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49715-04-0

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49715-04-0 Usage

Chemical Properties

Clear colourless to yellow liquid

Uses

Reagent for chloromethylation of Fmoc-protected amino acids without the generation of carcinogenic bis(chloromethyl)ether.

Check Digit Verification of cas no

The CAS Registry Mumber 49715-04-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,9,7,1 and 5 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 49715-04:
(7*4)+(6*9)+(5*7)+(4*1)+(3*5)+(2*0)+(1*4)=140
140 % 10 = 0
So 49715-04-0 is a valid CAS Registry Number.
InChI:InChI=1/CH2Cl2O4S/c2-1-6-8(4,5)7-3/h1H2

49715-04-0 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (C2660)  Chloromethyl Chlorosulfonate  >98.0%(GC)(T)

  • 49715-04-0

  • 5g

  • 690.00CNY

  • Detail
  • TCI America

  • (C2660)  Chloromethyl Chlorosulfonate  >98.0%(GC)(T)

  • 49715-04-0

  • 25g

  • 2,450.00CNY

  • Detail
  • Aldrich

  • (656682)  Chloromethylchlorosulfate  97%

  • 49715-04-0

  • 656682-2G

  • 948.87CNY

  • Detail

49715-04-0Synthetic route

dichloromethane
75-09-2

dichloromethane

A

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

B

[(chlorosulfonyl)oxy]methyl sulfurochloridate
92975-18-3

[(chlorosulfonyl)oxy]methyl sulfurochloridate

Conditions
ConditionsYield
With sulfuric acid; boron tribromide at 20 - 30℃; for 4h; Temperature;A 85%
B 12%
dichloromethane
75-09-2

dichloromethane

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
With Trimethyl borate; sulfur trioxide at 20℃; for 0.166667h;33%
With chlorosulfonic acid at 60 - 130℃;
formaldehyd
50-00-0

formaldehyd

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
Stage #1: formaldehyd With chlorosulfonic acid at 20 - 80℃;
Stage #2: With thionyl chloride at 60℃; Product distribution / selectivity;
30%
With chlorosulfonic acid at 70℃; und Destillation unter ca.13 mm Druck;
chlorobromomethane
74-97-5

chlorobromomethane

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid for 3h; Heating;30%
With chlorosulfonic acid for 3h; Heating;30%
formaldehyd
50-00-0

formaldehyd

A

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

B

[1,3,2]dioxathietane-2,2-dioxide
56639-44-2

[1,3,2]dioxathietane-2,2-dioxide

Conditions
ConditionsYield
With chlorosulfonic acid
bis(2-chloromethyl)ether
542-88-1

bis(2-chloromethyl)ether

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid at 70℃;
With sulfur trioxide durch Destillation das hergestellten Gemisch unter 28 mm Druck;
bischloromethyl sulfate
73455-05-7

bischloromethyl sulfate

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid at 70 - 80℃;
bischloromethyl sulfate
73455-05-7

bischloromethyl sulfate

A

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

B

[1,3,2]dioxathietane-2,2-dioxide
56639-44-2

[1,3,2]dioxathietane-2,2-dioxide

Conditions
ConditionsYield
With chlorosulfonic acid at 70 - 80℃;
[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide
20757-83-9

[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid bei der Destillation unter 12 mm Druck;
carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid at 100℃;
chlorosulfonic acid
7790-94-5

chlorosulfonic acid

carbonochloridic acid, chloromethyl ester
22128-62-7

carbonochloridic acid, chloromethyl ester

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
zuletzt unter Erwaermen auf dem Wasserbad;
chlorosulfonic acid
7790-94-5

chlorosulfonic acid

bis(2-chloromethyl)ether
542-88-1

bis(2-chloromethyl)ether

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
at 70℃; und nachfolgenden Destillieren unter 14 mm Druck;
chlorosulfonic acid
7790-94-5

chlorosulfonic acid

[1,3,2]dioxathietane-2,2-dioxide
56639-44-2

[1,3,2]dioxathietane-2,2-dioxide

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
under 12 Torr;
chlorosulfonic acid
7790-94-5

chlorosulfonic acid

dichloromethane
75-09-2

dichloromethane

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
at 60 - 130℃;
bischloromethyl sulfate
73455-05-7

bischloromethyl sulfate

chlorosulfonic acid (9 mol)

chlorosulfonic acid (9 mol)

