| Identification | More | [Name]
5-Fluoroindole-2-carboxylic acid | [CAS]
399-76-8 | [Synonyms]
2-CARBOXY-5-FLUOROINDOLE
5-FLUORO-1H-INDOLE-2-CARBOXYLIC ACID
5-FLUOROINDOLE-2-CARBOXYLIC ACID
AKOS JY2082860
TIMTEC-BB SBB010058
5-Fluoroindole-2-carboxylicacid,99%
5-Fluoroindole-2-carboxylic acid 99%
5-Fluoro-2-indolecarboxylic acid
5-F-ICA
5-Fluoroindole-2-carboxylic acid, 98+% | [EINECS(EC#)]
206-919-5 | [Molecular Formula]
C9H6FNO2 | [MDL Number]
MFCD00005612 | [Molecular Weight]
179.15 | [MOL File]
399-76-8.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow-brown crystalline powder | [Melting point ]
259 °C (dec.)(lit.)
| [Boiling point ]
422.2±25.0 °C(Predicted) | [density ]
1.3231 (estimate) | [storage temp. ]
0-6°C | [form ]
Crystalline Powder | [pka]
4.27±0.30(Predicted) | [color ]
Yellow-brown | [Water Solubility ]
Insoluble | [BRN ]
153217 | [InChI]
InChI=1S/C9H6FNO2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,(H,12,13) | [InChIKey]
WTXBRZCVLDTWLP-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=C(F)C=C2)C=C1C(O)=O | [CAS DataBase Reference]
399-76-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,F | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R15:Contact with water liberates extremely flammable gases.
R10:Flammable. | [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 .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S36:Wear suitable protective clothing .
S7/8:Keep container tightly closed and dry . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow-brown crystalline powder | [Uses]
5-Fluoroindole-2-carboxylic acid,is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff. | [Definition]
ChEBI: 5-fluoro-1H-indole-2-carboxylic acid is an indolyl carboxylic acid. | [General Description]
5-Fluoroindole-2-carboxylic acid is an antagonist of the glycine site within the NMDA (N-methyl-D-aspartate) receptor complex. | [Synthesis]
General procedure for the synthesis of 5-fluoroindole-2-carboxylic acid from ethyl 5-fluoroindole-2-carboxylate: 103.6 g of ethyl 5-fluoroindole-2-carboxylate was dissolved in a mixed solution consisting of 31.25 g of 96% sodium hydroxide, 183 mL of methanol, and 183 mL of water, and heated at reflux for 1 hour. After the reaction was completed, the reaction solution was cooled to 50 °C, and the pH was adjusted to 3-4 by slowly adding 10% hydrochloric acid solution dropwise.After the reaction solution was completely cooled, the precipitate was collected by filtration to obtain 84.7 g of off-white 5-fluoroindole-2-carboxylic acid in 95% yield, which was shown to contain ≥96% by HPLC analysis. | [References]
[1] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0040; 0043
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 3149 - 3157
[4] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1954, vol. 297, p. 229,233
[5] Journal of the Chemical Society, 1955, p. 1283,1284 |
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