Basic information
- Standard SMILES
NCc1ccccc1- InChIKey
WGQKYBSKWIADBV-UHFFFAOYSA-N- Molecular formula
- C7H9N
- Average molar mass
- 107.15 g/mol
- Monoisotopic mass
- 107.07349929
Names & identifiers
- Preferred name
- Benzylamine
- IUPAC
- phenylmethanamine
- English name
- Benzylamine
- Molecular formula
- C7H9N
- Molecular weight
- 107.15
Names & synonyms
Show more names
Database identifiers
- CAS
100-46-9、89551-24-6- PubChem CID
- 7504
- DTXSID
DTXSID5021839- ChEMBL
CHEMBL522- ChEBI
CHEBI:40538- UNII
- A1O31ROR09
- EC Number
- 202-854-1、810-242-6
- Nikkaji
- J4.008H
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 26 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 55
Experimental & physicochemical properties
LogP
1.09
log Kow = 1.09
1.09
1.09
Odor
Ammonia-like odor
Weak amine-like odor
Density
0.98 at 68 °F (USCG, 1999) - Less dense than water; will float
0.983 at 19 °C/4 °C
Density: 0.9813 g/cu cm at 20 °C
Density = 0.9272 at 86.6 °C/4 °C
Relative density (water = 1): 0.98
0.983 @ 19°C
Color/Form
Colorless liquid
Light amber liquid
Solubility
1000000
Miscible in ethanol and diethyl ether. Very soluble in acetone. Soluble in benzene. Slightly soluble in chloroform.
In water, 1.00X10+6 mg/L at 20 °C (miscible)
1000 mg/mL at 20 °C
Solubility in water: miscible
Flash Point
168 °F (USCG, 1999)
168 °F
65 °C (149 °F) - closed cup
60 °C
Boiling Point
364.1 °F at 760 mmHg (USCG, 1999)
185
185 °C
185.00 °C. @ 760.00 mm Hg
185 °C
185 °C @760 [mm Hg]
Melting Point
-51 °F (USCG, 1999)
10
10 °C
10 °C
Physicochemical properties
- Melting point
- 10 °C · 10 °C (lit.)
- Boiling point
- 184 · 184-185 °C (lit.)
- Density
- 0.981 g/mL · 0.981 g/mL at 25 °C (lit.)
- vapor pressure
- 1.2 hPa · 1.2 hPa (20 °C)
- refractive index
- 20 · n20/D 1.543(lit.)
- Flash point
- 140 °F · 140 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- alcohol: miscible
- form
- Liquid
- pka
- 9.33 · 9.33(at 25℃)
- color
- Clear colorless to slightly yellow
- PH
- 11.4 · 11.4 (100g/l, H2O, 20℃)
- Odor
- Strong ammonia.
- explosive limit
- 0.7 · 0.7-8.2%(V)
- Water Solubility
- soluble
- Specific Heat Capacity
- 1.93 J/ · Cp(liquid): 1.93 J/(g·K), at 25℃
- Sensitive
- Air Sensitive
- Merck
- 14 · 14,1125
- BRN
- 741984 · 741984
- Henry's Law Constant
- 7.1 · 7.1×10-1 mol/(m3Pa) at 25℃, Yao et al. (2002)
- Dielectric constant
- 4.6 · 4.6(Ambient)
- Stability
- Combustible. Incompatible with strong oxidizing agents, strong acids.
