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941-55-9 Usage

Chemical Description

Tosyl azide is a reagent used in organic synthesis to introduce azide functional groups into molecules.

Description

Tosyl azide is a reagent used in organic synthesis. It is prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.

Applications

Tosyl azide is utilized for the introduction of diazo and azide functional groups. Moreover, it is used as a nitrene and a substrate for [3+2] cycloaddition reactions.

Safety

Tosyl azide is a very volatile chemical that should be carefully stored and handled.

Uses

Different sources of media describe the Uses of 941-55-9 differently. You can refer to the following data:
1. Used for the introduction of azide and diazo functional groups. It is also used as a nitrene source and as a substrate for [3+2] cycloaddition reactions.
2. 4-Methylbenzenesulfonyl Azide can be used to target Bcl-2 family proteins to potentially treat cancer.
3. p-Toluenesulfonyl azide solution can be employed as a reagent along with alkyne, and amine in the three-component coupling reaction for the synthesis of N-sulfonylamidines in presence of copper catalyst.It can also be used in the synthesis of N-sulfonyl-1,2,3-triazoles by azide-alkyne cycloaddition reaction in the presence of copper catalyst.

Synthesis Reference(s)

Synthetic Communications, 17, p. 1015, 1987 DOI: 10.1080/00397918708063962Tetrahedron Letters, 28, p. 5091, 1987 DOI: 10.1016/S0040-4039(00)95598-9

Check Digit Verification of cas no

The CAS Registry Mumber 941-55-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,4 and 1 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 941-55:
(5*9)+(4*4)+(3*1)+(2*5)+(1*5)=79
79 % 10 = 9
So 941-55-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H8N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5,8H,1H3/q+1

941-55-9 Well-known Company Product Price

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  • Aldrich

  • (713589)  p-Toluenesulfonylazidesolution  11-15 % (w/w) in toluene, 97%

  • 941-55-9

  • 713589-25G

  • 1,932.84CNY

  • Detail
  • Aldrich

  • (713589)  p-Toluenesulfonylazidesolution  11-15 % (w/w) in toluene, 97%

  • 941-55-9

  • 713589-100G

  • 6,762.60CNY

  • Detail

941-55-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name P-Toluenesulfonyl Azide

1.2 Other means of identification

Product number -
Other names diazonio-(4-methylphenyl)sulfonylazanide

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:941-55-9 SDS

941-55-9Synthetic route

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
With sodium azide In water; isopropyl alcohol at 20℃; for 1h;100%
With sodium azide In water; acetone at 0 - 23℃; for 17h; Inert atmosphere;100%
With sodium azide In water; acetone at 0 - 23℃; for 17h; Inert atmosphere;100%
p-toluenesulfonyl fluoride
455-16-3

p-toluenesulfonyl fluoride

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
With trimethylsilylazide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 1.5h;98%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
Stage #1: toluene-4-sulfonic acid With trichloroisocyanuric acid; triphenylphosphine In tetrahydrofuran at 0 - 5℃; for 0.25h;
Stage #2: With sodium azide In tetrahydrofuran at 5 - 20℃; for 0.0166667h; Solvent;
97%
With sodium azide; trichloroacetonitrile; triphenylphosphine In acetonitrile at 20℃; for 3h;95%
Stage #1: toluene-4-sulfonic acid With 1-ethyl-3-methylimidazolium tetrafluoroborate; triethylamine at 0℃; for 0.0833333h;
Stage #2: With sodium azide; bis(trichloromethyl) carbonate at 0 - 25℃; for 1.5h;
89%
With sodium azide; trichloroisocyanuric acid; triphenylphosphine In tetrahydrofuran at 20℃;
toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
With SHNC In water for 0.75h; Ambient temperature;96%
With dinitrogen tetraoxide In tetrachloromethane; acetonitrile at -20℃; for 0.166667h; Product distribution; other t;95%
With dinitrogen tetraoxide In tetrachloromethane; acetonitrile at -20℃; for 0.166667h;95%
toluene-4-sulfonamide
70-55-3

toluene-4-sulfonamide

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
With 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate; potassium carbonate In water; isopropyl alcohol at 20℃; for 18h; Solvent; Concentration;90%
With sodium azide In water; acetone at 20℃; for 2h;87%
With copper(ll) sulfate pentahydrate; sodium hydrogencarbonate; perfluorobutanesulfonyl azide In methanol; diethyl ether; water at 20℃; for 6h;81%
(η5-cyclopentadienyl)(p-toluenesulfonylimido-kN-thio-kS-ethene-2-thiolato-kS)cobalt(III)

