p-carboxybenzenesulfonyl azide
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
With sodium tetrahydroborate; cetyltrimethylammonim bromide; cobalt(II) chloride In water at 25℃; for 0.166667h; Reduction; | 97% |
With ethyl acetoacetate; triethylamine In acetonitrile |
Conditions | Yield |
---|---|
With oxygen; cobalt(II) acetate; 3,5-dinitro-N-hydroxy-N-methylbenzamide; acetic acid at 100℃; under 760.051 Torr; for 10h; Temperature; Reagent/catalyst; | 94.05% |
With sodium hydroxide; potassium permanganate In water at 70 - 90℃; for 2h; | 90% |
Stage #1: toluene-4-sulfonamide With potassium permanganate In water for 12h; Reflux; Stage #2: With sulfuric acid In water at 0℃; | 66% |
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
With gadolinium(III) oxide; 2-methyl-4-hydroxy-3,6-dimethyloltoluene; acetylacetone at 50 - 78℃; for 1.83333h; Temperature; | 94% |
Conditions | Yield |
---|---|
With sodium metabisulfite; sodium azide; tetrabutylammomium bromide; triphenylphosphine In water; acetonitrile at 80℃; for 12h; Inert atmosphere; | 60% |
With sodium metabisulfite; sodium azide; tetrabutylammomium bromide; triphenylphosphine In water; acetonitrile at 80℃; for 4h; Inert atmosphere; Schlenk technique; | 60% |
p-carboxyphenylsulfonyl chloride
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
With ammonia In methanol at -5℃; | 53% |
With ammonia | |
Multi-step reaction with 2 steps 1: NaN3 / acetone; H2O 2: 3-oxo-butanoic acid ethyl ester, Et3N / acetonitrile View Scheme | |
With hydrogenchloride; ammonium hydroxide |
4-formyl-benzenesulfonamide
A
4-(aminosulfonyl)-benzoic acid
B
4-(hydroxymethyl)benzenesulfonamide
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With n-butyllithium; diethyl ether anschliessend mit Kohlendixid; |
Conditions | Yield |
---|---|
With phosphorus pentachloride und Erhitzen des Reaktionsprodukts mit wss.Ammoniumpolysulfid in Dioxan; |
N-tosylpyrrolidine
water
A
succinic acid
B
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
Erhitzen; |
4-formyl-benzenesulfonamide
A
4-(aminosulfonyl)-benzoic acid
B
4-(hydroxymethyl)benzenesulfonamide
4-(trichlorophosphoranylidene-sulfamoyl)-benzoyl chloride
water
4-(aminosulfonyl)-benzoic acid
4-sulfamoyl-cinnamic acid
4-(aminosulfonyl)-benzoic acid
water
chloramine T trihydrate
A
4-(aminosulfonyl)-benzoic acid
B
toluene-4-sulfonamide
Conditions | Yield |
---|---|
am Licht; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: pyridine; ammonium hydroxide / dichloromethane / 4 h / 0 - 20 °C 2.1: potassium permanganate / water / 12 h / Reflux 2.2: 0 °C View Scheme |
Conditions | Yield |
---|---|
With thionyl chloride at 20℃; for 2h; | 100% |
Stage #1: methanol With thionyl chloride at 0℃; for 0.5h; Stage #2: 4-(aminosulfonyl)-benzoic acid at 20℃; for 3h; | 100% |
With sulfuric acid for 8h; Reflux; | 95% |
ethanol
4-(aminosulfonyl)-benzoic acid
4-sulfamoylbenzoic acid ethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride at 20℃; | 98% |
With hydrogenchloride In water for 20h; Reflux; | 52% |
With hydrogenchloride | |
With sulfuric acid for 24h; Reflux; |
4-(aminosulfonyl)-benzoic acid
diazomethyl-trimethyl-silane
methyl 4-sulfamoylbenzoate
Conditions | Yield |
---|---|
In methanol; hexane; chloroform at 20℃; for 0.0833333h; | 98% |
In methanol; hexane; dichloromethane at 20℃; for 2h; | 95% |
Stage #1: 4-(aminosulfonyl)-benzoic acid; diazomethyl-trimethyl-silane In methanol; hexane; dichloromethane for 2h; Stage #2: With sodium hydroxide In methanol; hexane; dichloromethane; water | 95% |
In methanol; hexane; dichloromethane for 2h; |
4-(aminosulfonyl)-benzoic acid
potassium hydrogencarbonate
potassium 4-sulfamoylbenzoate
Conditions | Yield |
---|---|