- InChI
- 1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
- InChIKey
- WGQKYBSKWIADBV-UHFFFAOYSA-N
- SMILES
- NCc1ccccc1
- LogP
- 1 at · 1 at 25℃
- Surface tension
- 37.1 mN/m · 37.1mN/m at 293.15K
- CAS DataBase Reference
- 100 · 100-46-9(CAS DataBase Reference)
- EWG's Food Scores
- 2 · 2
- FDA UNII
- 1 O31ROR09 · A1O31ROR09
- NIST Chemistry Reference
- Benzylamine(100-46-9)
- EPA Substance Registry System
- Benzylamine (100-46-9)
- UNSPSC Code
- 12352116 · 12352116
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302+H312-H314-H402-H227
- Precautionary statements
- 501 · P501-P273-P270-P210-P264-P280-P370+P378-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C
- Risk Statements
- 21 · 21/22-34
- Safety Statements
- 26 · 26-36/37/39-45
- RIDADR
- 2735 · UN 2735 8/PG 2
- WGK Germany
- 1 · 1
- RTECS
- 1488500 · DP1488500
- F
- 34 · 34
- Autoignition Temperature
- 405 °C · 405 °C
- TSCA
- TSCA listed
- HS Code
- 2921 · 2921 49 00
- HazardClass
- 8 · 8
- PackingGroup
- II
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1Skin Corr. 1B
- Hazardous Substances Data
- 100 · 100-46-9(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 552 mg/kg LD50 dermal Rat 1350 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral];H312: Harmful in contact with skin [Warning Acute toxicity, dermal];H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 0.2% (1 of 518) of reports.
Hazard information
Regulatory Information
Chemical: Benzenemethanamine
Benzenemethanamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenemethanamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 20-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5667;Status: Active Update: 19-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20033
Benzylamine: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
Special Hazards of Combustion Products: Toxic nitrogen oxides may form in a fire. (USCG, 1999)
Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 60 °C explosive vapour/air mixtures may be formed.
Health Hazards
Inhalation of vapor causes irritation of the mucous membranes of the nose and throat, and lung irritation with respiratory distress and cough. Headache, nausea, faintness, and anxiety can occur. Exposure to vapor produces eye irritation with lachrymation, conjunctivitis, and corneal edema resulting in halos around lights. Direct local contact with liquid is known to produce severe and sometimes permanent eye damage and skin burns. Vapors may also produce primary skin irritation and dermatitis. (USCG, 1999)
Hazards Summary
Corrosive to skin; [Quick CPC] Inhalation of vapor can cause respiratory distress and cough; Effects on the eye include lacrimation and corneal edema associated with a perception of halos around lights; [CAMEO] A corrosive substance that can cause pulmonary edema; [ICSC]
Reactivity Profile
In presence of moisture, BENZYLAMINE may weakly corrode some metals. Liquid will attack some plastics (USCG, 1999). Neutralize acids to form salts plus water in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides.
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzylamine is produced, as an intermediate or a final product, by process units covered under this subpart.
Safety & protection
Fire Fighting
Fire Extinguishing Agents Not to Be Used: Water may be ineffective.;Fire Extinguishing Agents: Alcohol foam, dry chemical, carbon dioxide (USCG, 1999)
Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Do NOT induce vomiting. Refer for medical attention .
Fire Fighting Procedures
Powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
Wear self contained breathing apparatus for fire fighting if necessary.
Cleanup Methods
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Collect leaking liquid in sealable containers. Cautiously neutralize remainder. Then wash away with plenty of water. Extra personal protection: complete protective clothing including self-contained breathing apparatus.
Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number D002, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
The following wastewater treatment technologies have been investigated for benzylamine: concentration process: biological treatment.
This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material.
Spillage Disposal
Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Cautiously neutralize remainder. Then wash away with plenty of water.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Ventilation, local exhaust, or breathing protection.
Isolation and Evacuation
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.;SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)
Toxicology
Body Burden
A total of 224 expired air samples were collected from 28 healthy, non-smoking volunteers in Chicago(1); approximately 18% of the samples contained benzylamine at a geometric mean concentration of about 0.1 ng/L(1). In another study, a total of 387 expired air samples were collected from 54 healthy volunteers in Chicago(1); approximately 12% of the samples contained benzylamine at a geometric mean concentration of about 0.007 ng/L(2).
