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14752-66-0 Usage

Chemical Properties

white crystalline powder

Check Digit Verification of cas no

The CAS Registry Mumber 14752-66-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,7,5 and 2 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 14752-66:
(7*1)+(6*4)+(5*7)+(4*5)+(3*2)+(2*6)+(1*6)=110
110 % 10 = 0
So 14752-66-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H5ClO2S.Na/c7-5-1-3-6(4-2-5)10(8)9;/h1-4H,(H,8,9);/q;+1/p-1

14752-66-0 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (A12583)  4-Chlorobenzenesulfinic acid sodium salt hydrate, 97%   

  • 14752-66-0

  • 5g

  • 632.0CNY

  • Detail
  • Alfa Aesar

  • (A12583)  4-Chlorobenzenesulfinic acid sodium salt hydrate, 97%   

  • 14752-66-0

  • 25g

  • 1635.0CNY

  • Detail
  • Alfa Aesar

  • (A12583)  4-Chlorobenzenesulfinic acid sodium salt hydrate, 97%   

  • 14752-66-0

  • 100g

  • 5482.0CNY

  • Detail

14752-66-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Sodium 4-chlorobenzene sulfinate

1.2 Other means of identification

Product number -
Other names 4-ChloroBenzene sulfinic acid sodium

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:14752-66-0 SDS

14752-66-0Synthetic route

chlorobenzene
108-90-7

chlorobenzene

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
Stage #1: chlorobenzene With aluminum (III) chloride; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate In 1,2-dichloro-ethane at 25℃; for 2h;
Stage #2: With sodium hydrogencarbonate In water; 1,2-dichloro-ethane at 25℃;
98%
With 1,4-diaza-bicyclo[2.2.2]octane; aluminum (III) chloride; sodium hydrogencarbonate In dichloromethane; water at 25 - 35℃;88%
Multi-step reaction with 2 steps
1: chlorosulfonic acid / 1 h / 20 °C
2: sodium sulfite / water / 1 h / 80 - 90 °C
View Scheme
4-chlorobenzenesulfonyl chloride
98-60-2

4-chlorobenzenesulfonyl chloride

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium sulfite In water at 80℃; for 4h;96%
With sodium carbonate; sodium sulfite In water at 50℃; for 2h;94%
With sodium hydrogencarbonate; sodium sulfite In water for 3h; Reflux;75%
p-Chlorothiophenol
106-54-7

p-Chlorothiophenol

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
Stage #1: p-Chlorothiophenol With sodium acetate; acrylic acid methyl ester In tetrahydrofuran; water at 20℃;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;
Stage #3: With sodium hydroxide In tetrahydrofuran; methanol at 0℃; Inert atmosphere;
91%
phenyl 4-chlorobenzenethiosulfonate
1142-97-8

phenyl 4-chlorobenzenethiosulfonate

acetylacetone
123-54-6

acetylacetone

A

3-(phenylthio)pentane-2,4-dione
22805-23-8

3-(phenylthio)pentane-2,4-dione

B

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 50℃; for 2h;A 61.7%
B 67.9%
phenyl 4-chlorobenzenethiosulfonate
1142-97-8

phenyl 4-chlorobenzenethiosulfonate

A

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

B

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
With sodium ethanolate In ethanol at 20℃; for 1h;A 67.6%
B 65.5%
C43H49ClNO14S(1-)*Na(1+)

C43H49ClNO14S(1-)*Na(1+)

A

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

B

sodium 4-chlorobenzenesulfonate
5138-90-9

sodium 4-chlorobenzenesulfonate

C

rifamycin S
13553-79-2

rifamycin S

Conditions
ConditionsYield
In ethyl acetate at 70℃; for 4h; Product distribution;A n/a
B n/a
C 49%
sodium p-chlorothiophenolate
18803-44-6

sodium p-chlorothiophenolate

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
With oxygen
Toluene-4-sulfonic acid 4-chloro-benzenesulfonylmethyl ester
91817-01-5

Toluene-4-sulfonic acid 4-chloro-benzenesulfonylmethyl ester

A

formaldehyd
50-00-0

formaldehyd

B

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

C

sodium tosylate
657-84-1

sodium tosylate

Conditions
ConditionsYield
With sodium hydroxide; cetyltrimethylammonim bromide In water at 32.1℃; Rate constant; Mechanism; solvolysis in H2O-dioxane;
4-chlorobenzenesulfonyl chloride
98-60-2