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
at 70 - 80℃;
chlorosulfonic acid
7790-94-5

chlorosulfonic acid

bis(2-chloromethyl)ether
542-88-1

bis(2-chloromethyl)ether

A

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

B

bischloromethyl sulfate
73455-05-7

bischloromethyl sulfate

Conditions
ConditionsYield
at 70℃; beim Ausgiessen des erhaltenen Reaktionsprodukts auf Eis und folgender Vakuumdestillation;
bis(2-chloromethyl)ether
542-88-1

bis(2-chloromethyl)ether

sulfur trioxide
7446-11-9

sulfur trioxide

A

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

B

bischloromethyl sulfate
73455-05-7

bischloromethyl sulfate

Conditions
ConditionsYield
under 28 Torr; bei der Destillation;
bischloromethyl sulfate
73455-05-7

bischloromethyl sulfate

chlorosulfonic acid (1.4 mol)

chlorosulfonic acid (1.4 mol)

A

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

B

[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide
20757-83-9

[1,3,5,7,2,6]tetroxadithiocane 2,2,6,6-tetraoxide

Conditions
ConditionsYield
at 70 - 80℃;
Chloroiodomethane
593-71-5

Chloroiodomethane

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Conditions
ConditionsYield
With chlorosulfonic acid; thionyl chloride; sodium hydroxide In dichloromethane; water at 20 - 35℃; for 7.5h; Inert atmosphere;
Chloroiodomethane
593-71-5

Chloroiodomethane

A

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

B

bischloromethyl sulfate
73455-05-7

bischloromethyl sulfate

Conditions
ConditionsYield
With chlorosulfonic acid In dichloromethane at 0 - 21℃; for 18h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

t-Boc-L-valine
13734-41-3

t-Boc-L-valine

N-tert-butyloxycarbonyl-L-valine chloromethyl ester
40224-39-3

N-tert-butyloxycarbonyl-L-valine chloromethyl ester

Conditions
ConditionsYield
Stage #1: t-Boc-L-valine With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0℃; for 0.166667h;
Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 0 - 20℃; for 19.3333h;
100%
With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate In dichloromethane; water at 0 - 20℃; for 19.33h;100%
Stage #1: t-Boc-L-valine With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 0.0833333h;
Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 0 - 20℃; for 2h;
99%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid
51077-16-8

N-(tert-butoxycarbonyl)-(R)-thiazolidine-4-carboxylic acid

(R)-Thiazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-chloromethyl ester

(R)-Thiazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;100%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

butyric acid
107-92-6

butyric acid

chloromethyl n-butyrate
33657-49-7

chloromethyl n-butyrate

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 16h;100%
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In dichloromethane; water at 20℃; for 4h; Inert atmosphere;58%
With sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogen sulfate In dichloromethane; water41%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0℃; for 1h;31%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

fenofibric acid
42017-89-0

fenofibric acid

chloromethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate
1094101-30-0

chloromethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Conditions
ConditionsYield
Stage #1: fenofibric acid With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In water at 20℃; for 0.25h;
Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃; Cooling with ice;
100%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

N-tert-butoxycarbonyl-L-leucine
13139-15-6

N-tert-butoxycarbonyl-L-leucine

(S)-chloromethyl 2-((tert-butoxycarbonyl)amino)-4-methylvalerate
70579-73-6

(S)-chloromethyl 2-((tert-butoxycarbonyl)amino)-4-methylvalerate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;99%
Stage #1: N-tert-butoxycarbonyl-L-leucine With sodium hydrogencarbonate In water for 0.166667h;
Stage #2: With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 0.166667h;
Stage #3: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃; for 15h; Cooling with ice;
98.4%
Stage #1: N-tert-butoxycarbonyl-L-leucine With sodium hydrogencarbonate In water for 0.166667h;
Stage #2: With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 0.166667h;
Stage #3: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃; for 15h; Cooling with ice;
98.4%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

