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621-84-1 Usage

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 621-84-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 1 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 621-84:
(5*6)+(4*2)+(3*1)+(2*8)+(1*4)=61
61 % 10 = 1
So 621-84-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)

621-84-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A11569)  Benzyl carbamate, 99%   

  • 621-84-1

  • 25g

  • 140.0CNY

  • Detail
  • Alfa Aesar

  • (A11569)  Benzyl carbamate, 99%   

  • 621-84-1

  • 100g

  • 436.0CNY

  • Detail
  • Alfa Aesar

  • (A11569)  Benzyl carbamate, 99%   

  • 621-84-1

  • 250g

  • 865.0CNY

  • Detail
  • Aldrich

  • (B18200)  Benzylcarbamate  99%

  • 621-84-1

  • B18200-25G

  • 250.38CNY

  • Detail
  • Aldrich

  • (B18200)  Benzylcarbamate  99%

  • 621-84-1

  • B18200-100G

  • 780.39CNY

  • Detail

621-84-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzyl carbamate

1.2 Other means of identification

Product number -
Other names Carbamic acid benzyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:621-84-1 SDS

621-84-1Synthetic route

O-benzyl carbamate
621-84-1

O-benzyl carbamate

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

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%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

2,2-dihydroxyacetic acid
563-96-2

2,2-dihydroxyacetic acid

N-benzyloxycarbonyl-glycine
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;
O-benzyl carbamate
621-84-1

O-benzyl carbamate

sodium benzenesulfonate
873-55-2

sodium benzenesulfonate

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

benzyl (4-cyanophenyl)(phenylsulfonyl)methylcarbamate
1220349-77-8

benzyl (4-cyanophenyl)(phenylsulfonyl)methylcarbamate

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

glyoxylic acid ethyl ester

O-benzyl carbamate
621-84-1

O-benzyl carbamate

ethyl 2-(((benzyloxy)carbonyl)amino)-2-hydroxyacetate
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%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

O-benzyl carbamate
621-84-1

O-benzyl carbamate

ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate
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%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

ethyl glyoxalate hydrate
64805-08-9

ethyl glyoxalate hydrate

ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate
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;
O-benzyl carbamate
621-84-1

O-benzyl carbamate

benzyl glyoxalate monohydrate
87692-25-9

benzyl glyoxalate monohydrate

C17H16ClNO4

C17H16ClNO4

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

O-benzyl carbamate

ethyl glyoxalate hydrate
64805-08-9

ethyl glyoxalate hydrate

N-Cbz-α-bromoglycine ethyl ester
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%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

benzyl N-(4-formylphenyl)carbamate
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%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

(E)-1-phenyl-2-penten-1-one
61752-66-7

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

3-(N-benzyloxycarbonylamino)-1-phenylpentan-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%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

O-benzyl carbamate
621-84-1

O-benzyl carbamate

benzyl benzhydrylcarbamate
5180-34-7

benzyl benzhydrylcarbamate

Conditions
ConditionsYield
With perrhenic acid anhydride In dichloromethane at 20℃; for 8h;99%
With aluminium(III) triflate In nitromethane at 50℃; for 0.166667h; Microwave irradiation;99%
With iron(III) chloride at 60℃; neat (no solvent);96%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

C9H8BrNO3
70400-19-0

C9H8BrNO3

benzyl [1-(3-bromo-4-methoxyphenyl)-2,2-dichloro-2-nitroethyl]carbamate
1355707-71-9

benzyl [1-(3-bromo-4-methoxyphenyl)-2,2-dichloro-2-nitroethyl]carbamate

Conditions
ConditionsYield
With N-chloro-succinimide; potassium carbonate In dichloromethane at 20℃; for 8h; regioselective reaction;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

β-(1-naphthyl)nitroethylene
37630-26-5, 4735-49-3

β-(1-naphthyl)nitroethylene

benzyl [2,2-dichloro-1-(naphth-1-yl)-2-nitroethyl]carbamate
1355707-76-4

benzyl [2,2-dichloro-1-(naphth-1-yl)-2-nitroethyl]carbamate

Conditions
ConditionsYield
With N-chloro-succinimide; potassium carbonate In dichloromethane at 20℃; for 8h; regioselective reaction;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

4-fluoro-β-nitrostyrene
5153-69-5, 706-08-1

4-fluoro-β-nitrostyrene

benzyl [2,2-dichloro-1-(4-fluorophenyl)-2-nitroethyl]carbamate
1355707-67-3

benzyl [2,2-dichloro-1-(4-fluorophenyl)-2-nitroethyl]carbamate

Conditions
ConditionsYield
With N-chloro-succinimide; potassium carbonate In dichloromethane at 20℃; for 8h; regioselective reaction;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

