Benzyl carbamate
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Basic information
- CAS
621-84-1- Standard SMILES
NC(=O)OCc1ccccc1- InChIKey
PUJDIJCNWFYVJX-UHFFFAOYSA-N- Molecular formula
- C8H9NO2
- Average molar mass
- 151.16 g/mol
- Monoisotopic mass
- 151.06332853
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 propertiesFilling in
- XLogP
- 1.2
- Topological polar surface area
- 52.3 Ų
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
401 records
Compound notes
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