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2148-56-3

Basic Information
CAS No.: 2148-56-3
Name: 2-Amino-6-chlorobenzoic acid
Molecular Structure:
Molecular Structure of 2148-56-3 (2-Amino-6-chlorobenzoic acid)
Formula: C7H6ClNO2
Molecular Weight: 171.58
Synonyms: Anthranilicacid, 6-chloro- (6CI,7CI,8CI);6-Chloroanthranilic acid;
EINECS: 218-416-8
Density: 1.476 g/cm3
Melting Point: 158-160 °C(lit.)
Boiling Point: 339.3 °C at 760 mmHg
Flash Point: 159 °C
Solubility: Very soluble in water. Soluble in methanol.
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-37/39
Transport Information:
PSA: 63.32000
LogP: 2.20160
Synthetic route
5344-49-0

2-chloro-6-nitrobenzoic acid

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
With potassium bisulfite; cerium(III) chloride; potassium chloride; 2-methoxy-phenol In ethanol at 65℃; for 8h; Time;90%
With platinum Hydrogenation;
With ammonium hydroxide; iron(II) sulfate
With iron(II) sulfate
616224-61-4

2-[(tert-butoxycarbonyl)amino]-6-chlorobenzoic acid

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane; water at 90℃; under 760.051 Torr; for 1h; Temperature;99.5%
6575-11-7

2-amino-6-chlorobenzonitrile

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
With dihydrogen peroxide; potassium hydroxide Reflux;94%
With dihydrogen peroxide; potassium hydroxide In water for 12h; Reflux;94%
19407-42-2

2-(acetylamino)-6-chlorobenzoic acid

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride Zers. des entstandenen Hydrochlorids mit Natriumdicarbonat;
With hydrogenchloride at 80 - 90℃; for 1.5h;
7463-35-6

N-(3-chloro-2-methylphenyl)acetamide

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65.7 percent / potassium permanganate; magnesium sulfate heptahydrate / H2O / 5 h / 135 - 160 °C
2: hydrochloric acid / 1.5 h / 80 - 90 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium permanganate; magnesium sulfate
2: concentrated hydrochloric acid / Zers. des entstandenen Hydrochlorids mit Natriumdicarbonat
View Scheme
Multi-step reaction with 2 steps
1: potassium permanganate; magnesium sulfate; water
2: aqueous hydrochloric acid
View Scheme
6344-05-4

4-chloroisatin

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide
19407-43-3

2-benzoylamino-6-chloro-benzoic acid

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
With sodium hydroxide
6259-40-1

3-chloro-2-methyl-aniline; hydrochloride

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium acetate
2: potassium permanganate; magnesium sulfate; water
3: aqueous hydrochloric acid
View Scheme
87-60-5

3-chloro-2-methylbenzenamine

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90.2 percent / CH2Cl2
2: 65.7 percent / potassium permanganate; magnesium sulfate heptahydrate / H2O / 5 h / 135 - 160 °C
3: hydrochloric acid / 1.5 h / 80 - 90 °C
View Scheme
Multi-step reaction with 3 steps
1: fluorobenzene / 2 h / 50 °C
2: water / tetrahydrofuran / 9.17 h / 155 - 175 °C / 5320.36 - 7600.51 Torr / Inert atmosphere
3: hydrogenchloride / 1,4-dioxane; water / 1 h / 90 °C / 760.05 Torr
View Scheme
118-92-3

anthranilic acid

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
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;
4-chloro-isatin

4-chloro-isatin

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
With sodium azide; sulfuric acid
6575-07-1

2-chloro-6-nitrobenzonitrile

2148-56-3

2-chloro-6-aminobenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) H2SO4, (ii) aq. NaNO2
2: FeSO4
View Scheme
75-44-5

phosgene

2148-56-3

2-chloro-6-aminobenzoic acid

20829-96-3

5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione

Conditions
ConditionsYield
In 1,4-dioxane at 12 - 20℃;99%
In 1,4-dioxane at 0 - 23℃; for 24h;93%
With potassium hydroxide In water; toluene91%
32315-10-9

bis(trichloromethyl) carbonate

2148-56-3

2-chloro-6-aminobenzoic acid

20829-96-3

5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione

Conditions
ConditionsYield
In 1,4-dioxane for 2h; Reflux;99%
In 1,4-dioxane Reflux;99%
With pyridine In dichloromethane; acetonitrile at 50℃; for 2h;97%
306296-91-3

2-methyl-4-(piperidin-4-yl)-1-[1-(4-trifluoromethylphenyl)ethyl]piperazine

2148-56-3

2-chloro-6-aminobenzoic acid

C26H32ClF3N4O

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;80%
2148-56-3

2-chloro-6-aminobenzoic acid

75-36-5

acetyl chloride

20829-96-3

5-chloro-1H-benzo[d][1,3]oxazine-2,4-dione

Conditions
ConditionsYield
With chloroformic acid ethyl ester In 1,4-dioxane at 50℃; for 11h; Heating / reflux;97%
2148-56-3