3-chloroβ-nitrostyrene
37888-03-2, 3156-35-2

3-chloroβ-nitrostyrene

benzyl [2,2-dichloro-1-(3-chlorophenyl)-2-nitroethyl]carbamate
1355707-63-9

benzyl [2,2-dichloro-1-(3-chlorophenyl)-2-nitroethyl]carbamate

Conditions
ConditionsYield
With N-chloro-succinimide; potassium carbonate In dichloromethane at 20℃; for 8h; regioselective reaction;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

o-bromonitrostyrene
65185-68-4

o-bromonitrostyrene

benzyl [1-(2-bromophenyl)-2,2-dichloro-2-nitroethyl]carbamate
1355707-66-2

benzyl [1-(2-bromophenyl)-2,2-dichloro-2-nitroethyl]carbamate

Conditions
ConditionsYield
With N-chloro-succinimide; potassium carbonate In dichloromethane at 20℃; for 8h; regioselective reaction;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

1-chloro-2-(2-nitrovinyl)benzene
22568-07-6, 3156-34-1

1-chloro-2-(2-nitrovinyl)benzene

benzyl [2,2-dichloro-1-(2-chlorophenyl)-2-nitroethyl]carbamate
1355707-61-7

benzyl [2,2-dichloro-1-(2-chlorophenyl)-2-nitroethyl]carbamate

Conditions
ConditionsYield
With N-chloro-succinimide; potassium carbonate In dichloromethane at 20℃; for 8h; regioselective reaction;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

(R/S)-N-benzyloxycarbonyl-1,3-diphenylprop-2-en-1-ylamine
928765-35-9

(R/S)-N-benzyloxycarbonyl-1,3-diphenylprop-2-en-1-ylamine

Conditions
ConditionsYield
With perrhenic acid anhydride In dichloromethane at 20℃; for 0.166667h;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

4-phenylbut-3-en-2-ol
17488-65-2

4-phenylbut-3-en-2-ol

(E)-4-phenyl-3-buten-2-amine N-benzyloxycarbonyl ester
920285-74-1

(E)-4-phenyl-3-buten-2-amine N-benzyloxycarbonyl ester

Conditions
ConditionsYield
With perrhenic acid anhydride In dichloromethane at 20℃; for 3h;99%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

O-benzyl carbamate
621-84-1

O-benzyl carbamate

benzyl N-(thiophen-2-ylmethyl)carbamate

benzyl N-(thiophen-2-ylmethyl)carbamate

Conditions
ConditionsYield
With triethylsilane; perrhenic acid anhydride In dichloromethane at 20℃; for 0.5h; chemoselective reaction;99%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

O-benzyl carbamate
621-84-1

O-benzyl carbamate

N-benzyloxycarbonyloxy-3-phenylpropylamine
302569-84-2

N-benzyloxycarbonyloxy-3-phenylpropylamine

Conditions
ConditionsYield
With triethylsilane; perrhenic acid anhydride In dichloromethane at 20℃; for 1.5h; chemoselective reaction;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

2-bromo-4-nitrotoluene
7745-93-9

2-bromo-4-nitrotoluene

benzyl (2-methyl-5-nitrophenyl)carbamate
875118-52-8

benzyl (2-methyl-5-nitrophenyl)carbamate

Conditions
ConditionsYield
With di-tert-butyl(2,2-diphenyl-1-methyl-1-cyclopropyl)phosphine; bis(η3-allyl-μ-chloropalladium(II)); triisopropylsilanol; potassium hydroxide In water at 50℃; for 24h; Inert atmosphere; Green chemistry;99%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

ethyl-3,3,3-trifluoropyruvate
13081-18-0

ethyl-3,3,3-trifluoropyruvate

ethyl 2-(((benzyloxy)carbonyl)amino)-3,3,3-trifluoro-2-hydroxypropanoate
126535-86-2

ethyl 2-(((benzyloxy)carbonyl)amino)-3,3,3-trifluoro-2-hydroxypropanoate

Conditions
ConditionsYield
In dichloromethane98%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

benzyl (diethoxyphosphoryl)(p-tolyl)methylcarbamate
129960-70-9

benzyl (diethoxyphosphoryl)(p-tolyl)methylcarbamate

Conditions
ConditionsYield
With thionyl chloride; acetic acid 1) room temperature, 20 min, 2) reflux, 12 h;98%
With acetyl chloride for 6h; Ambient temperature; Yield given;
cyclohexenone
930-68-7

