N-BENZYLAMINE

N-benzylamine is a colorless to pale yellow liquid with a characteristic amine-like odor and exhibits basic properties due to the lone pair of electrons on the nitrogen atom. 
N-benzylamine is highly reactive in nucleophilic substitution and condensation reactions, making it an important building block in organic synthesis and medicinal chemistry. 
N-benzylamine is soluble in many organic solvents such as ethanol, ether, and chloroform, and moderately soluble in water. 

CAS Number: 100-46-9
Molecular Formula: C7H9N
Molecular Weight: 107.15
EINECS Number: 202-854-1

Synonyms: Benzylamine, phenylmethanamine, 100-46-9, Benzenemethanamine, Monobenzylamine, (Phenylmethyl)amine, alpha-Aminotoluene, (Aminomethyl)benzene, Moringine, Sumine 2005, Aminotoluene, omega-Aminotoluene, Sumine 2006, CHEBI:40538, A1O31ROR09, DTXSID5021839, NSC-8046, DTXCID201839, alpha Aminotoluene, CHEBI:22531, 202-854-1, RefChem:5598, 1-phenylmethanamine, 89551-24-6, N-Benzylamine, Phenylmethylamine, benzyl amine, a-Aminotoluene, .omega.-Aminotoluene, benzyl-amine, 1utj, 1utn, 2bza, NSC 8046, MFCD00008106, .alpha.-Aminotoluene, TOLUENE,ALPHA-AMINO, CHEMBL522, ABN, MFCD00145849, AM resin, HSDB 2795, EINECS 202-854-1, Lacosamide EP Impurity J, benzylarnine, bezylamine, BRN 0741984, UNII-A1O31ROR09, AI3-15299, Benzylamine; 1-Phenylmethanamine; Lacosamide Imp. J (Pharmeuropa), aminomethylbenzene, N-(phenylmethyl)amine, BnNH2, NH2Bn, QuadraPure(TM) BZA, Bzl-NH2, Benzenemethanamine, 9CI, BENZYLAMINE [MI], Benzylamine, reagent grade, SCHEMBL373, BENZYLAMINE [HSDB], Epitope ID:141489, EC 202-854-1, QuadraPure(TM) Benzylamine, C4X-183021Benzylamine, NCIOpen2_007746, SCHEMBL17695, SCHEMBL65919, SCHEMBL65920, 4-12-00-02155 (Beilstein Handbook Reference), laquo Omegaraquo -aminotoluene, SCHEMBL201838, SCHEMBL232726, SCHEMBL300292, SCHEMBL497858, SCHEMBL1077812, SCHEMBL4522847, SCHEMBL4626764, SCHEMBL9353950, SCHEMBL9452523, Benzylamine, analytical standard, SCHEMBL11190747, SCHEMBL16197776, BDBM10999, NSC8046, Benzylamine, redistilled from glass, SGA75079, STR00195, Benzylamine, ReagentPlus(R), 99%, Tox21_300933, MFCD00130502, MFCD00135579, SBB040473, STL115534, AKOS000119096, DB02464, FA29816, FB09449, NCGC00166029-01, NCGC00166029-02, NCGC00254835-01, BP-31247, CAS-100-46-9, LACOSAMIDE IMPURITY J [EP IMPURITY], B0406, NS00009841, ST45255426, EN300-16215, Benzylamine, for GC derivatization, >=99.0%, Benzylamine, purified by redistillation, >=99.5%, Q424000, BRD-K76133116-001-01-2, F2190-0388, 3F830B2A-ABAA-4E26-971C-53B1C7485954, Aminomethyl polystyrene resin (1.0-1.2 mmol/g, 100-200 mesh), InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H, QuadraPure(R) BZA, 400-1100 mum, extent of labeling: 20 mg/g loading, macroporous , Moringine;moringine[qr];omega-Aminotoluene;omega-aminotoluene[qr];Sumine 2005;sumine2005;sumine2006;BZA

N-benzylamine, also known as phenylmethylamine, is an organic chemical compound with the condensed structural formula C6H5CH2NH2 (sometimes abbreviated as PhCH2NH2 or BnNH2). 
N-benzylamine consists of a benzyl group, C6H5CH2, attached to an amine functional group, NH2. 
This colorless water-soluble liquid is a common precursor in organic chemistry and used in the industrial production of many pharmaceuticals. 