2-chloro-6-aminobenzoic acid

75-36-5

acetyl chloride

4743-17-3

5-Chloroisatoic anhydride

Conditions
ConditionsYield
Stage #1: 2-chloro-6-aminobenzoic acid With chloroformic acid ethyl ester In 1,4-dioxane for 1h; Heating / reflux;
Stage #2: acetyl chloride In 1,4-dioxane at 50℃; for 10h;
97%
2148-56-3

2-chloro-6-aminobenzoic acid

39885-08-0

(2-amino-6-chlorophenyl)methanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃;95%
With borane-THF In tetrahydrofuran at 0 - 30℃; for 1.66667h; Inert atmosphere;88%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h;87%
6061-04-7

1,1-dichloro-2-nitro ethylene

2148-56-3

2-chloro-6-aminobenzoic acid

2-chloro-6-(2-nitroacetamido)benzoic acid

Conditions
ConditionsYield
In water at 50℃; for 6h; Temperature; Green chemistry;95%
2148-56-3

2-chloro-6-aminobenzoic acid

731007-25-3

2-amino-3,5,6-trichloro-benzoic acid

Conditions
ConditionsYield
With N-chloro-succinimide In N,N-dimethyl-formamide at 80 - 90℃;95%
852029-79-9

{(1S)-1-[4-phenyl-1-(propylsulfonyl)piperidin-4-yl]ethyl}amine

2148-56-3

2-chloro-6-aminobenzoic acid

852029-50-6

2-amino-6-chloro-N-((4-phenyl-1-(propylsulfonyl)piperidin-4-yl)methyl)benzamide

Conditions
ConditionsYield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Polystyrene;94%
2148-56-3

2-chloro-6-aminobenzoic acid

74-88-4

methyl iodide

41632-04-6

methyl 6-chloroanthranilate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;82%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;82%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 18h;56%
2148-56-3

2-chloro-6-aminobenzoic acid

18107-18-1

diazomethyl-trimethyl-silane

41632-04-6

methyl 6-chloroanthranilate

Conditions
ConditionsYield
In methanol; hexane; benzene at 20℃; for 1h;91%
2148-56-3

2-chloro-6-aminobenzoic acid

79-04-9

chloroacetyl chloride

127603-58-1

6-Chloro-4,1-benzoxazepin-2,5-dione

Conditions
ConditionsYield
With sodium hydroxide In N-methyl-acetamide; water91%
306297-33-6

C19H28F3N3

2148-56-3

2-chloro-6-aminobenzoic acid

C26H32ClF3N4O

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine90%
16502-01-5

tetrahydrobetacarboline

2148-56-3

2-chloro-6-aminobenzoic acid

(2-amino-6-chlorophenyl)(1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indol-2-yl)methanone

Conditions
ConditionsYield
With triethylamine; HATU89%
2148-56-3

2-chloro-6-aminobenzoic acid

5918-97-8

4-chloro-1,3-dihydro-2H-benzoimidazol-2-one

Conditions
ConditionsYield
With sodium azide; ammonium chloride; trichlorophosphate; N,N-dimethyl-formamide at 0 - 20℃; Curtius rearrangement;88%
2148-56-3

2-chloro-6-aminobenzoic acid

108-24-7

acetic anhydride

5627-73-6

5-chloro-2-methyl-4-oxo-4H-benzo[d][1,3]oxazine

Conditions
ConditionsYield
at 130℃; for 6h; Inert atmosphere;87%
at 130℃;78%
Reflux;76%
for 0.666667h; cyclocondensation; Heating;32%
for 2h; Reflux;
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

2148-56-3

2-chloro-6-aminobenzoic acid

62-53-3

aniline

1615680-13-1

tert-butyl (S)-2-(5-chloro-4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: 1-(tert-butoxycarbonyl)-L-proline; 2-chloro-6-aminobenzoic acid With triphenyl phosphite In pyridine at 70℃; for 2h;
Stage #2: aniline In pyridine at 70℃; for 2h;
86%
Stage #1: 1-(tert-butoxycarbonyl)-L-proline; 2-chloro-6-aminobenzoic acid With pyridine; triphenyl phosphite at 70℃;
Stage #2: aniline at 70 - 80℃;
2148-56-3

2-chloro-6-aminobenzoic acid

77-78-1

dimethyl sulfate

41632-04-6

methyl 6-chloroanthranilate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;86%
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;75.8%
55183-45-4

hex-5-in-carboxyl chloride

2148-56-3

2-chloro-6-aminobenzoic acid

5-chloro-2-(pent-4-yn-1-yl)-4H-3,1-benzoxazin-4-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;86%
22065-57-2

ethyl 2-phenyldiazoacetate

2148-56-3

2-chloro-6-aminobenzoic acid

2-chloro-6-((2-ethoxy-2-oxo-1-phenylethyl)amino)benzoic acid

Conditions
ConditionsYield
With C43H37Br2CuN3P2(1+)*ClO4(1-) In methanol at 0 - 20℃; for 8h; Schlenk technique; Inert atmosphere; chemoselective reaction;85%
2148-56-3

