| Identification | More | [Name]
2-Chloro-6-fluorobenzoic acid | [CAS]
434-75-3 | [Synonyms]
2-CHLORO-6-FLUOROBENZOIC ACID
LABOTEST-BB LT00454355
RARECHEM AL BO 0022
Benzoic acid, 2-chloro-6-fluoro-
2-Chloro-6-fluorobenzoic acid, 98+%
2-Chloro-6-fluorobenzoic acid 97%
2-Chloro-6-fluorobenzoicacid97%
2-CHLORO-6-FLUROBENZOIC ACID pure | [EINECS(EC#)]
207-105-2 | [Molecular Formula]
C7H4ClFO2 | [MDL Number]
MFCD00002417 | [Molecular Weight]
174.56 | [MOL File]
434-75-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White to light yellow crystal powder | [Melting point ]
155-157 °C(lit.) | [Boiling point ]
263.7±20.0 °C(Predicted) | [density ]
1.4016 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
2.04±0.10(Predicted) | [color ]
White to Gray to Brown | [BRN ]
973857 | [InChI]
InChI=1S/C7H4ClFO2/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3H,(H,10,11) | [InChIKey]
XNTIGDVFBDJLTQ-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=C(F)C=CC=C1Cl | [CAS DataBase Reference]
434-75-3(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Chloro-6-fluorobenzoic acid(434-75-3) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R37/38:Irritating to respiratory system and skin .
R36:Irritating to the eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163900 |
| Hazard Information | Back Directory | [Chemical Properties]
White to light yellow crystal powder | [Uses]
2-Chloro-6-fluorobenzoic Acid is a versatile reactant used in the synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling with aryl iodides. Also used in the preparation of fluorinated biaryls and heterobiaryls using copper catalyzed decarboxylative cross-coupling of aryl and heteroalyl iodides or bromides with potassium polyfluorobenzoates. | [General Description]
2-Chloro-6-fluorobenzoic acid is a two-fold halogenated derivative of benzoic acid. | [Synthesis]
General procedure for the synthesis of 2-chloro-6-fluorobenzoic acid from 2-chloro-6-fluorobenzaldehyde: H3PO4 (454 mg, 3.78 mmol) was added to a solution of 2-chloro-6-fluorobenzamide (1.0 g, 6.31 mmol) in 25 mL of THF and 10 mL of H2O. The reaction mixture was stirred at room temperature for 10 min, followed by the addition of NaClO (1.88 g, 20.81 mmol) and 1.4 mL H2O2 (30% w/w). The reaction was continued to be stirred for 3 h at room temperature. After completion of the reaction, the reaction mixture was extracted with EtOAc. The combined organic layers were washed with 1 M NaOH aqueous solution. The combined aqueous layer was acidified with 1 M HCl aqueous solution to pH ≈ 1 and extracted again with EtOAc. The combined organic layers were washed with brine and dried with anhydrous Na2SO4. After filtration, the solvent was removed in vacuum to afford 1.10 g (99% yield) of 2-chloro-6-fluorobenzoic acid as a colorless solid, which could be used without further purification.1H NMR (400 MHz, CDCl3) δ: 7.44-7.37 (m, 1H), 7.31-7.27 (m, 1H) , 7.10-7.07 (m, 1H). | [References]
[1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] Patent: WO2018/52903, 2018, A1. Location in patent: Page/Page column 47-48
[3] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1967 - 1970
[4] Chemische Berichte, 1936, vol. 69, p. 2253,2255
[5] Tetrahedron Letters, 1988, vol. 29, # 16, p. 1967 - 1970 |
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