The hydrochloride salt was used to treat motion sickness on the Mercury-Atlas 6 mission in which NASA astronaut John Glenn became the first American to orbit the Earth.
N-benzylamine's α-methylated derivative has been found to act as a monoamine oxidase inhibitor (MAOI), including of both monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B).
N-Benzylamine is an organic compound that belongs to the class of primary amines, where a benzyl group (a phenyl ring attached to a methylene, –CH₂–) is directly bonded to the nitrogen atom of the amine. 

N-benzylamine can act as a precursor for the synthesis of various pharmaceuticals, agrochemicals, and dyes, as well as intermediates for fine chemicals.
A derivative, pargyline (N-methyl-N-propargylbenzylamine), is an MAOI that has been used pharmaceutically as an antihypertensive agent and antidepressant.
N-benzylamine is an MAOI, inhibiting both MAO-A and MAO-B, as well.[19]

Another derivative, N-benzylamine, partially substitutes for MDMA at high doses in drug discrimination tests in rats.
N-benzylamine is also similar in structure to benzylpiperazine (BZP), which is a monoamine releasing agent and psychostimulant.
However, both N-benzylamine and α-methylbenzylamine have been found to be inactive as norepinephrine releasing agents.

N-benzylamine can be produced by several methods, the main industrial route being the reaction of benzyl chloride and ammonia. 
It is also produced by the reduction of benzonitrile and reductive amination of benzaldehyde, both done over Raney nickel.
N-benzylamine occurs biologically from the action of the N-substituted formamide deformylase enzyme, which is produced by Arthrobacter pascens bacteria.

This hydrolase catalyses the conversion of N-benzylformamide into benzylamine with formate as a by-product.
N-benzylamine is degraded biologically by the action of the monoamine oxidase B enzyme, resulting in benzaldehyde.
The hydrochloride salt of N-benzylamine, C6H5CH2NH3Cl or C6H5CH2NH2·HCl, is prepared by reacting benzylamine with hydrochloric acid, and can be used in treating motion sickness. 

NASA astronaut John Glenn was issued with N-benzylamine hydrochloride for this purpose for the Mercury-Atlas 6 mission.
The cation in this salt is called benzylammonium and is a moiety found in pharmaceuticals such as the anthelmintic agent bephenium hydroxynaphthoate, used in treating ascariasis.
Other derivatives of N-benzylamine and its salts have been shown to have anti-emetic properties, including those with the N-(3,4,5-trimethoxybenzoyl)benzylamine moiety.

Commercially available motion-sickness agents including cinnarizine and meclizine are derivatives of benzylamine.
N-benzylamine is a methylated benzylamine derivative that is chiral; enantiopure forms are obtained by resolving racemates. 
Its racemic form is sometimes known as (±)-α-methylbenzylamine.

Both N-benzylamine and 1-phenylethylamine form stable ammonium salts and imines due to their relatively high basicity.
Because of its reactive amine group, N-benzylamine can be corrosive to tissues and irritating to the skin, eyes, and respiratory tract upon contact or inhalation. 
N-benzylamine may also pose hazards if ingested, potentially causing gastrointestinal discomfort, and it can form flammable vapors when exposed to heat or open flames. 

Proper handling requires personal protective equipment, adequate ventilation, and storage in tightly sealed containers away from strong oxidizers or acids.
N-Benzylamine is a primary aliphatic amine in which the nitrogen atom is directly bonded to a benzyl group, consisting of a phenyl ring attached through a methylene (–CH₂–) linkage. 
N-benzylamine is typically encountered as a colorless to pale yellow liquid with a sharp, characteristic amine odor, which can be irritating to the respiratory system and mucous membranes. 