L-tert-butyl 1-(chloromethoxycarbonyl)-2-phenylethylcarbamate
34573-39-2

L-tert-butyl 1-(chloromethoxycarbonyl)-2-phenylethylcarbamate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃;99%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;83%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃;
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

C24H46O8
1421487-17-3

C24H46O8

Conditions
ConditionsYield
Stage #1: C24H46O8 With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate In water at 20℃; for 0.333333h; Reflux; Inert atmosphere;
Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 0 - 20℃; for 19h;
99%
With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate In dichloromethane; water at 0 - 20℃; for 19h;2.19 g
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

(S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid chloromethyl ester

(S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;98%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

(S)-2-tert-Butoxycarbonylamino-malonic acid mono-tert-butyl ester

(S)-2-tert-Butoxycarbonylamino-malonic acid mono-tert-butyl ester

(S)-2-tert-Butoxycarbonylamino-malonic acid tert-butyl ester chloromethyl ester

(S)-2-tert-Butoxycarbonylamino-malonic acid tert-butyl ester chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;98%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

D-tert-butyl 1-(chloromethoxycarbonyl)-2-phenylethylcarbamate
1051916-41-6

D-tert-butyl 1-(chloromethoxycarbonyl)-2-phenylethylcarbamate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃;97%
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

(S)-tert-butyl chloromethyl pyrrolidine-1,2-dicarboxylate
34614-72-7

(S)-tert-butyl chloromethyl pyrrolidine-1,2-dicarboxylate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;96%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid chloromethyl ester

(S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;96%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid
84358-13-4

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid

1-tert-butyl 4-(chloromethyl)piperidine-1,4-dicarboxylate
150109-49-2

1-tert-butyl 4-(chloromethyl)piperidine-1,4-dicarboxylate

Conditions
ConditionsYield
Stage #1: N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0℃; for 0.166667h;
Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 0 - 20℃;
96%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;92%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 5h;86%
With sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 20℃; for 0.5h;
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 5h;
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

1-<(tert-butyloxy)carbonylamino>cyclopropane-1-carboxylic acid
88950-64-5

1-<(tert-butyloxy)carbonylamino>cyclopropane-1-carboxylic acid

1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropanecarboxylic acid chloromethyl ester
1581704-70-2

1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropanecarboxylic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; Cooling with ice;96%
With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate In dichloromethane; water at 0 - 20℃;73.3%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

N-[(1,1-dimethylethoxy)carbonyl]-L-alanine chloromethyl ester
150109-42-5

N-[(1,1-dimethylethoxy)carbonyl]-L-alanine chloromethyl ester

Conditions
ConditionsYield
Stage #1: L-N-Boc-Ala With sodium hydrogencarbonate In water for 0.5h;
Stage #2: With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 0.333333h;
Stage #3: chlorosulfuric acid chloromethyl ester In dichloromethane; water for 15h;
95.5%
Stage #1: L-N-Boc-Ala With sodium hydrogencarbonate In water for 0.5h;
Stage #2: With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 0.333333h;
Stage #3: chlorosulfuric acid chloromethyl ester In dichloromethane; water for 15h;
95.5%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;94%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

potassium di-tert-butylphosphate
33494-80-3

potassium di-tert-butylphosphate

di-tert-butyl chloromethyl phosphate
229625-50-7

di-tert-butyl chloromethyl phosphate

Conditions
ConditionsYield
Stage #1: potassium di-tert-butylphosphate With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0℃; for 0.166667h;
Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃; for 20h;
95.3%
With potassium hydrogenphosphate trihydrate; tert-butyl methyl ether; tetra(n-butyl)ammonium hydrogensulfate In water at 0 - 20℃; for 2.41667h;94%
With potassium hydrogenphosphate trihydrate; tetra(n-butyl)ammonium hydrogensulfate In tert-butyl methyl ether; water at 0 - 30℃; for 2.41667h;94%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

