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3144-09-0

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3144-09-0 Usage

Chemical Description

Methanesulfonamide is a solvent used in the dihydroxylation reaction.

Chemical Properties

White to yellow crystals, powder or flakes

Uses

Different sources of media describe the Uses of 3144-09-0 differently. You can refer to the following data:
1. Methanesulfonamide will react with thionyl chloride, cyanates, carbon disulfide and ketones and aldehydes to prepare pharmaceuticals, brightening agent and other target molecules. It is also used in biological studies to predict binding affinity and binding mode of protein ligand complexes.
2. Methanesulfonamide is used in the synthesis of important organic reagents such as N-(2-methylthio-1-p-toluenesufonyl)methanesulfonamide and tert-butyl ((2-(trimethylsilyl)ethyl)sulfonyl)carbamate.It can be used as a source of nitrogen in the conversion of carboxylic acids to corresponding nitriles.It is widely used as a reagent in the synthesis of medicinally important compounds such as derivatives of indole-N-acetamide, methanesulfonamide pyrimidine-substituted 3,5-dihydroxy-6-heptenoates and repertaxin.

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 4096, 1968 DOI: 10.1021/ja01017a032The Journal of Organic Chemistry, 60, p. 7682, 1995 DOI: 10.1021/jo00128a048Tetrahedron Letters, 35, p. 7201, 1994 DOI: 10.1016/0040-4039(94)85360-6

Check Digit Verification of cas no

The CAS Registry Mumber 3144-09-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,4 and 4 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 3144-09:
(6*3)+(5*1)+(4*4)+(3*4)+(2*0)+(1*9)=60
60 % 10 = 0
So 3144-09-0 is a valid CAS Registry Number.
InChI:InChI=1/CH5NO2S/c1-5(2,3)4/h1H3,(H2,2,3,4)

3144-09-0 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (A10885)  Methanesulfonamide, 98+%   

  • 3144-09-0

  • 10g

  • 234.0CNY

  • Detail
  • Alfa Aesar

  • (A10885)  Methanesulfonamide, 98+%   

  • 3144-09-0

  • 50g

  • 523.0CNY

  • Detail
  • Alfa Aesar

  • (A10885)  Methanesulfonamide, 98+%   

  • 3144-09-0

  • 250g

  • 1302.0CNY

  • Detail
  • Alfa Aesar

  • (A10885)  Methanesulfonamide, 98+%   

  • 3144-09-0

  • 500g

  • 2213.0CNY

  • Detail
  • Aldrich

  • (64275)  Methanesulfonamide  ≥97.0% (CHN)

  • 3144-09-0

  • 64275-10G

  • 610.74CNY

  • Detail
  • Aldrich

  • (64275)  Methanesulfonamide  ≥97.0% (CHN)

  • 3144-09-0

  • 64275-50G

  • 2,111.85CNY

  • Detail

3144-09-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Methanesulfonamide

1.2 Other means of identification

Product number -
Other names Methane sulfonamide

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:3144-09-0 SDS

3144-09-0Synthetic route

N-nitromethanesulfonimide
80284-02-2

N-nitromethanesulfonimide

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

CH3N2O4S(1-)*H4N(1+)

CH3N2O4S(1-)*H4N(1+)

Conditions
ConditionsYield
With ammonia In dichloromethane for 0.0833333h;A n/a
B 100%
N-(3-methylbut-2-en-1-yl)methanesulfonamide
1578267-78-3

N-(3-methylbut-2-en-1-yl)methanesulfonamide

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With silver hexafluoroantimonate In 1,2-dichloro-ethane at 140℃; for 0.0333333h; Inert atmosphere; Microwave irradiation;100%
methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane; ethyl acetate99%
With triethylamine In dichloromethane98%
97%
N,N-bis(3-methylbut-2-en-1-yl)methanesulfonamide

N,N-bis(3-methylbut-2-en-1-yl)methanesulfonamide

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With silver hexafluoroantimonate In 1,2-dichloro-ethane at 140℃; for 0.0333333h; Microwave irradiation; Inert atmosphere;98%
HCl(aq)

HCl(aq)

