Basic information
- Standard SMILES
CC(C)CN- InChIKey
KDSNLYIMUZNERS-UHFFFAOYSA-N- Molecular formula
- C4H11N
- Average molar mass
- 73.14 g/mol
- Monoisotopic mass
- 73.08914935
Overview
Isobutylamine appears as a clear colorless liquid with a fishlike odor. Flash point 15 °F. Less dense (6.1 lb / gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.
Names & identifiers
- Preferred name
- Isobutylamine
- IUPAC
- 2-methylpropan-1-amine
- English name
- Isobutylamine
- Molecular formula
- C4H11N
- Molecular weight
- 73.14
Names & synonyms
Show more names
Database identifiers
- CAS
78-81-9- PubChem CID
- 6558
- DTXSID
DTXSID9025459- ChEBI
CHEBI:15997- UNII
- 1H60H4LOHZ
- EC Number
- 201-145-4
- Nikkaji
- J46.573I
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 26 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 5
- Formal charge
- 0
- Complexity
- 17.6
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Amines, Aliphatic
Flammable agents - 3rd degree
LogP
log Kow = 0.73
0.73
0.73
0.73
Odor
Amine odor
Fish-like odor.
Density
0.739 at 68 °F (USCG, 1999) - Less dense than water; will float
0.724 at 25 °C/4 °C
Relative density (water = 1): 0.72
0.731-0.737
0.731 @ 20°C
Solubility
Very soluble (NTP, 1992)
Very sol in alcohol, ether; Sol in acetone, benzene
In water, 1X10+6 mg/L (miscible) at 25 °C
1000 mg/mL at 25 °C
Solubility in water: miscible
Soluble in water
Flash Point
15 °F (NTP, 1992)
15 °F (-9 °C) (closed cup)
-9.0 °C c.c.
Boiling Point
154 to 156 °F at 760 mmHg (NTP, 1992)
68-69 °C
68-69 °C
67.00 to 71.00 °C. @ 760.00 mm Hg
68-69 °C
68 °C
Physicochemical properties
- Melting point
- -85 °C · -85 °C (lit.)
- Boiling point
- 64 · 64-71 °C (lit.)
- Density
- 0.736 g/mL · 0.736 g/mL at 25 °C (lit.)
- vapor pressure
- 15.9 kPa · 15.9kPa at 20℃
- FEMA
- 4239 · 4239 | ISOBUTYLAMINE
- refractive index
- 20 · n20/D 1.397(lit.)
- FLAVIS Number
- 11.002 · 11.002 | Isobutylamine
- Flash point
- 15 °F · 15 °F
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 1000 g/l · 1000g/l
- form
- Liquid
- pka
- 1 · pK1:10.41(+1) (25°C)
- color
- Clear colorless to slightly yellow
- PH
- 12.2 · 12.2 (100g/l, H2O, 20℃)
- Odor
- Strong ammoniacal.
- explosive limit
- 2 · 2-9%(V)
- Odor Threshold
- 0.0015 ppm · 0.0015ppm
- Odor Type
- fishy
- Water Solubility
- soluble
- Specific Heat Capacity
- 2.5 J/ · Cp(liquid): 2.5 J/(g·K), at 25℃
- JECFA Number
- 1583 · 1583
- Merck
- 14 · 14,5132
- BRN
- 385626 · 385626
- Henry's Law Constant
- 7.3 · 7.3×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 4.4 · 4.4(Ambient)
- InChI
- 1S/C4H11N/c1-4(2)3-5/h4H,3,5H2,1-2H3
- InChIKey
- KDSNLYIMUZNERS-UHFFFAOYSA-N
- SMILES
- CC(C)CN
- LogP
- -0.3 at · -0.3 at 25℃
- CAS DataBase Reference
- 78 · 78-81-9(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ISOBUTYLAMINE
- EWG's Food Scores
- 2 · 2
- FDA UNII
- 1 H60H4LOHZ · 1H60H4LOHZ
- NIST Chemistry Reference
- 1 · 1-Propanamine, 2-methyl-(78-81-9)
- EPA Substance Registry System
- Isobutylamine (78-81-9)
- UNSPSC Code
- 12352116 · 12352116
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H314-H335-H225
- Precautionary statements
- 501 · P501-P270-P240-P261-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,C
- Risk Statements
- 11 · 11-22-35
- Safety Statements
- 26 · 26-36/37/39-45
- OEL
- 5 ppm; · STEL: 5.0 ppm; 15.0 mg/m3
- RIDADR
- 1214 · UN 1214
- WGK Germany
- 1 · 1
- RTECS
- 9900000 · NP9900000
- F
- 10 · 10-23
- Autoignition Temperature
- 400 °C · 400°C
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29211990 · 29211990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 OralFlam · Acute Tox. 3 OralFlam. Liq. 2Skin Corr. 1A
- Hazardous Substances Data
- 78 · 78-81-9(Hazardous Substances Data)
- Toxicity
- 50 · LD50 (14 day) in male, female rats (mg/kg): 224.4, 231.8 orally (Cheever)
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P361+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 208 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
Hazard information
Regulatory Information
Chemical: 1-Propanamine, 2-methyl-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Status: Active Update: 26-11-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/27674
Isobutylamine: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Special Hazards of Combustion Products: Toxic oxides of nitrogen may be formed in fire.
