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70-55-3

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70-55-3 Usage

Role and purpose

P-toluene sulfonamide is a kind of excellent solid plasticizer used for thermoset plastic. It is suitable for being applied to phenolic resin, melamine resin, urea-formaldehyde resins and polyamide resins. Combination with a small amount can improve workability and make the solidification be uniform, and thus endowing the products with a good gloss. However, P-toluene sulfonamide has no softening effect as the liquid plasticizer, and is incompatible with polyvinyl chloride and vinyl chloride copolymer and is partially compatible with cellulose acetate, cellulose acetate butyrate and cellulose nitrate. p-Toluene sulfonamide has a low toxicity. It has been approved by the US Food and Drug Administration for being applied into adhesives as food packaging materials. p-Toluene sulfonamide is briefly called TSH and is commonly used for nickel plating. It can improve the coating structure by the adsorption on the electrode so that it has some degree of surface glossing effect; it is generally not strictly limited for the added amount of brighteners lax; moreover it also has very light effects on the coating characteristics. However, it can only give semi-bright coatings, and the surface gloss is related to the polishing quality of the matrix before plating. Currently, the brightener agents of nickel plating used is mostly some kinds of organic compounds. And the used amount of these organic compound, although are very little, but with a significant effect. In addition to brightening the coating, it can also largely determine the mechanical properties and chemical properties of the coating. But it must be realized that, since the bright nickel plating solution has been added to the organic brightener, it naturally makes the nickel plating layer contain a relative big amount of organic sulfur and other impurities, thus inevitably enlarging the internal stress, so its mechanical properties is a bitter lower than the conventional nickel-plate, and is prone to crack layer when the plating gets stress; its antirust ability is also worse than the dark nickel. Thus, a single layer of bright nickel is unable to improve the corrosion resistance and mechanical properties of the nickel layer; it must need to form a bi-layer and multilayer nickel or chromium to form a multilayer combination of decorative protective coatings. When toluene sulfonamide is heated to 105 °C, it will be decomposed and there will be nitrogen released (gas evolution 130 mL/g); p-toluene sulfonamide foaming agents can give a fine foaming with small product shrinkage. It also has a high tear strength and good stability. Thereby, it has a wide range of applications. The above information is edited by the lookchem of Dai xiongfeng.

Uses

Different sources of media describe the Uses of 70-55-3 differently. You can refer to the following data:
1. 1. It is used in the manufacture of dyes, synthetic resins, paints, disinfectants and wood processing brightener. 2. It is used for the manufacture of plasticizers, disinfectants; it can also be used for the production of synthetic resins, paints, and fluorescent dyes. 3. It can be used as primary brightener in the bright nickel plating. It is sued for bright nickel plating for multilayer to obtain uniform bright coating. It has a commonly used amount of 0.2~0.3 g/L. 4. It can be used as plasticizers, also used for synthesis of organics, resins and saccharin.
2. p-Toluenesulfonamide was used to prepare the precursor required for synthesis of ethyl 6-phenyl-1-tosyl-1,2,5,6-tetrahydropyridine-3-carboxylate.
3. 4-Tolylsulfonamide is a carbonic anhydrase inhibitor used the synthesis of antiglaucoma and anticancer drugs.
4. Used in the manufacture of plasticizer, disinfectant, fungicide, fungicides, wood brightener. Also can be used in the production of synthetic resin, the coating, the fluorescent dye, pharmaceutical, etc.

Production methods

It is obtained by the reaction between toluenesulfonyl chloride and ammonia. First, add part of HN3 water into the reaction pot, stirring for adding p-toluenesulfonyl chloride with the temperature rising naturally to above 50 °C; after the temperature has dropped, add the remaining ammonia and have reaction for 0.5 h at 85~90 °C. Stop the reaction when the pH reaches 8 to 9. Cool to 20 °C, filter, and wash the filter cake with water to obtain the crude. Then further go through bleaching via activated carbon, alkali dissolution, acid precipitation, rejection filter, drying to get products.

Chemical Properties

White leaflets. Soluble in alcohol; very slightly soluble inwater.Combustible.

Definition

ChEBI: A sulfonamide that is benzenesulfonamide bearing a methyl group at position 4.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 4327, 1982 DOI: 10.1021/jo00143a031Synthetic Communications, 20, p. 293, 1990 DOI: 10.1080/00397919008052297Synthesis, p. 1031, 1986 DOI: 10.1055/s-1986-31862

General Description

p-Toluenesulfonamide undergoes FeCl3-catalyzed direct substitution reaction with benzylic and allylic alcohols.It is employed as nucleophile in tetrabutylammonium fluoride (TBAF) catalyzed vinyl aziridine opening reaction.

Purification Methods

Crystallise the amide from hot water, then from EtOH or Et2O/pet ether. [Beilstein 11 H 104, 11 IV 376.]

