Benzylamine

Benzylamine

Names
IUPAC name 1-Phenylmethanamine
Other names Benzyl amine Phenylmethylamine α-Aminotoluene
Identifiers
Jmol-3D images	Image
SMILES c1ccc(cc1)CN
Properties
Chemical formula	C7H9N C6H5CH2NH2
Molar mass	107.156 g/mol
Appearance	Colorless to slight yellowish liquid
Odor	Amine-like
Density	0.981 g/cm3 (20 °C)
Melting point	10 °C (50 °F; 283 K)
Boiling point	185 °C (365 °F; 458 K)
Solubility in water	Miscible
Solubility	Miscible in acetone, benzene, diethyl ether, ethanol, methanol, pyridine Partially miscible with chloroform
Vapor pressure	0.662 mmHg at 25 °C
Acidity (pKa)	9.34
Thermochemistry
Hazards
Safety data sheet	Sigma-Aldrich
Flash point	65 °C (149 °F; 338 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	552 mg/kg (rat, oral)
Related compounds
Related compounds	Aniline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzylamine is an organic chemical compound with the chemical formula C₆H₅CH₂NH₂ or C₇H₉N (sometimes abbreviated as PhCH₂NH₂ or BnNH₂).

Properties

Chemical

Benzylamine reacts with acids forming salts.

Benzylamine reacts with acetyl chloride to form N-benzylacetamide, an exemplar of the Schotten–Baumann reaction.

Physical

Benzylamine is a colorless viscous liquid that may turn slightly yellowish after prolonged contact with air. It is miscible with water and many organic solvents.

Availability

Benzylamine is sold by chemical suppliers in both liquid form and as salt.

Preparation

There are several routes for benzylamine.

The main industrial route being the reaction of benzyl chloride and ammonia. The reaction alone produces sufficient heat to maintain the temperature between 30-34 °C.

Benzylamine can also be produced in the lab by the reduction of benzonitrile with Raney nickel, and reductive amination of benzaldehyde with formamide or ammonium formate (Leuckart reaction).

Projects

• Make anti-nausea medication
• Make Hexanitrohexaazaisowurtzitane (HNIW)

Handling

Safety

Benzylamine, while irritant, exhibits modest oral toxicity in rats, with LD50 of 552-1,130 mg/kg. It is readily biodegraded.

Storage

Benzylamine should be kept in airtight bottles, away from air and light, if kept in liquid form. The salt form is somewhat more stable to oxidation, though not by much.

Disposal

Benzylamine should be mixed with a more flammable solvent and burned in an incinerator or outside.

References

Relevant Sciencemadness threads

• Benzylamine via the delepine reaction
• Benzylamine Hydrochloride to Benzylamine
• Bizzare observation about benzylamines- explanation?