Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With trimethylsilylazide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 1.5h; | 98% |
Conditions | Yield |
---|---|
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℃; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
A
4-toluenesulfonyl azide
B
(η(5)-cyclopentadienyl)[1,2-bis(methoxycarbonyl)ethenethiolato-κS]cobalt(III)
Conditions | Yield |
---|---|
In neat (no solvent) 177-178°C; | A 43% B 88% |
Conditions | Yield |
---|---|
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
A
4-toluenesulfonyl azide
B
7-Methoxy-2,4-dihydropyrrolo<4,3,2-de>quinolin-8(1H)-one
Conditions | Yield |
---|---|
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
A
4-toluenesulfonyl azide
B
4-hydroxy-3-methyl-5H-furan-2-one
Conditions | Yield |
---|---|
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
A
4-toluenesulfonyl azide
B
3-(3,4-dimethoxyphenyl)-4-hydroxy-5H-furan-2-one
Conditions | Yield |
---|---|
With sodium azide In methanol at 20℃; Substitution; | A n/a B n/a C 20% |
N-tosyl dimethylketenimine
A
4-toluenesulfonyl azide
B
Isobutyronitrile
C
N-[1-Amino-2-methyl-prop-2-en-(Z)-ylidene]-4-methyl-benzenesulfonamide
D
C22H28N2O5S2
Conditions | Yield |
---|---|
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 ether | A n/a B n/a C 14% D 3% |
N-[1-Chloro-2-methyl-prop-(Z)-ylidene]-4-methyl-benzenesulfonamide
A
4-toluenesulfonyl azide
B
Isobutyronitrile
Conditions | Yield |
---|---|
With lithium azide In diethyl ether; N,N-dimethyl-formamide at -20 - 20℃; Product distribution; |
4-toluenesulfonyl azide
Conditions | Yield |
---|---|
With acetic acid; sodium nitrite |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 70 percent / K2CO3 / acetone / 20 °C 2: NaN3 / methanol / 20 °C View Scheme |
4-(4-toluenesulfonyloxy)coumarin
4-toluenesulfonyl azide
Conditions | Yield |
---|---|
With sodium azide In dimethyl sulfoxide for 1h; |
Conditions | Yield |
---|---|
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
p-toluenesulfonyl chloride
A
4-toluenesulfonyl azide
B
1-azido-2,4-dinitrobenzene
C
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
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
A
4-toluenesulfonyl azide
B
2,4-Dinitrophenol
C
1-azido-2,4-dinitrobenzene
D
toluene-4-sulfonic acid
Conditions | Yield |
---|---|
With sodium azide In water; dimethyl sulfoxide; acetonitrile at 25℃; Kinetics; Mechanism; regioselective reaction; |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 18℃; | 100% |
4-toluenesulfonyl azide
Conditions | Yield |
---|---|
In dichloromethane-d2 at -78℃; for 144h; | 100% |
1,4-Dihydro-1,4-dimethyl-5-(2,2-dimethylpropyliden)-5H-tetrazol
4-toluenesulfonyl azide
Conditions | Yield |
---|---|
In toluene at 20℃; for 1h; | 100% |
4-toluenesulfonyl azide
thiolane-2,5-dione
benzylamine
N-(4-methylphenylsulfonyl)-N'-(phenylmethyl)-butanediamide
Conditions | Yield |
---|---|
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
4-toluenesulfonyl azide
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
Conditions | Yield |
---|---|
With copper(l) iodide In dichloromethane at 20℃; for 1h; Inert atmosphere; | 100% |
4-toluenesulfonyl azide
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; for 16h; | 100% |
4-toluenesulfonyl azide
Conditions | Yield |
---|---|
With copper(I) thiophene-2-carboxylate In dichloromethane at 20℃; for 3h; | 99.2% |
4-toluenesulfonyl azide
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
Conditions | Yield |
---|---|
With triethylamine In acetonitrile Diazotization; | 99% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With 4 A molecular sieve; chiral (CO)Ru(II)(salen) In dichloromethane at 20℃; for 24h; | 99% |
4-toluenesulfonyl azide
methyl-phenyl-thioether
