6388-47-2

Basic information

• Product Name: 2-Amino-3-chlorobenzoic acid
• Synonyms: BUTTPARK 24\07-98;3-CHLORO-2-AMINOBENZOIC ACID;3-CHLOROANTHRANILIC ACID;2-AMINO-3-CHLOROBENZOIC ACID;TIMTEC-BB SBB003844;2-Amino-3-chloro;2-Amino-3-chlorbenzoesure;3-Chloroanthranilic acid (COOH=1)
• CAS NO: 6388-47-2
• Molecular Formula: C₇H₆ClNO₂
• Molecular Weight: 171.58
• EINECS: 228-996-4
• Product Categories: FINE Chemical & INTERMEDIATES;benzene derivative;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Phenylacetic acid;Organic acids;Amines;Aromatics;Miscellaneous Reagents
• Mol File: 6388-47-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 189-191 °C(lit.)
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: Yellow to brown/Solid
• Density: 1.476 g/cm³
• Vapor Pressure: 0.000174mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanaol
• PKA: 4.57±0.10(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Air & Light Sensitive
• CAS DataBase Reference: 2-Amino-3-chlorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-chlorobenzoic acid(6388-47-2)
• EPA Substance Registry System: 2-Amino-3-chlorobenzoic acid(6388-47-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36
• WGK Germany: 1
• Hazardous Substances Data: 6388-47-2(Hazardous Substances Data)

Usage

Chemical Properties

white to yellow, tan or grey crystalline powder

Uses

Different sources of media describe the Uses of 6388-47-2 differently. You can refer to the following data:
1. 2-Amino-3-chlorobenzoic acid is used as pharmaceutical intermediates.
2. 2-Amino-3-chlorobenzoic Acid is a plant growth regulator.

Synthesis Reference(s)

The Journal of Organic Chemistry, 17, p. 141, 1952 DOI: 10.1021/jo01135a014

Synthesis

The synthesis of?2-Amino-3-chlorobenzoic acid is as follows:70 ml of methanol was added to an autoclave, and cooled to -70° C., and 16 g (942 mmol) of a generated ammonia gas was added. 30 g (157 mmol) of 2,3-dichlorobenzoic acid and 0.78 g (7.85 mmol) of copper(I) chloride were added. The autoclave was sealed, and heated in an oil bath at 130° C. and 30 atmospheres for 20 hours. After the completion of the reaction, the autoclave was cooled to room temperature, and the reaction mixture was transferred into a reaction flask. 100 ml of water was added to the reaction solution, and the reaction solution was heated in an oil bath to 100° C. to remove the ammonia and the methanol. Then, the reaction solution was cooled to room temperature, and hydrochloric acid was added to adjust the pH value to 3. The precipitated crystals were filtered and dried to obtain 21.8 g of 2-amino-3-chlorobenzoic acid as white crystals with a yield of 81%.

InChI:InChI=1/C7H6ClNO2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3H,9H2,(H,10,11)/p-1

Synthetic route

3-chloro-2-nitro-benzoic acid (4771-47-5) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol; water for 1h; Ambient temperature;	85%
With hydrogenchloride; tin	72%
With ammonium hydroxide; sodium dithionite In water at 20℃; for 1h;	70%

2,3-dichlorbenzoic acid (50-45-3) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With ammonia; copper(l) chloride In methanol at 130℃; under 22801.5 Torr; for 20h; Pressure; Solvent; Autoclave;	81%
With hydrogenchloride; sodium hydroxide; aqueous NH3; ammonia; copper(l) chloride In water
With sodium hydroxide; ammonia; copper(l) chloride In water

ammonium hydroxide (1336-21-6) + 3-chloro-2-nitro-benzoic acid (4771-47-5) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With sodium chloride In water
With sodium chloride In water
With sodium chloride In water

O-methylcaprolactim (2525-16-8) + 3-chloro-2-nitro-benzoic acid (4771-47-5) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
Ra-Ni In tetrahydrofuran

anthranilic acid (118-92-3) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With glucose dehydrogenase; D-glucose; 7-tryptophan FDH from the native organism Lechevalieria aerocolonigenes, 1K variant; NAD; flavin adenine dinucleotide; sodium chloride; flavin reductase In aq. buffer at 25℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;	38.2%
With D-glucose; Escherichia coli flavin reductase; Bacillus megaterium glucose dehydrogenase; Lechevalieria aerocolonigenes tryptophan-7-halogenase; flavin adenine dinucleotide; NADH; sodium chloride In aq. phosphate buffer; isopropyl alcohol pH=7.4; Enzymatic reaction;

