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ChemicalBook--->CAS DataBase List--->458-09-3

458-09-3

458-09-3 Structure

458-09-3 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack 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 InformationBack Directory
[Chemical Properties]

White to beige crystalline powder
[Synthesis]

3-Fluoro-4-methoxyphenylacetic acid

452-14-2

3-FLUORO-4-HYDROXYPHENYLACETIC ACID

458-09-3

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.,
Spectrum DetailBack Directory
[Spectrum Detail]

3-FLUORO-4-HYDROXYPHENYLACETIC ACID(458-09-3)MS
3-FLUORO-4-HYDROXYPHENYLACETIC ACID(458-09-3)1HNMR
3-FLUORO-4-HYDROXYPHENYLACETIC ACID(458-09-3)IR1
3-FLUORO-4-HYDROXYPHENYLACETIC ACID(458-09-3)IR2
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

3-Fluoro-4-hydroxyphenylacetic acid, 98%(458-09-3)
[Alfa Aesar]

3-Fluoro-4-hydroxyphenylacetic acid, 98%(458-09-3)
[Sigma Aldrich]

458-09-3(sigmaaldrich)
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403-14-5 395-33-5 452-14-2 458-09-3

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