Check Digit Verification of cas no

The CAS Registry Mumber 70-55-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 0 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 70-55:
(4*7)+(3*0)+(2*5)+(1*5)=43
43 % 10 = 3
So 70-55-3 is a valid CAS Registry Number.
InChI:InChI=1/C7H9NO2S/c1-6-2-4-7(5-3-6)11(8,9)10/h2-5H,1H3,(H2,8,9,10)

70-55-3 Well-known Company Product Price

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

  • (A12156)  p-Toluenesulfonamide, 98+%   

  • 70-55-3

  • 250g

  • 212.0CNY

  • Detail
  • Alfa Aesar

  • (A12156)  p-Toluenesulfonamide, 98+%   

  • 70-55-3

  • 500g

  • 257.0CNY

  • Detail
  • Alfa Aesar

  • (A12156)  p-Toluenesulfonamide, 98+%   

  • 70-55-3

  • 2500g

  • 1135.0CNY

  • Detail
  • Alfa Aesar

  • (A12156)  p-Toluenesulfonamide, 98+%   

  • 70-55-3

  • 10000g

  • 3820.0CNY

  • Detail
  • USP

  • (1672020)  p-Toluenesulfonamide  United States Pharmacopeia (USP) Reference Standard

  • 70-55-3

  • 1672020-200MG

  • 7,294.95CNY

  • Detail
  • Aldrich

  • (236330)  p-Toluenesulfonamide  ReagentPlus®, ≥99%

  • 70-55-3

  • 236330-10G

  • 322.92CNY

  • Detail
  • Aldrich

  • (236330)  p-Toluenesulfonamide  ReagentPlus®, ≥99%

  • 70-55-3

  • 236330-50G

  • 975.78CNY

  • Detail
  • Aldrich

  • (105902)  p-Toluenesulfonamide  reagent grade, 98%

  • 70-55-3

  • 105902-250G

  • 311.22CNY

  • Detail
  • Aldrich

  • (105902)  p-Toluenesulfonamide  reagent grade, 98%

  • 70-55-3

  • 105902-1KG

  • 738.27CNY

  • Detail
  • Vetec

  • (V900746)  p-Toluenesulfonamide  Vetec reagent grade, 98%

  • 70-55-3

  • V900746-250G

  • 53.82CNY

  • Detail

70-55-3SDS

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 toluene-4-sulfonamide

1.2 Other means of identification

Product number -
Other names 4-methylbenzenesulfonamide

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:70-55-3 SDS

70-55-3Synthetic route

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With C36H55N2*Pd(2+)*C7H7NO2S(2-); hydrogen In benzene-d6 at 75℃; for 12h; Temperature; Time;100%
With iron(III) oxide; hydrazine hydrate In water at 120℃; for 1.5h; Inert atmosphere;99%
With D-glucose; potassium hydroxide In water at 85℃; for 0.0833333h; Green chemistry; chemoselective reaction;99%
N-(p-tolylsulfonyl)diphenyltellurimide
78727-83-0

N-(p-tolylsulfonyl)diphenyltellurimide

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

bis oxide
107590-68-1

bis oxide

Conditions
ConditionsYield
In diethyl ether; dichloromethane for 0.5h;A 78%
B 100%
N-(2,3-dimethylbut-2-enyl)-4-methylbenzenesulfonamide

N-(2,3-dimethylbut-2-enyl)-4-methylbenzenesulfonamide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 1h;100%
With triethylsilane; trifluoroacetic acid In dichloromethane for 1h;100%
triphenylphosphine
603-35-0

triphenylphosphine

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

N-p-tolylsulfonylphosphine imide
1058-14-6

N-p-tolylsulfonylphosphine imide

Conditions
ConditionsYield
With [(tris[2-{N-tetramethylguanidyl}ethyl]amine)CoII-[N-(p-toluenesulfonyl)imino](2-tert-butylsulfonyl)phenyliodinane](OTf)2 In acetone at -40℃; Kinetics; Reagent/catalyst; Time; Inert atmosphere;A n/a
B 100%
[N-(p-tolylsulfonyl)imino]phenyliodinane
55962-05-5

[N-(p-tolylsulfonyl)imino]phenyliodinane

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With 1,3-dihydroisobenzofuran; manganese(ll) chloride In acetonitrile at 20℃; for 12h; Reagent/catalyst; Inert atmosphere;100%
With iodine; benzene In dichloromethane at 20℃; for 24h; Mechanism; Inert atmosphere;99%
tetrahydroxy-1,4-quinone
319-89-1

tetrahydroxy-1,4-quinone

A

diphenyl telluride
1202-36-4

diphenyl telluride

B

hexaketocyclohexane
527-31-1

hexaketocyclohexane

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With N-(p-tolylsulfonyl)diphenyltellurimide In methanol for 0.5h; Ambient temperature;A 97%
B 88%
C 99%
diphenyl ditelluride
32294-60-3

diphenyl ditelluride

Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide
62486-35-5

Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide

A

bis(4-methoxyphenyl)telluride
4456-34-2

bis(4-methoxyphenyl)telluride

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

N,N-bis(phenyltelluro)-p-toluenesulfonamide
116161-54-7

N,N-bis(phenyltelluro)-p-toluenesulfonamide

Conditions
ConditionsYield
In chloroform for 5h; Ambient temperature;A 97%
B 98%
C 99%
Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide
62486-35-5

Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide

A

bis(4-methoxyphenyl)telluride
4456-34-2

bis(4-methoxyphenyl)telluride

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

N,N-bis(phenyltelluro)-p-toluenesulfonamide
116161-54-7

N,N-bis(phenyltelluro)-p-toluenesulfonamide

Conditions
ConditionsYield
With diphenyl ditelluride In chloroform Ambient temperature;A 97%
B 98%
C 99%
diphenyl-N-(p-toluenesulfonyl)selenimide
52867-19-3

diphenyl-N-(p-toluenesulfonyl)selenimide

thiophenol
108-98-5

thiophenol

A

diphenylselenide
1132-39-4

diphenylselenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In chloroform for 0.25h; Product distribution; Ambient temperature;A 96%
B 99%
C 97%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

thiophenol
108-98-5

thiophenol

A

dibenzyl selenide
1842-38-2

dibenzyl selenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
ConditionsYield
In chloroform for 0.166667h; Product distribution; Ambient temperature;A 98%
B 99%
C 97%
diphenyl-N-(p-toluenesulfonyl)selenimide
52867-19-3

diphenyl-N-(p-toluenesulfonyl)selenimide

phenylmethanethiol
100-53-8

phenylmethanethiol

A

dibenzyl disulphide
150-60-7

dibenzyl disulphide

B

diphenylselenide
1132-39-4

diphenylselenide

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
In chloroform for 0.666667h; Product distribution; Ambient temperature;A 98%
B 97%
C 99%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

phenylmethanethiol
100-53-8

phenylmethanethiol

A

dibenzyl disulphide
150-60-7

dibenzyl disulphide

B

dibenzyl selenide
1842-38-2

dibenzyl selenide

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
In chloroform for 0.333333h; Product distribution; Ambient temperature;A 98%
B 99%
C 98%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

N,N-diphenylthiourea
102-08-9

N,N-diphenylthiourea

A

dibenzyl selenide
1842-38-2

dibenzyl selenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

1,3-Diphenylcarbodiimide
622-16-2

1,3-Diphenylcarbodiimide

Conditions
ConditionsYield
In methanol for 0.5h; Mechanism; Ambient temperature;A 99%
B 98%
C 76%
para-thiocresol
106-45-6

para-thiocresol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
Stage #1: para-thiocresol With dihydrogen peroxide; zirconium(IV) chloride In acetonitrile at 25℃;
Stage #2: With pyridine; ammonia In acetonitrile at 25℃; for 0.0333333h; chemoselective reaction;
99%
Stage #1: para-thiocresol With thionyl chloride; dihydrogen peroxide In water; acetonitrile at 25℃;
Stage #2: With pyridine; ammonia In water; acetonitrile at 25℃; for 0.0333333h;
97%
With tert.-butylhydroperoxide; ammonium hydroxide; iodine In water; acetonitrile at 100℃; for 16h;86%
N-formyl-N-tosylamide
4917-56-0

N-formyl-N-tosylamide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With hydrogenchloride; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) In dichloromethane; water at 40℃; for 10h; Schlenk technique;99%
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With ammonia; sodium hydrogencarbonate In water; acetone at 25℃; Schotten-Baumann Reaction; Flow reactor; Combinatorial reaction / High throughput screening (HTS);98%
With sodium isocyanate In water for 0.166667h; Reflux;97%
With ammonium hydroxide In tetrahydrofuran at 0 - 20℃;96%
tetrahydroxy-1,4-quinone
319-89-1

tetrahydroxy-1,4-quinone

A

rhodizonic acid
118-76-3

rhodizonic acid

B

bis(4-methoxyphenyl)telluride
4456-34-2

bis(4-methoxyphenyl)telluride

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide In methanol for 0.25h; Ambient temperature;A 89%
B 98%
C 98%
2,2,3,3,4,4,5,5-octafluoropentan-1-ol
355-80-6

