Benzylamine

Benzylamine
Names
	IUPAC name 1-Phenylmethanamine
	Other names α-Aminotoluene
Identifiers
CAS Number	100-46-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:40538 ;
ChEMBL	ChEMBL522 ;
ChemSpider	7223 ;
DrugBank	DB02464 ;
ECHA InfoCard	100.002.595
KEGG	C15562 ;
RTECS number	DP1488500;
UNII	A1O31ROR09 ;
CompTox Dashboard (EPA)	DTXSID5021839 ;
	InChI InChI=1S/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2 Key: WGQKYBSKWIADBV-UHFFFAOYSA-N ; 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	107.156 g·mol−1
Appearance	Colorless liquid
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
Acidity (pKa)	9.34
Basicity (pKb)	4.66
Refractive index (nD)	1.543
Structure
Dipole moment	1.38 D
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Flammable
NFPA 704 (fire diamond)	3 2
Flash point	65 °C (149 °F)
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox 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.

It is used as a masked source of ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis:^[4]

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

^ ^a ^b ^c ^d Benzylamine at Sigma-Aldrich
^ ^a ^b ^c ^d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ Hall, H.K. (1957). J. Am. Chem. Soc. 79 (20): 5441. doi:10.1021/ja01577a030. {{cite journal}}: Missing or empty |title= (help)
^ Gatto, V. J.; Miller, S. R.; Gokel, G. W. (1993). "4,13-Diaza-18-Crown-6". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 152. (example of alklylation of benzylamine followed by hydrogenolysis).