| Identification | More | [Name]
METHYL 2,4-DIFLUOROBENZOATE | [CAS]
106614-28-2 | [Synonyms]
2,4-DIFLUORO-BENZOIC ACID METHYL ESTER
METHYL 2,4-DIFLUOROBENZOATE
RARECHEM AL BF 0213 | [EINECS(EC#)]
600-756-7 | [Molecular Formula]
C8H6F2O2 | [MDL Number]
MFCD03093799 | [Molecular Weight]
172.13 | [MOL File]
106614-28-2.mol |
| Chemical Properties | Back Directory | [Boiling point ]
128-129 °C (lit.) | [density ]
1.384 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.4840(lit.)
| [Fp ]
180 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
clear liquid | [color ]
Colorless to Light yellow to Light orange | [InChI]
InChI=1S/C8H6F2O2/c1-12-8(11)6-3-2-5(9)4-7(6)10/h2-4H,1H3 | [InChIKey]
YQUHULOBTDYMAG-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC=C(F)C=C1F | [CAS DataBase Reference]
106614-28-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless to yellow liquid | [Uses]
Methyl 2,?4-Difluorobenzoate is a reagent used in the synthesis of pharmaceuticals. Used in the design and synthesis of integrin αvβ3 antagonists displaying antiplatelet activity. | [Synthesis]
General procedure for the synthesis of methyl 2,4-difluorobenzoate from 2,4-difluorobenzoic acid:
1. 2,4-difluorobenzoic acid (1.5808 g, 10.00 mmol) was dissolved in methanol (15 mL) and cooled to 0 °C in an ice-water bath.
2. a methanol (10 mL) solution of thionyl chloride (1.46 mL, 20.02 mmol) was added slowly and dropwise to the above cooled mixture.
3. Gradually warm the reaction mixture to room temperature with continuous stirring for 24 hours.
4. Upon completion of the reaction, the mixture was poured into saturated aqueous NaHCO3 solution and extracted three times with ether.
5. The organic phases were combined and dried over anhydrous MgSO4.
6. The organic phase was concentrated under pressure and purified by silica gel column chromatography (eluent: hexane/ether=5/1) to give methyl 2,4-difluorobenzoate (1.6743 g, 97% yield).
7. The product was characterized by 1H-NMR (CDCl3): δ 7.99 (td, 1H, J=8.2,6.6 Hz), 6.98-6.84 (m, 2H), 3.93 (s, 3H). | [References]
[1] Patent: US6194461, 2001, B1 |
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