Interactions
Semicarbazide-sensitive amine oxidase (SSAO) is highly expressed in adipose cells, and substrates of SSAO, such as benzylamine, in combination with low concentrations of vanadate strongly stimulate glucose transport and GLUT4 recruitment in 3T3-L1 and rat adipocytes. ... Acute intravenous administration of these drugs enhanced glucose tolerance in nondiabetic rats and in streptozotocin (STZ)-induced diabetic rats. This occurred in the absence of changes in plasma insulin concentrations. However, the administration of benzylamine or vanadate alone did not improve glucose tolerance. The improvement caused by benzylamine plus vanadate was abolished when rats were pretreated with the SSAO-inhibitor semicarbazide. Chronic administration of benzylamine and vanadate exerted potent antidiabetic effects in STZ-induced diabetic rats. Although daily administration of vanadate alone (50 and 25 umol/kg/day i.p.) for 2 weeks had little or no effect on glycemia, vanadate plus benzylamine reduced hyperglycemia in diabetic rats, enhanced basal and insulin-stimulated glucose transport, and upregulated GLUT4 expression in isolated adipocytes...
Benzylamine, a substrate of semicarbazide-sensitive amine oxidase (SSAO), stimulates glucose transport in rat adipocytes and improves glucose disposal in diabetic rats only in the presence of vanadate. These effects have been described to result from a synergism between the hydrogen peroxide formed during amine oxidation and vanadate, via the generation of pervanadate, a powerful insulin mimicker. However, it has also been reported that benzylamine alone can stimulate glucose uptake and inhibit lipolysis in human fat cells. ...This work ... investigated whether benzylamine on its own was able to induce both in vivo and in vitro insulin-like responses in animal models other than rat. In rabbits, the i.v. infusion of 7 umol/kg benzylamine before a glucose tolerance test resulted in a net reduction of the hyperglycemic response without a change in insulin secretion. Benzylamine also improved glucose tolerance and reduced lipid mobilization in hyperglycemic/obese mice. In vitro, 0.1 mM benzylamine stimulated glucose transport and inhibited lipolysis in mouse and rabbit adipocytes. These effects were blocked by previous treatments with semicarbazide, a SSAO inhibitor. Levels of benzylamine oxidation were more elevated in mouse than in rabbit adipose tissues, whereas the reverse was observed for skeletal muscles. Finally, benzylamine was unable to stimulate insulin secretion by isolated pancreatic islets from both species and SSAO activity was hardly detectable in pancreas. Together, /these/ results bring evidence that benzylamine on its own can improve glucose tolerance in rabbit and mouse, likely by stimulating glucose uptake via amine oxidase activation in insulin-sensitive tissues.
In mice deprived of food for 12 h, the i.c.v. or i.p. administration of benzylamine, a substrate common to both monoamine oxidase B and semicarbazide-sensitive benzylamine oxidases, dose-dependently inhibited feeding. This effect was significantly potentiated by selective monoamine oxidase A and B inhibition, suggesting that central monoamines, known to be substrates of these enzymes may be released. The i.p. administration of semicarbazide-sensitive benzylamine oxidase inhibitors, B24 (3,5-ethoxy-4-aminomethylpyridine) and MDL 72274 ((E)-2-phenyl-3-chloroallylamine) strongly potentiated the effect of i.p. but not i.c.v.-administered benzylamine. The hypophagic effect of benzylamine was evaluated following i.c.v. administration, in comparison with the effect of the sympathomimetic compound amphetamine or the K(+) channel blocker tetraethylammonium, as reference compounds. Our results make it possible to define benzylamine as a centrally acting hypophagic compound devoid of amphetamine-like motor stimulatory effects and point to a role of B24 and MDL 72274 as specific peripheral enhancers of the pharmacological effects of benzylamine.
Streptozotocin induced diabetic rats were treated with benzylamine (BZA) +/- vanadate (V) or insulin. In contrast to insulin, BZA + V treatment did not reduce HbA(1C) levels. However, it reduced the elevated serum semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 (SSAO) activity, decreased the accumulation of advanced-glycation end products and increased the bioavailability of nitric oxide in diabetic animals, similarly to insulin. BZA alone did not affect any of these parameters.
For more Interactions (Complete) data for Benzylamine (7 total), please visit the HSDB record page.
