Benzylamine

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Benzylamine
Skeletal formula of benzylamine
Benzylamine-3D-spacefill.png
Names
IUPAC name
1-Phenylmethanamine
Other names
α-Aminotoluene
Identifiers
100-46-9 YesY
ChEBI CHEBI:40538 YesY
ChEMBL ChEMBL522 YesY
ChemSpider 7223 YesY
DrugBank DB02464 YesY
Jmol-3D images Image
KEGG C15562 YesY
PubChem 7504
RTECS number DP1488500
UNII A1O31ROR09 YesY
Properties
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]
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
1.543
Structure
Dipole moment 1.38 D
Hazards
MSDS Fischer Scientific
Main hazards Flammable
R-phrases R21/22 R34[1]
S-phrases S26 S36/37/39 S45[1]
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 is 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, the main industrial route being the reaction of benzyl chloride and ammonia. It is also produced by the reduction of benzonitrile and reductive amination of benzaldehyde over Raney nickel.[4]

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:[5]

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 of the IFA
  3. ^ Hall, H.K. (1957). J. Am. Chem. Soc. 79 (20): 5441. doi:10.1021/ja01577a030.  Missing or empty |title= (help)
  4. ^ Heuer, Lutz (2006). "Benzylamines". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a04_009.pub2. 
  5. ^ Gatto, V. J.; Miller, S. R.; Gokel, G. W. (1993). "4,13-Diaza-18-Crown-6". Org. Synth. ; Coll. Vol. 8, p. 152  (example of alklylation of benzylamine followed by hydrogenolysis).