14543-45-4

Basic information

• Product Name: 4-AMINO-3-MERCAPTOBENZOIC ACID
• Synonyms: 4-AMINO-3-MERCAPTOBENZOIC ACID;4-AMINO-3-SULFANYLBENZENECARBOXYLIC ACID;4-AMINO-3-MERCAPTOBENZOIC ACID 98+%;4-aMino-3-sulfanylbenzoic acid
• CAS NO: 14543-45-4
• Molecular Formula: C₇H₇NO₂S
• Molecular Weight: 169.2
• Product Categories: MOFS COFS
• Mol File: 14543-45-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 290 °C (decomp)
• Boiling Point: 383.333 °C at 760 mmHg
• Flash Point: 185.633 °C
• Appearance: /
• Density: 1.448 g/cm³
• Vapor Pressure: 1.46E-06mmHg at 25°C
• Refractive Index: 1.708
• PKA: 4.61±0.10(Predicted)
• CAS DataBase Reference: 4-AMINO-3-MERCAPTOBENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-3-MERCAPTOBENZOIC ACID(14543-45-4)
• EPA Substance Registry System: 4-AMINO-3-MERCAPTOBENZOIC ACID(14543-45-4)

Safety Data

• Hazardous Substances Data: 14543-45-4(Hazardous Substances Data)

Usage

General Description

4-Amino-3-Mercaptobenzoic Acid, commonly referred to as 3-AB, is a chemical compound known for its properties as a radical scavenger and metal-chelating agent. Its molecular formula is C7H7NO2S and the molecular weight is 169.20 g/mol. The compound contains one sulfur atom which gives it the ability to bond with metals, thus making it a useful agent in laboratories for binding and removing heavy metals. Its mercaptobenzoic acid component can eliminate harmful free radicals and protects against oxidative stress. Owing to its antioxidant property, 4-Amino-3-MercaptoBenzoic Acid is mainly used in research fields, particularly in cell defense mechanism studies against oxidative stress.

InChI:InChI=1/C7H7NO2S/c8-5-2-1-4(7(9)10)3-6(5)11/h1-3,11H,8H2,(H,9,10)

Synthetic route

4-amino-3-thiocyanatobenzoic acid (18330-64-8) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With sodium sulfide In ethanol; water at 90℃; for 2h;	96%
Multi-step reaction with 2 steps 1: hydrochloric acid / H2O / 0.5 h / Heating 2: potassium hydroxide / H2O / 4 h / Heating View Scheme

2-aminobenzo[d]thiazole-6-carboxylic acid methyl ester (66947-92-0) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With water; potassium hydroxide for 16h; Inert atmosphere;	90%

2-amino-6-cyanobenzthiazole (19759-66-1) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With sodium hydroxide for 72h; Heating;	76%

2-aminobenzothiazole-6-carboxylic acid (93-85-6) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Stage #1: 2-aminobenzothiazole-6-carboxylic acid With water; potassium hydroxide for 24h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice;	67.9%
Stage #1: 2-aminobenzothiazole-6-carboxylic acid With water; potassium hydroxide for 24h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride In water Cooling with ice;	67.9%
With potassium hydroxide In water for 24h; Inert atmosphere; Reflux;	67.9%
With water; potassium hydroxide for 3h; Reflux;	66.1%
With potassium hydroxide In water

2-aminobenzothiazole-6-carboxylic acid hydrochloride → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With potassium hydroxide for 4h; Heating;
With potassium hydroxide In water for 4h; Heating;

2-amino-benzothiazole-carboxylic acid-(6) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
With potassium hydroxide

4-Aminobenzonitrile (873-74-5) + [(Xantphos)2Pd(η3-CH2Ph]OTf → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 82 percent / Br2; AcOH / 3 h / 20 °C 2: 76 percent / aq. NaOH / 72 h / Heating View Scheme

4-amino-benzoic acid (150-13-0) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine / methanol / 2 h / -5 °C 2: hydrochloric acid / H2O / 0.5 h / Heating 3: potassium hydroxide / H2O / 4 h / Heating View Scheme

ethyl 2-aminobenzothiazole-6-carboxylate (50850-93-6) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1N aq. HCl / Heating 2: KOH / 4 h / Heating View Scheme

p-aminoethylbenzoate (94-09-7) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2 / methanol / 2 h / -5 °C 2: 1N aq. HCl / Heating 3: KOH / 4 h / Heating View Scheme

4-Aminobenzonitrile (873-74-5) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: acetic acid / 3.5 h / 20 °C / Cooling with ice 2.1: hydrogenchloride; water / 6 h / 100 °C 3.1: potassium hydroxide; water / 24 h / Inert atmosphere; Reflux 3.2: Cooling with ice View Scheme
Multi-step reaction with 3 steps 1: acetic acid; bromine / 3.5 h / 20 °C / Cooling with ice 2: hydrogenchloride / water / 6 h / 100 °C 3: potassium hydroxide / water / 24 h / Inert atmosphere; Reflux View Scheme