S-methyl-S-phenyl-N-(p-tolylsulfonyl)sulfimide
Conditions | Yield |
---|---|
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
4-trifluoromethylphenylacetylene
diisopropylamine
Conditions | Yield |
---|---|
With copper(l) iodide In tetrahydrofuran at 20℃; for 1h; | 99% |
4-toluenesulfonyl azide
phenylacetylene
1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With copper(l) iodide; water; triethylamine at 25℃; for 1h; | 99% |
4-toluenesulfonyl azide
2-ethynyl-1-nitrobenzene
1-(4-methylbenzensulfonyl)-4-(2-nitrophenyl)-1H-1,2,3-triazole
Conditions | Yield |
---|---|
With [Tpm*,BrCu(NCMe)]BF4 In chloroform at 40℃; for 72h; Inert atmosphere; | 99% |
4-toluenesulfonyl azide
propargyl benzene
4-benzyl-1-(p-tosyl)-1H-1,2,3-triazole
Conditions | Yield |
---|---|
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
1-ethynylcyclopentanol
1-(1-(p-tosyl)-1H-1,2,3-triazol-4-yl)cyclopentan-1-ol
Conditions | Yield |
---|---|
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
4-(1-phenylvinyl)morpholine
4-methyl-N-[morpholino(phenyl)methylene]benzenesulfonamide
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.333333h; | 99% |
4-toluenesulfonyl azide
4-methoxyphenylacetylen
4-(4-methoxyphenyl)-1-tosyl-1H-1,2,3-triazole
Conditions | Yield |
---|---|
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
para-bromoacetophenone
N-(2-acetyl-5-bromophenyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
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
acetophenone
N-(2-acetylphenyl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
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
benzoic acid ethyl ester
ethyl 2-(4-methylphenylsulfonamido)benzoate
Conditions | Yield |
---|---|
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
5-bromo-N-acetylindoline
N-(1-acetyl-5-bromoindolin-7-yl)-4-methylbenzenesulfonamide
Conditions | Yield |
---|---|
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
4-methylphenylboronic acid
4-methyl-N-(4-methylphenyl)benzenesulfonamide
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With copper(I) thiophene-2-carboxylate In toluene at 20℃; Schlenk technique; Inert atmosphere; | 99% |
4-toluenesulfonyl azide
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With copper(I) thiophene-2-carboxylate In toluene at 0 - 20℃; for 1h; Inert atmosphere; Schlenk technique; | 99% |
The Tosyl azide, with the CAS registry number 941-55-9, is also known as p-Methylphenylsulfonyl azide. Its EINECS number is 213-381-5. This chemical's molecular formula is C7H7N3O2S and molecular weight is 197.21. What's more, its systematic name is 4-Methylbenzenesulfonyl azide. It is stable at common pressure and temperature. When heating, it may cause an explosion, so you should keep it away from sources of ignition - No smoking. This material and its container must be disposed of in a safe way. Tosyl azide is a reagent used in organic synthesis. This chemical is used for the introduction of azide and diazo functional groups. It is also used as a nitrene source and as a substrate for cycloaddition reactions. It can be prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.
Physical properties of Tosyl azide are: (1)ACD/LogP: 0.918; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.92; (4)ACD/LogD (pH 7.4): 0.92; (5)ACD/BCF (pH 5.5): 2.94; (6)ACD/BCF (pH 7.4): 2.94; (7)ACD/KOC (pH 5.5): 75.23; (8)ACD/KOC (pH 7.4): 75.23; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 70.67 Å2.
You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)([N-][N+]#N)c1ccc(cc1)C
(2)Std. InChI: InChI=1S/C7H7N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5H,1H3
(3)Std. InChIKey: NDLIRBZKZSDGSO-UHFFFAOYSA-N
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