(S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid
57133-29-6

(S)-2,5-bis((tert-butoxycarbonyl)amino)pentanoic acid

(S)-2,5-Bis-tert-butoxycarbonylamino-pentanoic acid chloromethyl ester

(S)-2,5-Bis-tert-butoxycarbonylamino-pentanoic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;95%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

[2-(2,6-dichloroanilino)phenyl]acetic acid
15307-86-5

[2-(2,6-dichloroanilino)phenyl]acetic acid

chloromethyl 2-(2-((2,6-dichlorophenyl)amino)phenyl)acetate

chloromethyl 2-(2-((2,6-dichlorophenyl)amino)phenyl)acetate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 1h;95%
With Bu4HSO4 In dichloromethane; water at 20℃; for 1h;
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

(3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid
764639-63-6

(3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid

C20H33ClN2O6

C20H33ClN2O6

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; for 3h;95%
Stage #1: (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water for 0.5h;
Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water at 20℃; for 5h;
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

4-((bis(benzyloxy)phosphoryl)oxy)-3-methoxybenzoic acid

4-((bis(benzyloxy)phosphoryl)oxy)-3-methoxybenzoic acid

chloromethyl 4-((bis (benzyloxy)phosphoryl)oxy)-3-methoxy benzoate

chloromethyl 4-((bis (benzyloxy)phosphoryl)oxy)-3-methoxy benzoate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0 - 20℃; for 16h;95%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

ibuprofen
15687-27-1

ibuprofen

chloromethyl 2-(4-isobutylphenyl)propanoate
135922-50-8

chloromethyl 2-(4-isobutylphenyl)propanoate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate In dichloromethane; water at 30℃; for 0.5h;94%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane at 25℃; for 1h;50%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

(S)-2-phenylbutanoic acid
4593-90-2, 772-15-6

(S)-2-phenylbutanoic acid

(S)-chloromethyl 3-phenylbutanoate
909785-77-9

(S)-chloromethyl 3-phenylbutanoate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃;94%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

N-tert-butyloxycarbonyl-L-tert-leucine
62965-35-9

N-tert-butyloxycarbonyl-L-tert-leucine

N-[(1,1-dimethylethoxy)carbonyl]-L-tert-leucine chloromethyl ester

N-[(1,1-dimethylethoxy)carbonyl]-L-tert-leucine chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; Cooling with ice;94%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

3-(tert-Butoxycarbonyl)amino-2,2-dimethylpropanoic Acid
180181-02-6

3-(tert-Butoxycarbonyl)amino-2,2-dimethylpropanoic Acid

3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethylpropanoic acid chloromethyl ester

3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2-dimethylpropanoic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; Cooling with ice;94%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-3-methylbutanoic acid

2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-3-methylbutanoic acid

2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-3-methylbutanoic acid chloromethyl ester

2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-3-methylbutanoic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane at 20℃; Cooling with ice;94%
BOC-glycine
4530-20-5

BOC-glycine

chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

N-[(1,1-dimethylethoxy)carbonyl]glycine chloromethyl ester
34573-36-9

N-[(1,1-dimethylethoxy)carbonyl]glycine chloromethyl ester

Conditions
ConditionsYield
Stage #1: BOC-glycine With sodium hydrogencarbonate In water for 0.5h;
Stage #2: With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 0.333333h;
Stage #3: chlorosulfuric acid chloromethyl ester In dichloromethane; water for 15h;
93.7%
Stage #1: BOC-glycine With sodium hydrogencarbonate In water for 0.5h;
Stage #2: With tetra(n-butyl)ammonium hydrogensulfate In dichloromethane for 0.333333h;
Stage #3: chlorosulfuric acid chloromethyl ester In dichloromethane for 15h;
93.8%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;87%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