4-amino-3-thiocyanatobenzonitrile (68867-21-0) → 4-amino-3-mercaptobenzoic acid (14543-45-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; water / 6 h / 100 °C 2.1: potassium hydroxide; water / 24 h / Inert atmosphere; Reflux 2.2: Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 6 h / 100 °C 2: potassium hydroxide / water / 24 h / Inert atmosphere; Reflux View Scheme

4-amino-3-mercaptobenzoic acid (14543-45-4) + bis(trichloromethyl) carbonate (32315-10-9) → 2-oxo-2,3-dihydro-1,3-benzothiazole-6-carboxylic acid (99615-68-6)

Conditions	Yield
Stage #1: 4-amino-3-mercaptobenzoic acid With potassium carbonate In tetrahydrofuran at 20℃; for 0.5h; Stage #2: bis(trichloromethyl) carbonate In tetrahydrofuran at -78℃; for 1h;	95%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-nitrobenzaldehdye (555-16-8) → 2-(4-nitrophenyl)-1,3-benzothiazole-6-carboxylic acid (65644-51-1)

Conditions	Yield
With oxygen In ethanol	90%
In nitrobenzene for 6h; Heating;	55%

4-amino-3-mercaptobenzoic acid (14543-45-4) + thioacetamide (62-55-5) → 2-methyl-1,3-benzothiazole-6-carboxylic acid (6941-28-2)

Conditions	Yield
With hydrogenchloride In ethylene glycol Heating;	90%
With hydrogenchloride In water; ethylene glycol at 100℃; for 7h;	78%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2-phenoxyethanethioamide (35370-80-0) → 2-Phenoxymethyl-benzothiazole-6-carboxylic acid

Conditions	Yield
With hydrogenchloride In ethylene glycol Heating;	85%

4-amino-3-mercaptobenzoic acid (14543-45-4) + isopropenylbenzene (98-83-9) → 3-methyl-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]thiazine-7-carboxylic acid

Conditions	Yield
With dipotassium peroxodisulfate; sodium iodide In acetonitrile at 80℃; for 16h; regioselective reaction;	84%

4-amino-3-mercaptobenzoic acid (14543-45-4) + methyl chloroformate (79-22-1) → 2-oxo-2,3-dihydro-1,3-benzothiazole-6-carboxylic acid (99615-68-6)

Conditions	Yield
Stage #1: 4-amino-3-mercaptobenzoic acid With sodium carbonate In water at 45℃; Inert atmosphere; Stage #2: methyl chloroformate In water at 45 - 80℃; Stage #3: With hydrogenchloride In water pH=2 - 3;	82.2%
Stage #1: 4-amino-3-mercaptobenzoic acid; methyl chloroformate With sodium carbonate In water at 80℃; Inert atmosphere; Stage #2: In water pH=2 - 3; Cooling with ice; Acidic conditions;	82.2%
With sodium carbonate In water at 45 - 80℃; Inert atmosphere;	82.2%

5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 4-amino-3-mercaptobenzoic acid (14543-45-4) → 2-(5-nitro-2-thienyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	81%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-dimethylamino-benzaldehyde (100-10-7) → 2-(4-Dimethylamino-phenyl)-benzothiazole-6-carboxylic acid

Conditions	Yield
With oxygen In ethanol	80%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-methoxymethylbenzothioamide (653568-68-4) → 2-(4-methoxymethyl-phenyl)-benzothiazole-6-carboxylic acid (723316-68-5)

Conditions	Yield
With hydrogenchloride In 1-methyl-pyrrolidin-2-one for 8h; Heating;	80%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-methoxy-benzaldehyde (123-11-5) → 2-(4-methoxyphenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	79%
With oxygen In ethanol	65%

4-amino-3-mercaptobenzoic acid (14543-45-4) + ortho-anisaldehyde (135-02-4) → 2-(2-methoxyphenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	79%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2-benzoyloxythioacetamide (40516-65-2) → 2-benzoyloxymethyl-benzothiazole-6-carboxylic acid (351465-00-4)

Conditions	Yield
With hydrogenchloride In ethylene glycol at 100℃; for 8h;	75%

5-nitrofurane-2-carboxaldehyde (698-63-5) + 4-amino-3-mercaptobenzoic acid (14543-45-4) → 2-(5-nitro-2-furyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	73%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 3-methoxy-benzaldehyde (591-31-1) → 2-(3-methoxyphenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	73%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-hydroxy-benzaldehyde (123-08-0) → 2-(4-hydroxyphenyl)benzo[d]thiazole-6-carboxylic acid

