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Benzyl carbamate

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Name

Benzyl carbamate

EINECS 210-710-4
CAS No. 621-84-1 Density 1.168 g/cm3
PSA 52.32000 LogP 1.98220
Solubility 68.02g/L(37 oC) Melting Point 86-89 °C(lit.)
Formula C8H9NO2 Boiling Point 318.723 °C at 760 mmHg
Molecular Weight 151.165 Flash Point 182.584 °C
Transport Information N/A Appearance Off-white to light beige powder or flakes
Safety 22-24/25-36-26 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 621-84-1 (Benzyl carbamate) Hazard Symbols HarmfulXn
Synonyms

Carbamicacid, benzyl ester (6CI,7CI,8CI);Benzyl aminoformate;Carbamyl benzyl ester;NSC 25317;O-Benzylcarbamate;

Article Data 95

Benzyl carbamate Synthetic route

621-84-1

O-benzyl carbamate

35660-91-4, 35845-66-0, 495-41-0

(E)-1-phenyl-2-buten-1-one

benzyl N-(4-oxo-4-phenylbutan-2-yl)carbamate

Conditions
ConditionsYield
With gold(III) chloride In dichloromethane at 20℃; for 2h; Product distribution; Further Variations:; Reagents; Aza-Michael reaction;100%
iridium tetrachloride for 2h; Product distribution / selectivity; Aza-Michael reaction;100%
osmium (III) chloride for 6h; Product distribution / selectivity; Aza-Michael reaction;96%
621-84-1

O-benzyl carbamate

563-96-2

2,2-dihydroxyacetic acid

79002-45-2

N-benzyloxycarbonyl-glycine

Conditions
ConditionsYield
In toluene at 40℃;100%
In toluene at 40℃; for 3.5h;100%
In toluene at 40℃; for 3.5h; Large scale reaction;96%
In diethyl ether at 20℃; for 10h;
621-84-1

O-benzyl carbamate

873-55-2

sodium benzenesulfonate

105-07-7

4-cyanobenzaldehyde

1220349-77-8

benzyl (4-cyanophenyl)(phenylsulfonyl)methylcarbamate

Conditions
ConditionsYield
With formic acid In tetrahydrofuran; water at 22℃; Inert atmosphere;100%
924-44-7

glyoxylic acid ethyl ester

621-84-1

O-benzyl carbamate

104473-51-0

ethyl 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetate

Conditions
ConditionsYield
In ethyl acetate at 60℃; for 24h;100%
With acetic acid In ethyl acetate; toluene at 60℃; for 14h; Inert atmosphere;97%
With acetic acid In ethyl acetate at 60℃; for 14h; Inert atmosphere;81%
924-44-7

glyoxylic acid ethyl ester

621-84-1

O-benzyl carbamate

134746-23-9

ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate

Conditions
ConditionsYield
With acetic acid; acetyl chloride In chloroform at 60℃; for 12h; Solvent; Inert atmosphere;100%
With acetic acid; acetyl chloride In chloroform at 60℃; for 12h;98%
With thionyl chloride In chloroform; toluene for 12h; Inert atmosphere; Schlenk technique; Reflux;93%
621-84-1

O-benzyl carbamate

64805-08-9

ethyl glyoxalate hydrate

134746-23-9

ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate

Conditions
ConditionsYield
With thionyl chloride In chloroform; toluene at 60℃; for 6h; Reagent/catalyst; Inert atmosphere;100%
With acetic acid; acetyl chloride In chloroform at 60℃; for 12h; Inert atmosphere;
621-84-1

O-benzyl carbamate

87692-25-9

benzyl glyoxalate monohydrate

C17H16ClNO4

Conditions
ConditionsYield
With acetic acid; acetyl chloride In chloroform at 60℃; for 16h; Inert atmosphere;100%
621-84-1

O-benzyl carbamate

64805-08-9

ethyl glyoxalate hydrate

577973-96-7

N-Cbz-α-bromoglycine ethyl ester

Conditions
ConditionsYield
With Acetyl bromide; acetic acid In chloroform; toluene at 20℃; for 6.5h; Reagent/catalyst; Inert atmosphere;100%
621-84-1

O-benzyl carbamate

1122-91-4

4-bromo-benzaldehyde

71150-68-0

benzyl N-(4-formylphenyl)carbamate

Conditions
ConditionsYield
With palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In tetrahydrofuran at 45℃; for 19h; Arylation;99%
621-84-1

O-benzyl carbamate

61752-66-7

(E)-1-phenyl-2-penten-1-one

3-(N-benzyloxycarbonylamino)-1-phenylpentan-1-one

Conditions
ConditionsYield
copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 3h;99%
With Nafion(R) SAC-13 In acetonitrile at 20℃; for 24h;99%
With toluene-4-sulfonic acid In acetonitrile at 20℃; for 72h; Product distribution; Further Variations:; Reagents; reaction times; aza-Michael addition;99%
With copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 3h; aza-Michael addition;99%
dichloro bis(acetonitrile) palladium(II) In dichloromethane at 20℃; for 24h;99%

Benzyl carbamate Specification

The Benzyl carbamate, with the CAS registry number 621-84-1, is also known as Carbamyl benzyl ester. It belongs to the product categories of Heterocycles; Nitrogen Compounds; Organic Building Blocks; Protected Amines; Building Blocks; Chemical Synthesis; Nitrogen Compounds. Its EINECS number is 210-710-4. This chemical's molecular formula is C8H9NO2 and molecular weight is 151.16. What's more, its systematic name is Benzyl carbamate. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides. It is used as organic synthesis intermediates. This chemical is a carbamate which is often used an amine protecting group in organic synthesis. It is commonly used in peptide synthesis. It is used to protect amines from electrophiles.

Physical properties of Benzyl carbamate are: (1)ACD/LogP: 1.31; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.31; (4)ACD/LogD (pH 7.4): 1.31; (5)ACD/BCF (pH 5.5): 5.83; (6)ACD/BCF (pH 7.4): 5.83; (7)ACD/KOC (pH 5.5): 122.91; (8)ACD/KOC (pH 7.4): 122.91; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 52.32 Å2; (13)Index of Refraction: 1.548; (14)Molar Refractivity: 41.112 cm3; (15)Molar Volume: 129.41 cm3; (16)Polarizability: 16.298×10-24cm3; (17)Surface Tension: 46.3 dyne/cm; (18)Density: 1.168 g/cm3; (19)Flash Point: 182.584 °C; (20)Enthalpy of Vaporization: 56.025 kJ/mol; (21)Boiling Point: 318.723 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by carbonochloridic acid benzyl ester at the temperature of 0 °C. This reaction will need reagent conc. ammonium hydroxide. The yield is about 92%.

Benzyl carbamate can be prepared by carbonochloridic acid benzyl ester at the temperature of 0 °C

Uses of Benzyl carbamate: it can be used to produce Malonyl-di-benzylurethan at the temperature of 100 - 110 °C. It will need reagent acetic anhydride. The yield is about 84%.

Benzyl carbamate can be used to produce Malonyl-di-benzylurethan at the temperature of 100 - 110 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing. You should not breathe dust. When using it, you must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCc1ccccc1)N
(2)Std. InChI: InChI=1S/C8H9NO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
(3)Std. InChIKey: PUJDIJCNWFYVJX-UHFFFAOYSA-N 

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