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6452-47-7

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6452-47-7 Usage

Description

Methylcarbamoyl Chloride is used as a reagent in the synthesis of acylprolinamides as a new class of peptide deformylase inhibitors with in vivo antibacterial activity. Methylcarbamoyl Chloride is also used as a reagent in the synthesis of carbamate derivatives as potential dual-binding site acetylcholinesterase inhibitors. The decomposition tail gas hydrogen chloride of Methylaminoformyl chloride is also useful during the cartap synthesis.

Uses

Different sources of media describe the Uses of 6452-47-7 differently. You can refer to the following data:
1. Methylaminoformyl chloride can be widely used as an intermediate of carbamate insecticides such as Zhongdingwei, carbofuran, isoprocarb, methomyl, chlorhexidine and carbaryl. Methylaminoformyl chloride is also used as a reagent in the synthesis of carbamate derivatives as potential dual-binding site acetylcholinesterase inhibitors. The decomposition tail gas hydrogen chloride of Methylaminoformyl chloride is also useful during the cartap synthesis.
2. Methylcarbamoyl Chloride is used as a reagent in the synthesis of acylprolinamides as a new class of peptide deformylase inhibitors with in vivo antibacterial activity. Methylcarbamoyl Chloride is also used as a reagent in the synthesis of carbamate derivatives as potential dual-binding site acetylcholinesterase inhibitors.

Preparation

Methylaminoformyl chloride is prepared by reacting methylamine with phosgene. Reaction equation: CH3NH2+COCl2→CH3NHCOCl. A 40% aqueous solution of methylamine is vaporized, and after drying, it is combined with phosgene at a ratio of 1:1.3 (methanol), methylamine at 4 m3/h, and phosgene at a rate of 8.6 m3/h (content 60%-70%). Preheating into the preheater, the preheating temperature of methylamine is controlled at 220-260°C, and the phosgene is controlled at 200-240°C. The preheated two gases enter the test tube and are synthesized at 280-300°C to obtain gaseous methaqualyl chloride. Then, carbon tetrachloride (or chlorobenzene solution) is circulated and absorbed at 0-20°C to obtain a solution of about 10% of carbamoyl chloride (or chlorobenzene), or cooled to a liquid product after 35-40°C or lower[2,3].

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 1888, 1950 DOI: 10.1021/ja01161a009

Check Digit Verification of cas no

The CAS Registry Mumber 6452-47-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,4,5 and 2 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 6452-47:
(6*6)+(5*4)+(4*5)+(3*2)+(2*4)+(1*7)=97
97 % 10 = 7
So 6452-47-7 is a valid CAS Registry Number.
InChI:InChI=1/C2H4ClNO/c1-4-2(3)5/h1H3,(H,4,5)

6452-47-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Methylaminoformyl Chloride

1.2 Other means of identification

Product number -
Other names N-methylcarbamoyl chloride

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:6452-47-7 SDS

6452-47-7Synthetic route

methycarbamoyl chloride

methycarbamoyl chloride

1,1-Dimethylurea
598-94-7

1,1-Dimethylurea

methyl isocyanate
624-83-9

methyl isocyanate

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

Conditions
ConditionsYield
In chloroform96.7%
Ethyl N-methylcarbamate
105-40-8

Ethyl N-methylcarbamate

A

methyl isocyanate
624-83-9

methyl isocyanate

B

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

Conditions
ConditionsYield
With Phenyltrichlorosilane at 100 - 150℃; for 1h;A 77.3%
B n/a
methyl isocyanate
624-83-9

methyl isocyanate

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane at 15℃; for 0.5h;54.4%
With hydrogenchloride In tetrachloromethane
With hydrogenchloride
phosgene
75-44-5

phosgene

methylamine hydrochloride
593-51-1

methylamine hydrochloride

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

Conditions
ConditionsYield
at 250 - 300℃;
at 250 - 300℃;
phosgene
75-44-5

phosgene

methylamine
74-89-5

methylamine

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

Conditions
ConditionsYield
at 275℃;
N-methyl-thiocarbamic acid S-methyl ester
22013-97-4

N-methyl-thiocarbamic acid S-methyl ester

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

Conditions
ConditionsYield
With chlorine In Dimethyldisulphide at -15 - -10℃; for 0.833333h;
3-(oxetan-3-ylmethoxy)-4-phenoxyaniline

3-(oxetan-3-ylmethoxy)-4-phenoxyaniline

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

1-methyl-3-[3-(oxetan-3-ylmethoxy)-4-phenoxyphenyl]urea

1-methyl-3-[3-(oxetan-3-ylmethoxy)-4-phenoxyphenyl]urea

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 16h;100%
4'-ethyl-2-methylbiphenyl-4-amine