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

4-(4-bromophenyl)-4-hydroxy-piperidine

4-(4-bromophenyl)-4-hydroxy-piperidine

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane; water95.6%
With triethylamine In dichloromethane; water95.6%
With triethylamine In dichloromethane; water
Methanesulfonyl azide
624-90-8, 1516-70-7

Methanesulfonyl azide

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With benzyltriethylammonium tetrathiomolybdate In water; acetonitrile at 25℃; for 0.1h;95%
With zinc In methanol at 20℃; for 2h;92%
With iron In water at 20℃; for 2h; Inert atmosphere;87%
N,N-bis[(E)-3,7-dimethylocta-2,6-dien-1-yl]methanesulfonamide

N,N-bis[(E)-3,7-dimethylocta-2,6-dien-1-yl]methanesulfonamide

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With silver hexafluoroantimonate In 1,2-dichloro-ethane at 140℃; for 0.0333333h; Microwave irradiation; Inert atmosphere;81%
tert-butylsulfinyl chloride
31562-43-3

tert-butylsulfinyl chloride

N-hydroxylmethanesulfonamide
50695-55-1

N-hydroxylmethanesulfonamide

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

di-tert-butyl thiosulfonate
31562-41-1

di-tert-butyl thiosulfonate

C

trifluoromethane sulfonic anhydride
75975-45-0

trifluoromethane sulfonic anhydride

D

C5H13NO4S2
75975-41-6

C5H13NO4S2

Conditions
ConditionsYield
With pyridine In acetone at 20℃; for 2h; Mechanism; Product distribution; other N-hydroxy sulfonamides;A 80%
B 13%
C 22%
D 15%
N-[(E)-morpholin-4-ylmethylidene]methanesulfonamide

N-[(E)-morpholin-4-ylmethylidene]methanesulfonamide

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20℃; for 2h;80%
N-methanesulfonyl-3-phenylpropylamine
362665-07-4

N-methanesulfonyl-3-phenylpropylamine

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

methanesulfonamide
3144-09-0

methanesulfonamide

C

3-(4-iodophenyl)propionaldehyde
213264-51-8

3-(4-iodophenyl)propionaldehyde

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene; iodine In 1,2-dichloro-ethane at 30 - 40℃; for 3h; ultrasonic irradiation;A 24%
B 66%
C 39%
N-Isopropylidene-methanesulfonamide
110955-56-1

N-Isopropylidene-methanesulfonamide

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

acetone
67-64-1

acetone

Conditions
ConditionsYield
With water for 1h; Heating;A 56%
B n/a
4-{2-[3,4-bis(difluoromethoxy)phenyl]-2-[6-(4-aminophenoxy)-pyridin-3-yl]ethyl}pyridine
303165-07-3

4-{2-[3,4-bis(difluoromethoxy)phenyl]-2-[6-(4-aminophenoxy)-pyridin-3-yl]ethyl}pyridine

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

A

4-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(methylsulfonylamino)phenoxy]-pyridin-3-yl}ethyl}pyridine

4-{2-[3,4-Bis(difluoromethoxy)phenyl]-2-{6-[4-(methylsulfonylamino)phenoxy]-pyridin-3-yl}ethyl}pyridine

B

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With potassium carbonate; triethylamine In tetrahydrofuran; methanol; dichloromethaneA 51%
B n/a
sodium methansulfinate
20277-69-4

sodium methansulfinate

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
Stage #1: sodium methansulfinate With iodine at 20℃; for 0.333333h; Green chemistry;
Stage #2: With ammonium hydroxide; water at 20℃; for 3h; Green chemistry;
23%
mavacoxib
170569-88-7

mavacoxib

methyl iodide
74-88-4

methyl iodide

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

4-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-N-methylbenzenesulfonamide

4-[5-(4-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]-N-methylbenzenesulfonamide