(η5-cyclopentadienyl)(p-toluenesulfonylimido-kN-thio-kS-ethene-2-thiolato-kS)cobalt(III)

A

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

B

(η(5)-cyclopentadienyl)[1,2-bis(methoxycarbonyl)ethenethiolato-κS]cobalt(III)
86543-67-1

(η(5)-cyclopentadienyl)[1,2-bis(methoxycarbonyl)ethenethiolato-κS]cobalt(III)

Conditions
ConditionsYield
In neat (no solvent) 177-178°C;A 43%
B 88%
1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole
1028-19-9

1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
With sodium azide; water In acetonitrile for 4h; Heating;88%
7-Methoxy-1-<(4-methylphenyl)sulfonyl>-3,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one
153718-76-4

7-Methoxy-1-<(4-methylphenyl)sulfonyl>-3,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one

A

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

B

7-Methoxy-2,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one
160208-44-6

7-Methoxy-2,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one

Conditions
ConditionsYield
With sodium azide; N,N-dimethyl-formamide at 25℃; for 4h;A n/a
B 84%
toluene-4-sulfonic acid 4-methyl-5-oxo-2,5-dihydro-furan-3-yl ester
263765-02-2

toluene-4-sulfonic acid 4-methyl-5-oxo-2,5-dihydro-furan-3-yl ester

A

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

B

4-hydroxy-3-methyl-5H-furan-2-one
516-09-6

4-hydroxy-3-methyl-5H-furan-2-one

C

4-azido-3-methyl-5H-furan-2-one

4-azido-3-methyl-5H-furan-2-one

Conditions
ConditionsYield
With sodium azide In methanol at 20℃; Substitution;A n/a
B n/a
C 20%
toluene-4-sulfonic acid 4-(3,4-dimethoxy-phenyl)-5-oxo-2,5-dihydro-furan-3-yl ester
263765-03-3

toluene-4-sulfonic acid 4-(3,4-dimethoxy-phenyl)-5-oxo-2,5-dihydro-furan-3-yl ester

A

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

B

3-(3,4-dimethoxyphenyl)-4-hydroxy-5H-furan-2-one
263764-91-6

3-(3,4-dimethoxyphenyl)-4-hydroxy-5H-furan-2-one

C

4-azido-3-(3,4-dimethoxyphenyl)-5H-furan-2-one

4-azido-3-(3,4-dimethoxyphenyl)-5H-furan-2-one

Conditions
ConditionsYield
With sodium azide In methanol at 20℃; Substitution;A n/a
B n/a
C 20%
N-tosyl dimethylketenimine
76227-58-2

N-tosyl dimethylketenimine

A

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

B

Isobutyronitrile
78-82-0

Isobutyronitrile

C

N-[1-Amino-2-methyl-prop-2-en-(Z)-ylidene]-4-methyl-benzenesulfonamide
86439-37-4

N-[1-Amino-2-methyl-prop-2-en-(Z)-ylidene]-4-methyl-benzenesulfonamide

D

C22H28N2O5S2
86439-38-5

C22H28N2O5S2

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine In diethyl ether Product distribution;A n/a
B n/a
C 14%
D 3%
With tris-(2-chloro-ethyl)-amine In diethyl etherA n/a
B n/a
C 14%
D 3%
N-[1-Chloro-2-methyl-prop-(Z)-ylidene]-4-methyl-benzenesulfonamide
86439-36-3

N-[1-Chloro-2-methyl-prop-(Z)-ylidene]-4-methyl-benzenesulfonamide

A

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

B

Isobutyronitrile
78-82-0

Isobutyronitrile

Conditions
ConditionsYield
With lithium azide In diethyl ether; N,N-dimethyl-formamide at -20 - 20℃; Product distribution;
p-toluenesulfonic acid hydrazide

p-toluenesulfonic acid hydrazide

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
With acetic acid; sodium nitrite
p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

