Benzylamine
| Benzylamine | |
|---|---|
 |
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1-Phenylmethanamine |
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Other names
α-Aminotoluene |
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| Identifiers | |
| CAS number | 100-46-9  |
| ChemSpider | 7223 |
| UNII | A1O31ROR09 |
| DrugBank | DB02464 |
| KEGG | C15562 |
| ChEBI | CHEBI:40538 |
| ChEMBL | CHEMBL522 |
| RTECS number | DP1488500 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C7H9N |
| Molar mass | 107.15 g mol−1 |
| Appearance | Colorless liquid |
| 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] |
| 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
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| Flash point | 65 °C (149 °F)[2][1] |
| Related compounds | |
| Related amines | aniline |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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.
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).
[edit] References
- ^ a b c d Benzylamine at Sigma-Aldrich
- ^ a b c d Record in the GESTIS Substance Database from the IFA
- ^ Hall, H.K. (1957). J. Am. Chem. Soc. 79 (20): 5441. doi:10.1021/ja01577a030.
- ^ Gatto, V. J.; Miller, S. R.; Gokel, G. W. (1993), "4,13-Diaza-18-Crown-6", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv8p0152; Coll. Vol. 8: 152 (example of alklylation of benzylamine followed by hydrogenolysis).