4'-ethyl-2-methylbiphenyl-4-amine

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

1-(4'-ethyl-2-methylbiphenyl-4-yl)-3-methylurea

1-(4'-ethyl-2-methylbiphenyl-4-yl)-3-methylurea

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 16h; Inert atmosphere;100%
1-iodo-5, 6,7,8-tetrahydroimidazo[1,5-a]pyrazine hydrochloride

1-iodo-5, 6,7,8-tetrahydroimidazo[1,5-a]pyrazine hydrochloride

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

1-iodo-N-methyl-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carboxamide

1-iodo-N-methyl-6,8-dihydro-5H-imidazo[1,5-a]pyrazine-7-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 1h;98%
methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

N-methyl-5-(trifluoromethyl)-1 3,4-thiadiazol-2-amine
25366-22-7

N-methyl-5-(trifluoromethyl)-1 3,4-thiadiazol-2-amine

1-methyl-3-methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)urea
25366-23-8

1-methyl-3-methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)urea

Conditions
ConditionsYield
With triethylamine In toluene at 30 - 75℃; for 5h; Temperature; Reagent/catalyst;97.5%
methyl 1H-pyrazole 3-carboxylate
15366-34-4

methyl 1H-pyrazole 3-carboxylate

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

methyl 1-(methylcarbamoyl)-1H-pyrazole-3-carboxylate

methyl 1-(methylcarbamoyl)-1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at -78 - 20℃; for 18h;96%
N-(7-hydroxy-8-methoxy-2-oxo-2H-chromen-3-yl)-3',6-dimethoxy-[1,1'-biphenyl]-3-carboxamide
1160952-27-1

N-(7-hydroxy-8-methoxy-2-oxo-2H-chromen-3-yl)-3',6-dimethoxy-[1,1'-biphenyl]-3-carboxamide

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

3-(3',6-dimethoxy-[1,1'-biphenyl]-3-ylcarboxamido)-8-methoxy-2-oxo-2H-chromen-7-yl methylcarbamate
1160952-33-9

3-(3',6-dimethoxy-[1,1'-biphenyl]-3-ylcarboxamido)-8-methoxy-2-oxo-2H-chromen-7-yl methylcarbamate

Conditions
ConditionsYield
In pyridine for 12h;90%
4-amino-1-(3-bromophenyl)-1H-pyrazole-3-carboxamide
850727-84-3

4-amino-1-(3-bromophenyl)-1H-pyrazole-3-carboxamide

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

1-(3-bromophenyl)-4-[(methylcarbamoyl)amino]-1H-pyrazole-3-carboxamide

1-(3-bromophenyl)-4-[(methylcarbamoyl)amino]-1H-pyrazole-3-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;89%
1-(6-chloropyrimidin-4-yl)-3,5-dimethyl-1H-pyrazol-4-ol

1-(6-chloropyrimidin-4-yl)-3,5-dimethyl-1H-pyrazol-4-ol

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

1-(6-chloropyrimidin-4-yl)-3,5-dimethyl-1H-pyrazol-4-yl methylcarbamate

1-(6-chloropyrimidin-4-yl)-3,5-dimethyl-1H-pyrazol-4-yl methylcarbamate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;89%
C19H28N2O4S

C19H28N2O4S

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

C21H30N2O5S

C21H30N2O5S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;89%
2-hydroxy-S-allylthiophenol
5656-45-1

2-hydroxy-S-allylthiophenol

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

2-(allylthio)phenyl-N-methylcarbamate
948-85-6

2-(allylthio)phenyl-N-methylcarbamate

Conditions
ConditionsYield
Stage #1: 2-hydroxy-S-allylthiophenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: methylcarbamoyl chloride In tetrahydrofuran at 0 - 20℃; for 24.25h;
88%
ethyl 2-amino-4-(3-nitrophenyl)thiophene-3-carboxylate
433701-34-9

ethyl 2-amino-4-(3-nitrophenyl)thiophene-3-carboxylate

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

C15H15N3O5S

C15H15N3O5S

Conditions
ConditionsYield
In dichloromethane at 0℃;87.5%
3-(1-benzyl-1H‑1,2,3‑triazol-4-yl)phenol

3-(1-benzyl-1H‑1,2,3‑triazol-4-yl)phenol

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

N-methyl-3-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl carbamate
1128193-61-2

