Benzylamine
From Wikipedia, the free encyclopedia
| Benzylamine | |
|---|---|
 |
|
| IUPAC name | 1-Phenylmethanamine |
| Other names | Aminotoluene |
| Identifiers | |
| CAS number | [100-46-9] |
| RTECS number | DP1488500 |
| SMILES | NCc1ccccc1 |
| Properties | |
| Molecular formula | C7H9N |
| Molar mass | 107.16 g/mol |
| Appearance | Colorless liquid |
| Density | 0.981 g/mL |
| Melting point |
-30 °C (22°F) |
| Boiling point |
183 °C (361.4°F) |
| Solubility in water | 3.24 g / 100 g water @ 25 °C |
| Solubility in other solvents | all organic solvents |
| Acidity (pKa) | 9.33 (value for protonated amine, pKaH) |
| Basicity (pKb) | 4.67 |
| Refractive index (nD) | 1.543 |
| Structure | |
| Dipole moment | 1.38 D |
| Hazards | |
| MSDS | ScienceLab.com |
| Main hazards | Flammable |
| NFPA 704 |
 2
3
0
|
| R-phrases | R11/22-34 |
| S-phrases | S(1/2-)-26-36/37/39-45 |
| Flash point | 72 °C (161.6°F) |
| Related compounds | |
| Related amines | aniline |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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.
- 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:[1]
- 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
- ^ 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).
 |
This article about an amine is a stub. You can help Wikipedia by expanding it. |