2,2,3,3,4,4,5,5-octafluoropentan-1-ol

Sb,Sb,Sb-tripropyl-N-(p-tolylsulfonyl)stibine imide
80920-02-1

Sb,Sb,Sb-tripropyl-N-(p-tolylsulfonyl)stibine imide

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

bis(octafluoropentaloxy)tripropylantimony
80927-38-4

bis(octafluoropentaloxy)tripropylantimony

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 35 - 37℃;A 98%
B 83%
diphenyl ditelluride
32294-60-3

diphenyl ditelluride

N-(p-tolylsulfonyl)diphenyltellurimide
78727-83-0

N-(p-tolylsulfonyl)diphenyltellurimide

A

diphenyl telluride
1202-36-4

diphenyl telluride

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

N,N-bis(phenyltelluro)-p-toluenesulfonamide
116161-54-7

N,N-bis(phenyltelluro)-p-toluenesulfonamide

Conditions
ConditionsYield
In chloroform Ambient temperature;A 95%
B 96%
C 98%
N-[(4-methylphenyl)sulfonyl]-S,S-diphenyl-sulfilimine
13150-76-0

N-[(4-methylphenyl)sulfonyl]-S,S-diphenyl-sulfilimine

A

diphenyl sulfide
139-66-2

diphenyl sulfide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With sodium tetrahydroborate; meso-tetraphenylporphyrin iron(III) chloride In ethanol; benzene at 25℃; for 0.1h;A 98%
B n/a
C19H16N2O4S2
24698-06-4

C19H16N2O4S2

A

4-nitrophenyl phenyl sulfide
952-97-6

4-nitrophenyl phenyl sulfide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With 1-Benzyl-1,4-dihydronicotinamide; meso-tetraphenylporphyrin iron(III) chloride In benzene at 25℃; for 0.1h; NaBH4;A 98%
B n/a
In neat (no solvent) at 300℃; for 2h;
N-(p-tolylsulfonyl)diphenyltellurimide
78727-83-0

N-(p-tolylsulfonyl)diphenyltellurimide

A

diphenyl telluride
1202-36-4

diphenyl telluride

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

N,N-bis(phenyltelluro)-p-toluenesulfonamide
116161-54-7

N,N-bis(phenyltelluro)-p-toluenesulfonamide

Conditions
ConditionsYield
With diphenyl ditelluride In chloroform Ambient temperature;A 95%
B 96%
C 98%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

thiourea
17356-08-0

thiourea

A

CYANAMID
420-04-2

CYANAMID

B

dibenzyl selenide
1842-38-2

dibenzyl selenide

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
In methanol for 0.5h; Mechanism; Ambient temperature;A 72%
B 98%
C 98%
N-(p-tolylsulfonyl)dibenzylselenimide
55986-20-4

N-(p-tolylsulfonyl)dibenzylselenimide

benzenecarbothioamide
2227-79-4

benzenecarbothioamide

A

dibenzyl selenide
1842-38-2

dibenzyl selenide

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

C

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
In methanol for 0.5h; Mechanism; Ambient temperature;A 98%
B 98%
C 81%
C25H22NO2S2(1+)*ClO4(1-)

C25H22NO2S2(1+)*ClO4(1-)

A

diphenyl sulphone
127-63-9

diphenyl sulphone

B

S,S,S-triphenyloxosulfonium perchlorate

S,S,S-triphenyloxosulfonium perchlorate

C

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With potassium hydroxide In methanol; water for 1h; Ambient temperature;A 20%
B 77%
C 98%
di(p-tolyl) disulfide
103-19-5

di(p-tolyl) disulfide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
Stage #1: di(p-tolyl) disulfide With dihydrogen peroxide; zirconium(IV) chloride In acetonitrile at 25℃;
Stage #2: With pyridine; ammonia In acetonitrile at 25℃; for 0.0166667h; chemoselective reaction;
98%
N-(9-phenyl-9-fluorenyl)toluenesulfonamide
78388-16-6

N-(9-phenyl-9-fluorenyl)toluenesulfonamide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With chlorotriisopropylsilane; trifluoroacetic acid In dichloromethane for 0.25h;98%
1,1-Diphenylmethanol
91-01-0

1,1-Diphenylmethanol

A

benzhydryl ether
574-42-5

benzhydryl ether

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
With N-sulfinyl-p-toluenesulfonamide In diethyl ether at 25℃; for 20h;A 94%
B 97%
1,1-diphenylethanol
599-67-7

1,1-diphenylethanol

A

1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

B

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Conditions
ConditionsYield
In toluene for 20h; Heating;A 507 mg
B 97%
N-(p-tolylsulfonyl)(diacetylmethyl)-o-nitrophenylsulfimide

N-(p-tolylsulfonyl)(diacetylmethyl)-o-nitrophenylsulfimide

A

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

B

diacetylmethyl o-nitrophenyl sulfoxide
112128-28-6

diacetylmethyl o-nitrophenyl sulfoxide

Conditions
ConditionsYield
With sulfuric acid for 2h; Heating;A 97%
B 62%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide
18303-04-3

