Benzylamine

Benzylamine

Names
IUPAC name 1-Phenylmethanamine
Other names α-Aminotoluene Benzyl amine Phenylmethylamine
Identifiers
CAS Number	100-46-9 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:40538 Y
ChEMBL	ChEMBL522 Y
ChemSpider	7223 Y
DrugBank	DB02464 Y
ECHA InfoCard	100.002.595
KEGG	C15562 Y
PubChem	7504
RTECS number	DP1488500
UNII	A1O31ROR09 Y
InChI InChI=1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2 Y Key: WGQKYBSKWIADBV-UHFFFAOYSA-N Y InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2 Key: WGQKYBSKWIADBV-UHFFFAOYAL
SMILES c1ccc(cc1)CN
Properties
Chemical formula	C7H9N
Molar mass	107.16 g·mol−1
Appearance	Colorless liquid
Odor	weak, ammonia-like
Density	0.981 g/mL
Melting point	10 °C (50 °F; 283 K)
Boiling point	185 °C (365 °F; 458 K)
Solubility in water	Miscible
Solubility	miscible in ethanol, diethyl ether very soluble in acetone soluble in benzene, chloroform
Acidity (pKa)	9.34
Basicity (pKb)	4.66
Magnetic susceptibility (χ)	-75.26·10−6 cm3/mol
Refractive index (nD)	1.543
Structure
Dipole moment	1.38 D
Hazards
Main hazards	Flammable
Safety data sheet	Fischer Scientific
R-phrases	R21/22 R34
S-phrases	S26 S36/37/39 S45
NFPA 704	2 3 0
Flash point	65 °C (149 °F; 338 K)
Related compounds
Related amines	aniline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Benzylamine is an organic chemical compound with the condensed structural formula C₆H₅CH₂NH₂ (sometimes abbreviated as PhCH₂NH₂ or BnNH₂). It consists of a benzyl group, C₆H₅CH_2, attached to an amine functional group, NH₂. This colorless liquid is a common precursor in organic synthesis 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.

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 over Raney nickel.

It was produced accidentally by Rudolf Leuckart in the reaction of benzaldehyde with formamide in a process now known as the Leuckart reaction, a general process in which reductive amination of aldehydes or ketones yields the corresponding amine.