Conditions	Yield
With oxygen In ethanol	65%

4-amino-3-mercaptobenzoic acid (14543-45-4) + benzaldehyde (100-52-7) → 2-phenyl-1,3-benzothiazole-6-carboxylic acid (19989-69-6)

Conditions	Yield
With oxygen In ethanol	60%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2,4-dinitrobenzaldehyde (528-75-6) → 2-(2,4-dinitrophenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	56%

methanol (67-56-1) + 4-amino-3-mercaptobenzoic acid (14543-45-4) → dimethyl 3,3'-disulfanediylbis(4-aminobenzoate) (93015-74-8)

Conditions	Yield
With sulfuric acid for 8h; Reflux;	52.2%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2-nitro-benzaldehyde (552-89-6) → 2-(2-nitrophenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	45%
In nitrobenzene Reflux;	20%

4-chlorosalicylaldehyde (2420-26-0) + 4-amino-3-mercaptobenzoic acid (14543-45-4) → 2-(4-chloro-2-hydroxyphenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene at 185℃; for 0.25h; Heating / reflux;	44%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 3-nitro-benzaldehyde (99-61-6) → 2-(3-nitrophenyl)-1,3-benzothiazole-6-carboxylic acid

Conditions	Yield
In nitrobenzene for 6h; Heating;	43%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 3,3-bis(methylthio)-2-(4-trifluoromethylpyrimidin-2-yl)acrylonitrile (1219483-62-1) → 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethyl-pyrimidin-2-yl)acetonitrile (1219483-86-9)

Conditions	Yield
With dmap; potassium carbonate In ethanol at 160℃; for 0.4h; Microwave;	40%

4-amino-3-mercaptobenzoic acid (14543-45-4) + 4-nitro-benzoyl chloride (122-04-3) → 2-(4-nitrophenyl)-1,3-benzothiazole-6-carboxylic acid (65644-51-1)

Conditions	Yield
With pyridine

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2-cyclohexylidenecyclohexanone (1011-12-7) → 1',3',4',11'a-tetrahydro-2'H-spiro[cyclohexane-1,11'-dibenzo[b,e][1,4]thiazepine]-8'-carboxylic acid

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2,3-dichloroquinoxaline (2213-63-0) → 12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxaline-3-carboxylic acid (19843-53-9)

4-amino-3-mercaptobenzoic acid (14543-45-4) + 2,3-dichloro-6-methylquinoxaline (39267-05-5) → 8-methyl-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxaline-3-carboxylic acid (31639-75-5)

Conditions	Yield
In ethanol Heating;

Upstream product

• 19759-66-1 2-amino-6-cyanobenzthiazole 
• 66947-92-0 2-aminobenzo[d]thiazole-6-carboxylic acid methyl ester 
• 68867-21-0 4-amino-3-thiocyanatobenzonitrile 
• 873-74-5 4-Aminobenzonitrile 
• 93-85-6 2-aminobenzothiazole-6-carboxylic acid 
• 50850-93-6 ethyl 2-aminobenzothiazole-6-carboxylate 
• 150-13-0 4-amino-benzoic acid 
• 18330-64-8 4-amino-3-thiocyanatobenzoic acid 
• 18330-76-2 2-aminobenzothiazole-6-carboxylic acid hydrochloride 
• 94-09-7 p-aminoethylbenzoate 

Downstream Products

• 723316-68-5 2-(4-methoxymethyl-phenyl)-benzothiazole-6-carboxylic acid 
• 99615-68-6 2-oxo-2,3-dihydro-1,3-benzothiazole-6-carboxylic acid 
• 1221408-57-6 N-{4-[4-(2-methoxyphenyl)piperazinyl]butyl}benzothiazolin-2-one-6-carboxamide 
• 93015-74-8 dimethyl 3,3'-disulfanediylbis(4-aminobenzoate) 
• 73302-00-8 4-(6-methyl-[2,6';2',6'']terbenzothiazol-2''-yl)-aniline 
• 855266-37-4 6-methyl-2'-(4-nitro-phenyl)-[2,6']bibenzothiazolyl 
• 95-22-7 4-(6-methyl-[2,6']bibenzothiazolyl-2'-yl)-aniline 
• 875846-26-7 2-(4-nitrophenyl)benzothiazole-6-carbonyl chloride 
• 13127-94-1 2-(4-aminophenyl)benzo[d]thiazole-6-carboxylic acid 
• 351465-01-5 2-hydroxymethyl-benzothiazole-6-carboxylic acid 
• 351465-00-4 2-benzoyloxymethyl-benzothiazole-6-carboxylic acid 
• 6941-28-2 2-methyl-1,3-benzothiazole-6-carboxylic acid 

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