· Flammable/combustible material.
Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.
Fire Potential
Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire.
DANGEROUS, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS
Health Hazards
Inhalation causes severe coughing and chest pain due to irritation of air passages; can cause lung edema. Compound is sympathomimetic and is also a cardiac depressant and convulsant; ingestion causes nausea and profuse salivation. Contact with eyes causes severe irritation and edema of the cornea. Contact with skin causes severe irritation. (USCG, 1999)
· May cause toxic effects if inhaled or ingested.
Hazards Summary
Corrosive to skin; [Quick CPC] High inhalation exposure can cause pulmonary edema; [ICSC] Contact with skin may cause erythema and blistering; [Merck Index] Causes convulsions and ataxia in oral lethal-dose studies of rats; [RTECS] Short-term exposure causes second- and third-degree burns and corneal edema; Inhalation causes intense coughing, chest pain, and possibly pulmonary edema; [CHRIS] Safe when used as a flavoring agent in food; [JECFA]
Reactivity Profile
ISOBUTYLAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Safety & protection
Fire Fighting
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
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. Give one or two glasses of water to drink. Refer for medical attention .
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
General First Aid:
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
2.0 [ppm], Ceiling = 5 ppm[German Research Foundation (DFG)]
Fire Fighting Procedures
Dry chemical, foam, carbon dioxide, or alcohol foam.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.
Storage Conditions
Fireproof. Separated from strong oxidants, strong acids, food and feedstuffs
Store in refrigerator. Keep under an inert atmosphere for long-term storage. /Butyl Amines/
Cleanup Methods
Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking liquid in sealable containers. Cautiously neutralize spilled liquid. Absorb remaining liquid in sand or inert absorbent and remove to safe place. Then wash away with plenty of water.
Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable. /Butyl Amines/
Small Spill: Use absorbent paper to pick up spilled material. Follow by washing surfaces well with soap and water. Seal all wastes in vapor-tight plastic bags for eventual disposal.
Environmental considerations-land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Apply appropriate foam to diminish vapor and fire hazard. Neutralize with sodium bisulfate (NaHSO4).
For more Cleanup Methods (Complete) data for ISOBUTYLAMINE (6 total), please visit the HSDB record page.
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Incineration; Incinerator is equipped with a scrubber or thermal unit to reduce NOx emissions. Alternatively it may be poured into sodium bisulfate, neutralized and flushed with water. /n-Butylamine/
Burn the paper in a suitable location away from combustible material. Large quantities can be reclaimed or collected and atomized in suitable combustion chamber equipped with appropriate effluent gas cleaning device. /N-butylamine/
/Absorb small spills with paper and/ burn the paper in a suitable location away from combustible materials. Large quantities can be reclaimed or collected & atomized in suitable combustion chamber equipped with appropriate effluent gas cleaning device.
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 spilled liquid. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wash away remainder with plenty of water.
Toxicology
Ecotoxicity Values
LC50 Danio rerio (Zebrafish, embryo) 1,267 umol/L/48 hr (95% confidence 1,093-1,610 umol/L); static (DarT test) /from table/
LD50 Danio rerio (Zebrafish, embryo) 3,282 umol/kg (calculated); static (DarT test) /from table/
LC100 Semotilus atromaculatus /(Creek chub)/ 820 umol/L/24 hr; static, 15-21 °C /from table/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 0.73(2) and a regression-derived equation(3), indicates that isobutylamine is expected to have high mobility in soil(SRC). The pKa of isobutylamine is 10.68(4) indicating that this compound will exist almost entirely 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 isobutylamine from moist soil surfaces is not expected to be an important fate process given its cation state(SRC). Isobutylamine is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). Isobutylamine was 87 percent and 68 percent biodegraded during a 2 week incubation period using a Japanese MITI test(7), suggesting that biodegradation may occur in soils(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 60(SRC), determined from a log Kow of 0.73(2) and a regression-derived equation(3), indicates that isobutylamine is not expected to adsorb to suspended solids and sediment in water(SRC). A pKa of 10.68(4) indicates isobutylamine 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(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Isobutylamine was 87 percent and 68 percent biodegraded during a 2 week incubation period using a Japanese MITI test(8), suggesting that biodegradation may occur in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isobutylamine, which has a vapor pressure of 138 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isobutylamine 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) from its estimated rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC), derived using a structure estimation method(3). Isobutylamine 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
Volatile amines /including isobutylamine were/ isolated ... from 4 month old Chanakh cheese.
The concn of various amines in 13 red and 10 white Italian wines were determined. ... The mean value for the red and white wines were 0.06 mg/L and 0.23 mg/L for isobutylamine, respectively.
