Identification | More | [Name]
3-FLUORO-4-HYDROXYPHENYLACETIC ACID | [CAS]
458-09-3 | [Synonyms]
3-FLUORO-4-HYDROXYPHENYLACETIC ACID 3-Fluoro-4-hydroxybenzeneacetic acid | [EINECS(EC#)]
207-275-8 | [Molecular Formula]
C8H7FO3 | [MDL Number]
MFCD00004348 | [Molecular Weight]
170.14 | [MOL File]
458-09-3.mol |
Chemical Properties | Back Directory | [Appearance]
White to beige crystalline powder | [Melting point ]
132-134 °C (lit.) | [Boiling point ]
320.3±27.0 °C(Predicted) | [density ]
1.423±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
4.30±0.10(Predicted) | [color ]
White to beige | [CAS DataBase Reference]
458-09-3(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 . S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29182900 |
Hazard Information | Back Directory | [Chemical Properties]
White to beige crystalline powder | [Synthesis]
General procedure for the synthesis of 3-fluoro-4-hydroxyphenylacetic acid from 3-fluoro-4-methoxyphenylacetic acid: Aluminum chloride (42.8 g, 0.32 mol) was slowly added to 500 mL of toluene solution containing 3-fluoro-4-methoxyphenylacetic acid (45 g, 0.245 mol), and the temperature of the reaction was controlled to be no more than 25 °C. Subsequently, the reaction mixture was heated to reflux for 5 hours. Upon completion of the reaction, 260 mL of 10% hydrochloric acid was added to the cooled solution. The precipitate was collected by filtration and the filtrate was extracted twice with 75 mL of 1,2-dichloroethane. The organic extracts were combined and washed sequentially with 5% sodium hydroxide solution and water. The alkaline washings were combined with the previously collected precipitate and filtered through activated carbon after adjusting the pH to 12 with 5% sodium hydroxide solution. The filtrate was acidified with 50% sulfuric acid and the resulting oil was extracted with ether. The organic phase was dried and the solvent was evaporated to give 3-fluoro-4-hydroxyphenylacetic acid in a yield of 25 g (62% yield). The melting point of the product was 109-111 °C. Mass spectrum (ESI) m/z (relative abundance): 193.0 [M + Na]+. | [Purification Methods]
Crystallise the acid from water. [Beilstein 10 III 440.] | [References]
[1] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 1, p. 296 - 306 [2] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 508 - 518 [3] Chemische Berichte, 1952, vol. 85, p. 577,580 [4] DRP/DRBP Org.Chem., |
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