4-chlorobenzenesulfonyl chloride

sodium sulfite
7757-83-7

sodium sulfite

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
In not given in alkaline media;
In not given in alkaline media;
4-Chlorophenylboronic acid
1679-18-1

4-Chlorophenylboronic acid

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C
1.2: 20 °C
2.1: iron(III) chloride; sodium hydroxymethanesulfinate dihydrate / N,N-dimethyl-formamide; acetonitrile / 0.33 h / 20 °C
View Scheme
bis(4-chlorophenyl)iodonium tetrafluoroborate

bis(4-chlorophenyl)iodonium tetrafluoroborate

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
With iron(III) chloride; sodium hydroxymethanesulfinate dihydrate In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.333333h;
p-chlorophenylsulfinyl chloride
2901-92-0

p-chlorophenylsulfinyl chloride

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Conditions
ConditionsYield
With sodium hydrogencarbonate; sodium sulfite In N,N-dimethyl-formamide at 80℃; for 4h;
(2-Bromomethylbenzyloxy)-t-butyldiphenylsilane
558466-20-9

(2-Bromomethylbenzyloxy)-t-butyldiphenylsilane

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

t-butyl [[2-[[(4-chlorophenyl)sulfonyl]methyl]benzyl]oxy]diphenylsilane
558464-21-4

t-butyl [[2-[[(4-chlorophenyl)sulfonyl]methyl]benzyl]oxy]diphenylsilane

Conditions
ConditionsYield
In propan-1-ol at 90℃; for 14h;100%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

sodium 4-chlorobenzenesulfonothioate
76219-32-4

sodium 4-chlorobenzenesulfonothioate

Conditions
ConditionsYield
With sulfur; N-butylamine at 20℃; for 1h; Other amines;99%
With 5,6,7,8,9-pentathiabenzocycloheptene In methanol; benzene for 10h; Ambient temperature;82%
bis(2,2,2-trichloroethyl)azodicarboxylate
38857-88-4

bis(2,2,2-trichloroethyl)azodicarboxylate

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

bis(2,2,2-trichloroethyl) 1-[(4-chlorophenyl)sulfonyl]hydrazine-1,2-dicarboxylate

bis(2,2,2-trichloroethyl) 1-[(4-chlorophenyl)sulfonyl]hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With trifluoroacetic acid In tetrahydrofuran at 0℃; for 0.5h;99%
4-(benzoyloxy)morpholine
5765-65-1

4-(benzoyloxy)morpholine

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

4-((4-chlorophenyl)sulfonyl)morpholine
22771-99-9

4-((4-chlorophenyl)sulfonyl)morpholine

Conditions
ConditionsYield
Stage #1: 4-(benzoyloxy)morpholine; sodium p-chlorobenzenesulphinate In 1,2-dichloro-ethane at 30℃; for 12h; Schlenk technique; Inert atmosphere;
Stage #2: With copper(ll) bromide In 1,2-dichloro-ethane for 12h; Schlenk technique; Inert atmosphere;
99%
1-dodecene
112-41-4

1-dodecene

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

1-chloro-4-(dodecylsulfonyl)benzene
105891-06-3

1-chloro-4-(dodecylsulfonyl)benzene

Conditions
ConditionsYield
With [Ir(dF(CF3)ppy)2(dtbbpy)]PF6; water; acetic acid In dichloromethane at 20℃; for 12h; Inert atmosphere; Irradiation; regioselective reaction;99%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

methyl chloroacetate
96-34-4

methyl chloroacetate

methyl 4-chlorophenylsulphinylacetate
15446-25-0

methyl 4-chlorophenylsulphinylacetate

Conditions
ConditionsYield
98%
In N,N-dimethyl-formamide at 120℃; for 3h;98%
In N,N-dimethyl-formamide at 45 - 115℃; for 3h;98%
indole
120-72-9

indole

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

2-((4-chlorophenyl)sulfonyl)-1H-indole
1505521-32-3

2-((4-chlorophenyl)sulfonyl)-1H-indole

Conditions
ConditionsYield
With tert.-butylhydroperoxide; ammonium iodide; acetic acid at 60℃; for 2h; regioselective reaction;98%
With iodine In methanol at 20℃; for 2h; regioselective reaction;88%
With tert.-butylhydroperoxide; iodine In acetic acid at 20 - 35℃; for 4h; regioselective reaction;82%
With Oxone; potassium iodide In water at 20℃; for 1h; Green chemistry; regioselective reaction;66%
4-vinylbenzyl chloride
1073-67-2