Conditions
ConditionsYield
In dimethyl sulfoxideA n/a
B 21%
styrene
292638-84-7

styrene

[N-(methylsulfonyl)imino]phenyliodinane

[N-(methylsulfonyl)imino]phenyliodinane

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

(N-methanesulfonyl)-2-phenylaziridine
102535-89-7

(N-methanesulfonyl)-2-phenylaziridine

Conditions
ConditionsYield
With copper acetylacetonate In acetonitrile Ambient temperature;A n/a
B 7%
tetrachloromethane
56-23-5

tetrachloromethane

N,N-bis-methanesulfonyl-alanine

N,N-bis-methanesulfonyl-alanine

methanesulfonamide
3144-09-0

methanesulfonamide

N,N-bis-methanesulfonyl-glycine
859980-70-4

N,N-bis-methanesulfonyl-glycine

1-methyl-4-nitrosobenzene
623-11-0

1-methyl-4-nitrosobenzene

A

glycolic Acid
79-14-1

glycolic Acid

B

methanesulfonamide
3144-09-0

methanesulfonamide

C

2-(methylsulfonylamino)acetic acid
35688-18-7

2-(methylsulfonylamino)acetic acid

N-(trimethylsilyl)methanesulfonamide
999-96-2

N-(trimethylsilyl)methanesulfonamide

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With water
dimethylsulfone
67-71-0

dimethylsulfone

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
Yield given. Multistep reaction;
ethyl methyl sulfone
594-43-4

ethyl methyl sulfone

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

Ethanesulfonamide
1520-70-3

Ethanesulfonamide

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
C9H9ClF2N2O3S2
78488-82-1

C9H9ClF2N2O3S2

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With acidic media Product distribution; heating;
C9H9Cl2FN2O3S2
78488-80-9

C9H9Cl2FN2O3S2

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With acidic media Product distribution; heating;
Trimesylhydroxylamine
75142-05-1

Trimesylhydroxylamine

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

dimesylamine
5347-82-0

dimesylamine

C

methanesulfonic acid sodium salt
2386-57-4

methanesulfonic acid sodium salt

D

N-methylsulfamic acid monosodium salt
41921-91-9

N-methylsulfamic acid monosodium salt

Conditions
ConditionsYield
With sodium hydroxide In water Mechanism; Product distribution; Heating; hydrolysis with basic, neutral and acidic aqu. solutions (other products);A 6 % Spectr.
B 20 % Spectr.
C 70 % Spectr.
D 4 % Spectr.
N-chlorosulphonyl-methanesulphonamide

N-chlorosulphonyl-methanesulphonamide

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With water In methanol Mechanism;
methanesulfonyl bromide
41138-92-5

methanesulfonyl bromide

methanesulfonamide
3144-09-0

methanesulfonamide

Conditions
ConditionsYield
With ammonia; triethylamine In acetonitrile at 0 - 20℃; Yield given;
methanesulfonyl isocyanate
3611-92-5

methanesulfonyl isocyanate

ethanol
64-17-5

ethanol

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

carbon dioxide
124-38-9

carbon dioxide

methanesulfonyl isocyanate
3611-92-5

methanesulfonyl isocyanate

water
7732-18-5

water

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

carbon dioxide
124-38-9

carbon dioxide

methanesulfonyl isocyanate
3611-92-5

methanesulfonyl isocyanate

A

methanesulfonamide
3144-09-0

methanesulfonamide

B

carbon dioxide
124-38-9

carbon dioxide

Conditions
ConditionsYield
With water
methanesulfonamide
3144-09-0

methanesulfonamide

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl (methylsulfonyl)carbamate
147751-16-4

tert-butyl (methylsulfonyl)carbamate

Conditions
ConditionsYield
With trimethylamine In dichloromethane at 0 - 20℃; for 16h;100%
With triethylamine; dmap In dichloromethane for 2h; Ambient temperature;88%
With triethylamine; dmap In dichloromethane at 25℃; for 2h;83%
methanesulfonamide
3144-09-0

methanesulfonamide

2-nitro-2-nitrosopropane
5275-46-7

2-nitro-2-nitrosopropane

C4H9N3O5S

C4H9N3O5S

Conditions
ConditionsYield
With phenformin In dichloromethane at 20℃;100%
methanesulfonamide
3144-09-0

