ベンジルアミン

Benzylamine

HCID 7504CAS 100-46-9

基本情報

標準SMILES
NCc1ccccc1
InChIKey
WGQKYBSKWIADBV-UHFFFAOYSA-N
分子式
C7H9N
平均分子量
107.15 g/mol
単同位体質量
107.07349929

名称と識別子

優先名称
Benzylamine
IUPAC
phenylmethanamine
現地名
ベンジルアミン
英語名
Benzylamine
分子式
C7H9N
分子量
107.15

名称と別名

BENZYLAMINE100-46-9phenylmethanamineBenzenemethanamineMonobenzylamine(Phenylmethyl)amine(Aminomethyl)benzenealpha-AminotolueneMoringineAminotolueneSumine 2005omega-Aminotoluene
名称をさらに表示
ベンジルアミンモリンギンアミノメチルベンゼンω-アミノトルエン(アミノメチル)ベンゼンアミノトルエンフェニルメタンアミンベンゼンメタンアミンベンゼン(メタンアミン)フェニルメチルアミン1-(アミノメチル)ベンゼン1-フェニルメタンアミンα-アミノトルエンBnnh2BZABenzylaminPHENYLMETHYLAMINEN-BENZYLAMINEBenzenethanamine
Sumine 2006DTXSID5021839A1O31ROR09CHEBI:40538NSC-8046DTXCID201839alpha AminotolueneRefChem:5598

データベース識別子

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

物性

構造計算による物性

XLogP
1.1
極性表面積
26 Ų
水素結合供与体数
1
水素結合受容体数
1
回転可能結合数
1
重原子数
8

実験および物理化学的性質

pHpH = 11.6 in water at a concentration of 100 g/L
LogP · 4 件

1.09

log Kow = 1.09

1.09

1.09

Odor · 2 件

Ammonia-like odor

Weak amine-like odor

Density · 6 件

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

Viscosity1.78 mPa-s at 21.2 °C, 0.295 mPa-s at 178.2 °C
Color/Form · 2 件

Colorless liquid

Light amber liquid

物理化学的性質

融点
10 °C · 10 °C (lit.)
沸点
184 · 184-185 °C (lit.)
比重(密度)
0.981 g/mL · 0.981 g/mL at 25 °C (lit.)
蒸気圧
1.2 hPa · 1.2 hPa (20 °C)
屈折率
20 · n20/D 1.543(lit.)
闪点
140 °F · 140 °F

化学的性質

化学的特性colourless liquid with an ammoniacal odour

安全と法規制

GHS分類

GHS Classification · 6 件

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.

危険有害性情報

Regulatory Information · 4 件

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

DOT LabelCorrosive
Fire Hazards · 2 件

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.

Fire PotentialFlammable
Health Hazards · 1 件

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 · 1 件

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]

安全と保護具

Fire Fighting · 2 件

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 · 4 件

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 .

First AidINHALATION: remove victim from exposure; if breathing is difficult, administer oxygen; if breathing has stopped, begin artificial respiration.;EYES or SKIN: wash with copious amounts of water for 15 min. (USCG, 1999)
Safe StorageFireproof. Separated from strong oxidants, strong acids and food and feedstuffs.
Fire Fighting Procedures · 2 件

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.

Storage ConditionsFireproof. Separated from strong oxidants, strong acids, food and feedstuffs.

毒性情報

Body Burden · 1 件

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 · 5 件

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 · 3 件

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 · 3 件

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 · 1 件

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).

Adverse EffectsDermatotoxin - Skin burns.;Lacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.;Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.

法規制情報

Regulatory Information · 4 件

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

RCRA RequirementsD002; A solid waste containing benzylamine may become characterized as a hazardous waste when subjected to testing for corrosivity as stipulated in 40 CFR 261.21, and if so characterized, must be managed as a hazardous waste.
Atmospheric Standards · 1 件

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.

安全データ

F
34
wgk
1
tsca
TSCA listed
rtecs
DP1488500
ridadr
UN 2735 8/PG 2
毒性
LD50 orally in Rabbit: 552 mg/kg LD50 dermal Rat 1350 mg/kg

化学と産業

薬理情報

Mechanism of Action · 2 件

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 · 5 件

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.