4-vinylbenzyl chloride

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

(E)-4-chlorostyryl 4-chlorophenyl sulfone
6178-26-3

(E)-4-chlorostyryl 4-chlorophenyl sulfone

Conditions
ConditionsYield
With iodine In water at 20℃; for 2h; Schlenk technique; Green chemistry;98%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

phenol
108-95-2

phenol

4-chlorobenzolsulfonsaeure-phenylester
2437-33-4

4-chlorobenzolsulfonsaeure-phenylester

Conditions
ConditionsYield
In water; acetonitrile at 20℃; for 2h; Electrochemical reaction;98%
indole
120-72-9

indole

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

3-((4-chlorophenyl)thio)-1H-indole
32884-73-4

3-((4-chlorophenyl)thio)-1H-indole

Conditions
ConditionsYield
With iodine; triphenylphosphine In ethanol at 80℃; for 2h; Green chemistry;97%
With iodine; triphenylphosphine In water Reflux; Inert atmosphere; Schlenk technique; Green chemistry;94%
With Diethyl phosphonate; iodine; dimethyl sulfoxide at 100℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;93%
2-methyl-1H-indole
95-20-5

2-methyl-1H-indole

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

3-((4-chlorophenyl)thio)-2-methyl-1H-indole

3-((4-chlorophenyl)thio)-2-methyl-1H-indole

Conditions
ConditionsYield
With iodine; triphenylphosphine In water Reflux; Inert atmosphere; Schlenk technique; Green chemistry;97%
With dipotassium peroxodisulfate In water; acetonitrile at 100℃; for 24h; Inert atmosphere; Green chemistry;88%
3-cyclopropylidene-1,2-diphenyl-3-prop-2-en-1-one
1376626-55-9

3-cyclopropylidene-1,2-diphenyl-3-prop-2-en-1-one

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

3-(4-chlorophenylsulfonyl)-3-cyclopropylidene-1,2-diphenylpropan-1-one

3-(4-chlorophenylsulfonyl)-3-cyclopropylidene-1,2-diphenylpropan-1-one

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 0.166667h;97%
C22H22O3

C22H22O3

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

1-[{(4-chlorophenyl)sulfonyl}(phenyl)methyl]-2-((S)-2-methoxy-1-phenylethoxy)benzene

1-[{(4-chlorophenyl)sulfonyl}(phenyl)methyl]-2-((S)-2-methoxy-1-phenylethoxy)benzene

Conditions
ConditionsYield
With chloro-trimethyl-silane; tin(II) bromide In nitromethane at -15℃; for 3h; Inert atmosphere; diastereoselective reaction;97%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

3-(bromomethyl)benzonitrile
28188-41-2

3-(bromomethyl)benzonitrile

3-(4-Chlorophenylsulfonylmethyl)benzonitrile

3-(4-Chlorophenylsulfonylmethyl)benzonitrile

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 70℃; for 72h;96%
1,4-epoxy-1,4-dihydronaphthalene
573-57-9

1,4-epoxy-1,4-dihydronaphthalene

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

(1S*2R*)-2-(4-chlorophenyl)-1,2-dihydronaphthalen-1-ol

(1S*2R*)-2-(4-chlorophenyl)-1,2-dihydronaphthalen-1-ol

Conditions
ConditionsYield
With palladium diacetate; tricyclohexylphosphine In water; 1,2-dichloro-ethane at 65℃; for 2h;96%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

4-methoxy-N-(8-quinolinyl)benzamide
33757-50-5

4-methoxy-N-(8-quinolinyl)benzamide

N-(5-((4-chlorophenyl)sulfonyl)quinolin-8-yl)-4-methoxybenzamide

N-(5-((4-chlorophenyl)sulfonyl)quinolin-8-yl)-4-methoxybenzamide

Conditions
ConditionsYield
With manganese(III) triacetate dihydrate; copper dichloride at 25℃; for 1.5h; regioselective reaction;96%
2-methoxy-4-benzoylamino-5-methyl-aniline
99-21-8

2-methoxy-4-benzoylamino-5-methyl-aniline

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

N-(4-amino-3-((4-chlorophenyl)sulfonyl)-5-methoxy-2-methylphenyl)benzamide

N-(4-amino-3-((4-chlorophenyl)sulfonyl)-5-methoxy-2-methylphenyl)benzamide

Conditions
ConditionsYield
With perchloric acid In ethanol; water Electrolysis;96%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