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With dmap; triethylamine In 1,2-dichloro-ethane at 20℃;100%
With dmap; triethylamine In dichloromethane at 20℃;98%
With N,N,N',N'-tetramethylguanidinium acetate at 20℃; for 0.5h; Neat (no solvent);94%
cis,trans-2,5-dimethoxytetrahydrofuran
696-59-3

cis,trans-2,5-dimethoxytetrahydrofuran

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-p-toluenesulfonylpyrrole
17639-64-4

N-p-toluenesulfonylpyrrole

Conditions
ConditionsYield
With phosphorus pentoxide In toluene at 110℃; for 0.333333h;100%
With scandium tris(trifluoromethanesulfonate) In 1,4-dioxane at 100℃; for 0.666667h; Clauson-Kaas condensation;95%
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h;90%
1,8-bis(p-toluenesulfonyloxy)-3,6-bis(p-toluenesulfonyl)-3,6-diazaoctane
56234-52-7

1,8-bis(p-toluenesulfonyloxy)-3,6-bis(p-toluenesulfonyl)-3,6-diazaoctane

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N,N',N-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane
52667-89-7

N,N',N-tris(p-toluenesulfonyl)-1,4,7-triazacyclononane

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 240h; Cyclization; Heating;100%
With potassium carbonate In acetonitrile for 144h; Heating;97%
benzaldehyde
100-52-7

benzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

isopropenylbenzene
98-83-9

isopropenylbenzene

N-(1,3-diphenylbut-3-en-1-yl)-4-methylbenzenesulfonamide
258851-74-0

N-(1,3-diphenylbut-3-en-1-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 1h;100%
With trimethylsilyl trifluoromethanesulfonate; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 1h;92%
With trimethylsilyl trifluoromethanesulfonate; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 1h; Condensation; imino ene reaction;90%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

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

N,N-dimethyl-formamide dimethyl acetal

N,N-Dimethyl-N'-<(4-methylphenyl)sulfonyl>formamidine

N,N-Dimethyl-N'-<(4-methylphenyl)sulfonyl>formamidine

Conditions
ConditionsYield
In dichloromethane for 0.5h; Heating;100%
diphenylmethylenecyclopropene
7632-57-7

diphenylmethylenecyclopropene

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N,N-bis-(2-benzhydryl-allyl)-4-methyl-benzenesulfonamide

N,N-bis-(2-benzhydryl-allyl)-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With palladium diacetate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In toluene at 110℃; for 3h;100%
bis(p-methoxyphenyl)methylenecyclopropane
28228-81-1

bis(p-methoxyphenyl)methylenecyclopropane

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N,N-bis-{2-[bis-(4-methoxy-phenyl)-methyl]-allyl}-4-methyl-benzenesulfonamide

N,N-bis-{2-[bis-(4-methoxy-phenyl)-methyl]-allyl}-4-methyl-benzenesulfonamide

Conditions
ConditionsYield
With palladium diacetate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In toluene at 115℃; for 3h;100%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

methylheptylmethylenecyclopropane

methylheptylmethylenecyclopropane

4-methyl-N,N-bis-[2-(1-methyl-octyl)-allyl]-benzenesulfonamide

4-methyl-N,N-bis-[2-(1-methyl-octyl)-allyl]-benzenesulfonamide

Conditions
ConditionsYield
With palladium diacetate; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine In toluene at 110℃; for 8h;100%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

N,N-diphenyl-p-toluenesulfonamide
4703-19-9

N,N-diphenyl-p-toluenesulfonamide

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 20℃; for 24h;100%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(benzylidene)-p-methylbenzenesulfonamide
51608-60-7

N-(benzylidene)-p-methylbenzenesulfonamide

Conditions
ConditionsYield
at 170℃;100%
at 170℃;95%
at 180℃; for 0.75h;91%
at 120 - 130℃; for 4h;82%
at 150℃; for 2h;
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(4-fluorobenzylidene)-4-methylbenzenesulfonamide
193675-43-3

N-(4-fluorobenzylidene)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With Amberlyst(R) 15 ion-exchange resin In toluene for 16h; Inert atmosphere; Reflux; Molecular sieve;100%
With amberlyst 15 In toluene for 16h; Heating; Molecular sieve;98%
With Amberlyst 15 In toluene for 12h; Molecular sieve; Reflux; Dean-Stark;98%
2-Phenylbenzaldehyde
1203-68-5

2-Phenylbenzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(2-phenylbenzylidene)-4-methylbenzenesulfonamide
1292302-62-5

N-(2-phenylbenzylidene)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With boron trichloride - methyl sulfide complex In toluene at 20℃; for 7.5h;100%
With copper diacetate In toluene Reflux;97%
With tetraethoxy orthosilicate Heating;47%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

hept-6-en-1-yl 4-methylbenzenesulfonate
110046-51-0

hept-6-en-1-yl 4-methylbenzenesulfonate

N-(hept-6-en-1-yl)-4-methylbenzenesulfonamide
1353723-21-3

N-(hept-6-en-1-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 15h; Inert atmosphere; Reflux;100%
3-(trifluoromethyl)dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate
1469876-14-9