The molecule’s nitrogen atom contains a lone pair of electrons, giving it strong nucleophilic properties and basicity, which allows it to readily participate in a variety of chemical reactions such as alkylation, acylation, and condensation with carbonyl compounds. 
This chemical reactivity makes N-benzylamine an important intermediate in synthetic organic chemistry, particularly in the preparation of pharmaceuticals, agrochemicals, dyes, polymers, and fine chemical reagents.

Melting point: 10 °C (lit.)
Boiling point: 184-185 °C (lit.)
Density: 0.981 g/mL at 25 °C (lit.)
Vapor pressure: 1.2 hPa (20 °C)
Refractive index: n20/D 1.543 (lit.)
Flash point: 140 °F
Storage temp.: Store below +30 °C
Solubility: Alcohol: miscible
Form: Liquid
pKa: 9.33 (at 25 ℃)
Color: Clear colorless to slightly yellow
pH: 11.4 (100 g/L, H₂O, 20 ℃)
Odor: Strong ammonia
Explosive limit: 0.7-8.2% (V)
Water solubility: Soluble
Sensitive: Air sensitive
Merck: 14,1125
BRN: 741984
Dielectric constant: 4.6 (Ambient)
Stability: Combustible. Incompatible with strong oxidizing agents, strong acids.
InChIKey: WGQKYBSKWIADBV-UHFFFAOYSA-N
LogP: 1 at 25 ℃
Surface tension: 37.1 mN/m at 293.15 K

N-benzylamine is often used as a building block for the synthesis of secondary and tertiary amines, Schiff bases, and heterocyclic compounds.
N-benzylamine can also act as a protective group donor for amine functionalities in multistep organic synthesis because the benzyl group can later be removed under specific conditions to regenerate the free amine. 
Furthermore, it is employed in the production of specialty polymers, where its amine functionality can react with epoxides or isocyanates to modify polymer properties, and in analytical chemistry, it is sometimes used for derivatization of carboxylic acids and aldehydes to improve chromatographic detection.

From a safety perspective, N-benzylamine should be handled with great care because it is corrosive and can cause severe irritation to the skin, eyes, and respiratory tract upon direct contact or inhalation of vapors. 
Ingestion can lead to gastrointestinal disturbances such as nausea, vomiting, and abdominal pain, while prolonged or repeated exposure may pose additional risks including sensitization. The compound is flammable, with vapors capable of forming explosive mixtures with air, and it can react violently with strong oxidizing agents, acids, or halogens. 

Safe handling practices include the use of appropriate personal protective equipment, working in well-ventilated areas or fume hoods, storing it in tightly sealed containers away from sources of ignition, and following proper spill and disposal protocols to prevent environmental contamination.
N-benzylamine may weakly corrode some metals. Liquid will attack some plastics. 

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.

N-benzylamine can undergo oxidation to form benzaldehyde or benzoic acid under strong oxidative conditions, and it can be converted into N-substituted derivatives through reductive amination or acylation reactions. 
Its moderate solubility in water and high solubility in organic solvents such as ethanol, methanol, ether, and chloroform make it versatile in both polar and non-polar reaction media. 
Due to its widespread use in medicinal chemistry, agrochemical production, and polymer synthesis, N-benzylamine is considered a key intermediate whose chemical properties and hazards must be carefully managed to ensure safe and efficient use in both laboratory and industrial contexts.

N-benzylamine is slowly oxidized on contact with air and forms benzalbenzylamine. 
N-benzylamine also reacts with carbon dioxide to form its solid carbamic acid salt. 
It therefore should be stored in a tight closed container for not more than one year. 

Uses Of N-benzylamine:
N-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.

N-benzylamine 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. 
N-benzylamine 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. 

N-benzylamine 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.