2-chloro-6-aminobenzoic acid

79-30-1

isobutyryl chloride

57334-25-5

5-chloro-2-isopropyl-4H-3,1-benzoxazin-4-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;85%
189999-35-7

[1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate

2148-56-3

2-chloro-6-aminobenzoic acid

2′-iodo-[1,1′-biphenyl]-2-yl 2-amino-6-chlorobenzoate

Conditions
ConditionsYield
With copper(l) iodide; 1,10-Phenanthroline; sodium carbonate In 1,4-dioxane at 95℃; for 17h; Molecular sieve; Green chemistry;84%
With copper(l) iodide; 1,10-Phenanthroline; sodium carbonate In 1,4-dioxane at 95℃; for 17h; Sealed tube;
2148-56-3

2-chloro-6-aminobenzoic acid

54166-95-9

2-amino-6-chlorobenzamide

Conditions
ConditionsYield
Stage #1: 2-chloro-6-aminobenzoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: With ammonium hydroxide In tetrahydrofuran at 20℃; for 23h;
83%
Stage #1: 2-chloro-6-aminobenzoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: With ammonium hydroxide at 20℃; for 23h;
83%
Multi-step reaction with 2 steps
1: pyridine / dichloromethane; acetonitrile / Inert atmosphere
2: ethanol; ammonia / 2 h / 20 °C
View Scheme
7031-27-8

(phenylthio)acetic acid chloride

2148-56-3

2-chloro-6-aminobenzoic acid

1265087-53-3

2-chloro-6-(2-phenylsulfanyl-acetylamino)benzoic acid

Conditions
ConditionsYield
Stage #1: (phenylthio)acetic acid chloride; 2-chloro-6-aminobenzoic acid With sodium hydroxide In water at 0 - 20℃; for 3h;
Stage #2: With hydrogenchloride In water pH=4 - 5;
82%
2148-56-3

2-chloro-6-aminobenzoic acid

3030-19-1

2-amino-5-bromo-6-chlorobenzoic acid

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 16h;82%
2148-56-3

2-chloro-6-aminobenzoic acid

90-04-0

2-methoxy-phenylamine

371243-74-2

2-Amino-6-chloro-N-(2-methoxyphenyl)benzamide

Conditions
ConditionsYield
With thionyl chloride In dichloromethane; chloroform; benzene81%
Stage #1: 2-chloro-6-aminobenzoic acid With sulfuryl dichloride In benzene for 24h; Heating / reflux;
Stage #2: 2-methoxy-phenylamine In chloroform at 65℃; for 2h;
2148-56-3

2-chloro-6-aminobenzoic acid

75-03-6

ethyl iodide

172217-11-7

ethyl 2-amino-6-chlorobenzoate

Conditions
ConditionsYield
Stage #1: 2-chloro-6-aminobenzoic acid With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: ethyl iodide In N,N-dimethyl-formamide at 20℃; for 48h;
80%
In N,N-dimethyl-formamide; mineral oil; Petroleum ether
In N,N-dimethyl-formamide; mineral oil; Petroleum ether
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Chemistry

IUPAC Name: 2-amino-6-chlorobenzoic acid 
Empirical Formula: C7H6ClNO2
Molecular Weight: 171.581g/mol
EINECS: 218-416-8 
Structure of 2-Amino-6-chlorobenzoic acid (CAS NO.2148-56-3):

Index of Refraction: 1.648
Molar Refractivity: 42.31 cm3
Molar Volume: 116.1 cm3
Polarizability: 16.77×10-24cm3
Surface Tension: 65.9 dyne/cm
Density: 1.476 g/cm3
Flash Point: 159 °C
Enthalpy of Vaporization: 61.5 kJ/mol 
Melting Point: 158-160 °C(lit.)
Boiling Point: 339.3 °C at 760 mmHg
Vapour Pressure: 3.61E-05 mmHg at 25°C 
Physical Appearance: white to light yellow crystal powder
Product Categories: benzene derivative;Amino Acids and Derivatives;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Organic acids 
Canonical SMILES: C1=CC(=C(C(=C1)Cl)C(=O)O)N
InChI: InChI=1S/C7H6ClNO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,9H2,(H,10,11)
InChIKey: SZCPTRGBOVXVCA-UHFFFAOYSA-N

Uses

 2-Amino-6-chlorobenzoic acid (2148-56-3)is used as intermediate for medicine and pesticides.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
Hazard Note: Irritant

Specification

First Aid Measures of 2-Amino-6-chlorobenzoic acid (2148-56-3):
Ingestion:Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Skin:Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Eyes:Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Storage of 2-Amino-6-chlorobenzoic acid (2148-56-3):
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.