3-(trifluoromethyl)dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

9-tosyl-2-(trifluoromethyl)-9H-carbazole
1469876-08-1

9-tosyl-2-(trifluoromethyl)-9H-carbazole

Conditions
ConditionsYield
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol at 90℃; for 16h; Inert atmosphere;100%
With copper diacetate; sodium carbonate; ethylene glycol In isopropyl alcohol at 85℃; for 16h; Ullmann Condensation; Inert atmosphere;55%
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol for 16h; Inert atmosphere; Reflux; Green chemistry;
[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

9-tosyl-9H-carbazole
3165-71-7

9-tosyl-9H-carbazole

Conditions
ConditionsYield
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol at 90℃; for 16h; Inert atmosphere;100%
With copper diacetate; sodium carbonate; ethylene glycol In isopropyl alcohol at 85℃; for 16h; Ullmann Condensation; Inert atmosphere;60%
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol for 16h; Inert atmosphere; Reflux; Green chemistry;
nonan-1-al
124-19-6

nonan-1-al

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-octylidene-p-toluenesulfonamide

N-octylidene-p-toluenesulfonamide

Conditions
ConditionsYield
With anthranilic acid In dichloromethane at 60℃; for 24h; Molecular sieve;100%
estragole oxide
51410-45-8

estragole oxide

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(2-hydroxy-3-(4-methoxyphenyl)propyl)-4-methylbenzenesulfonamide

N-(2-hydroxy-3-(4-methoxyphenyl)propyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 6h;100%
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In 1,4-dioxane at 90℃; for 5h;98%
diethylphosphonoacetic acid
3095-95-2

diethylphosphonoacetic acid

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

2-(diethoxyphosphoryl)-N-(p-toluenesulfonyl)ethanamide

2-(diethoxyphosphoryl)-N-(p-toluenesulfonyl)ethanamide

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 71h; Inert atmosphere;100%
4-methyl-1,2-dihydronaphthalene
4373-13-1

4-methyl-1,2-dihydronaphthalene

benzaldehyde
100-52-7

benzaldehyde

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-(2-(3,4-dihydronaphthalen-1-yl)-1-phenylethyl)-4-methylbenzenesulfonamide

N-(2-(3,4-dihydronaphthalen-1-yl)-1-phenylethyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 0.0166667h;100%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

N-d2-p-toluenesulfonamide

N-d2-p-toluenesulfonamide

Conditions
ConditionsYield
With deuteromethanol for 5h; Sealed tube; Inert atmosphere;100%
1-acetoxy-1,2-benziodoxol-3-one
1829-26-1

1-acetoxy-1,2-benziodoxol-3-one

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

Zhdankin’s reagent

Zhdankin’s reagent

Conditions
ConditionsYield
Stage #1: 1-acetoxy-1,2-benziodoxol-3-one With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: toluene-4-sulfonamide In dichloromethane at 20℃; for 3h; Inert atmosphere;
100%
1-(2-methoxyphenyl)ethanol
13513-82-1

1-(2-methoxyphenyl)ethanol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

A

N-(1-(2-methoxyphenyl)ethyl)-4-methylbenzenesulfonamide
93027-83-9

N-(1-(2-methoxyphenyl)ethyl)-4-methylbenzenesulfonamide

B

di[1-(2-methoxyphenyl)ethyl]ether
859312-83-7

di[1-(2-methoxyphenyl)ethyl]ether

Conditions
ConditionsYield
With acidic mesoporous zeolite β-catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube; Inert atmosphere;A 100%
B n/a
α-methyl-4-(methylthio)benzenemethanol
32293-73-5

α-methyl-4-(methylthio)benzenemethanol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

A

1-(4-methylthiophenyl)-1-(p-toluenesulfonamido)ethane

1-(4-methylthiophenyl)-1-(p-toluenesulfonamido)ethane

B

C18H22OS2

C18H22OS2

Conditions
ConditionsYield
With acidic mesoporous zeolite β-catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube; Inert atmosphere;A 100%
B n/a
4,4'-dimethylbenzhydrol
885-77-8

4,4'-dimethylbenzhydrol

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

A

bis[bis(p-tolyl)methyl] ether
37858-01-8

bis[bis(p-tolyl)methyl] ether

B

C22H23NO2S
1581274-94-3

C22H23NO2S

Conditions
ConditionsYield
With acidic mesoporous zeolite β-catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Sealed tube; Inert atmosphere;A n/a
B 100%
4,4'-dimethoxychalcone
2373-89-9

4,4'-dimethoxychalcone

toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

2-bromo-1-(4'-methoxyphenyl)-3-(4-methoxyphenyl)-3-(p-toluenesulfonamido)propan-1-one

