ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Hydrocarbon halides 1-Bromo-2,3-difluorobenzene

1-Bromo-2,3-difluorobenzene

Product Name1-Bromo-2,3-difluorobenzene
CAS38573-88-5
MFC6H3BrF2
MW192.99
EINECS609-564-8
MOL File38573-88-5.mol

Chemical Properties

Boiling point	234 °C (765 mmHg)
Density	1.724 g/mL at 25 °C(lit.)
refractive index	n20/D 1.509(lit.)
Flash point	142 °F
storage temp.	2-8°C
form	clear liquid
color	Colorless to Almost colorless
Specific Gravity	1.724
InChIKey	RKWWASUTWAFKHA-UHFFFAOYSA-N
CAS DataBase Reference	38573-88-5(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,F
Risk Statements	36/37/38
Safety Statements	26-36/37/39-37/39
RIDADR	1993
WGK Germany	3
Hazard Note	Flammable
HazardClass	3.2
PackingGroup	III
HS Code	29039990

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

Clear colorless to peach liquid

Uses

1-Bromo-2,3-difluorobenzene may be used in the synthesis of potent, orally active Calcitonin gene-related peptide (CGRP) receptor antagonist (BMS-846372). It may be used in the preparation of 2,3-difluorophenyl(dimethyl)phosphane.

Uses

intermediate for liquid crystal and drugs

General Description

Microbial oxidation of 1-bromo-2,3-difluorobenzene by Pseudomonas putida strain 39/D and Escherichia coli recombinant microorganism (strain JM 109(pDTG601)) has been reported.

Synthesis

Add 50% aqueous solution of KOH (18.0 g, 160 mmol) to a mixture of 1-bromo-5,5,6,6-tetrafluorocyclohex-1-ene (11.65 g) and triethylbenzylammonium chloride (0.15 g, 0.7 mmol) at 30-35°C for 30 minutes. Keep the reaction mixture at 75-85°C for 2 hours. Cool the reaction mixture. Dilute the reaction mixture with water. Extract the organic product with CH2Cl2. Dry the organic product over CaCl2. Distill the organic product. 1H NMR (CDCl3, 300.1 MHz), δ: 7.00-7.16 (m, 1H, Ar); 7.17-7.29 (m, 1H, Ar); 7.34-7.47 (m, 1H, Ar). 13C NMR (CDCl3, 75.5 MHz), δ: 110.40 (d, C(1), J = 17.5 Hz); 116.40 (d, C(4), J = 17.7 Hz); 124.70 (dd, C(5), J = 7.1 Hz, J = 5.0 Hz); 128.23 (d, C(6), J = 3.6 Hz); 148.10 (dd, C(2), J = 248.8 Hz, J = 14.3 Hz); 150.92 (dd, C(3), J = 251.9 Hz, J = 13.3 Hz). 19F NMR (CDCl3, 282.4 MHz), δ: -130.9 (m, 1 F, Ar), -134.8 (m, 1 F, Ar). BP 157-158°C. Elemental Analysis Found (%): C, 37.54; H, 1.50. C6H3BrF2. Calculated (%): C, 37.34; H, 1.52. Mass Spec MS, m/z (Irel (%)): 194, 192 [M]+ (100, 99), 113 [M-Br]+ (88), 63 (60).

Fig The synthetic method of 1-Bromo-2,3-difluorobenzene