22892-96-2

Basic information

• Product Name: 4-Chloro-3-nitro-5-sulphamoylbenzoic acid
• Synonyms: TIMTEC-BB SBB003020;4-CHLORO-3-NITRO-5-SULFAMOYLBENZOIC ACID;4-Chloro-3-nitro-5-sulphamoylbenzoic acid;LABOTEST-BB LT00847210;4-Chloro-3-Nitro-5-Sulfomyl Benzoic Acid;5-Aminosulfonyl-4-Chloro-3-Nitrobenzoic Acid;3-Nitro-4-Chloro-5-Sulfamoylbenzoic acid;4-Chloro-3-nitro-5-sulfonamidobenzoic acid
• CAS NO: 22892-96-2
• Molecular Formula: C₇H₅ClN₂O₆S
• Molecular Weight: 280.64
• EINECS: 245-310-9
• Product Categories: API intermediates;Intermediates of Bumetanide;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 22892-96-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 227-231 °C
• Boiling Point: 563.5 °C at 760 mmHg
• Flash Point: 294.6 °C
• Appearance: /
• Density: 1.814 g/cm³
• Vapor Pressure: 1.56E-13mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.82±0.10(Predicted)
• CAS DataBase Reference: 4-Chloro-3-nitro-5-sulphamoylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3-nitro-5-sulphamoylbenzoic acid(22892-96-2)
• EPA Substance Registry System: 4-Chloro-3-nitro-5-sulphamoylbenzoic acid(22892-96-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 22892-96-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 22892-96-2 differently. You can refer to the following data:
1. Intermediate in the production of Bumetanide
2. 4-Chloro-3-nitro-5-sulfamoylbenzoic acid has been used in preparation of 4-((2-(2-hydroxyphenyl)quinolin-3-yl)methylamino)-3-nitro-5-sulfamoylbenzoic acid.

InChI:InChI=1/C7H5ClN2O6S/c8-6-4(10(13)14)1-3(7(11)12)2-5(6)17(9,15)16/h1-2H,(H,11,12)(H2,9,15,16)

Synthetic route

N-methylhomoveratrylamine (3490-06-0) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-3-nitro-5-sulfamoylbenzoic acid (1415960-92-7)

Conditions	Yield
Stage #1: N-methylhomoveratrylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 11h; Reflux; Stage #2: With hydrogenchloride In water pH=Ca. 2;	94%

2-(3-Fluorophenyl)ethylamine (404-70-6) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-{[2-(3-fluorophenyl)ethyl]amino}-3-nitro-5-sulfamoylbenzoic acid (1415960-91-6)

Conditions	Yield
Stage #1: 2-(3-Fluorophenyl)ethylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 2.5h; Reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=Ca. 11; Stage #3: With hydrogenchloride In diethyl ether; water pH=Ca. 2;	91%

4-Methoxyphenethylamine (55-81-2) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-{[2-(4-methoxyphenyl)ethyl]amino}-3-nitro-5-sulfamoylbenzoic acid (1415960-88-1)

Conditions	Yield
Stage #1: 4-Methoxyphenethylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 2.5h; Reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=Ca. 11; Stage #3: With hydrogenchloride In diethyl ether; water pH=Ca. 2;	87%

phenethylamine (64-04-0) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 3-nitro-4-[(2-phenylethyl)amino]-5-sulfamoylbenzoic acid (28395-45-1)

Conditions	Yield
Stage #1: phenethylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 2.5h; Reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=Ca. 11; Stage #3: With hydrogenchloride In diethyl ether; water pH=Ca. 2;	85%
With hydrogenchloride In water

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-{[2-(3,4-dimethoxyphenyl)ethyl]amino}-3-nitro-5-sulfamoylbenzoic acid

Conditions	Yield
Stage #1: 2-(3,4-dimethoxyphenyl)-ethylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 2.5h; Reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=Ca. 11; Stage #3: With hydrogenchloride In diethyl ether; water pH=Ca. 2;	80%

2-(3-methoxyphenyl)-1-ethanamine (2039-67-0) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-{[2-(3-methoxyphenyl)ethyl]amino}-3-nitro-5-sulfamoylbenzoic acid (1415960-87-0)

