Benzylamine

Benzylamine

Chembox new
Name = Benzylamine
ImageFile = Benzylamine-2D-skeletal.png ImageName = Skeletal formula of benzylamine
IUPACName = 1-Phenylmethanamine
OtherNames = Aminotoluene
Section1 = Chembox Identifiers
SMILES = NCc1ccccc1
CASNo = 100-46-9
RTECS = DP1488500
Section2 = Chembox Properties
C=7|H=9|N=1
Appearance = Colorless liquid
Density = 0.981 g/mL
Solubility = 3.24 g / 100 g water @ 25 °C
Solvent = other solvents
SolubleOther = all organic solvents
MeltingPt = -30 °C (22°F)
BoilingPt = 183 °C (361.4°F)
pKa = 9.33 (value for protonated amine, p"KaH")
pKb = 4.67
Viscosity =
RefractIndex = 1.543
Section3 = Chembox Structure
Dipole = 1.38 D
Section7 = Chembox Hazards
ExternalMSDS = [http://www.sciencelab.com/xMSDS-Benzylamine-9923068 ScienceLab.com]
MainHazards = Flammable
NFPA-H = 3
NFPA-F = 2
NFPA-R =
FlashPt = 72 °C (161.6°F)
RPhrases = R11/22-34
SPhrases = S(1/2-)-26-36/37/39-45
Section8 = Chembox Related
Function = amines
OtherFunctn = aniline

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: [OrgSynth | author = Gatto, V. J.; Miller, S. R.; Gokel, G. W. | title = 4,13-Diaza-18-Crown-6 | collvol = 8 | collvolpages = 152 | year = 1993 | prep = cv8p0152 (example of alklylation of benzylamine followed by hydrogenolysis).] :C6H5CH2NH2 + 2 RBr → C6H5CH2NR2 + 2 HBr:C6H5CH2NR2 + H2 → C6H5CH3 + R2NHTypically a base is employed in the first step to absorb the HBr (or related acid for other kinds of alkylating agents).

References


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