Benzylammonium

Benzylamine
Identifiers
CAS number 100-46-9 YesY
PubChem 7504
ChemSpider 7223 YesY
UNII A1O31ROR09 YesY
DrugBank DB02464
KEGG C15562 YesY
ChEBI CHEBI:40538 YesY
RTECS number DP1488500
Jmol-3D images Image 1
Properties
Molecular formula C7H9N
Molar mass 107.15 g mol−1
Appearance Colorless liquid
Odor weak, ammonia-like
Density 0.981 g/mL[1]
Melting point

10 °C, 283 K, 50 °F ([2])

Boiling point

185 °C, 458 K, 365 °F ([2])

Solubility in water Miscible[2]
Solubility miscible in ethanol, diethyl ether
very soluble in acetone
soluble in benzene, chloroform
Acidity (pKa) 9.34[3]
Basicity (pKb) 4.66
Refractive index (nD) 1.543
Structure
Dipole moment 1.38 D
Hazards
MSDS Fischer Scientific
R-phrases R21/22 R34[1]
S-phrases S26 S36/37/39 S45[1]
Main hazards Flammable
NFPA 704
2
3
0
Flash point 65 °C (149 °F)[2][1]
Related compounds
Related amines aniline
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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: from the reaction of benzyl chloride and ammonia; by the reduction of benzonitrile; from the reaction between benzyl bromide and acetamide; from the reaction between N-benzylphthalimide and hydrazine hydrate.

Uses

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

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