Isobutylamine has been qualitatively detected in various Italian cheeses, in German wine, in American beef, in Valencia oranges, lemons from CA and cooked and boiled beef(1-6).
Isobutylamine concentrations in various foods(1). [Table#1715]
Milk Concentrations
... The presence of volatile aliphatic amines ... in human breast milk and amniotic fluid /was measured/ to assess their role in neonatal hypergastrinemia. These volatile nitrogenous amino acid metabolites have been previously demonstrated to stimulate gastrin release in in vivo and in vitro laboratory preparations. ... The present study ... demonstrated that these gastrin-stimulatory volatile amines were present in significant concentrations in breast milk during the first several weeks after parturition and in amniotic fluid. The individual amines that were identified in both human milk and amniotic fluid samples were methylamine, dimethylamine, ethylamine, trimethylamine, propylamine, isobutylamine, and butylamine. This study provides indirect evidence to support the possibility that the hypergastrinemia measured in the fetus/neonate during the period immediately before and after birth may be attributable, in part, to the ingestion of fluid containing high concentrations of gastrin-stimulating amines.
Signs and Symptoms
Burning sensation. Cough. Shortness of breath. Laboured breathing. Symptoms may be delayed.
Pain. Redness. Skin burns.
Redness. Pain. Severe deep burns.
Abdominal pain. Burning sensation. Shock or collapse.
Soil Adsorption/Mobility
The Koc of isobutylamine is estimated as 60(SRC), using a log Kow of 0.73(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that isobutylamine is expected to have high mobility in soil. The pKa of isobutylamine is 10.68(4) indicating that this compound will exist almost entirely 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).
Natural Pollution Sources
... amines from decomposing fish ... /Amines/
/The microbe/ ... Proteus mirabilis was found to produce isobutylamine.
Isobutylamine is a natural component of tobacco(1) and has been detected in marine algae(2).
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ INHALATION: Burning sensation. Cough. Shortness of breath. Labored breathing. Symptoms may be delayed. SKIN: Pain. Redness. EYES: Redness. Pain. Severe deep burns. Skin burns. INGESTION: Abdominal pain. Burning sensation. Shock or collapse.
/SIGNS AND SYMPTOMS/ SKIN CONTACT CAN RESULT IN ERYTHEMA, BLISTERING. INHALATION CAUSES HEADACHE, DRYNESS OF NOSE & THROAT.
/SIGNS AND SYMPTOMS/ Isobutylamine induces nausea and unpleasant salivation in man at 40 mg/kg orally.
/SIGNS AND SYMPTOMS/ Skin contact can result in erythema and blistering; inhalation causes headache and dryness of the nose and throat.
For more Human Toxicity Excerpts (Complete) data for ISOBUTYLAMINE (8 total), please visit the HSDB record page.
Regulatory information
CERCLA Reportable Quantities
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Clean Water Act Requirements
Isobutyamine is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.
Safety data
- F
- 10-23
- OEL
- STEL: 5.0 ppm; 15.0 mg/m3
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- NP9900000
- ridadr
- UN 1214
- hs_code
- 29211990
- Toxicity
- LD50 (14 day) in male, female rats (mg/kg): 224.4, 231.8 orally (Cheever)
- risk_code
- 11-22-35
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS06
- hazard_code
- F,C
- safety_code
- 26-36/37/39-45
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H301-H314-H335-H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 OralFlam. Liq. 2Skin Corr. 1A
- Autoignition Temperature
- 400°C
- Precautionary statements
- P501-P270-P240-P261-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
- Hazardous Substances Data
- 78-81-9(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Used in the production of insecticides and other organic chemicals; [HSDB]
Organic synthesis, insecticides.
Dehairing agent
Methods of Manufacturing
From isobutyl alcohol + ammonia; British patent 847,799 (1960 to Cellulose-polymeres et Derives "Cepede"); Shirley, Speranza, US patent 3,128,311 (1964 to Jefferson Chem). Isolation from fungi: von Kamienski, Planta 50, 331 (1958).
THERMAL DECOMP PRODUCT FROM VALINE & LEUCINE. /FROM TABLE/
Use Classification
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
1-Propanamine, 2-methyl-: ACTIVE
With isobutylamine, crotonic acid forms interpolymerization products suitable for sizing and wood sealing.
Aziridines are hydrogenated in the presence of typical hydrogenation catalysts to give alkyl amines.
Applications
UsesIsobutylamine may be used in the synthesis of N-i-butyl-9(Z),12(Z),15(Z)-octadecatrienamide by reacting with trilinolenin. It can also react with tropolone to form a hydrogen-bonded complex, iso-butyl-ammonium 7-oxo-cyclo-hepta-1,3,5-trien-1-olate. Fullerene (C60) can undergo oxyamination with isobutylamine to form polyamines.
General DescriptionIsobutylamine is a clear colorless liquid with a fishlike odor. Flash point 15°F. Less dense (6.1 lb / gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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