Conditions	Yield
Stage #1: 2-(3-methoxyphenyl)-1-ethanamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 2.5h; Reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=Ca. 11; Stage #3: With hydrogenchloride In diethyl ether; water pH=Ca. 2;	78%

o-methoxy-2-phenylethylamine (2045-79-6) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-{[2-(2-methoxyphenyl)ethyl]amino}-3-nitro-5-sulfamoylbenzoic acid (1415960-89-2)

Conditions	Yield
Stage #1: o-methoxy-2-phenylethylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 2.5h; Reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=Ca. 11; Stage #3: With hydrogenchloride In diethyl ether; water pH=Ca. 2;	75%

morpholine (110-91-8) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-morpholino-3-nitro-5-sulfamoylbenzoic acid (28395-56-4)

Conditions	Yield
Reflux;	67%

3-METHOXYBENZYLAMINE (5071-96-5) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-[(3-methoxybenzyl)amino]-3-nitro-5-sulfamoylbenzoic acid (1415960-94-9)

Conditions	Yield
Stage #1: 3-METHOXYBENZYLAMINE; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water at 20℃; for 15h; Stage #2: With hydrogenchloride In water Heating;	64%

4-Fluorophenol (371-41-5) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-(4-fluorophenoxy)-3-nitro-5-sulfamoylbenzoic acid (1357465-13-4)

Conditions	Yield
With sodium hydrogencarbonate In water at 85℃; for 16h;	61%
With sodium hydrogencarbonate In water at 85℃; for 16h;	61%
Stage #1: 4-Fluorophenol; 4-chloro-3-nitro-5-sulfamoylbenzoic acid With sodium hydrogencarbonate In water at 0 - 100℃; for 12h; Stage #2: With hydrogenchloride In water at 20℃;

4-methoxy-benzylamine (2393-23-9) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-[(4-methoxybenzyl)amino]-3-nitro-5-sulfamoylbenzoic acid (1415960-95-0)

Conditions	Yield
Stage #1: 4-methoxy-benzylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water at 20℃; for 3h; Stage #2: With sodium hydroxide In water pH=Ca. 9; Stage #3: With hydrogenchloride In diethyl ether; water	61%

2-(3-chlorophenyl)ethylamine (13078-79-0) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-{[2-(3-chlorophenyl)ethyl]amino}-3-nitro-5-sulfamoylbenzoic acid (1415960-90-5)

Conditions	Yield
Stage #1: 2-(3-chlorophenyl)ethylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water for 2.5h; Reflux; Stage #2: With sodium hydroxide In water at 20℃; pH=Ca. 11; Stage #3: With hydrogenchloride In diethyl ether; water pH=Ca. 2;	60%

4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) + phenol (108-95-2) → 3-nitro-4-phenoxy-5-sulfamoylbenzoic acid (28328-53-2)

Conditions	Yield
With sodium hydrogencarbonate In water at 85℃;	57%
With sodium hydrogencarbonate In water at 85℃; for 15h;	38%
With sodium hydrogencarbonate In water
Stage #1: 4-chloro-3-nitro-5-sulfamoylbenzoic acid; phenol With sodium hydrogencarbonate In water at 85℃; Stage #2: With hydrogenchloride In water at 20℃;
With sodium hydrogencarbonate In water at 85℃;	1.9 g

benzylamine (100-46-9) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-(benzylamino)-3-nitro-5-sulfamoylbenzoic acid (28395-43-9)

Conditions	Yield
Stage #1: benzylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water at 20℃; for 3.5h; Stage #2: With hydrogenchloride In water Heating;	53%
In water

2-methoxybenzylamine (6850-57-3) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-[(2-methoxybenzyl)amino]-3-nitro-5-sulfamoylbenzoic acid (1415960-96-1)

Conditions	Yield
Stage #1: 2-methoxybenzylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water at 20℃; for 15h; Stage #2: With sodium hydroxide In water at 20℃; Stage #3: With hydrogenchloride In diethyl ether; water	51%

4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 3-amino-5-sulfamoylbenzoic acid

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen; sodium hydroxide In methanol; water under 760.051 Torr; for 3h;	42%
With 5%-palladium/activated carbon; hydrogen; sodium hydroxide In methanol; water under 760.051 Torr; for 3h;	42%

2-(3-(aminomethyl)quinolin-2-yl)phenol (1357063-78-5) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-((2-(2-hydroxyphenyl)quinolin-3-yl)methylamino)-3-nitro-5-sulfamoylbenzoic acid (1357063-79-6)