Desyl chloride
447-31-4

Desyl chloride

1,2-diphenyl-1-(p-chlorophenylsulfonyl)-2-ethanone
125039-59-0

1,2-diphenyl-1-(p-chlorophenylsulfonyl)-2-ethanone

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 0.5h; Heating;95%
bis(4-fluorophenyl)disulfide
405-31-2

bis(4-fluorophenyl)disulfide

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

(S)-p-Fluorophenyl p-chlorobenzenethiosulfonate
361477-25-0

(S)-p-Fluorophenyl p-chlorobenzenethiosulfonate

Conditions
ConditionsYield
With iodine at 40℃; for 5h;95%
With N-Bromosuccinimide In acetonitrile at 25℃; for 15h;84%
3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione
58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

8-(4-chlorophenyl)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione
1136519-32-8

8-(4-chlorophenyl)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; copper diacetate In 1,4-dioxane; dimethyl sulfoxide at 20 - 110℃; for 24.08h; Inert atmosphere;95%
dibenzyl disulphide
150-60-7

dibenzyl disulphide

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

S-benzyl 4-chlorobenzenesulfonothioate

S-benzyl 4-chlorobenzenesulfonothioate

Conditions
ConditionsYield
With N-Bromosuccinimide In acetonitrile at 25℃; for 15h;95%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

2-phenylimidazo[1,2-a]pyridine
4105-21-9

2-phenylimidazo[1,2-a]pyridine

3-((4-chlorophenyl)thio)-2-phenylimidazo[1,2-α]pyridine
306278-24-0

3-((4-chlorophenyl)thio)-2-phenylimidazo[1,2-α]pyridine

Conditions
ConditionsYield
With iodine; triphenylphosphine In dichloromethane at 100℃; for 12h; Sealed tube;95%
With iodine; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 12h;93%
With ammonium iodide In N,N-dimethyl-formamide at 135℃; for 20h; Sealed tube; regioselective reaction;65%
2-phenylimidazo[2,1-b]benzothiazole
17833-07-7

2-phenylimidazo[2,1-b]benzothiazole

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

3-((4-chlorophenyl)thio)-2-phenylbenzo[d]imidazo[2,1-b]thiazole

3-((4-chlorophenyl)thio)-2-phenylbenzo[d]imidazo[2,1-b]thiazole

Conditions
ConditionsYield
With iodine; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 12h;95%
styrene
292638-84-7

styrene

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

(E)-1-chloro-4-(styrylsulfonyl)benzene
16215-12-6

(E)-1-chloro-4-(styrylsulfonyl)benzene

Conditions
ConditionsYield
With iodine In water at 20℃; for 2h; Schlenk technique; Green chemistry;95%
With tetrabutylammonium tetrafluoroborate; acetic acid; potassium iodide In dimethyl sulfoxide at 50℃; for 10h; Inert atmosphere; Electrochemical reaction;73%
With dipotassium peroxodisulfate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; silver nitrate In toluene at 100℃; for 10h; Schlenk technique; stereoselective reaction;71%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

4-chloro-N-(quinolin-8-yl)benzamide
33757-54-9

4-chloro-N-(quinolin-8-yl)benzamide

4-chloro-N-(5-((4-chlorophenyl)sulfonyl)quinolin-8-yl)benzamide

4-chloro-N-(5-((4-chlorophenyl)sulfonyl)quinolin-8-yl)benzamide

Conditions
ConditionsYield
With manganese(III) triacetate dihydrate; copper dichloride at 25℃; for 1.5h; regioselective reaction;95%
N-quinolin-8-yl-benzamide
33757-48-1

N-quinolin-8-yl-benzamide

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

N-(5-((4-chlorophenyl)sulfonyl)quinolin-8-yl)benzamide

N-(5-((4-chlorophenyl)sulfonyl)quinolin-8-yl)benzamide

Conditions
ConditionsYield
With manganese(III) triacetate dihydrate; copper dichloride at 25℃; for 1.5h; regioselective reaction;95%
N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