N-methyl-3-(1-benzyl-1H-1,2,3-triazol-4-yl)phenyl carbamate

Conditions
ConditionsYield
Stage #1: 3-(1-benzyl-1H‑1,2,3‑triazol-4-yl)phenol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: methylcarbamoyl chloride In tetrahydrofuran; water
86%
methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

β-naphthol
135-19-3

β-naphthol

naphthalen-2-yl methylcarbamate
4089-04-7

naphthalen-2-yl methylcarbamate

Conditions
ConditionsYield
In Isopropylbenzene85%
3,5-diethylphenol
1197-34-8

3,5-diethylphenol

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

3,5-diethylphenyl-N-methylcarbamate
30087-47-9

3,5-diethylphenyl-N-methylcarbamate

Conditions
ConditionsYield
In o-xylene85%
N-(4-{3-[(4-methylphenyl)amino]-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-2-yl}pyridin-2-yl)acetamide

N-(4-{3-[(4-methylphenyl)amino]-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridin-2-yl}pyridin-2-yl)acetamide

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

2-[2-(acetylamino)pyridin-4-yl]-N-methyl-3-[(4-methylphenyl)amino]-4-oxo-1,4,5,7-tetrahydro-6H-pyrrolo[2,3-c]pyridine-6-carboxamide

2-[2-(acetylamino)pyridin-4-yl]-N-methyl-3-[(4-methylphenyl)amino]-4-oxo-1,4,5,7-tetrahydro-6H-pyrrolo[2,3-c]pyridine-6-carboxamide

Conditions
ConditionsYield
With pyridine at 20℃; for 16h;85%
2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester

2,7-diaza-spiro[3.5]nonane-2-carboxylic acid tert-butyl ester

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

tert-butyl 7-(methylcarbamoyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate

tert-butyl 7-(methylcarbamoyl)-2,7-diazaspiro[3.5]nonane-2-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane Inert atmosphere;85%
8-chloro-6-(4-methylpyridin-3-yl)isoquinolin-3-amine

8-chloro-6-(4-methylpyridin-3-yl)isoquinolin-3-amine

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

1-[8-chloro-6-(4-methyl-3-pyridyl)-3-isoquinolyl]-3-methylurea

1-[8-chloro-6-(4-methyl-3-pyridyl)-3-isoquinolyl]-3-methylurea

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 120℃; for 16h;84%
C16H22N2O3S

C16H22N2O3S

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

C18H24N2O4S

C18H24N2O4S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;84%
5-(1,3-dioxoisoindolin-2-yl)-N-(piperidin-4-yl)naphthalene-1-sulfonamide

5-(1,3-dioxoisoindolin-2-yl)-N-(piperidin-4-yl)naphthalene-1-sulfonamide

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

C25H24N4O5S

C25H24N4O5S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 8h;83%
With triethylamine In dichloromethane at 25℃; for 8h;83%
3-(3,3-difluorocyclobutyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine

3-(3,3-difluorocyclobutyl)-5,6,7,8-tetrahydroimidazo[1,5-a]pyrazine

methylcarbamoyl chloride
6452-47-7

methylcarbamoyl chloride

3-(3,3-difluorocyclobutyl)-N-methyl-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxamide

3-(3,3-difluorocyclobutyl)-N-methyl-5,6-dihydroimidazo[1,5-a]pyrazine-7(8H)-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 3h;83%

6452-47-7Relevant articles and documents

-

Buder,Schmidt

, p. 1429,1430, 1434 (1973)

-

Preparation of carbamoyl halides

-

, (2008/06/13)

Compounds of formula I, RNHCOCl (I), where R is an optionally substituted alkyl or aryl group, are obtained by chlorinating a compound of formula II, RNHCHO (II), in the absence of a solvent.

Preparation of alkyl isocyanates

-

, (2008/06/13)

A novel process for the preparation of alkyl isocyanates comprising reacting COX2 and an alkyl amine hydrohalide of the formula wherein R is alkyl of 1 to 3 carbon atoms and X is a halogen either under pressure in an inert organic solvent or under atmospheric pressure in a high boiling organic solvent to form the corresponding alkyl carbamoyl halide, reacting the latter in an organic solvent with an urea of the formula STR1 wherein X' is selected from the group consisting of oxygen and sulfur, R1 and R3 are individually selected from the group consisting of alkyl of 1 to 7 carbon atoms, cycloalkyl of 4 to 6 carbon atoms and phenyl and R2 and R4 are individually selected from the group consisting of hydrogen, alkyl of 1 to 7 carbon atoms, cycyloalkyl of 4 to 6 carbon atoms and phenyl to obtain the corresponding alkyl isocyanate.

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