Identification | More | [Name]
3-Fluoro-4-hydroxybenzaldehyde | [CAS]
405-05-0 | [Synonyms]
3-FLUORO-4-HYDROXYBENZALDEHYDE 4-HYDROXY-3-FLUOROBENZALDEHYDE | [EINECS(EC#)]
609-839-2 | [Molecular Formula]
C7H5FO2 | [MDL Number]
MFCD00016626 | [Molecular Weight]
140.11 | [MOL File]
405-05-0.mol |
Chemical Properties | Back Directory | [Melting point ]
121-124°C | [Boiling point ]
225.6±20.0 °C(Predicted) | [density ]
1.4710 (estimate) | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
powder to crystal | [pka]
6.52±0.18(Predicted) | [color ]
Light yellow to Yellow to Orange | [Sensitive ]
Air Sensitive | [BRN ]
3234259 | [InChI]
InChI=1S/C7H5FO2/c8-6-3-5(4-9)1-2-7(6)10/h1-4,10H | [InChIKey]
QSBHJTCAPWOIIE-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC=C(O)C(F)=C1 | [CAS DataBase Reference]
405-05-0(CAS DataBase Reference) |
Questions And Answer | Back Directory | [Uses]
3-Fluoro-4-hydroxybenzaldehyde can be used to synthesize 3-Cyclopropylmethoxy-4-difluoromethoxybenzoic Acid, which is an impurity and intermediate in the preparation of Roflumilast. |
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 . S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . S27:Take off immediately all contaminated clothing . | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29145090 |
Hazard Information | Back Directory | [Chemical Properties]
White crystalline powder | [Synthesis]
The general procedure for the synthesis of 3-fluoro-4-hydroxybenzaldehyde from 3-fluoro-4-methoxybenzaldehyde was as follows: 3-fluoro-4-methoxybenzaldehyde (1 g, 6.5 mmol) was mixed with boron tribromide (1 M solution in dichloromethane, 19.5 mmol) in dichloromethane, and the reaction was stirred for 24 hours under ice bath conditions. Upon completion of the reaction, an excess of anhydrous methanol was added to the reaction system, followed by removal of the solvent and the resulting trimethyl borate by distillation under reduced pressure. The residue was dissolved in methanol and again subjected to reduced pressure distillation to completely remove the residual trimethyl borate. The resulting solid residue was dissolved in ethyl acetate, the organic phase was washed with water (3 x 100 ml) and dried with anhydrous sodium sulfate. The organic solvent was removed by concentration under reduced pressure, and the crude product obtained was purified by silica gel column chromatography (eluent ratio of petroleum ether:ethyl ether=8:2) to finally obtain the pure 3-fluoro-4-hydroxybenzaldehyde. The yield was 91%; the melting point was 120-123 °C; the 1H NMR (CDCl3) data were as follows: δ 6.04 (s, exchangeable with D2O, 1H, OH); 7.16 (m, 1H, aromatic hydrogen); 7.62-7.67 (m, 2H, aromatic hydrogen); 9.86 (s, 1H, CHO). Elemental analysis results (C7H5FO2) Calculated values: C 60.01, H 3.60; measured values: C 59.93, H 3.77. | [References]
[1] European Journal of Medicinal Chemistry, 2014, vol. 71, p. 112 - 127 [2] Patent: WO2012/11125, 2012, A1. Location in patent: Page/Page column 88-89 [3] Journal of Medicinal Chemistry, 2000, vol. 43, # 4, p. 690 - 705 [4] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 14, p. 5032 - 5038 |
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