Cellular LocationsCytoplasm;Extracellular

用途と製造

Uses · 6 件

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 · 4 件

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.

Industry UsesIntermediate;Monomers
Methods of Manufacturing · 2 件

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 · 2 件

Paint and Coating Manufacturing;All Other Basic Organic Chemical Manufacturing

Benzenemethanamine: ACTIVE

応用分野 · 6 件

解説ベンジルアミン,液体.沸点185 ℃,90 ℃(1.6 kPa).d194 0.9826.n20D 1.540.水,エタノール,エーテルに可溶.強い塩基性を示す.pKa 9.6(25 ℃).空気中の二酸化炭素を吸収する.医薬品,染料,界面活性剤などの合成原料に用いられる.不快な刺激臭があり,眼,鼻,口腔などの粘膜に対し強い刺激性を有する。トルエンの存在下での光塩素化によって塩化ベンザルとベンゾトリクロリドとともに生成する。加水分解によりベンジルアルコールを生じる。消毒剤の中間体,アミン類のベンジル化剤として使用される。香料,医薬品,染料などの製造原料の一つとして用いられる。

用途有機合成原料、界面活性剤

用途医薬品、染料、界面活性剤、化学薬品の合成原料

使用Benzylamine 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.

一般的な説明Colorless to light yellow liquid with a strong odor of ammonia. Floats and mixes with water.

使用用途ベンジルアミンは、医薬品はじめ染料や界面活性剤の原料など産業上の基礎材料として幅広く活用されています。例えば、、シアン化ベンジルなど化合物の製造原料です。 工業用途では、農薬や染料、防腐剤、プラスチック、香料、ゴムなどの製造に広く使用されます。さらに、さまざまな医薬品や農薬を合成する際の官能基の導入や置換反応の起点としても使用される、重要なビルディングブロックでもあります。

調製方法 · 2 件

製造方法ベンジルアミンの製造方法 ベンジルアミンの製造には、とアンモニアを反応させる方法やトルエンとアンモニアを反応させて得られる方法などで合成することができます。 最も一般的な方法は、アンモニアまたはアミンの存在下、アルカリ金属またはアルカリ土類金属を用いてを還元する方法です。 まず、ベンジルアルコールとを反応させ、塩化ベンジルを調製します。次に、合成した塩化ベンジルを、アンモニアまたは/などのアミン存在下、などのアルカリ金属あるいはアルカリ土類金属と混合します。 この混合物を約80〜100℃の温度まで加熱することで、塩化ベンジルをベンジルラジカルに還元する反応が起こります。生じたベンジルラジカルは、アンモニアまたはアミンと反応してベンジルアミンが合成されます。 その後、エーテルやなどの溶媒を用いて反応混合物から生成物を抽出します。この合成法は複数あるベンジルアミン合成法の中で最も効率的であり、高い純度の生成物を得ることが可能です。

純化方法Dry it with NaOH or KOH, then distil it under N2, through a column packed with glass helices, taking the middle fraction. Also distil it from zinc dust under reduced pressure. The picrate has m 196o (from EtOH), and the p-toluenesulfonamide has m 116o (from MeOH). [Beilstein 12 IV 2155.]

上流・下流製品情報

下流製品

(3R)-(+)-3-(tert-ブトキシカルボニルアミノ)ピロリジン2,6-ジメチルピペラジン3-(ベンジルアミノ)プロピオン酸エチルN-[4-(アミノスルホニル)ベンジル]アセトアミドホモスルファミン 塩酸塩N-ベンジル-N-(メトキシメチル)-N-トリメチルシリルメチルアミン1-ベンジル-4-オキソ-3-ピペリジンカルボン酸メチル塩酸塩メチル(4-ピペリジル)カルバミン酸 tert-ブチルTERT-ブチル 3-(アミノメチル)アゼチジン-1-カルボキシレート(S)-1-ベンジル-3-ピロリジノール(S)-3-ヒドロキシピロリジン塩酸塩(+)-N-ベンジル-(3R,4R)-ビス(ジフェニルホスフィノ)ピロリジン

サプライヤー44 社

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補足説明

定義ChEBI: A primary amine compound having benzyl as the N-substituent. It has been isolated from Moringa oleifera (horseradish tree).

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