CH2=CMeCHMeCH2X, X=Br or tosyl

CH2=CMeCHMeCH2X, X=Br or tosyl

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / K2CO3 / acetone / 20 °C
2: NaN3 / methanol / 20 °C
View Scheme
4-(4-toluenesulfonyloxy)coumarin
200055-89-6

4-(4-toluenesulfonyloxy)coumarin

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
With sodium azide In dimethyl sulfoxide for 1h;
para-thiocresol
106-45-6

para-thiocresol

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-chloro-succinimide; tetrabutyl-ammonium chloride; water / acetonitrile / 0 °C
2: sodium azide / acetonitrile / 0.75 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: tetrabutyl-ammonium chloride; water; N-chloro-4-methylbenzenesulfonamide / acetonitrile / 0.5 h / 0 °C
2: sodium azide / acetonitrile / 0.75 h / 0 - 20 °C
View Scheme
2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

A

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

B

1-azido-2,4-dinitrobenzene
4096-88-2

1-azido-2,4-dinitrobenzene

C

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / diethyl ether
2: sodium azide / dimethyl sulfoxide; water; acetonitrile / 25 °C
View Scheme
2,4-dinitrophenyl 4-methylbenzenesulfonate
742-25-6

2,4-dinitrophenyl 4-methylbenzenesulfonate

A

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

B

2,4-Dinitrophenol
51-28-5

2,4-Dinitrophenol

C

1-azido-2,4-dinitrobenzene
4096-88-2

1-azido-2,4-dinitrobenzene

D

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

Conditions
ConditionsYield
With sodium azide In water; dimethyl sulfoxide; acetonitrile at 25℃; Kinetics; Mechanism; regioselective reaction;
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%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

(1S,3aS,6aR,9aR)-1,8,8-Trimethyl-4,7-dioxo-decahydro-cyclopenta[d]indene-5-carbaldehyde

(1S,3aS,6aR,9aR)-1,8,8-Trimethyl-4,7-dioxo-decahydro-cyclopenta[d]indene-5-carbaldehyde

C16H21N2O3(1+)*C7H8NO2S(1-)

C16H21N2O3(1+)*C7H8NO2S(1-)

Conditions
ConditionsYield
With triethylamine In dichloromethane at 18℃;100%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

C24H30O2P2

C24H30O2P2

11,17-di-tert-butyl-2-tosyltiazenyliden-3,2-12-oxadiphosphapentacyclo<11.5.1.02,11.04,10.012,16>nonadeca-4(10),5,8,14,17-pentaen-19-one

11,17-di-tert-butyl-2-tosyltiazenyliden-3,2-12-oxadiphosphapentacyclo<11.5.1.02,11.04,10.012,16>nonadeca-4(10),5,8,14,17-pentaen-19-one

Conditions
ConditionsYield
In dichloromethane-d2 at -78℃; for 144h;100%
1,4-Dihydro-1,4-dimethyl-5-(2,2-dimethylpropyliden)-5H-tetrazol
54986-16-2

1,4-Dihydro-1,4-dimethyl-5-(2,2-dimethylpropyliden)-5H-tetrazol

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

5-{2,2-dimethyl-1-{3-[(4-methylphenyl)sulfonyl]triaz-1-enyl}propyl}-1,4-dimethyl-1H-tetrazolium inner salt

5-{2,2-dimethyl-1-{3-[(4-methylphenyl)sulfonyl]triaz-1-enyl}propyl}-1,4-dimethyl-1H-tetrazolium inner salt

Conditions
ConditionsYield
In toluene at 20℃; for 1h;100%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

thiolane-2,5-dione
3194-60-3

thiolane-2,5-dione

benzylamine
100-46-9

benzylamine

N-(4-methylphenylsulfonyl)-N'-(phenylmethyl)-butanediamide
104816-53-7

N-(4-methylphenylsulfonyl)-N'-(phenylmethyl)-butanediamide

Conditions
ConditionsYield
Stage #1: thiolane-2,5-dione; benzylamine In methanol for 0.5h;
Stage #2: 4-toluenesulfonyl azide With 2,6-dimethylpyridine In methanol for 0.5h; Further stages.;
100%
methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-D-glycero-D-galacto-non-2-enonate
909103-59-9