2-bromo-1-(4'-methoxyphenyl)-3-(4-methoxyphenyl)-3-(p-toluenesulfonamido)propan-1-one

Conditions
ConditionsYield
With N-Bromosuccinimide; aluminium In dichloromethane at 25℃; for 0.166667h; regioselective reaction;99.8%
With N-Bromosuccinimide; silicon In dichloromethane at 25℃; for 1h; Aerobic conditions; stereoselective reaction;98%
With N-Bromosuccinimide; copper In dichloromethane at 25℃; for 1h; stereoselective reaction;97.5%
With N-Bromosuccinimide; potassium iodide In dichloromethane at 25℃; for 2h; Aerobic conditions; regioselective reaction;97%

70-55-3Relevant articles and documents

Cellular AND Gates: Synergistic Recognition to Boost Selective Uptake of Polymeric Nanoassemblies

Fernandez, Ann,Gao, Jingjing,Thayumanavan, S.,Wu, Peidong,Zhuang, Jiaming

, p. 10456 - 10460 (2020)

The development of nanoparticle-based biomedical applications has been hampered due to undesired off-target effects. Herein, we outline a cellular AND gate to enhance uptake selectivity, in which a nanoassembly–cell interaction is turned on, only in the concurrent presence of two different protein functions, an enzymatic reaction (alkaline phosphatase, ALP) and a ligand–protein (carbonic anhydrase IX, CA IX) binding event. Selective uptake of nanoassemblies was observed in cells that overexpress both of these proteins (unicellular AND gate). Interestingly, selective uptake can also be achieved in CA IX overexpressed cells, when cocultured with ALP overexpressed cells, where the nanoassembly presumably acts as a mediator for cell–cell communication (bicellular AND gate). This logic-gated cellular uptake could find use in applications such as tumor imaging or theranostics.

Synthesis of 8-Alkoxy-5 H-isochromeno[3,4- c]isoquinolines and 1-Alkoxy-4-arylisoquinolin-3-ols through Rh(III)-Catalyzed C-H Functionalization of Benzimidates with 4-Diazoisochroman-3-imines and 4-Diazoisoquinolin-3-ones

Li, Zhenmin,Lu, Ping,Wang, Yanguang,Xie, Jianwei

, p. 5525 - 5535 (2020)

Rh(III)-catalyzed C-H activation/annulation of benzimidates with 4-diazoisochroman-3-imines furnished 8-alkoxy-5H-isochromeno[3,4-c]isoquinolines in moderate to excellent yields with a broad range of substrate scope. The reaction was carried out under mild reaction conditions and could be scaled up with practical usage. Similar reaction between benzimidates and 4-diazoisoquinolin-3-ones provided 1-alkoxy-4-arylisoquinolin-3-ols in excellent yields. Moreover, the synthesized products could be conveniently transformed to the corresponding heterocycles with a 1,8-naphthyridinone or isochromenopyridinone core, which are privileged structures in medicinal chemistry.

Anisole alkylation with N-arenesulfonylimines of dichloro(phenyl)acetaldehyde and derivatives thereof

Drozdova,Mirskova

, p. 819 - 821 (2001)

N-[1-4-Methoxyphenyl-2-phenyl-2,2-dichloroethyl]arenesulfonamides are formed in reaction of N-(2-phenyl-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide and N-(2-phenyl-2,2-dichloroethylidene)-4-methylbenzenesulfonamide with anisole catalyzed by boron t

Structural, vibrational spectra and normal coordinate analysis for two tautomers of 4(5)-(2′-furyl)-imidazole

Ledesma,Zinczuk,Gonzalez, J.J. Lopez,Altabef, A. Ben,Brandan

, p. 587 - 597 (2010)

We have synthesized both the 4 and 5 tautomeric forms of 4(5)-(2′-furyl)-imidazole (1) and investigated their molecular vibrations by infrared and Raman spectroscopies as well as by calculation based on the density functional theory (DFT) approach. Examination of the temperature dependence of IR intensity revealed the band characteristics of the 4 and 5 tautomersof(1).Comparisonofexperimentalandcalculatedchemicalshiftsinnucl earmagneticresonance(NMR)spectroscopy was made in order to identify the two tautomeric forms. The assignment of vibrational normal modes was performed, and the forcefieldobtainedreproduced theexperimentalvibrationalwavenumbers with a root mean-squaredeviation (RMSD)value of ca. 13 cm-1 for both tautomers. The natural bond orbital (NBO) study reveals the characteristics of the electronic delocalization of the two tautomeric structures.

Formation and Isolation of the Disulphide Dication of 1,5-Dithiacyclo-octane in the Reactions of the Corresponding S-Oxide and S-(N-tosylimide) in Concentrated Sulphuric Acid

Furukawa, Naomichi,Kawada, Akira,Kawai, Tsutomu

, p. 1151 - 1152 (1984)

The disulphide dication of 1,5-dithiacyclo-octane was generated in the reaction of the corresponding S-oxide and S-(N-tosylimide) with conc.H2SO4 and isolated in crystalline form.