methanesulfonamide

2,2-dimethyl-5-nitro-5-nitroso-1,3-dioxane
139308-14-8

2,2-dimethyl-5-nitro-5-nitroso-1,3-dioxane

C7H13N3O7S

C7H13N3O7S

Conditions
ConditionsYield
With phenformin In dichloromethane at 20℃;100%
methanesulfonamide
3144-09-0

methanesulfonamide

trifluoronitrosomethane
334-99-6

trifluoronitrosomethane

trifluoromethylazosulfonylmethane

trifluoromethylazosulfonylmethane

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 12h;100%
methanesulfonamide
3144-09-0

methanesulfonamide

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N-[1-Dimethylamino-meth-(E)-ylidene]-methanesulfonamide
78523-02-1

N-[1-Dimethylamino-meth-(E)-ylidene]-methanesulfonamide

Conditions
ConditionsYield
In dichloromethane for 0.5h; Heating;100%
methanesulfonamide
3144-09-0

methanesulfonamide

para-bromotoluene
106-38-7

para-bromotoluene

N-(4-methylphenyl)methanesulfonamide
4284-47-3

N-(4-methylphenyl)methanesulfonamide

Conditions
ConditionsYield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In tert-Amyl alcohol at 80℃; Kinetics; Inert atmosphere;100%
With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; tert-butyl XPhos In 2-methyltetrahydrofuran at 80℃; for 6h; Inert atmosphere;93%
With potassium phosphate; copper(l) iodide; dimethylaminoacetic acid In N,N-dimethyl-formamide for 48h; Heating;89%
C38H44FNO6

C38H44FNO6

methanesulfonamide
3144-09-0

methanesulfonamide

C39H47FN2O7S

C39H47FN2O7S

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃;100%
methanesulfonamide
3144-09-0

methanesulfonamide

1-(3-Iodophenyl)-2-methoxy-6-(3-methoxyphenyl)naphthalene
1064681-32-8

1-(3-Iodophenyl)-2-methoxy-6-(3-methoxyphenyl)naphthalene

molybdenum hexacarbonyl
13939-06-5, 199620-15-0

molybdenum hexacarbonyl

3-(2-Methoxy-6-(3-methoxyphenyl)naphthalene-1-yl)-N-(methylsulfonyl)-benzamide
1064681-28-2

3-(2-Methoxy-6-(3-methoxyphenyl)naphthalene-1-yl)-N-(methylsulfonyl)-benzamide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium diacetate In 1,4-dioxane at 110℃; for 0.25h; microwave irradiation;100%
methanesulfonamide
3144-09-0

methanesulfonamide

4-Methylphenyl 5-chloro-4-(3,4-dichlorophenoxy)-2-fluorobenzoate
1354960-59-0

4-Methylphenyl 5-chloro-4-(3,4-dichlorophenoxy)-2-fluorobenzoate

5-Chloro-4-(3,4-dichlorophenoxy)-2-fluoro-N-(methylsulfonyl)benzamide
1354955-37-5

5-Chloro-4-(3,4-dichlorophenoxy)-2-fluoro-N-(methylsulfonyl)benzamide

Conditions
ConditionsYield
Stage #1: methanesulfonamide With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.516667h;
Stage #2: 4-Methylphenyl 5-chloro-4-(3,4-dichlorophenoxy)-2-fluorobenzoate In tetrahydrofuran; mineral oil at 70℃;
100%
2-n-butyl-5-bromo-benzofuran
497225-66-8

2-n-butyl-5-bromo-benzofuran

methanesulfonamide
3144-09-0

methanesulfonamide

N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide
437652-07-8

N-(2-butyl-2,3-dihydro-5-benzofuranyl)methanesulfonamide

Conditions
ConditionsYield
With bis(dibenzylideneacetone)-palladium(0); tert-butyl XPhos In 1,4-dioxane at 100℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere;100%
methanesulfonamide
3144-09-0

methanesulfonamide

4-(4-chlorophenoxy)-2-fluoro-5-iodobenzoic acid
1445862-88-3

4-(4-chlorophenoxy)-2-fluoro-5-iodobenzoic acid

4-(4-chlorophenoxy)-2-fluoro-5-iodo-N-(methylsulfonyl)benzamide
1445862-89-4

4-(4-chlorophenoxy)-2-fluoro-5-iodo-N-(methylsulfonyl)benzamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
methanesulfonamide
3144-09-0