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-(2-propynyl)-D-glycero-D-galacto-non-2-enonate

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

diisopropylamine
108-18-9

diisopropylamine

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate
1304780-03-7

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-8,9-O-isopropylidene-4-O-[3-(diisopropylamino)-3-(4-methylbenzenesulfonylimino)propoxy]-D-glycero-D-galacto-non-2-enonate

Conditions
ConditionsYield
With copper(l) iodide In dichloromethane at 20℃; for 1h; Inert atmosphere;100%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

methyl 3-oxo-4-phenylhexanoate

methyl 3-oxo-4-phenylhexanoate

methyl 2-diazo-3-oxo-4-phenylhexanoate

methyl 2-diazo-3-oxo-4-phenylhexanoate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 16h;100%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

benzyl(3S,4S)-4-(2-(4-bromophenyl)-2-oxoethyl)-3-ethynyl-1-(mesitylsulfonyl)-1,2,3,4-tetrahydroquinoline-3-carboxylate

benzyl(3S,4S)-4-(2-(4-bromophenyl)-2-oxoethyl)-3-ethynyl-1-(mesitylsulfonyl)-1,2,3,4-tetrahydroquinoline-3-carboxylate

benzyl(3R,4S)-4-(2-(4-bromophenyl)-2-oxoethyl)-1-(mesitylsulfonyl)-3-(1-tosyl-1H-1,2,3-triazol-4-yl)-1,2,3,4-tetrahydroquinoline-3-carboxylate

benzyl(3R,4S)-4-(2-(4-bromophenyl)-2-oxoethyl)-1-(mesitylsulfonyl)-3-(1-tosyl-1H-1,2,3-triazol-4-yl)-1,2,3,4-tetrahydroquinoline-3-carboxylate

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate In dichloromethane at 20℃; for 3h;99.2%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-3-oxohept-6-enoate
316380-13-9

ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-3-oxohept-6-enoate

ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-diazo-3-oxohept-6-enoate
316380-15-1

ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-diazo-3-oxohept-6-enoate

Conditions
ConditionsYield
With triethylamine In acetonitrile Diazotization;99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

C26H24N2O4PS2(1-)*Na(1+)

C26H24N2O4PS2(1-)*Na(1+)

Conditions
ConditionsYield
Stage #1: chloro-diphenylphosphine With sodium In tetrahydrofuran for 18h; Heating;
Stage #2: 4-toluenesulfonyl azide In tetrahydrofuran; acetone at 20℃; for 48h; Staudinger reaction;
99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

1-methylthio-4-nitro-benzene
701-57-5

1-methylthio-4-nitro-benzene

C14H14N2O4S2

C14H14N2O4S2

Conditions
ConditionsYield
With 4 A molecular sieve; chiral (CO)Ru(II)(salen) In dichloromethane at 20℃; for 24h;99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

methyl-phenyl-thioether
100-68-5

methyl-phenyl-thioether

S-methyl-S-phenyl-N-(p-tolylsulfonyl)sulfimide
205581-06-2, 543681-35-2, 543681-36-3

S-methyl-S-phenyl-N-(p-tolylsulfonyl)sulfimide

Conditions
ConditionsYield
With MS 4 Angstroem; bis(salicylaldehyde)ethylenediiminatocarbonylruthenium(II) In dichloromethane at 20℃;99%
With (5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)iron(III) chloride In 1,2-dichloro-ethane for 24h; Molecular sieve; Inert atmosphere; Reflux;94%
With D-glucose; cytochrome P-I263F A328V variant; NADPH In aq. phosphate buffer; dimethyl sulfoxide at 20℃; for 20h; pH=8; Reagent/catalyst; Enzymatic reaction;63%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

