| Identification | More | [Name]
5-Amino-2-chlorobenzoic acid | [CAS]
89-54-3 | [Synonyms]
2-AMINO-4-CARBOXY-5-CHLOROBENZENE
2-CHLORO-5-AMINO BENZOIC ACID
3-AMINO-6-CHLOROBENZOIC ACID
3-CARBOXY-4-CHLOROANILINE
4-AMINO-2-CARBOXY-1-CHLOROBENZENE
5-AMINO-2-CHLOROBENZOIC ACID
5-amino-2-chloro-benzoicaci
5-Amino-2-Chlorobenzoic Acid 2-Chloro-5-Aminobenzoic Acid
sodium salt of mnitrobenzoic acid
5-AMINO-2-CHLOROBENZOIC ACID TECH. 85%
2,5-CABA
5-Amino-2-chlorobenzoic acid, 98+% | [EINECS(EC#)]
201-916-5 | [Molecular Formula]
C7H6ClNO2 | [MDL Number]
MFCD00007845 | [Molecular Weight]
171.58 | [MOL File]
89-54-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
184-188 °C (lit.) | [Boiling point ]
250°C (rough estimate) | [density ]
1.5 | [refractive index ]
1.5570 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
479mg/l | [form ]
powder to crystal | [pka]
1.99±0.25(Predicted) | [color ]
White to Light yellow | [BRN ]
2090422 | [InChI]
InChI=1S/C7H6ClNO2/c8-6-2-1-4(9)3-5(6)7(10)11/h1-3H,9H2,(H,10,11) | [InChIKey]
GVCFFVPEOLCYNN-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC(N)=CC=C1Cl | [CAS DataBase Reference]
89-54-3(CAS DataBase Reference) | [EPA Substance Registry System]
89-54-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29224999 |
| Hazard Information | Back Directory | [Chemical Properties]
White solid | [Uses]
5-Amino-2-chlorobenzoic Acid is a reagent in the preparation of potent and selective benzothiazole hydrazone inhibitors of Bcl-XL. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
General procedure for the synthesis of 5-amino-2-chlorobenzoic acid from 2-chloro-5-nitrobenzoic acid: 75 g of 2-chloro-5-nitrobenzoic acid, 59 g of iron powder, 800 mL of ethanol, 150 mL of water, and 115 g of ammonium chloride were added to a reaction flask equipped with a stirrer. The mixture was heated to 78-80°C and the reaction was refluxed for 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent was petroleum ether/ethyl acetate=1:3) during the reaction. Upon completion of the reaction, the reaction mixture was filtered while hot and the solids were washed with 150 mL of hot ethanol. The filtrate was dried at 60°C to obtain the crude product. Subsequently, the crude product was dissolved in 400 mL of ethyl acetate and heated to reflux pulping for 2 hours. The mixture was cooled to 0~5°C in a salt bath and then naturally reduced to room temperature and crystallized for more than 30 minutes. The crystals were separated by centrifugation and washed with 50 mL of ethyl acetate. Finally, it was dried under reduced pressure at 50°C to give 60.7 g of yellow solid 5-amino-2-chlorobenzoic acid with 99.1% purity and 95.1% yield. | [References]
[1] Arzneimittel-Forschung/Drug Research, 1982, vol. 32, # 3, p. 183 - 186
[2] Chemical and Pharmaceutical Bulletin, 1988, vol. 36, # 9, p. 3462 - 3467
[3] Patent: CN106748721, 2017, A. Location in patent: Paragraph 0029; 0030
[4] Angewandte Chemie - International Edition, 1999, vol. 38, # 18, p. 2777 - 2779
[5] Justus Liebigs Annalen der Chemie, 1868, vol. 147, p. 258 |
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