methanesulfonamide

4-bromo-3-(difluoromethoxy)benzoic acid

4-bromo-3-(difluoromethoxy)benzoic acid

4-bromo-3-(difluoromethoxy)-N-(methylsulfonyl)benzamide

4-bromo-3-(difluoromethoxy)-N-(methylsulfonyl)benzamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;100%
methanesulfonamide
3144-09-0

methanesulfonamide

6-bromo-3-(chloromethyl)benzofuran

6-bromo-3-(chloromethyl)benzofuran

N-((6-bromobenzofuran-3-yl)methyl)methanesulfonamide

N-((6-bromobenzofuran-3-yl)methyl)methanesulfonamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 80℃; for 11h;100%
methanesulfonamide
3144-09-0

methanesulfonamide

(S)-3-(((benzyloxy)carbonyl)amino)-4-((tert-butyldiphenylsilyl)oxy)butanoic acid
461009-54-1

(S)-3-(((benzyloxy)carbonyl)amino)-4-((tert-butyldiphenylsilyl)oxy)butanoic acid

benzyl (S)-(1-((tert-butyldiphenylsilyl)oxy)-4-(methylsulfonamido)-4-oxobutan-2-yl)carbamate

benzyl (S)-(1-((tert-butyldiphenylsilyl)oxy)-4-(methylsulfonamido)-4-oxobutan-2-yl)carbamate

Conditions
ConditionsYield
Stage #1: (S)-3-(((benzyloxy)carbonyl)amino)-4-((tert-butyldiphenylsilyl)oxy)butanoic acid With 1,1'-carbonyldiimidazole at 20℃; for 3h; Inert atmosphere;
Stage #2: methanesulfonamide With 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; Inert atmosphere;
100%
bromobenzene
108-86-1

bromobenzene

methanesulfonamide
3144-09-0

methanesulfonamide

N-phenylmethanesulfonamide
1197-22-4

N-phenylmethanesulfonamide

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; dimethylaminoacetic acid In N,N-dimethyl-formamide for 48h; Heating;99%
With potassium phosphate; copper(l) iodide In N,N-dimethyl-formamide at 130℃; for 18h; Sealed tube;75%
With copper(l) iodide; potassium carbonate In various solvent(s) at 195℃; for 2h; microwave irradiation;67%
With copper(I) oxide; caesium carbonate In water at 130℃; for 24h; Sealed tube;36%
iodobenzene
591-50-4

iodobenzene

methanesulfonamide
3144-09-0

methanesulfonamide

N-phenylmethanesulfonamide
1197-22-4

N-phenylmethanesulfonamide

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; sarcosine In N,N-dimethyl-formamide at 100℃; for 24h;99%
With copper(I) oxide; caesium carbonate In water at 130℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;90%
With copper(I) oxide; caesium carbonate In water at 130℃; for 24h; Sealed tube;90%
methanesulfonamide
3144-09-0

methanesulfonamide

methyl 3-iodo-benzoate
618-91-7

methyl 3-iodo-benzoate

3-methanesulfonylaminobenzoic acid methyl ester
32087-05-1

3-methanesulfonylaminobenzoic acid methyl ester

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; sarcosine In N,N-dimethyl-formamide at 100℃; for 24h;99%
methanesulfonamide
3144-09-0

methanesulfonamide

tert-butyl benzylidenecarbamate
177896-09-2

tert-butyl benzylidenecarbamate

tert-butyl N-[(4-methylsulfonamido)(phenyl)methyl]carbamate

tert-butyl N-[(4-methylsulfonamido)(phenyl)methyl]carbamate

Conditions
ConditionsYield
With bis(trifluoromethanesulfonyl)amide In diethyl ether at 20℃; for 0.333333h;99%
methanesulfonamide
3144-09-0

