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 ;
PubChem CID	7504;
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
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
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 0
Flash point	65 °C (149 °F; 338 K)
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.

Manufacturing

Benzylamine can be produced through a number of ways, 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.^[4]

Uses

It is used as a masked source of ammonia, since after N-alkylation, the benzyl group can be removed by hydrogenolysis:^[5]

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)
^ Heuer, Lutz (2006). "Benzylamines". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a04_009.pub2.
^ 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).

[Aldrich-1] Benzylamine at Sigma-Aldrich

[GESTIS-2] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[3] Hall, H.K. (1957). J. Am. Chem. Soc. 79 (20): 5441. doi:10.1021/ja01577a030. {{cite journal}}: Missing or empty |title= (help)

[4] Heuer, Lutz (2006). "Benzylamines". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a04_009.pub2.

[5] 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).

[1]

[2]

[3]

[4]

[5]