4-trifluoromethylphenylacetylene
705-31-7

4-trifluoromethylphenylacetylene

diisopropylamine
108-18-9

diisopropylamine

N1,N1-diisopropyl-N2-(4-methylbenzenesulfonyl)-2-(4-trifluoromethylphenyl)acetamidine

N1,N1-diisopropyl-N2-(4-methylbenzenesulfonyl)-2-(4-trifluoromethylphenyl)acetamidine

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran at 20℃; for 1h;99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

phenylacetylene
536-74-3

phenylacetylene

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
884866-01-7

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; benzoic acid In benzene at 60℃; for 0.05h; Flow reactor;99%
With (N,N’-bis-{2,6-(di-iso-propyl)phenyl}imidazole-2-ylidene)tri-tert-butylphosphinetetrafluoroborate copper (I) In toluene at 20℃; for 15h; Reagent/catalyst; Solvent; Temperature;97%
With copper(II) acetate monohydrate; 2-amino-phenol In acetonitrile at 20℃; for 0.333333h; regioselective reaction;95%
C10H16O4

C10H16O4

4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

C17H25NO7S

C17H25NO7S

Conditions
ConditionsYield
With copper(l) iodide; water; triethylamine at 25℃; for 1h;99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

2-ethynyl-1-nitrobenzene
16433-96-8

2-ethynyl-1-nitrobenzene

1-(4-methylbenzensulfonyl)-4-(2-nitrophenyl)-1H-1,2,3-triazole
1215090-01-9

1-(4-methylbenzensulfonyl)-4-(2-nitrophenyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
With [Tpm*,BrCu(NCMe)]BF4 In chloroform at 40℃; for 72h; Inert atmosphere;99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

propargyl benzene
10147-11-2

propargyl benzene

4-benzyl-1-(p-tosyl)-1H-1,2,3-triazole
1078739-21-5

4-benzyl-1-(p-tosyl)-1H-1,2,3-triazole

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; benzoic acid In benzene at 60℃; for 0.05h; Flow reactor;99%
With copper(I) thiophene-2-carboxylate In toluene at 20℃; for 3h;75%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

1-ethynylcyclopentanol
17356-19-3

1-ethynylcyclopentanol

1-(1-(p-tosyl)-1H-1,2,3-triazol-4-yl)cyclopentan-1-ol
1253966-26-5

1-(1-(p-tosyl)-1H-1,2,3-triazol-4-yl)cyclopentan-1-ol

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; benzoic acid In benzene at 60℃; for 0.05h; Flow reactor;99%
With copper(I) thiophene-2-carboxylate In toluene at 20℃; for 3h;90%
With copper(I) thiophene-2-carboxylate In toluene at 20℃; for 2h;83%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

4-(1-phenylvinyl)morpholine
7196-01-2

4-(1-phenylvinyl)morpholine

4-methyl-N-[morpholino(phenyl)methylene]benzenesulfonamide
17260-48-9

4-methyl-N-[morpholino(phenyl)methylene]benzenesulfonamide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 0.333333h;99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

4-(4-methoxyphenyl)-1-tosyl-1H-1,2,3-triazole
1078739-24-8

4-(4-methoxyphenyl)-1-tosyl-1H-1,2,3-triazole

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate; benzoic acid In benzene at 60℃; for 0.05h; Flow reactor;99%
With copper(II) acetate monohydrate; 2-amino-phenol In acetonitrile at 20℃; for 0.5h; regioselective reaction;96%
With (N,N’-bis-{2,6-(di-iso-propyl)phenyl}imidazole-2-ylidene)tri-tert-butylphosphinetetrafluoroborate copper (I) In toluene at 20℃; for 15h;93%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

para-bromoacetophenone
99-90-1

para-bromoacetophenone

N-(2-acetyl-5-bromophenyl)-4-methylbenzenesulfonamide
1438400-32-8

N-(2-acetyl-5-bromophenyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium carbonate; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 25℃; for 12h; Inert atmosphere;99%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 80℃; for 12h;71%
With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 100℃; for 24h; Inert atmosphere; Schlenk technique;70%
With silver hexafluoroantimonate; dichloro(p-cymene)ruthenium(II) dimer; copper diacetate In 1,2-dichloro-ethane at 80℃; for 48h; Inert atmosphere;46%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