In water at 45℃; for 0.5h; | 98% |
4-(aminosulfonyl)-benzoic acid
tert-butyl N-(3-{2-[2-(3-aminopropoxy)ethoxy]ethoxy}propyl)carbamate
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In chloroform; N,N-dimethyl-formamide | 97% |
Conditions | Yield |
---|---|
With thionyl chloride In Isopropyl acetate at 80 - 90℃; Solvent; Temperature; | 96% |
Stage #1: 4-(aminosulfonyl)-benzoic acid; 2-Methoxybenzoic acid With p-nitrobenzenesulfonic acid In toluene for 4h; Reflux; Stage #2: With thionyl chloride In toluene at 50℃; for 5h; Temperature; Reagent/catalyst; |
4-(aminosulfonyl)-benzoic acid
5-tert-butoxycarbonylamino-1-aminopentane
C17H27N3O5S
Conditions | Yield |
---|---|
Stage #1: 4-(aminosulfonyl)-benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide Inert atmosphere; Stage #2: 5-tert-butoxycarbonylamino-1-aminopentane With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 94% |
4-(aminosulfonyl)-benzoic acid
Propargylamine
N-(prop-2-yn-1-yl)-4-sulfamoylbenzamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere; | 93% |
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; | 82% |
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate | 82% |
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; | 82% |
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide | 74% |
4-(aminosulfonyl)-benzoic acid
1-amino-4-[(tert-butyloxycarbonyl)amino]butane
Conditions | Yield |
---|---|
Stage #1: 4-(aminosulfonyl)-benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 1-amino-4-[(tert-butyloxycarbonyl)amino]butane In N,N-dimethyl-formamide at 20℃; for 16h; | 93% |
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
Stage #1: 4-(aminosulfonyl)-benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: N-(2-(2-(2-aminoethoxy)ethoxy)ethyl)pent-4-ynamide With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; | 92% |
4-(aminosulfonyl)-benzoic acid
1-Ethyl-2,2-dimethoxy-pyrrolidine
Conditions | Yield |
---|---|
In diethyl ether for 6h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With thionyl chloride In chlorobenzene at 120℃; for 7 - 9h; | 91% |
4-fluoropiperidine
4-(aminosulfonyl)-benzoic acid
4-[(4-fluoropiperidin-1-yl)carbonyl]benzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: 4-(aminosulfonyl)-benzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0 - 20℃; for 3h; Stage #2: 4-fluoropiperidine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 2h; | 91% |
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
With 4-methyl-morpholine; HATU In N,N-dimethyl-formamide at 0℃; | 91% |
4-(aminosulfonyl)-benzoic acid
4-sulfamoylbenzoyl chloride
Conditions | Yield |
---|---|
With thionyl chloride for 5h; Heating; | 90% |
With thionyl chloride for 0.5h; Heating; | |
With thionyl chloride Heating / reflux; |
4-(aminosulfonyl)-benzoic acid
N-benzyloxycarbonyl-1,6-hexanediamine
benzyl (6-(4-sulfamoylbenzamido)hexyl)carbamate
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 90% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 14h; | 73.8 mg |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 24h; | 90% |
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 16h; Ambient temperature; | 89% |
4-(aminosulfonyl)-benzoic acid
1-cyclopropyl-4-{4-[(5-methyl-3-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]pyridin-2-yl}piperazine
1-cyclopropyl-4-{4-[(5-methyl-3-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]pyridin-2-yl}piperazine 4-sulfamoylbenzoate
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; | 88% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; | 88% |
tert-butyl 2,7-diazaspiro[3.5]nonane-7-carboxylate hydrochloride
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; | 88% |
1-hydroxy-pyrrolidine-2,5-dione
