2-Chlor-6-fluorbenzoesaeure

Bezeichnung:2-Chlor-6-fluorbenzoesaeure

CAS-Nr434-75-3

Englisch Name:2-Chloro-6-fluorobenzoic acid

CBNumberCB1688854

SummenformelC7H4ClFO2

Molgewicht174.56

MOL-Datei434-75-3.mol

Synonyma

2-Chlor-6-fluorbenzoesaeure

2-Chlor-6-fluorbenzoesaeure physikalisch-chemischer Eigenschaften

Schmelzpunkt	155-157 °C(lit.)
Siedepunkt	263.7±20.0 °C(Predicted)
Dichte	1.4016 (estimate)
storage temp.	Sealed in dry,Room Temperature
pka	2.04±0.10(Predicted)
Aggregatzustand	powder to crystal
Farbe	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 Datenbank	434-75-3(CAS DataBase Reference)
NIST chemische Informationen	2-Chloro-6-fluorobenzoic acid(434-75-3)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	36/37/38-37/38-36-20/21/22
S-Sätze:	26-36-37/39
WGK Germany	3
HazardClass	IRRITANT
HS Code	29163900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

2-Chloro-6-fluorobenzoic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R37/38:Reizt die Atmungsorgane und die Haut.
R36:Reizt die Augen.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
White to light yellow crystal powder
Verwenden
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.
Allgemeine Beschreibung
2-Chloro-6-fluorobenzoic acid is a two-fold halogenated derivative of benzoic acid.
Synthese

387-45-1

434-75-3

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).
Einzelnachweise
[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

2-Chloro-6-fluorobenzoic acid Upstream-Materialien And Downstream Produkte

2-Chlor-6-fluorbenzoesaeure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

434-75-3, 2-Chloro-6-fluorobenzoic acid Verwandte Suche:

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