N-Benzylamine serves as a highly versatile intermediate in organic and medicinal chemistry due to the presence of its reactive primary amine group, which can participate in a wide range of chemical transformations including alkylation, acylation, reductive amination, and condensation reactions with carbonyl-containing compounds. 
In pharmaceutical chemistry, it is frequently employed as a building block for the synthesis of various drug molecules, including analgesics, antiviral agents, and central nervous system active compounds, where its benzyl group can serve both as a structural motif and as a protective group for amine functionalities that can later be removed under controlled conditions.

In addition to drug synthesis, N-benzylamine is widely used in the production of agrochemicals such as herbicides, insecticides, and fungicides, where its reactive amine allows for the introduction of nitrogen-containing functional groups that enhance biological activity or modify solubility and stability properties. 
N-benzylamine is also utilized in the preparation of dyes, pigments, and specialty polymers, often reacting with epoxides, isocyanates, or other functional monomers to modify polymer characteristics, such as crosslinking density, thermal stability, and adhesion properties.

Analytically, N-benzylamine is sometimes employed for the derivatization of carboxylic acids, aldehydes, or ketones, improving their detectability in chromatographic and spectroscopic methods, and in solid-phase synthesis, it can be attached to polymeric supports to create functionalized resins used in combinatorial chemistry and peptide synthesis.
Furthermore, in industrial chemical processes, N-benzylamine can act as a precursor to secondary and tertiary amines through reductive amination, contributing to the production of surfactants, corrosion inhibitors, and specialty lubricants. 
Its combination of nucleophilicity, basicity, and solubility in both polar and non-polar solvents makes it an indispensable compound for chemical research and large-scale manufacturing applications where controlled reactivity and versatility are required.

N-benzylamine 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.
N-benzylamine is used as a masked source of ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis: C6H5CH2NH2 + 2 RBr → C6H5CH2NR2 + 2 HBr
C6H5CH2NR2 + H2 → C6H5CH3 + R2NH

Typically a base is employed in the first step to absorb the HBr (or related acid for other kinds of alkylating agents).
N-benzylamine reacts with acetyl chloride to form N-benzylacetamide.
Isoquinolines can be prepared from benzylamine and glyoxal acetal by an analogous approach known as the Schlittler-Müller modification to the Pomeranz–Fritsch reaction. 

This modification can also be used for preparing substituted isoquinolines.
N-benzylamine is used in the manufacture of other pharmaceuticals, including alniditan, lacosamide, moxifloxacin, and nebivolol.

N-benzylamine is also used to manufacture the military explosive hexanitrohexaazaisowurtzitane (HNIW), which is superior to older nitroamine high explosives like HMX and RDX. 
Illustrating the debenzylation tendency of benzylamines, four of the benzyl groups are removed from hexabenzylhexaazaisowurtzitane by hydrogenolysis catalysed by palladium on carbon.

Health Hazard Of N-benzylamine:
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.

Safety Profile Of N-benzylamine:
N-Benzylamine is considered a hazardous chemical primarily because of its corrosive and irritating properties, which can affect the skin, eyes, and respiratory system upon direct contact or inhalation of its vapors, causing redness, pain, coughing, and shortness of breath. Prolonged or repeated exposure may lead to sensitization of the skin or respiratory tract, increasing the likelihood of allergic reactions in susceptible individuals. 
If ingested, N-benzylamine can cause gastrointestinal distress, including nausea, vomiting, abdominal pain, and diarrhea, and in severe cases, systemic toxicity may occur due to absorption into the bloodstream.

From a flammability perspective, N-benzylamine is classified as a combustible liquid, and its vapors can form explosive mixtures with air, meaning that exposure to heat, sparks, or open flames can lead to fire or explosion if proper precautions are not taken. 
N-benzylamine can also react violently with strong oxidizing agents, acids, halogens, and other reactive chemicals, potentially producing hazardous byproducts or heat that can initiate secondary hazards. 
Additionally, accidental release into the environment can pose risks to aquatic and terrestrial organisms, as N-benzylamine is moderately soluble in water and can alter local chemical balances if spilled in large quantities.