4-(aminosulfonyl)-benzoic acid
4-uulfamoyl-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere; | 87% |
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide | 80% |
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at -20℃; for 21h; | 75% |
1-Butyl-2,2-dimethoxy-pyrrolidine
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
In diethyl ether for 6h; Ambient temperature; | 87% |
4-(aminosulfonyl)-benzoic acid
4-(hydroxymethyl)benzenesulfonamide
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 0 - 20℃; for 12h; | 86% |
With diborane In tetrahydrofuran at 0 - 20℃; for 19h; Inert atmosphere; | 74% |
Stage #1: 4-(aminosulfonyl)-benzoic acid With diborane In tetrahydrofuran at 0 - 20℃; for 18.5h; Stage #2: With hydrogenchloride In methanol; water at 0℃; for 1.5h; Reflux; | 67% |
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 10℃; for 12h; | 64.47% |
Stage #1: 4-(aminosulfonyl)-benzoic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water at 0℃; |
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
With pyridine; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 72h; | 86% |
4-(aminosulfonyl)-benzoic acid
5-iodooctafluoro-3-oxapentanesulfonyl fluoride
Conditions | Yield |
---|---|
Stage #1: 4-(aminosulfonyl)-benzoic acid With 19-oxaheptatriacontane; potassium carbonate; potassium hydroxide In water; toluene at 20℃; Stage #2: 5-iodooctafluoro-3-oxapentanesulfonyl fluoride In water; toluene for 0.5h; | 86% |
4-(aminosulfonyl)-benzoic acid
Conditions | Yield |
---|---|
Stage #1: 4-(aminosulfonyl)-benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3-bromobenzoylpiperazine In N,N-dimethyl-formamide at 20℃; | 86% |
The Benzoic acid,4-(aminosulfonyl)-, with the CAS registry number 138-41-0, is also known as 4-Carboxybenzenesulfonamide. Its EINECS number is 205-327-4. This chemical's molecular formula is C7H7NO4S and molecular weight is 201.21. What's more, its systematic name is 4-sulfamoylbenzoic acid. Its classification code is Drug / Therapeutic Agent. It is used as an organic intermediate and in synthetizing pharmaceuticals.
Physical properties of Benzoic acid,4-(aminosulfonyl)- are: (1)ACD/LogP: 0.50; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.38; (4)ACD/LogD (pH 7.4): -2.56; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 72.06 Å2; (13)Index of Refraction: 1.611; (14)Molar Refractivity: 45.46 cm3; (15)Molar Volume: 130.9 cm3; (16)Polarizability: 18.02×10-24cm3; (17)Surface Tension: 66.2 dyne/cm; (18)Density: 1.536 g/cm3; (19)Flash Point: 225.4 °C; (20)Enthalpy of Vaporization: 74.57 kJ/mol; (21)Boiling Point: 449 °C at 760 mmHg; (22)Vapour Pressure: 7.56E-09 mmHg at 25°C.
Preparation: this chemical can be prepared by 4-chlorosulfonyl-benzoic acid at the temperature of -5 °C. This reaction will need reagent ammonia and solvent methanol. The yield is about 53%.
Uses of Benzoic acid,4-(aminosulfonyl)-: it can be used to produce 4-sulfamoyl-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester. It will need reagent dicyclohexylcarbodiimide and solvent dimethylformamide. The yield is about 80%.
When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. You should not breathe dust. When using it, you must avoid contact with eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(N)c1ccc(C(=O)O)cc1
(2)Std. InChI: InChI=1S/C7H7NO4S/c8-13(11,12)6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)(H2,8,11,12)
(3)Std. InChIKey: UCAGLBKTLXCODC-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 1gm/kg (1000mg/kg) | Journal of Medicinal Chemistry. Vol. 8, Pg. 548, 1965. | |
rat | LD50 | intraperitoneal | 350mg/kg (350mg/kg) | Pharmazie. Vol. 38, Pg. 102, 1983. |
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