acetophenone
98-86-2

acetophenone

N-(2-acetylphenyl)-4-methylbenzenesulfonamide
1859-70-7

N-(2-acetylphenyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium carbonate; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 25℃; for 12h; Inert atmosphere;99%
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; sodium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 80℃; for 12h; Reagent/catalyst; Temperature; Time;97%
With bromopentacarbonylmanganese(I); dimethyl zinc(II); copper diacetate In 1,4-dioxane; toluene at 0 - 80℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction;90%
With silver hexafluoroantimonate; dichloro(p-cymene)ruthenium(II) dimer; copper diacetate In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere;75%
With silver hexafluoroantimonate; [RhCl2(p-cymene)]2; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 100℃; for 24h; Solvent; Reagent/catalyst; Inert atmosphere; Schlenk technique;72%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

benzoic acid ethyl ester
93-89-0

benzoic acid ethyl ester

ethyl 2-(4-methylphenylsulfonamido)benzoate
223526-78-1

ethyl 2-(4-methylphenylsulfonamido)benzoate

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium carbonate; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 50℃; for 12h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

5-bromo-N-acetylindoline
22190-38-1

5-bromo-N-acetylindoline

N-(1-acetyl-5-bromoindolin-7-yl)-4-methylbenzenesulfonamide
1612872-73-7

N-(1-acetyl-5-bromoindolin-7-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) triflimide In 1,2-dichloro-ethane at 20℃; for 3h;99%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 25℃; for 6h; Inert atmosphere; regioselective reaction;95%
With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; silver(I) acetate In 1,2-dichloro-ethane at 80℃; for 10h; Schlenk technique;75%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

4-methyl-N-(4-methylphenyl)benzenesulfonamide
599-86-0

4-methyl-N-(4-methylphenyl)benzenesulfonamide

Conditions
ConditionsYield
With copper(l) chloride In methanol at 20℃; for 0.5h; Chan-Lam Coupling;99%
With L-proline-functionalized MCM-41-immobilized-CuCl; air In methanol at 20℃; for 2h;97%
With Copper(II) immobilized into prolinamide-modified polyacrylonitrile fiber In methanol at 60℃; for 0.5h; Chan-Lam Coupling;94%
With air; Graphene supported-1-N-ferrocenylmethylimidazole-Copper complex In ethanol at 70℃; for 0.75h; Catalytic behavior;92%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

2-Methoxybenzoic acid
579-75-9

2-Methoxybenzoic acid

2-methoxy-6-[(4-methylphenyl)sulfonamido]benzoic acid

2-methoxy-6-[(4-methylphenyl)sulfonamido]benzoic acid

Conditions
ConditionsYield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium carbonate; acetic acid; silver(I) triflimide In 1,2-dichloro-ethane at 80℃; for 12h; Inert atmosphere;99%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 80℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube;92%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 50℃; for 24h;88%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

C16H14O

C16H14O

4-(2-((2-methylbenzyl)oxy)phenyl)-1-tosyl-1H-1,2,3-triazole

4-(2-((2-methylbenzyl)oxy)phenyl)-1-tosyl-1H-1,2,3-triazole

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate In toluene at 20℃; Schlenk technique; Inert atmosphere;99%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

C13H14ClNO

C13H14ClNO

N-(4-chloro-1-pivaloyl-1H-indol-7-yl)-4-methylbenzenesulfonamide

N-(4-chloro-1-pivaloyl-1H-indol-7-yl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With [Cp*Ir(OCOCH3)2]; silver(I) triflimide In 1,2-dichloro-ethane at 25℃; for 12h; regioselective reaction;99%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate; silver(I) triflimide In 1,2-dichloro-ethane at 80℃; Sealed tube; Inert atmosphere; regioselective reaction;78%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; lithium acetate; silver(I) triflimide In 1,2-dichloro-ethane at 120℃; for 1h; regioselective reaction;76%
4-toluenesulfonyl azide
941-55-9

4-toluenesulfonyl azide

((2S,3S)-3-ethynyl-1-tosylindolin-2-yl)(phenyl)methanone

((2S,3S)-3-ethynyl-1-tosylindolin-2-yl)(phenyl)methanone

C31H26N4O5S2

C31H26N4O5S2

Conditions
ConditionsYield
With copper(I) thiophene-2-carboxylate In toluene at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique;99%

941-55-9Relevant articles and documents

Kice et al.

