Benzyl carbamate Chemical Properties

Melting point:

86-89 °C (lit.)

Boiling point:

273.17°C (rough estimate)

Density 

1.2023 (rough estimate)

refractive index 

1.5810 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Powder or Flakes

pka

13.42±0.50(Predicted)

color 

Off-white to light beige

Water Solubility 

68.02g/L(37 ºC)

BRN 

1865635

InChIKey

PUJDIJCNWFYVJX-UHFFFAOYSA-N

CAS DataBase Reference

621-84-1(CAS DataBase Reference)

NIST Chemistry Reference

Carbamic acid, benzyl ester(621-84-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

HS Code 

29242995

MSDS

• Language:English Provider:Benzyl carbamate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Benzyl carbamate Usage And Synthesis

Chemical Properties

Off-white to light beige powder or flakes, melting point 87-89 ℃. Insoluble in water, soluble in organic solvents such as benzene.

Uses

Benzyl carbamate is a reagent used for the nucleophilic introduction of an amino-protected group, Benzyl carbamates can be considered as a benzyloxycarbonyl (otherwise known as carbobenzyloxy, Cbz or Z) protecting group for amino groups. It was introduced as a versatile alternative to the ethoxy carbamate group in peptide synthesis.

Application

Benzyl carbamate is an intermediate in the synthesis of various pharmaceutical compounds. It can be also used as nondeuterated internal standards for the quantitative analysis of carisoprodol in blood.

Preparation

Benzyl carbamate is prepared by reacting benzyl chloroformate with ammonia. Benzyl chloroformate was slowly added to 5 times the volume of cold ammonia water (relative density 0.90) under vigorous stirring, the reaction mixture was placed at room temperature for 30 minutes, the precipitate was filtered out, washed with water and dried to obtain the finished product of benzyl carbamate.

Purification Methods

If it smells of NH3, then dry it in a vacuum desiccator and recrystallise it from 2 volumes of toluene and dry it in a vacuum desiccator again. It forms glistening plates from toluene, and can be recrystallised from H2O [Martell & Herbst J Org Chem 6 878 1941, Carter et al. Org Synth Coll Vol III 168 1955]. [Beilstein 6 IV 2278.]

Benzyl carbamate(621-84-1)Related Product Information

• Benzyl alcohol
• Chlorpropham
• Benzyl benzoate
• Benzyl formate
• Benzyl chloroformate
• POLYURETHANE
• Carbobenzoxyhydrazide
• 4-Nitrobenzyl chloroformate
• AMINOGUANIDINE HEMISULFATE
• Aminoguanidine bicarbonate
• Sulfamic acid
• 2,6-DI-TERT-BUTYLNAPHTHALENE SULFONIC ACID SODIUM SALT
• Trimethylstearylammonium Chloride
• 2,3-Butanediol
• Ethylene Glycol Dibutyl Ether
• Ethylene dimethacrylate
• 2,2-Diethoxyethylamine
• N-Benzyloxycarbonyl-L-asparagine