7-chloroisatin (7477-63-6) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate (582319-05-9) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: ozone / methanol / 1.5 h / 785.91 Torr / Cooling with acetone-dry ice 2: hydrogenchloride / water / 4 h / Reflux 3: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme

ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(3-chloro-2-aminophenyl)pentanoate (1446522-61-7) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 4 h / Reflux 2: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme

4,10-dichloro-5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione (106038-61-3) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With potassium hydroxide

8-chloro-3-(2-chloro-phenyl)-1H-quinazoline-2,4-dione (106782-55-2) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With potassium hydroxide

3-chloro-phthalamic acid (98557-43-8) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With potassium hydroxide; bromine

o-chlorophenyl isocyanate (3320-83-0) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3; NaCl 2: aqueous KOH View Scheme

3-chloro-DL-kynurenine → L-alanin (56-41-7) + 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
With Pseudomonas fluorescens kynureninase In aq. phosphate buffer at 37℃; pH=8; Kinetics; Enzymatic reaction;

anthranilic acid (118-92-3) → 2-amino-3-chlorobenzoic acid (6388-47-2) + 5-chloroanthranilic acid (635-21-2)

Conditions	Yield
With Pseudomonas fluorescens BL915 halogenase F454K mutant; flavin adenine dinucleotide; NADH; magnesium chloride In aq. phosphate buffer at 30℃; for 1h; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction;

N-(2-chloro-6-methylphenyl)acetamide (21352-09-0) → 2-amino-3-chlorobenzoic acid (6388-47-2)

Conditions	Yield
(i) aq. KMnO4, (ii) aq. H2SO4; Multistep reaction;

4-chloro-1H-isoindole-1,3(2H)-dione (51108-30-6) + water (7732-18-5) + furan-2,3,5(4H)-trione pyridine (1:1) + sodium hypobromite → 2-amino-3-chlorobenzoic acid (6388-47-2)

2-amino-3-chlorobenzoic acid (6388-47-2) → 2-amino-5-bromo-3-chloro-benzoic acid (58026-21-4)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1h;	100%
With N-Bromosuccinimide In dichloromethane at 20℃; for 2h;	89%
With N-Bromosuccinimide In dichloromethane at 20℃; for 2.5h;	85%

2-amino-3-chlorobenzoic acid (6388-47-2) + acetic anhydride (108-24-7) → 8-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one (5627-74-7)

Conditions	Yield
for 1h; Heating / reflux;	97%
Reflux;	76%
With acetic acid Heating;
for 3h; Heating / reflux;

2-amino-3-chlorobenzoic acid (6388-47-2) → 2-amino-3-chloro-benzamide (18343-44-7)

Conditions	Yield
Stage #1: 2-amino-3-chlorobenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Inert atmosphere; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide	97%
Stage #1: 2-amino-3-chlorobenzoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: With ammonium hydroxide at 20℃; for 20h;	81%
Stage #1: 2-amino-3-chlorobenzoic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide at 70℃; for 16h; Reagent/catalyst; Time; Temperature;	60%

dichloroacethyl chloride (79-36-7) + 2-amino-3-chlorobenzoic acid (6388-47-2) → 8-Chloro-2-dichloromethyl-benzo[d][1,3]oxazin-4-one (95632-30-7)

Conditions	Yield
	96%

2-amino-3-chlorobenzoic acid (6388-47-2) + dimethyl sulfate (77-78-1) → methyl 3-chloroanthranilate (77820-58-7)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In toluene at 80℃; for 1h; Solvent; Temperature; Reagent/catalyst;	96%

2-amino-3-chlorobenzoic acid (6388-47-2) → 2-amino-5-iodo-3-chlorobenzoic acid (101012-31-1)

Conditions	Yield
With N-iodo-succinimide In N,N-dimethyl-formamide at 20 - 80℃; for 2h;	95%
With N-iodo-succinimide In dichloromethane at 20℃; for 6h;	76%
With N-iodosuccinimide In DMF (N,N-dimethyl-formamide) at 60℃;

2-amino-3-chlorobenzoic acid (6388-47-2) → (2-amino-3-chlorophenyl)methanol (61487-25-0)

