| Identification | More | [Name]
5-Bromoindole-2-carboxylic acid | [CAS]
7254-19-5 | [Synonyms]
1H-INDOLE-2-CARBOXYLIC ACID, 5-BROMO-
5-BROMO-1H-INDOLE-2-CARBOXYLIC ACID
5-BROMO-2-INDOLECARBOXYLIC ACID
5-BROMOINDOLE-2-CARBOXYLIC ACID
AKOS JY2082545
5-bromoindole-2-carboxylicacid5-Bromoindole-2-carboxylicacid | [Molecular Formula]
C9H6BrNO2 | [MDL Number]
MFCD00022705 | [Molecular Weight]
240.05 | [MOL File]
7254-19-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
287-288 | [Boiling point ]
470.9±25.0 °C(Predicted) | [density ]
1.838±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [form ]
Solid | [pka]
4.25±0.30(Predicted) | [color ]
White to Light yellow to Light orange | [InChI]
InChI=1S/C9H6BrNO2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,(H,12,13) | [InChIKey]
YAULOOYNCJDPPU-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(Br)C=C2)C=C1C(O)=O | [CAS DataBase Reference]
7254-19-5(CAS DataBase Reference) |
| 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 .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Uses]
5-Bromoindole-2-carboxylic acid,Reactant involved in studies of biologically active molecules including:Discovery of indole inhibitors of MMP-13 for treatment of arthritic diseases1;Synthesis of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors2 ;cis-Diaminocyclohexane derivatives prepared for use as factor Xa inhibitors3 ;Synthesis of tubulin polymerization inhibitors and cancer cell growth inhibitors4 ;Preparation of dual PPARγ/δ agonists5;Synthesis of chemical probes to examine the role of hFPRL1 receptor .
| [Synthesis]
The general procedure for the synthesis of 5-bromoindole-2-carboxylic acid from ethyl 5-bromoindole-2-carboxylate was as follows: 134 g of ethyl 5-bromoindole-2-carboxylate was dissolved in a solvent mixture of 31.25 g of 96% methanol and 183 mL of water, and was heated and refluxed for 0.5 h. The reaction was completed with the addition of 10% hydrochloric acid. After completion of the reaction, it was cooled to 40 °C and the pH was adjusted to 3-4 by slowly adding 10% hydrochloric acid solution.Subsequently, the reaction mixture was filtered to give 109.1 g of off-white solid 5-bromoindole-2-carboxylic acid in 91% yield, which was analyzed by high-performance liquid chromatography (HPLC) and showed ≥96% purity. | [References]
[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 23, p. 7512 - 7527
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[3] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0050; 0053 |
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