, p. 5516,5517,5518,5519 (1969)

Synthesis and characterization of redox active cyrhetrene-triazole click products

Day, David P.,Dann, Thomas,Blagg, Robin J.,Wildgoose, Gregory G.

, p. 29 - 34 (2014)

We report the synthesis and characterization of two new cyclopentadienyl tricarbonyl rhenium(I) (cyrhetrene) complexes modified with a 1,4-disubstituted 1,2,3-triazole moiety. The two compounds, (η5-[4-phenyltriazol-1-yl]cyclopentadienyl) trica

Copper(I)-Catalyzed Ketenimine Formation/Aza-Claisen Rearrangement Cascade for Stereoselective Synthesis of α-Allylic Amidines

Wang, Cheng-Gang,Wu, Rui,Li, Ting-Peng,Jia, Tao,Li, Yang,Fang, Dongmei,Chen, Xiaozhen,Gao, Yuanji,Ni, Hai-Liang,Hu, Ping,Wang, Bi-Qin,Cao, Peng

, p. 3234 - 3238 (2020)

A copper-catalyzed three-component reaction of terminal alkynes, TsN3, and tertiary allylic amines is developed toward the one-pot synthesis of α-allylic amidines. The product was synthesized on gram scale under 1 mol % of catalyst loading. Transformations of products into alkenyl amine and other nitrogen-containing compounds are demonstrated without any loss of stereochemical information.

Powerful Direct C-H Amidation Polymerization Affords Single-Fluorophore-Based White-Light-Emitting Polysulfonamides by Fine-Tuning Hydrogen Bonds

Choi, Tae-Lim,Hwang, Soon-Hyeok,Kim, Hongsik,Lee, Dongwhan,Ryu, Hanseul,Serdiuk, Illia E.

supporting information, p. 1778 - 1785 (2022/01/19)

The development of white-light-emitting polymers has been actively pursued because of the importance of such polymers in various applications, such as lighting sources and displays. To generate white-light, numerous research efforts have focused on synthe

Ambruticins: tetrahydropyran ring formation and total synthesis

Bowen, James I.,Crump, Matthew P.,Wang, Luoyi,Willis, Christine L.

supporting information, p. 6210 - 6215 (2021/07/28)

The ambruticins are a family of polyketide natural products which exhibit potent antifungal activity. Gene knockout experiments are in accord with the proposal that the tetrahydropyran ring of the ambruticins is formedviathe AmbJ catalysed epoxidation of the unsaturated 3,5-dihydroxy acid, ambruticin J, followed by regioselective cyclisation to ambruticin F. Herein, a convergent approach to the total synthesis of ambruticin J is described as well as model studies involving epoxidation and cyclisations of unsaturated hydroxy esters to give tetrahydropyrans and tetrahydrofurans. The total synthesis involves preparation of three key fragments which were unitedviaa Suzuki-Miyaura cross-coupling and Julia-Kocienski olefination to generate the required carbon framework. Global deprotection to a triol and selective oxidation of the primary alcohol gave, after hydrolysis of the lactone, ambruticin J.

Catalyst-free one-pot, four-component approach for the synthesis of di- And tri-substituted: N -sulfonyl formamidines

Liu, Ai-Ran,Zhang, Lei,Li, Jiao,Wusiman, Abudureheman

, p. 15161 - 15166 (2021/05/19)

A straightforward one-pot, multicomponent approach was developed to synthesize di- and tri-substituted N-sulfonyl formamidines from sulfonyl chlorides, NaN3, ethyl propiolate, and primary/secondary amines under mild conditions without catalysts or additives. Structural analysis of the di-substituted sulfonyl formamidines indicated formation of the E-syn/anti isomeric form. Tri-substituted analogues only formed E-isomers.

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