acetophenone
98-86-2

acetophenone

2-(((4-chlorophenyl)sulfonyl)methyl)-1-phenylprop-2-en-1-one

2-(((4-chlorophenyl)sulfonyl)methyl)-1-phenylprop-2-en-1-one

Conditions
ConditionsYield
With iron(III) chloride; dipotassium peroxodisulfate; sodium dodecyl-sulfate at 110℃; for 14h;95%
With iron(III) chloride; dipotassium peroxodisulfate; sodium dodecyl-sulfate at 110℃; for 14h; Green chemistry;95%
sodium p-chlorobenzenesulphinate
14752-66-0

sodium p-chlorobenzenesulphinate

2-bromoindanone
1775-27-5

2-bromoindanone

(1R,2S)-2-((4-chlorophenyl)sulfonyl)-2,3-dihydro-1H-inden-1-ol

(1R,2S)-2-((4-chlorophenyl)sulfonyl)-2,3-dihydro-1H-inden-1-ol

Conditions
ConditionsYield
With chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); sodium formate In water; isopropyl alcohol at 60℃; for 5h; stereoselective reaction;95%

14752-66-0Relevant articles and documents

Convenient method for preparation of aryl sulfinates from arenes and DABSO as the SO2 surrogates

Wang, Tianlei,Wang, Fumin,Shen, Jinghua,Pang, Tianting,Ren, Yanfei,Wu, Botao,Zhang, Xubin

, p. 1183 - 1187 (2018)

A safe and efficient protocol for the synthesis of aryl sulfinates from arenes and 1,4-diazabicyclo[2,2,2]octane bis(sulfur dioxide) (DABSO) under mild conditions is described. Through in situ infrared spectroscopic studies, a plausible mechanism for the sulfination reaction is proposed as well.

Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates

Xiong, Yan-Shi,Zhang, Bin,Yu, Yang,Weng, Jiang,Lu, Gui

, p. 13465 - 13472 (2019)

Copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates to construct substituted lactones has been realized. This protocol employs inexpensive CuCl2 as the catalyst, di-tert-butyl peroxide or O2 as the terminal oxidant, and readily available sodium sulfinates as sulfonylation reagents. High functional group tolerance and excellent yields were demonstrated by the efficient preparation of a wide range of γ-sulfonylated phthalides.

Copper-mediated ortho C-H sulfonylation of benzoic acid derivatives with sodium sulfinates

Liu, Jidan,Yu, Lin,Zhuang, Shaobo,Gui, Qingwen,Chen, Xiang,Wang, Wenduo,Tan, Ze

, p. 6418 - 6421 (2015)

Copper-mediated direct ortho C-H bond sulfonylation of benzoic acid derivatives with sodium sulfinates was achieved by employing an 8-aminoquinoline moiety as the bidentate directing group. Various aryl sulfones were synthesized in good yields with excellent regioselectivity. This journal is

Electrosynthesis of N-unsubstituted enaminosulfones from vinyl azides and sodium sulfinates mediated by NH4I

Mulina, Olga M.,Doronin, Mikhail M.,Terent'ev, Alexander O.

supporting information, (2021/10/16)

A wide range of N-unsubstituted enaminosulfones were obtained via electrochemical sulfonylation of vinyl azides with sulfonyl radicals generated from sodium sulfinates. The discovery of N-unsubstituted enaminosulfones synthesis is based on a unique ability of the azido group to eliminate the N2 molecule. The process is performed under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode applying NH4I both as the redox catalyst and the supporting electrolyte.

Direct α-Acylation of Alkenes via N-Heterocyclic Carbene, Sulfinate, and Photoredox Cooperative Triple Catalysis

Liu, Kun,Studer, Armido

supporting information, p. 4903 - 4909 (2021/05/04)

N-Heterocyclic carbene (NHC) catalysis has emerged as a versatile tool in modern synthetic chemistry. Further increasing the complexity, several processes have been introduced that proceed via dual catalysis, where the NHC organocatalyst operates in concert with a second catalytic moiety, significantly enlarging the reaction scope. In biological transformations, multiple catalysis is generally used to access complex natural products. Guided by that strategy, triple catalysis has been studied recently, where three different catalytic modes are merged in a single process. In this Communication, direct α-C-H acylation of various alkenes with aroyl fluorides using NHC, sulfinate, and photoredox cooperative triple catalysis is reported. The method allows the preparation of α-substituted vinyl ketones in moderate to high yields with excellent functional group tolerance. Mechanistic studies reveal that these cascades proceed through a sequential radical addition/coupling/elimination process. In contrast to known triple catalysis processes that operate via two sets of interwoven catalysis cycles, in the introduced process, all three cycles are interwoven.

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