Benzylamine

Benzylamine
IUPAC name	1-Phenylmethanamine
Other names	Aminotoluene
Identifiers
CAS number	100-46-9
RTECS number	DP1488500
SMILES	NCc1ccccc1
Properties
Molecular formula	C7H9N
Molar mass	107.16 g/mol
Appearance	Colorless liquid
Density	0.981 g/mL
Melting point	-30 °C (22°F)
Boiling point	183 °C (361.4°F)
Solubility in water	3.24 g / 100 g water @ 25 °C
Solubility in other solvents	all organic solvents
Basicity (pKb)	4.67
Refractive index (nD)	1.543
Structure
Dipole moment	1.38 D
Hazards
MSDS	ScienceLab.com
Main hazards	Flammable
NFPA 704	2 3 0
R-phrases	R11/22-34
S-phrases	S(1/2-)-26-36/37/39-45
Flash point	72 °C (161.6°F)
Related Compounds
Related amines	aniline
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Benzylamine is the chemical compound with the formula C₆H₅CH₂NH₂. It consists of a benzyl group, C₆H₅CH₂, attached to an amine functional group. This colorless liquid is a common precursor in organic synthesis. Benzylamine is preprared by hydrogenation of benzonitrile.

C₆H₅CN + 2 H₂ → C₆H₅CH₂NH₂

It is used as a masked source of ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis:^[1]

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).

References

1. ^ Gatto, V. J.; Miller, S. R.; Gokel, G. W. (1993). "4,13-Diaza-18-Crown-6". Org. Synth.; Coll. Vol. 8: 152.  (example of alklylation of benzylamine followed by hydrogenolysis).