Ecotoxicity Values
LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow through, 23.9 °C, pH 7.9, dissolved oxygen 6.9 mg/L, hardness 44.7 mg/L CaCO3, alkalinity 44.0 mg/L CaCO3; Concentration: 102 mg/L for 96 hr (confidence limit: 97.9-106 mg/L)
EC50; Species: Pimephales promelas (fathead minnow); Conditions: flow through, 23.9 °C, pH 7.9, dissolved oxygen 6.9 mg/L, hardness 44.7 mg/L CaCO3, alkalinity 44.0 mg/L CaCO3; Concentration: 98 mg/L for 96 hr (confidence limit: 94.5-102 mg/L); Effect: loss of equilibrium
LC50; Species: Pimephales promelas (fathead minnow, age 30 days, 0.087 g, 18.2 mm); Conditions: freshwater, flow through, 23.9 °C, pH 7.9, hardness 44.7 mg/L CaCO3, alkalinity 44.0 mg/L CaCO3, dissolved oxygen 6.9 mg/L; Concentration: 102000 ug/L (97900-106000 ug/L) for 96 hr /99% pure/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 270(SRC), determined from a log Kow of 1.09(2) and a regression-derived equation(3), indicates that benzylamine is expected to have moderate mobility in soil(SRC). The pKa of benzylamine is 9.33(4), indicating that this compound will entirely exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of benzylamine from moist soil surfaces is not expected to be an important fate process(SRC) given the predominance of the cationic state at pH values of 5 to 9(7). Benzylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.662 mm Hg at 25 °C(8). Multiple biodegradation screening studies reported that benzylamine degraded 53-101% after 4-30 days(9,10)suggesting that biodegradation is expected to be an important fate process in terrestrial environments(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 270(SRC), determined from a log Kow of 1.09(2) and a regression-derived equation(3), indicates that benzylamine is expected to adsorb to suspended solids and sediment(SRC). A pKa of 9.33(6) indicates benzylamine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(7). According to a classification scheme(8), an estimated BCF of 2.4(SRC), from its log Kow(2) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Benzylamine degraded 96.1-98.9% after 6 days in lake water(10), indicating benzylamine will biodegrade in aquatic environments(SRC). However, biodegradation may be attenuated by adsorption to suspended sediments(11,12).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), benzylamine, which has a vapor pressure of 0.662 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase benzylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 11 hours(SRC), calculated from its rate constant of 3.3X10-11 cu cm/molecule-sec at 25 °C(3). Benzylamine does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
The following concentrations of benzylamine (in mg/kg) were detected in samples of fresh vegetables: spinach, 6.1; red cabbage, 3.3; cabbage, 2.8; cauliflower, 1.4; kale, 3.8; white beet, 5.3; carrots, 2.8; red beet, 0.1; large radish, 1.8; red radish, 4.8; celery, 3.4. Benzylamine concentrations (in mg/kg) were detected in the following foods: maize, grains, 3.4; green salad, 11.5; rhubard, 2.9; apple flesh, 0.3; apple peel, 0.6(1).
Signs and Symptoms
Sore throat. Cough. Burning sensation. Shortness of breath. Laboured breathing. Symptoms may be delayed.
Pain. Redness. Skin burns. Blisters.
Pain. Redness. Severe deep burns.
Burning sensation. Abdominal pain. Shock or collapse.
Soil Adsorption/Mobility
The Koc of benzylamine is estimated as 270(SRC), using a log Kow of 1.09(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that benzylamine is expected to have moderate mobility in soil. The pKa of benzylamine is 9.33(4), indicating that this compound will almost entirely exist in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Corrosive to the eyes, the skin and the respiratory tract. Inhalation of vapor may cause lung edema ... The symptoms of lung edema often do not become manifest until a few hours have passed, and they are aggravated by physical effort. Rest and medical observation is therefore essential. Immediate administration of an appropriate spray, by a doctor or a person authorized by him/her, should be considered.
/SIGNS AND SYMPTOMS/ Inhalation: Sore throat. Cough. Burning sensation. Shortness of breath. Labored breathing. Symptoms may be delayed. Skin: Pain. Redness. Skin burns. Blisters. Eyes: Pain. Redness. Severe deep burns. Ingestion: Burning sensation. Abdominal pain. Shock or collapse.