cyclohexenone

O-benzyl carbamate
621-84-1

O-benzyl carbamate

benzyl (3-oxocyclohexyl)carbamate

benzyl (3-oxocyclohexyl)carbamate

Conditions
ConditionsYield
With chloro-trimethyl-silane; tributylphosphine In dichloromethane at 30℃; for 24h; aza-Michael reaction;98%
With bismuth(III) nitrate In dichloromethane at 20℃;94%
[Pd(MeCN)2(DPCBH)](OTf)2 at 20℃; for 0.5h;92%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

trans-3-penten-2-one
3102-33-8

trans-3-penten-2-one

benzyl N-(4-oxopentan-2-yl)carbamate

benzyl N-(4-oxopentan-2-yl)carbamate

Conditions
ConditionsYield
With chloro-trimethyl-silane; tributylphosphine In dichloromethane at 30℃; for 24h; aza-Michael reaction;98%
With Nafion(R) SAC-13 In acetonitrile at 20℃; for 12h;78%
O-benzyl carbamate
621-84-1

O-benzyl carbamate

(E)-1,3-diphenyl-2-propen-1-ol
62668-02-4

(E)-1,3-diphenyl-2-propen-1-ol

(R/S)-N-benzyloxycarbonyl-1,3-diphenylprop-2-en-1-ylamine
928765-35-9

(R/S)-N-benzyloxycarbonyl-1,3-diphenylprop-2-en-1-ylamine

Conditions
ConditionsYield
With C36H40O20S4 In water at 60℃; for 24h;98%
With potassium hexafluorophosphate; bismuth(lll) trifluoromethanesulfonate; calcium sulfate In 1,4-dioxane at 23 - 26℃; for 0.2h;97%
With sodium tetrachloroaurate(III) dihyrate In dichloromethane for 1h; Reflux;94%

621-84-1Relevant articles and documents

Simple synthesis of variously N-protected α-aminomethanesulfinate salts

Dujols, Frederic J. M.,Mulliez, Michel E.

, p. 5648 - 5649 (1996)

-

Synthesis of N-carbobenzoxy-N,N-acetals

Ding,Silverman

, p. 1467 - 1471 (1993)

A series of N-carbobenzoxy-N,N-acetals have been synthesized by the reaction of aromatic aldehydes or certain aliphatic aldehydes with benzyl carbamate and morpholine. The N,N-acetals can be converted into N-carbobenzoxy-N,S-acetals with benzyl thiol.

A PROCESS FOR THE PREPARATION OF UPADACITINIB AND ITS INTERMEDIATES

-

Page/Page column 5; 6, (2021/09/11)

The present invention provides novel intermediates of formula IV and formula VI, which are key intermediates in the process of Upadacitinib.

Triazinetriamine-derived porous organic polymer-supported copper nanoparticles (Cu-NPs@TzTa-POP): an efficient catalyst for the synthesis of: N -methylated products via CO2fixation and primary carbamates from alcohols and urea

Haque, Najirul,Biswas, Surajit,Basu, Priyanka,Haque Biswas, Imdadul,Khatun, Resmin,Khan, Aslam,Islam, Sk Manirul

supporting information, p. 15446 - 15458 (2020/10/22)

In recent times, carbon dioxide fixation has received much attention for its potential application as an abundant C1 source and a range of important fine chemicals can be manufactured via this fixation. Here, a copper nanoparticle-decorated porous organic polymer-based (Cu-NPs@TzTa-POP) material was prepared by a simple in situ process. The catalyst was characterized by various techniques such as UV-vis spectra, FTIR spectra, HR-TEM, PXRD, N2 adsorption-desorption, TG-DTA, XPS, and AAS analysis. The synthesized heterogeneous catalyst showed excellent activity in an atmospheric carbon dioxide fixation reaction to produce N-methylated products from aromatic/heterocyclic amines in the presence of polymethyl-hydrosiloxane (PMHS) as the reducing agent at 80 °C within 12 h of the reaction. Through this catalytic N-methylation reaction, we obtained 98% yield of the product with turnover frequency ranging from 18 to 42 h-1. The catalyst is also very stable for the formation of primary carbamates from alcohols using the eco-friendly carbonylating agent, urea. Diverse alcohols (such as benzylic alcohols, phenols, heterocyclic alcohols, as well as aliphatic alcohols) showed much acceptance to this catalytic reaction and produced moderate to excellent yields of the respective carbamate products under ambient reaction conditions. Moreover, Cu-NPs@TzTa-POP is effortlessly recyclable and reusable without the extensive loss of active copper metal centres for many catalytic rounds (up to six catalytic rounds were examined).

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