methanesulfonamide

10-bromodecanoic acid methyl ester
26825-94-5

10-bromodecanoic acid methyl ester

methyl 10-(methylsulfonamido)decanoate
1161364-44-8

methyl 10-(methylsulfonamido)decanoate

Conditions
ConditionsYield
Stage #1: methanesulfonamide With sodium hydride In N,N-dimethyl-formamide at 100℃; for 2h;
Stage #2: 10-bromodecanoic acid methyl ester In N,N-dimethyl-formamide at 100℃;
99%
methanesulfonamide
3144-09-0

methanesulfonamide

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

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

N-[(2E)-1,3-diphenyl-2-propen-1-yl]methanesulfonamide
1262765-49-0

N-[(2E)-1,3-diphenyl-2-propen-1-yl]methanesulfonamide

Conditions
ConditionsYield
With 3-tetradecyl-1-(4-sulfobutyl)imidazolium trifluoromethanesulfonate In 1,4-dioxane at 80℃; for 2h;99%
With [BsTdmim]OTf In 1,4-dioxane at 80℃; for 2h;99%
With iron(III) chloride hexahydrate In 1,4-dioxane at 25℃; for 24h;89%
(1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II)

(1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II)

methanesulfonamide
3144-09-0

methanesulfonamide

(η6-cymene)Ru(TsN(CHPh)2NH2)(NHSO2Me)

(η6-cymene)Ru(TsN(CHPh)2NH2)(NHSO2Me)

Conditions
ConditionsYield
In dichloromethane 23°C, 0.5-1 min;99%
methanesulfonamide
3144-09-0

methanesulfonamide

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

N,N-bis(4-methoxybenzyl)methanesulfonamide

N,N-bis(4-methoxybenzyl)methanesulfonamide

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In butanone at 75℃;99%
With potassium carbonate; potassium iodide In butanone at 81℃; for 18h; Concentration; Temperature;81%
Stage #1: methanesulfonamide With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h;
Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 20℃; for 19h;
17.1 g
With potassium carbonate; potassium iodide In butanone at 75℃;
3-bromo-5-fluorobenzaldehyde
188813-02-7

3-bromo-5-fluorobenzaldehyde

methanesulfonamide
3144-09-0

methanesulfonamide

N-(3-bromo-5-fluorobenzyl) methanesulfonamide
1467083-70-0

N-(3-bromo-5-fluorobenzyl) methanesulfonamide

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; triethylamine In 1,2-dichloro-ethane at 20℃;99%
With sodium tris(acetoxy)borohydride; triethylamine In 1,2-dichloro-ethane at 20℃;93.9%
methanesulfonamide
3144-09-0

methanesulfonamide

tert-butyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylate
207743-78-0

tert-butyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylate

tert-butyl 2-(3-(methylsulfonyl)thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
1452776-84-9

tert-butyl 2-(3-(methylsulfonyl)thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Conditions
ConditionsYield
Stage #1: methanesulfonamide With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.25h;
Stage #2: tert-butyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylate In N,N-dimethyl-formamide; mineral oil at 60℃; for 1h;
99%
methanesulfonamide
3144-09-0

methanesulfonamide

AZD 6482
1173900-33-8

AZD 6482

C23H27N5O5S
1622905-82-1

C23H27N5O5S

Conditions
ConditionsYield
With dmap for 72h;99%
methanesulfonamide
3144-09-0

methanesulfonamide

4-bromo-2-fluoro-5-methylbenzoic acid
415965-24-1

4-bromo-2-fluoro-5-methylbenzoic acid

4-bromo-2-fluoro-5-methyl-N-(methylsulfonyl)benzamide

4-bromo-2-fluoro-5-methyl-N-(methylsulfonyl)benzamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;99%
methanesulfonamide
3144-09-0

methanesulfonamide

2-(5-((S)-1-((tert-butoxycarbonyl)amino)ethyl)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)oxazole-4-carboxamido)-2-(2,4-difluorophenyl)acetic acid

