2-Amino-3-chlorobenzoic acid supplier

Name
2-Amino-3-chlorobenzoic acid
EINECS 228-996-4
CAS No. 6388-47-2
Article Data25
CAS DataBase
Density 1.476 g/cm³
Solubility Soluble in water.
Melting Point 189-195 °C
Formula C₇H₆ClNO₂
Boiling Point 316.3 °C at 760 mmHg
Molecular Weight 171.583
Flash Point 145.1 °C
Transport Information
Appearance White to yellow, tan or grey crystalline powder
Safety 26-37/39-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Benzoic acid, 2-amino-3-chloro-;3-Chloro-2-aminobenzoic acid;3-Chloroanthranilic acid;Anthranilic acid, 3-chloro-;TL8007342;AC1Q3OUF;
PSA 63.32000
LogP 2.20160

Synthetic route

: 4771-47-5
3-chloro-2-nitro-benzoic acid

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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%

: 50-45-3
2,3-dichlorbenzoic acid

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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

: 1336-21-6
ammonium hydroxide

: 4771-47-5
3-chloro-2-nitro-benzoic acid

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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

: 2525-16-8
O-methylcaprolactim

: 4771-47-5
3-chloro-2-nitro-benzoic acid

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

Conditions	Yield
Ra-Ni In tetrahydrofuran

: 118-92-3
anthranilic acid

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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;

: 7477-63-6
7-chloroisatin

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide

: 582319-05-9
ethyl 7-chloroindole-3-(3-acetamido-3-carboethoxy)butanoate

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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

: 1446522-61-7
ethyl 2-acetamido-2-carboethoxy-5-oxo-5-(3-chloro-2-aminophenyl)pentanoate

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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

: 106038-61-3
4,10-dichloro-5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 106782-55-2
8-chloro-3-(2-chloro-phenyl)-1H-quinazoline-2,4-dione

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 98557-43-8
3-chloro-phthalamic acid

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

Conditions	Yield
With potassium hydroxide; bromine

: 3320-83-0
o-chlorophenyl isocyanate

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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

: 3-chloro-DL-kynurenine

A: 56-41-7
L-alanin

B: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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

: 118-92-3
anthranilic acid

A: 6388-47-2
2-amino-3-chlorobenzoic acid

B: 635-21-2
5-chloroanthranilic acid

Conditions

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;

: 21352-09-0
N-(2-chloro-6-methylphenyl)acetamide

: 6388-47-2
2-amino-3-chlorobenzoic acid

Conditions

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

: 51108-30-6
4-chloro-1H-isoindole-1,3(2H)-dione

: 7732-18-5
water

: furan-2,3,5(4H)-trione pyridine (1:1)

sodium hypobromite: sodium hypobromite

: 6388-47-2
2-amino-3-chlorobenzoic acid

...Expand

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 58026-21-4
2-amino-5-bromo-3-chloro-benzoic acid

Conditions

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%

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 108-24-7
acetic anhydride

: 5627-74-7
8-chloro-2-methyl-4H-benzo[d][1,3]oxazin-4-one

Conditions

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

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 18343-44-7
2-amino-3-chloro-benzamide

Conditions

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%

: 79-36-7
dichloroacethyl chloride

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 95632-30-7
8-Chloro-2-dichloromethyl-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
	96%

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 77-78-1
dimethyl sulfate

: 77820-58-7
methyl 3-chloroanthranilate

Conditions

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

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 101012-31-1
2-amino-5-iodo-3-chlorobenzoic acid

Conditions

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℃;

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 61487-25-0
(2-amino-3-chlorophenyl)methanol

Conditions

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%

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 953039-28-6
2-amino-5-bromo-3-chlorobenzoic acid hydrobromide

Conditions

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

: 32315-10-9
bis(trichloromethyl) carbonate

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 63497-60-9
8-chloro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione

Conditions

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%

: 50-00-0
formaldehyd

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 1056452-97-1
5,5'-methylenebis(2-amino-3-chlorobenzoic acid)

Conditions

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

: 7031-27-8
(phenylthio)acetic acid chloride

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 1265087-56-6
5-chloro-6-(2-phenylsulfanyl-acetylamino)benzoic acid

Conditions

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%

: 6388-47-2
2-amino-3-chlorobenzoic acid

CF3COX: CF3COX

: 91457-67-9
8-Chloro-2-trifluoromethyl-benzo[d][1,3]oxazin-4-one

Conditions

Conditions	Yield
	85%

: 16096-32-5
4-methyl-1H-indole

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 4-chloro-7-methylindolo[2,1-b]quinazoline-6,12-dione

Conditions

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

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 4771-47-5
3-chloro-2-nitro-benzoic acid

Conditions

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

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 51908-29-3
4-isothiocyanatobenzene sulfonamide

: 8-chloro-3-(4-aminosulphonylphenyl)-2-mercapto-3H-quinazolin-4-one

Conditions

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

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 70-11-1
α-bromoacetophenone