N-(tert-butoxycarbonyl)sarcosine
13734-36-6

N-(tert-butoxycarbonyl)sarcosine

chloromethyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate

chloromethyl 2-((tert-butoxycarbonyl)(methyl)amino)acetate

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water Ambient temperature;93%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

1-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid
35264-09-6

1-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid

1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopentane carboxylic acid chloromethyl ester

1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopentane carboxylic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; Cooling with ice;93%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

1-(<<(tert-butoxy)carbonyl>amino>methyl)cyclopentane-1-carboxylic acid
204514-22-7

1-(<<(tert-butoxy)carbonyl>amino>methyl)cyclopentane-1-carboxylic acid

1-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]cyclopentane carboxylic acid chloromethyl ester

1-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]cyclopentane carboxylic acid chloromethyl ester

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 20℃; Cooling with ice;93%
chlorosulfuric acid chloromethyl ester
49715-04-0

chlorosulfuric acid chloromethyl ester

(E)-3-t-butoxycarbonyl-2-butenoic acid
45022-27-3, 120515-28-8, 135355-96-3

(E)-3-t-butoxycarbonyl-2-butenoic acid

tert-butyl chloromethyl (2E)-but-2-enedioate

tert-butyl chloromethyl (2E)-but-2-enedioate

Conditions
ConditionsYield
Stage #1: (E)-3-t-butoxycarbonyl-2-butenoic acid With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water at 0℃; for 0.166667h;
Stage #2: chlorosulfuric acid chloromethyl ester In dichloromethane; water for 16h;
93%

49715-04-0Relevant articles and documents

Chloromethyl chlorosulfate: A new, catalytic method of preparation and reactions with some nucleophiles

Power, Nicholas P.,Bethell, Donald,Proctor, Lee,Latham, Elliot,Dawson, Paul

, p. 1554 - 1562 (2004)

A catalytic method of preparing chloromethyl chlorosulfate (CMCS) was described. The reaction of liquid SO3 with CH2Cl 2 at room temperature led to SO3 insertion into the C-Cl bonds, giving CMCS. The product mixtures consists entirely of CMCS and the product of further sulfation, methylene bis(chlorosulfate) (MBCS). The reaction was shown to be first order in the catalyst and third order in SO3 by measuring initial rates of CMCS formation or total CH2Cl2 consumption. The results show that the reaction between dichloromethane and SO3 at room temperature is accelerated by very low concentrations.

Development of a process for the preparation of chloromethyl chlorosulfate

Zheng, Bin,Sugiyama, Masano,Eastgate, Martin D.,Fritz, Alan,Murugesan, Saravanababu,Conlon, David A.

, p. 1827 - 1831 (2012)

A new and efficient synthesis of chloromethyl chlorosulfate (CMCS) from chloroiodomethane and chlorosulfonic acid is described. This process leverages a chlorosulfonic acid-mediated iodide oxidation to drive the equilibrating displacement process to full conversion. The resulting iodine byproduct is further oxidized and removed as iodate, to prevent iodide-induced decomposition of CMCS. This new process provides an efficient and scalable protocol for the preparation of CMCS in 92% solution yield and high purity (>99 GC area %).

Preparation method of methyl bichlorosulfonate

-

Paragraph 0011; 0024-0039, (2018/05/16)

The invention discloses a preparation method of methyl bichlorosulfonate. The methyl bichlorosulfonate is prepared through the catalytic addition reaction of fuming sulphuric acid and dichloromethaneunder the condition that boron tribromide is taken as a catalyst. Compared with the prior art, the preparation method of the methyl bichlorosulfonate has the following advantages: (1) the novel catalyst of boron tribromide is cheap and easy to get, and the production cost is lowered; (2) due to the optimized catalyst and reaction condition, the MBCS (Methyl Bichlorosulfonate) yield is increased, and a byproduct CMCS is also reduced; (3) the use of the hazardous difficult-to-treat material sulfur trioxide is avoided, the operability is strong, and the industrial value is high; and (4) the problem of difficulties in storing and fusing the liquid sulfur trioxide in use is avoided.

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