Benzyl carbamate (HCID 12136)

Names & identifiers

Preferred name: Benzyl carbamate
IUPAC: benzyl carbamate
English name: Benzyl carbamate
Molecular formula: C8H9NO2
Molecular weight: 151.16

Names & synonyms

BENZYL CARBAMATE621-84-1Carbamic acid, phenylmethyl esterCarbamic acid benzyl esterBenzylcarbamateCCRIS 5070AI3-52524EINECS 210-710-4NSC 25317DTXSID00211159UNII-7890Q001S7NSC-25317

Show more names

Z-NH2CARBAMO-BenzylcarbamateBenzyl aminoformateN-CARBOBENZOXY-AMIDEZ-AMIDEBenzyl urethane

PHENYLMETHYL CARBAMATE7890Q001S7RefChem:118862DTXCID50133650210-710-4InChI=1/C8H9NO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10PUJDIJCNWFYVJX-UHFFFAOYSA-NCarbamyl Benzyl Ester

Database identifiers

CAS: 621-84-1
PubChem CID: 12136
DTXSID: DTXSID00211159
ChEMBL: CHEMBL2259788
UNII: 7890Q001S7
EC Number: 210-710-4
Nikkaji: J95.774G

Properties

Computed structural properties

XLogP: 1.2
Topological polar surface area: 52.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 3
Heavy atoms: 11
Formal charge: 0
Complexity: 130

Physicochemical properties

Melting point: 86 · 86-89 °C (lit.)
Boiling point: 273.17 °C · 273.17°C (rough estimate)
Density: 1.2023 · 1.2023 (rough estimate)
refractive index: 1.581 · 1.5810 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), Methanol (Slightly)
pka: 13.42 · 13.42±0.50(Predicted)
form: Powder or Flakes
color: Off-white to light beige
Water Solubility: 68.02 g/L · 68.02g/L(37 ºC)
BRN: 1865635 · 1865635
InChI: InChI=1S/C8H9NO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
InChIKey: PUJDIJCNWFYVJX-UHFFFAOYSA-N
SMILES: C(OCC1=CC=CC=C1)(=O)N
CAS DataBase Reference: 621 · 621-84-1(CAS DataBase Reference)
FDA UNII: 7890 Q001S7 · 7890Q001S7
NIST Chemistry Reference: Carbamic acid, benzyl ester(621-84-1)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 271 · P271-P280
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xn
Risk Statements: 20 · 20/21/22-36/37/38
Safety Statements: 22 · 22-24/25-36-26
WGK Germany: 3 · 3
HS Code: 29242995 · 29242995
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (50%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29242995
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 22-24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319-H335
Precautionary statements: P271-P280

Chemistry & industry

Applications · 1 item

UsesBenzyl 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.

Preparation methods · 1 item

PreparationBenzyl 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.