Cyclopropyl aziridines: Solvolytic reactions of the N-tosylaziridines of (+)-2-carene and (+)-3-carene

Silverberg, Lee J.,Rabb, Javon M.,Reno, Joseph M.,He, Gang

, p. 193 - 199 (2014)

The N-tosylaziridine 4 of (+)-2-carene 1 was prepared and subjected to solvolytic reactions with weak protic acids. For comparison, the solvolytic reactions of cis-3-carene-N-tosylaziridine 8 were also studied. The solvolyses of 4 were more rapid than those of 8, and both rings were opened in 4, whereas only the aziridine was opened in 8. This leads to the conclusion that the aziridine and cyclopropane rings in 4 can achieve a conjugated transition state.

Data-Driven Identification of Hydrogen Sulfide Scavengers

Yang, Chun-tao,Wang, Yingying,Marutani, Eizo,Ida, Tomoaki,Ni, Xiang,Xu, Shi,Chen, Wei,Zhang, Hui,Akaike, Takaaki,Ichinose, Fumito,Xian, Ming

, p. 10898 - 10902 (2019)

Hydrogen sulfide (H2S) is an important signaling molecule whose up- and down-regulation have specific biological consequences. Although significant advances in H2S up-regulation, by the development of H2S donors, have been achieved in recent years, precise H2S down-regulation is still challenging. The lack of potent/specific inhibitors for H2S-producing enzymes contributes to this problem. We expect the development of H2S scavengers is an alternative approach to address this problem. Since chemical sensors and scavengers of H2S share the same criteria, we constructed a H2S sensor database, which summarizes key parameters of reported sensors. Data-driven analysis led to the selection of 30 potential compounds. Further evaluation of these compounds identified a group of promising scavengers, based on the sulfonyl azide template. The efficiency of these scavengers in in vitro and in vivo experiments was demonstrated.

Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls

Bai, Jiaxing,Ding, Pin,Han, Lingbo,Liu, Jingjing,Luan, Xinjun

, (2022/03/19)

Transition metal-catalyzed diamination by hydroxylamines is a common approach for making three-membered aziridines, while its use for building the larger N-heterocycles is still underdeveloped. Herein, we report an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation of o-bromo(or chloro)-biaryls with bifunctional secondary hydroxylamines for the one-step assembly of synthetically useful carbazoles. Noteworthily, a linchpin for this domino reaction was the judicious selection of both the amino-sources and Pd(0)-catalysts for enabling the prerequisite oxidative addition of aryl halides to Pd(0)-species in the presence of hydroxylamines with a labile N-O bond. [Figure not available: see fulltext.].

Mechanically Strong Heterogeneous Catalysts via Immobilization of Powderous Catalysts to Porous Plastic Tablets

Li, Tingting,Xu, Bo

supporting information, p. 2673 - 2678 (2021/08/03)

Main observation and conclusion: We describe a practical and general protocol for immobilization of heterogeneous catalysts to mechanically robust porous ultra-high molecular weight polyethylene tablets using inter-facial Lifshitz-van der Waals Interactions. Diverse types of powderous catalysts, including Cu, Pd/C, Pd/Al2O3, Pt/C, and Rh/C have been immobilized successfully. The immobilized catalysts are mechanistically robust towards stirring in solutions, and they worked well in diverse synthetic reactions. The immobilized catalyst tablets are easy to handle and reused. Moreover, the metal leaching of immobilized catalysts was reduced significantly.

Inhibitory Evaluation and Molecular Docking Analysis of Benzenesulfonamides on Carbonic Anhydrase II

Zhang,Wei,Liu,Wu,Xuan

, p. 261 - 269 (2021/03/23)

Abstract: Sulfonamides is an important class of compounds, which can be used as carbonic anhydrase inhibitors. Nine different benzenesulfonamide compounds were synthesized, and their inhibitory effects on carbonic anhydrase II were studied by esterase method and molecular docking. The results showed that compounds (IId)–(IIg) with nitro and acetamide groups on the benzene ring exhibited excellent carbonic anhydrase II inhibitory activities. Molecular docking showed that compared with the control inhibitor acetazolamide, the compounds (IId)–(IIg) docked at the carbonic anhydrase II active site and showed higher binding energy and stronger binding ability. The physical and chemical properties of all compounds were studied by Molinspiration, which showed outstanding drug-like properties and ADME properties. Cytotoxicity assay results showed that compounds (IIe) and (IIf) were almost non-toxic to HepG2 and RAW264.7 cells. In conclusion, the compounds (IIe) and (IIf) have a certain application prospect as new inhibitors of carbonic anhydrase II.

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