Conditions	Yield
In butan-1-ol at 80 - 90℃;	41%

3,4-dimethoxybenzylamine (5763-61-1) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-[(3,4-dimethoxybenzyl)amino]-3-nitro-5-sulfamoylbenzoic acid (1415960-93-8)

Conditions	Yield
Stage #1: 3,4-dimethoxybenzylamine; 4-chloro-3-nitro-5-sulfamoylbenzoic acid In water at 20℃; for 15h; Stage #2: With hydrogenchloride In water Heating;	36%

4-amino-phenol (123-30-8) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-(p-hydroxyanilino)-3-nitro-5-sulphamyl-benzoic acid (28395-39-3)

Conditions	Yield
In water Heating;

m-Anisidine (536-90-3) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-(m-methoxyanilino)-3-nitro-5-sulphamyl-benzoic acid (28337-65-7)

Conditions	Yield
In water Heating;

2-methoxy-phenylamine (90-04-0) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-(o-methoxyanilino)-3-nitro-5-sulphamyl-benzoic acid (28337-64-6)

Conditions	Yield
In water Heating;

3-trifluoromethylaniline (98-16-8) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 3-nitro-5-sulphamyl-4-(m-trifluoromethylanilino)-benzoic acid (28395-33-7)

Conditions	Yield
In water Heating;

1-amino-3-(dimethylamino)propane (109-55-7) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-(3-dimethylaminopropylamino)-3-nitro-5-sulphamyl-benzoic acid

Conditions	Yield
In water
In water

Benzenesulfinic acid (618-41-7) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 3-nitro-4-phenylsulphonyl-5-sulphamyl-benzoic acid (28395-67-7)

Conditions	Yield
With sodium acetate In ethanol

2-methoxyethylamine (109-85-3) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-(2methoxyethylamino)-3-nitro-5-sulphamyl-benzoic acid (28395-49-5)

Conditions	Yield
In ethanol
In ethanol

o-toluidine (95-53-4) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 3-nitro-5-sulphamyl-4-(o-toluidino)-benzoic acid (28337-63-5)

Conditions	Yield
In water Heating;

(2-hydroxyethyl)(methyl)amine (109-83-1) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-[(2-Hydroxy-ethyl)-methyl-amino]-3-nitro-5-sulfamoyl-benzoic acid (28395-52-0)

Conditions	Yield
In ethanol

3-monochlorophenol (108-43-0) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-(m-chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid (28337-54-4)

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate In water
With sodium hydrogencarbonate

ethanol (64-17-5) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → ethyl-4-chloro-3-nitro-5-sulphamyl-benzoate (28394-90-3)

Conditions	Yield
With hydrogenchloride

sodium methylate (124-41-4) + 4-chloro-3-nitro-5-sulfamoylbenzoic acid (22892-96-2) → 4-methoxy-3-nitro-5-sulphamyl-benzoic acid (28337-56-6)

Conditions	Yield
In methanol

Downstream Products

• 25317-76-4 3-sulphamoyl-4-chloro-5-aminobenzoic acid 
• 28337-60-2 3-nitro-5-sulphamyl-4-(m-toluidino)-benzoic acid 
• 28328-65-6 3-Nitro-4-(4'-methoxyphenoxy)-5-sulphamoylbenzoic acid 
• 28395-43-9 4-(benzylamino)-3-nitro-5-sulfamoylbenzoic acid 
• 28395-65-5 3-nitro-5-sulphamyl-4-(o-tolylthio)-benzoic acid 
• 945397-39-7 2-chloro-5-(hydroxymethyl)-3-nitro-benzenesulfonamide 
• 28395-40-6 3-amino-4-(p-hydroxyanilino)-5-sulphamyl-benzoic acid 
• 28395-68-8 3-amino-4-phenylsulphonyl-5-sulphamyl-benzoic acid 
• 22893-01-2 ethyl 3-amino-4-chloro-5-sulfamoyl benzoate 
• 28337-56-6 4-methoxy-3-nitro-5-sulphamyl-benzoic acid 
• 28394-90-3 ethyl-4-chloro-3-nitro-5-sulphamyl-benzoate 
• 28337-54-4 4-(m-chlorophenoxy)-3-nitro-5-sulphamyl-benzoic acid 
• 28395-52-0 4-[(2-Hydroxy-ethyl)-methyl-amino]-3-nitro-5-sulfamoyl-benzoic acid 
• 28395-49-5 4-(2methoxyethylamino)-3-nitro-5-sulphamyl-benzoic acid