/SIGNS AND SYMPTOMS/ Highly irritating to skin, mucous membranes.
/SIGNS AND SYMPTOMS/ Benzylamine is an irritating, corrosive liquid. The vapor irritates the eyes and the mucous membranes of the respiratory tract. The solution irritates and corrodes the skin. Long-term exposure can cause eczema.
/CASE REPORTS/ The case of a 48 year old chemist who developed a work related dermatitis after handling epichlorohydrin, benzylamine, and benzyl-1-amino-3-chloro-2-hydroxypropane was described. The patient presented with a dermatitis of the hands and face which subsided after a few days away from work. He used the compounds as chemical intermediates in the potential synthesis of agricultural chemicals, and his dermatitis developed shortly after he had contact with the materials. The clinical history included hay fever, and positive inhalation responses to house dust, grass pollen, and animal dander were obtained. A weak reaction to formaldehyde was found in patch tests with the ICDRG standard series. Patch tests to epichlorohydrin were negative. Patch tests to benzylamine and benzyl-1-amino-3-chloro-2-hydroxypropane were positive. These compounds were tested at 0.1 and 1% in 70% ethanol. Ten comparisons had negative patch tests to these compounds. It was concluded that the positive reactions in the patient are allergic reactions which probably demonstrate cross sensitivity.
Regulatory information
Regulatory Information
Chemical: Benzenemethanamine
Benzenemethanamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenemethanamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 20-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5667;Status: Active Update: 19-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/20033
Benzylamine: Does not have an individual approval but may be used under an appropriate group standard
Atmospheric Standards
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Benzylamine is produced, as an intermediate or a final product, by process units covered under this subpart.
Safety data
- F
- 34
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- DP1488500
- ridadr
- UN 2735 8/PG 2
- hs_code
- 2921 49 00
- Toxicity
- LD50 orally in Rabbit: 552 mg/kg LD50 dermal Rat 1350 mg/kg
- risk_code
- 21/22-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H302+H312-H314-H402-H227
- Limited Quantities
- 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 OralEye Dam. 1Skin Corr. 1B
- Autoignition Temperature
- 405 °C
- Precautionary statements
- P501-P273-P270-P210-P264-P280-P370+P378-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
- Hazardous Substances Data
- 100-46-9(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Mechanism of Action
Glucose, 3-deoxyglucosone (3-DG), and methylglyoxal (MG) oxidatively deaminated benzylamine to benzaldehyde in the presence of Cu(2+) at a physiological pH and temperature but not glyoxal. 3-DG and MG were more effective oxidants than glucose. We have determined the effects of metal ions, pH, oxygen, and radical scavengers on the oxidative deamination. The formation of benzaldehyde was greatest with Cu(2+), and was accelerated at a higher pH and in the presence of oxygen. EDTA, catalase, and dimethyl sulfoxide significantly inhibited the oxidation, suggesting the participation of reactive oxygen species. From these results, we propose a mechanism for the oxidative deamination by the Strecker-type reaction and the reactive oxygen species-mediated oxidation during glycoxidation.
Human semicarbazide-sensitive amine oxidase (SSAO) is a target for novel anti-inflammatory drugs that inhibit enzymatic activity. However, progress in developing such drugs has been hampered by an incomplete understanding of mechanisms involved in substrate turnover. We report here results of a comparative study of human and bovine SSAO enzymes that reveal binding of substrates and other ligands to at least two (human) and up to four (bovine) distinct sites on enzyme monomers. Anaerobic spectroscopy reveals binding of substrates (spermidine and benzylamine) and of an imidazoline site ligand (clonidine) to the reduced active site of bovine SSAO, whereas interactions with oxidized enzyme are evident in kinetic assays and crystallization studies. Radioligand binding experiments with [(3)H]tetraphenylphosphonium, an inhibitor of bovine SSAO that binds to an anionic cavity outside the active site, reveal competition with spermidine, benzylamine, and clonidine, indicating that these ligands also bind to this second anionic region. Kinetic models of bovine SSAO are consistent with one spermidine molecule straddling the active and secondary sites on both oxidized and reduced enzyme, whereas these sites are occupied by two individual molecules of smaller substrates such as benzylamine. Clonidine and other imidazoline site ligands enhance or inhibit activity as a result of differing affinities for both sites on oxidized and reduced enzyme. In contrast, although analyses of kinetic data obtained with human SSAO are also consistent with ligands binding to oxidized and reduced enzyme, ... no apparent requirement for substrate or modulator binding to any secondary site to model enzyme behavior /was observed/.