Conditions	Yield
Stage #1: 2-amino-3-chlorobenzoic acid With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1.83333h; Stage #2: With water In tetrahydrofuran at 10℃;	94%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1.83333h;	94%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h;	93%

2-amino-3-chlorobenzoic acid (6388-47-2) → 2-amino-5-bromo-3-chlorobenzoic acid hydrobromide (953039-28-6)

Conditions	Yield
With bromine In chloroform at 20℃; for 16h;	87%

bis(trichloromethyl) carbonate (32315-10-9) + 2-amino-3-chlorobenzoic acid (6388-47-2) → 8-chloro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione (63497-60-9)

Conditions	Yield
With pyridine In dichloromethane; acetonitrile at 20℃; for 5h;	87%
With pyridine In dichloromethane; acetonitrile at 55℃; for 2.16667h;	83%
With pyridine In dichloromethane; acetonitrile at 55℃; for 5.5h;	78.2%

formaldehyd (50-00-0) + 2-amino-3-chlorobenzoic acid (6388-47-2) → 5,5'-methylenebis(2-amino-3-chlorobenzoic acid) (1056452-97-1)

Conditions	Yield
With hydrogenchloride In water at 50 - 70℃; for 4h;	86%

(phenylthio)acetic acid chloride (7031-27-8) + 2-amino-3-chlorobenzoic acid (6388-47-2) → 5-chloro-6-(2-phenylsulfanyl-acetylamino)benzoic acid (1265087-56-6)

Conditions	Yield
Stage #1: (phenylthio)acetic acid chloride; 2-amino-3-chlorobenzoic acid With sodium hydroxide In water at 0 - 20℃; for 3h; Stage #2: With hydrogenchloride In water pH=4 - 5;	86%

2-amino-3-chlorobenzoic acid (6388-47-2) + CF3COX → 8-Chloro-2-trifluoromethyl-benzo[d][1,3]oxazin-4-one (91457-67-9)

Conditions	Yield
	85%

4-methyl-1H-indole (16096-32-5) + 2-amino-3-chlorobenzoic acid (6388-47-2) → 4-chloro-7-methylindolo[2,1-b]quinazoline-6,12-dione

Conditions	Yield
With oxygen; N,N,N',N'-tetramethylguanidine In acetonitrile at 30℃; under 760.051 Torr; for 48h; Irradiation; Green chemistry;	85%

2-amino-3-chlorobenzoic acid (6388-47-2) → 3-chloro-2-nitro-benzoic acid (4771-47-5)

Conditions	Yield
With sodium perborate; titanium(IV) hydroxide; acetic acid at 85 - 90℃; for 1h; Temperature; Inert atmosphere;	84.9%

2-amino-3-chlorobenzoic acid (6388-47-2) + 4-isothiocyanatobenzene sulfonamide (51908-29-3) → 8-chloro-3-(4-aminosulphonylphenyl)-2-mercapto-3H-quinazolin-4-one

Conditions	Yield
With triethylamine In ethanol for 3h; Inert atmosphere; Reflux;	84%

2-amino-3-chlorobenzoic acid (6388-47-2) + α-bromoacetophenone (70-11-1) → 2-amino-3-chloro-benzoic acid 2-oxo-2-phenyl-ethyl ester

Conditions	Yield
Stage #1: 2-amino-3-chlorobenzoic acid With sodium carbonate In N,N-dimethyl-formamide at 20 - 65℃; for 0.916667h; Stage #2: α-bromoacetophenone In N,N-dimethyl-formamide at 30 - 70℃; for 1h;	81%

2-amino-3-chlorobenzoic acid (6388-47-2) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 8-chloroquinazolin-4(3H)-one (101494-95-5)

Conditions	Yield
at 140℃;	79%
at 175℃;
at 135 - 175℃; for 3h;
at 135 - 175℃; for 3h;

2-amino-3-chlorobenzoic acid (6388-47-2) + 2-Chloroaniline (95-51-2) → 2-Amino-3-chloro-N-(2-chlorophenyl)benzamide (371243-71-9)

Conditions	Yield
With thionyl chloride In chloroform; benzene	78%

2-amino-3-chlorobenzoic acid (6388-47-2) + N (2'-chlorophenyl)cyanothioformamide (4955-65-1) → 4-chloro-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one

Conditions	Yield
With triethylamine In ethanol for 3h; Heating;	77%

2-amino-3-chlorobenzoic acid (6388-47-2) → (S)-2-amino-3-chloro-N-(3-(2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)oxazolidin-5-yl)propyl)benzamide (1422210-53-4)

