Benzylamine

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Benzylamine
Skeletal formula of benzylamine
Benzylamine-3D-spacefill.png
Identifiers
CAS number 100-46-9 YesY
PubChem 7504
ChemSpider 7223 YesY
UNII A1O31ROR09 YesY
DrugBank DB02464
KEGG C15562 YesY
ChEBI CHEBI:40538 YesY
ChEMBL CHEMBL522 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 (50 °F; 283 K)[2]
Boiling point 185 °C (365 °F; 458 K)[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
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 65 °C (149 °F; 338 K)[2][1]
Related compounds
Related amines aniline
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

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.

Benzonitrile hydrogenation.svg

Uses[edit]

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[edit]

  1. ^ a b c d Benzylamine at Sigma-Aldrich
  2. ^ a b c d Record in the GESTIS Substance Database from the IFA
  3. ^ Hall, H.K. (1957). J. Am. Chem. Soc. 79 (20): 5441. doi:10.1021/ja01577a030. 
  4. ^ 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).