2-(5-((S)-1-((tert-butoxycarbonyl)amino)ethyl)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)oxazole-4-carboxamido)-2-(2,4-difluorophenyl)acetic acid

tert-butyl ((1S)-1-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-4-((1-(2,4-difluorophenyl)-2-(methylsulfonamido)-2-oxoethyl)carbamoyl)oxazol-5-yl)ethyl)carbamate

tert-butyl ((1S)-1-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-4-((1-(2,4-difluorophenyl)-2-(methylsulfonamido)-2-oxoethyl)carbamoyl)oxazol-5-yl)ethyl)carbamate

Conditions
ConditionsYield
Stage #1: 2-(5-((S)-1-((tert-butoxycarbonyl)amino)ethyl)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)oxazole-4-carboxamido)-2-(2,4-difluorophenyl)acetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 60℃; for 0.5h;
Stage #2: methanesulfonamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60℃; for 10h;
99%

3144-09-0Relevant articles and documents

-

Boyer,Ellzey

, p. 127 (1958)

-

Development of succinimide-based inhibitors for the mitochondrial rhomboid protease PARL

Andrews, Charlotte L.,Cardozo, Joaquin M.,Chow, Alyssa S.,Crainic, Jennifer A.,Parsons, William H.,Rutland, Nicholas T.,Sheehan, Brendan K.

supporting information, (2021/08/04)

While the biochemistry of rhomboid proteases has been extensively studied since their discovery two decades ago, efforts to define the physiological roles of these enzymes are ongoing and would benefit from chemical probes that can be used to manipulate the functions of these proteins in their native settings. Here, we describe the use of activity-based protein profiling (ABPP) technology to conduct a targeted screen for small-molecule inhibitors of the mitochondrial rhomboid protease PARL, which plays a critical role in regulating mitophagy and cell death. We synthesized a series of succinimide-containing sulfonyl esters and sulfonamides and discovered that these compounds serve as inhibitors of PARL with the most potent sulfonamides having submicromolar affinity for the enzyme. A counterscreen against the bacterial rhomboid protease GlpG demonstrates that several of these compounds display selectivity for PARL over GlpG by as much as two orders of magnitude. Both the sulfonyl ester and sulfonamide scaffolds exhibit reversible binding and are able to engage PARL in mammalian cells. Collectively, our findings provide encouraging precedent for the development of PARL-selective inhibitors and establish N-[(arylsulfonyl)oxy]succinimides and N-arylsulfonylsuccinimides as new molecular scaffolds for inhibiting members of the rhomboid protease family.

An optimised series of substituted N-phenylpyrrolamides as DNA gyrase B inhibitors

Tiz, Davide Benedetto,Skok, ?iga,Durcik, Martina,Toma?i?, Tihomir,Ma?i?, Lucija Peterlin,Ila?, Janez,Zega, Anamarija,Draskovits, Gábor,Révész, Tamás,Nyerges, ákos,Pál, Csaba,Cruz, Cristina D.,Tammela, P?ivi,?igon, Du?an,Kikelj, Danijel,Zidar, Nace

, p. 269 - 290 (2019/02/20)

ATP competitive inhibitors of DNA gyrase and topoisomerase IV have great therapeutic potential, but none of the described synthetic compounds has so far reached the market. To optimise the activities and physicochemical properties of our previously reported N-phenylpyrrolamide inhibitors, we have synthesized an improved, chemically variegated selection of compounds and evaluated them against DNA gyrase and topoisomerase IV enzymes, and against selected Gram-positive and Gram-negative bacteria. The most potent compound displayed IC50 values of 6.9 nM against Escherichia coli DNA gyrase and 960 nM against Staphylococcus aureus topoisomerase IV. Several compounds displayed minimum inhibitory concentrations (MICs) against Gram-positive strains in the 1–50 μM range, one of which inhibited the growth of Enterococcus faecalis, Enterococcus faecium, S. aureus and Streptococcus pyogenes with MIC values of 1.56 μM, 1.56 μM, 0.78 μM and 0.72 μM, respectively. This compound has been investigated further on methicillin-resistant S. aureus (MRSA) and on ciprofloxacin non-susceptible and extremely drug resistant strain of S. aureus (MRSA VISA). It exhibited the MIC value of 2.5 μM on both strains, and MIC value of 32 μM against MRSA in the presence of inactivated human blood serum. Further studies are needed to confirm its mode of action.

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