: 2-amino-3-chloro-benzoic acid 2-oxo-2-phenyl-ethyl ester

Conditions

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%

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 77287-34-4, 77287-35-5, 60100-09-6
formamide

: 101494-95-5
8-chloroquinazolin-4(3H)-one

Conditions

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

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 95-51-2
2-Chloroaniline

: 371243-71-9
2-Amino-3-chloro-N-(2-chlorophenyl)benzamide

Conditions

Conditions	Yield
With thionyl chloride In chloroform; benzene	78%

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 4955-65-1
N (2'-chlorophenyl)cyanothioformamide

: 4-chloro-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one

Conditions

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

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 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

Conditions

Conditions	Yield
	74%

: 16502-01-5
tetrahydrobetacarboline

: 6388-47-2
2-amino-3-chlorobenzoic acid

: (2-amino-3-chlorophenyl)(1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)methanone

Conditions

Conditions	Yield
With triethylamine; HATU	74%

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 108-24-7
acetic anhydride

: 19407-54-6
8-chloro-2-methylquinazolin-4(3H)-one

Conditions

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

: 67-56-1
methanol

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 77820-58-7
methyl 3-chloroanthranilate

Conditions

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;

: 120-72-9
indole

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 4-chloroindolo[2,1-b]quinazoline-6,12-dione

Conditions

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

: 73217-11-5
(2-bromomethylphenyl)acetonitrile

: 6388-47-2
2-amino-3-chlorobenzoic acid

A: C32H20N4O2Cl2

B: 1062308-78-4
4-chloro-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one

Conditions

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

...Expand

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 23165-62-0
3-isothiocyanato-benzenesulfonamide

: 3-(8-chloro-2-mercapto-4-oxoquinazolin-3(4H)-yl)benzenesulfonamide

Conditions

Conditions	Yield
In ethanol Reflux;	69%

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 393-52-2
2-Fluorobenzoyl chloride

: 8-chloro-2-(2'-fluorophenyl)-4H-benzo[d][1,3]oxazin-4-one

Conditions

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

: 6388-47-2
2-amino-3-chlorobenzoic acid

: 57-13-6
urea

: 62484-22-4
8-chloro-2,4-dioxo-1,2,3,4-tetrahydroquinazoline

Conditions

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

2-Amino-3-chlorobenzoic acid Specification

The 2-Amino-3-chlorobenzoic acid with CAS registry number of 6388-47-2 is also known as 3-Chloroanthranilic acid. The IUPAC name and product name are the same. It belongs to product categories of Fine chemical & Intermediates; Benzene Derivative; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Phenylacetic Acid; Organic Acids. Its EINECS registry number is 228-996-4. In addition, the formula is C₇H₆ClNO₂ and the molecular weight is 171.58. This chemical is a white to yellow, tan or grey crystalline powder and should be sealed in cool, dry place without light.

Physical properties about 2-Amino-3-chlorobenzoic acid are: (1)ACD/LogP: 2.60; (2)ACD/LogD (pH 5.5): 1.26; (3)ACD/LogD (pH 7.4): -0.29; (4)ACD/BCF (pH 5.5): 2.58; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 28.69; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.648; (12)Molar Refractivity: 42.31 cm³; (13)Molar Volume: 116.1 cm³; (14)Surface Tension: 65.9 dyne/cm; (15)Density: 1.476 g/cm³; (16)Flash Point: 145.1 °C; (17)Enthalpy of Vaporization: 58.88 kJ/mol; (18)Boiling Point: 316.3 °C at 760 mmHg; (19)Vapour Pressure: 0.000174 mmHg at 25 °C.

Preparation of 2-Amino-3-chlorobenzoic acid: it is prepared by reaction of 3-chloro-2-nitro-benzoic acid. The reaction needs reagents NiCL₂*6H₂O, NaBH₄ and solvents methanol, H₂O at ambient temperature for 1 hour. The yield is about 85%.

2-Amino-3-chlorobenzoic acid is prepared by reaction of 3-chloro-2-nitro-benzoic acid.

Uses of 2-Amino-3-chlorobenzoic acid: it is used to produce 4-chloro-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one by reaction with thiooxalsaeure-nitril-(2-chlor-anilid). The reaction occurs with reagent Et₃N and solvent ethanol with other condition of heating for 3 hours. The yield is about 77%.

2-Amino-3-chlorobenzoic acid is used to produce 4-chloro-benzo[4,5]thiazolo[2,3-b]quinazolin-12-one by reaction with thiooxalsaeure-nitril-(2-chlor-anilid).

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC(=C(C(=C1)Cl)N)C(=O)O
2. InChI: InChI=1S/C7H6ClNO2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3H,9H2,(H,10,11)
3. InChIKey: LWUAMROXVQLJKA-UHFFFAOYSA-N

Product Name

2-Amino-3-chlorobenzoic acid

Synthetic route

2-Amino-3-chlorobenzoic acid Specification

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