Conditions	Yield
	74%

tetrahydrobetacarboline (16502-01-5) + 2-amino-3-chlorobenzoic acid (6388-47-2) → (2-amino-3-chlorophenyl)(1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)methanone

Conditions	Yield
With triethylamine; HATU	74%

2-amino-3-chlorobenzoic acid (6388-47-2) + acetic anhydride (108-24-7) → 8-chloro-2-methylquinazolin-4(3H)-one (19407-54-6)

Conditions	Yield
Stage #1: 2-amino-3-chlorobenzoic acid; acetic anhydride at 20℃; Stage #2: With ammonia In water at 20℃; for 7h;	73%

methanol (67-56-1) + 2-amino-3-chlorobenzoic acid (6388-47-2) → methyl 3-chloroanthranilate (77820-58-7)

Conditions	Yield
With sulfuric acid for 28h; Heating;	72%
With sulfuric acid	67%
With thionyl chloride at 0℃; for 24h;	60%
With sulfuric acid for 12h; Heating;
With sulfuric acid for 12h; Reflux;

indole (120-72-9) + 2-amino-3-chlorobenzoic acid (6388-47-2) → 4-chloroindolo[2,1-b]quinazoline-6,12-dione

Conditions	Yield
With oxygen; N,N,N',N'-tetramethylguanidine In acetonitrile at 30℃; under 760.051 Torr; for 36h; Irradiation; Green chemistry;	72%

(2-bromomethylphenyl)acetonitrile (73217-11-5) + 2-amino-3-chlorobenzoic acid (6388-47-2) → C32H20N4O2Cl2 + 4-chloro-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one (1062308-78-4)

Conditions	Yield
at 175℃; for 3.5h;	A n/a B 70%

2-amino-3-chlorobenzoic acid (6388-47-2) + 3-isothiocyanato-benzenesulfonamide (23165-62-0) → 3-(8-chloro-2-mercapto-4-oxoquinazolin-3(4H)-yl)benzenesulfonamide

Conditions	Yield
In ethanol Reflux;	69%

2-amino-3-chlorobenzoic acid (6388-47-2) + 2-Fluorobenzoyl chloride (393-52-2) → 8-chloro-2-(2'-fluorophenyl)-4H-benzo[d][1,3]oxazin-4-one

Conditions	Yield
With pyridine at 20℃; for 16h;	67%
With pyridine at 20℃; for 16h;

2-amino-3-chlorobenzoic acid (6388-47-2) + urea (57-13-6) → 8-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinazoline (62484-22-4)

Conditions	Yield
at 140 - 180℃; for 26h;	67%
In 1-methyl-pyrrolidin-2-one at 180 - 190℃; for 4h;
at 200℃; for 2h;

Upstream product

• 51108-30-6 4-chloro-1H-isoindole-1,3(2H)-dione 
• 7732-18-5 water 
• 1446522-61-7 ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(3-chloro-2-aminophenyl)pentanoate 
• 118-92-3 anthranilic acid 
• 582319-05-9 ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate 
• 1336-21-6 ammonium hydroxide 
• 4771-47-5 3-chloro-2-nitro-benzoic acid 
• 2525-16-8 O-methylcaprolactim 
• 50-45-3 2,3-dichlorbenzoic acid 
• 3320-83-0 o-chlorophenyl isocyanate 
• 21352-09-0 N-(6-chloro-2-methylphenyl)acetamide 
• 98557-43-8 3-chloro-phthalamic acid 
• 106782-55-2 8-chloro-3-(2-chloro-phenyl)-1H-quinazoline-2,4-dione 
• 106038-61-3 4,10-dichloro-5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione 

Downstream Products

• 437998-71-5 3-chloro-2-[4-(4-phenyl-3,6-dihydro-2H-pyridin-1-yl)-butyrylamino]-benzamide 
• 62484-22-4 8-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 
• 1259944-19-8 8-chloro-2-heptyl-3-hydroxyquinolin-4-(1H)-one 
• 1017540-70-3 3-chloro-2-iodobenzoyl chloride 
• 1422210-53-4 (S)-2-amino-3-chloro-N-(3-(2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-6-yl)oxazolidin-5-yl)propyl)benzamide 
• 19407-54-6 8-chloro-2-methylquinazolin-4(3H)-one 

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