Metabolism/Metabolites
The in vivo and in vitro disposition of benzylamine was investigated in rats. Benzylamine was metabolized to only a small extent by rat liver subcellular fractions. In contrast, it was extensively metabolized in vivo in rats. In vivo studies performed with stable isotope-labeled benzylamine enabled rapid mass spectrometric identification of metabolites present in rat bile and urine. The major metabolite of benzylamine was the hippuric acid formed by glycine conjugation of benzoic acid. LC/MS analysis of bile and urine obtained from rats dosed with 1:1 equimolar mixture of either d(0):d(7)- or d(0):d(2)-benzylamine showed the presence of several glutathione adducts in addition to the hippuric acid metabolite. The presence of various glutathione adducts indicated that benzylamine was metabolized to a number of reactive intermediates. Various metabolic pathways, including those independent of P450, were found to produce these intermediates. A previously undocumented pathway included the formation of a new carbon-nitrogen bond that led to a potentially reactive intermediate, Ar-CH(2)-NH(CO)-X, capable of interacting with various nucleophiles. The origin of this reactive intermediate is postulated to occur via the formation of either a formamide or carbamic acid metabolites. Metabolites which were produced by the reaction of this intermediate, Ar-CH(2)-NH(CO)-X with nucleophiles included S-[benzylcarbamoyl] glutathione, N-acetyl-S-[benzylcarbamoyl]cysteine, S-[benzylcarbamoyl] cysteinylglycine, S-[benzylcarbamoyl] cysteinylglutamate, N-[benzylcarbamoyl] glutamate, and an oxidized glutathione adduct. Bioactivation of amines via this pathway has not been previously described. The oxidative deamination of benzylamine yielding the benzaldehyde was demonstrated to be a precursor to the hippuric acid metabolite and S-benzyl-L-glutathione. The formation of the S-benzyl-L-glutathione conjugate showed that a net displacement of amine from benzylamine had taken place with a subseq
In mammals, benzylamine is metabolized by semicarbazide-sensitive amine oxidase (SSAO) to benzaldehyde and hydrogen peroxide. This latter product has insulin-mimicking action, and is involved in the effects of benzylamine on human adipocytes: stimulation of glucose transport and inhibition of lipolysis.
Hippuric acid was excreted after ingestion of benzylamine by humans.
The activity of monoamine oxidase was studied in the mitochondria fraction of the brain stem of active sleeping, or hibernating ground squirrels. During hibernation, deamination of serotonin and conversion of monoamine oxide serotonin complex decr more than benzylamine deamination and monoamine oxide benzylamine complex conversion.
For more Metabolism/Metabolites (Complete) data for Benzylamine (7 total), please visit the HSDB record page.
Uses & manufacturing
Uses
Used as a chemical intermediate; [HSDB]
In organic synthesis
Chemical intermediate for dyes, pharmaceuticals and polymers
... raw material for the production of biotin (Vitamin H), as an intermediate for certain photographic materials..
In synthetic textiles, in paints, and as a corrosion inhibitor ... an intermediate in the production of ... compounds for plant and material protection. In this case ... as "protected nitrogen"
Reaction with glyoxal hemiacetal to synthesize 1-substituted isoquinolines.
U.S. Production
2023: <75,000 lb;2022: <75,000 lb;2021: <75,000 lb;2020: 75,000 - <500,000 lb
Benzenemethanamine is listed as an Extended High Production Volume (EHPV). Chemicals listed as EHPV were produced in or imported into the U.S. in >1 million pounds according to the 2002 Toxic Substances Control Act (TSCA) Inventory Update. The EHPV program is a voluntary initiative that allows companies to demonstrate that adequate screening data exist for organic HPV chemicals.
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4171]
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzenemethanamine. Aggregated National Production Volume: < 500,000 pounds.
Methods of Manufacturing
Benzylamine is produced by the reaction of benzyl chloride with ammonia in aqueous solution. The catalytic hydrogenation of benzonitrile and the reaction of benzaldehyde with ammonia in the presence of hydrogen and catalysts are alternatives.
Preparation: benzyl chloride and ammonia; by reduction of benzonitrile; from benzyl bromide and acetamide; from N-benzylphthalimide and hydrazine hydrate.
General Manufacturing Information
Paint and Coating Manufacturing;All Other Basic Organic Chemical Manufacturing
Benzenemethanamine: ACTIVE
Applications
UsesBenzylamine is used as a chemical intermediate for dyes, pharmaceuticals, and polymers.It is also employed as a corrosion inhibitor and as a brightener in electroplating baths. It also finds use in the manufacture of explosives.
UsesBenzylamine is a valuable intermediate for various applications and a building block for chemical synthesis used in pharmaceuticals and crop protection agents. It finds application in the coating industry. It is involved as a carrier electrolyte for separation of alkali, alkaline earth and ammonium cations in water samples by capillary electrophoresis with indirect UV detection. It is also used in synthesis of cross-linked porous copolymer supports based on N-(p-vinylbenzoyl)-2-methylalanine, styrene and divinylbenzene. In the textile industry, it is used in colored dyes. It is often used for medicinal purposes in topical creams and antifungal solutions as well as in vitamins.
UsesBenzylamine may be used as a derivatization agent to increase the sensitivity of 5-hydroxyindoles, catecholamines and catechols in biological samples prior to their determination using high performance liquid chromatography (HPLC) coupled with fluorescence detection.
General DescriptionColorless to light yellow liquid with a strong odor of ammonia. Floats and mixes with water.
Preparation methods
Preparation28% Aqueous Ammonia, 810g Benzyl chloride, 84.3g 49% Aqueous NaOH, 52.3g Diethyl Ether, 200g A three-necked flask was equipped with a reflux condenser dropping funnel and an agitator. All of the aqueous ammonium hydroxide solution was poured into the flask, then the benzyl chloride was introduced drop by drop; over a period of two hours with constant stirring of the mixture. The exothermic heat of reaction kept the temperature between 30-34°C during this period. When it is desired to introduce the benzyl chloride at a faster rate, conventional cooling means can be employed to control the temperature. A large excess of ammonia was employed as the molar ratio of reactants was 20:1. An additional two hours was allowed to insure completion of the following reaction: Then the equimolecular quantity of caustic soda solution was added. When quiescent, the mixture split into an aqueous layer and an oily layer. After separating these two layers by use of a separatory funnel, the aqueous phase was made available for further repeated use by merely adding sufficient ammonium hydroxide to bring the total quantity of ammonia up to the original figure. The oily layer was steam distilled until no further oily constituent was visible in the condensed distillate as it dripped down the condenser tube. This distillate was saturated with sodium chloride and successively extracted with an initial 80 and three 40 gram batches of ethyl ether. Upon evaporation of the ether from the extract, 52g of crude benzylamine remain which was distilled at atmospheric pressure. 41g grams of substantially pure benzylamine distilled over in the boiling range 185-192°C, while the residue was found to contain an additional 2.3g of benzylamine and 8.7g of other matter which was believed to consist entirely of dibenzyl amine. Thus the total yield of benzylamine was 43.3g or 60.7% based on the weight of benzyl chloride.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers44 total
Additional notes
DefinitionChEBI: A primary amine compound having benzyl as the N-substituent. It has been isolated from Moringa oleifera (horseradish tree).
Related reactions
Linked notes
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