5-Bromo-2-chlorophenol Chemical Properties

Melting point:

46-47

Boiling point:

234°C(lit.)

Density 

1.788±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

7.53±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C6H4BrClO/c7-4-1-2-5(8)6(9)3-4/h1-3,9H

InChIKey

UEVFFMZHGNYDKM-UHFFFAOYSA-N

SMILES

C1(O)=CC(Br)=CC=C1Cl

CAS DataBase Reference

183802-98-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-36/37

Hazard Note 

Corrosive

HS Code 

29089990

5-Bromo-2-chlorophenol Usage And Synthesis

Chemical Properties

Light yellow to White crystals

Synthesis

General procedure for the synthesis of 5-bromo-2-chlorophenol from 5-bromo-2-chloroanisole: BBr3 (8.2 mL, 84.9 mmol) was slowly added dropwise to a solution of 5-bromo-2-chloroanisole (18.26 g, 82.4 mmol) in dichloromethane (45 mL) under stirring conditions at 0-5 °C. The reaction mixture was stirred continuously for 4 hours at room temperature. Upon completion of the reaction, the mixture was carefully poured into a pre-cooled 2N NaOH/ice mixture and washed twice with tert-butyl methyl ether (TBME). The aqueous phase was acidified with 2N HCl to a suitable pH and then extracted again with TBME twice. All organic phases were combined and dried with anhydrous Na2SO4, followed by evaporation of the solvent under reduced pressure to afford the target product 5-bromo-2-chlorophenol as colorless crystals (16.35 g, 95% yield). The product was confirmed by 1H-NMR (400 MHz, DMSO-d6) and mass spectrometry (ES+) analysis: 1H-NMR δ (ppm): 6.97 (dd, 1H), 7.09 (d, 1H), 7.26 (d, 1H), 10.65 (bs, 1H, OH); MS (m/z) ES+: 210 (15), 208 (70, M+) , 206 (50), 179 (20), 177 (15), 63 (100).

References

[1] Patent: WO2007/91152, 2007, A1. Location in patent: Page/Page column 43
[2] Patent: US2006/25349, 2006, A1. Location in patent: Page/Page column 17
[3] Patent: US2006/35841, 2006, A1. Location in patent: Page/Page column 18
[4] Patent: WO2005/103054, 2005, A2. Location in patent: Page/Page column 158-159
[5] Patent: WO2003/105853, 2003, A1. Location in patent: Page 57

5-Bromo-2-chlorophenol(183802-98-4)Related Product Information

• 2-Chlorophenol
• BCDMH
• 4-Chlorophenol
• Chlorobromoisocyanurate
• 3-Bromophenol
• 5-Bromo-2-chlorobenzoic acid
• Bromine
• 3-Bromo-2-chlorophenol
• 1-BROMO-4-CHLORO-2-FLUORO-5-METHOXY-BENZENE
• 2,6-DIBROMO-4-CHLOROPHENOL
• 2-BROMO-4-CHLOROPHENOL,2-Bromo-4-chlorophenol, 98+%,2-Bromo-4-chlorophenol, 99+%
• 2-ACETYL-6-BROMO-4-CHLOROPHENOL
• 3-Bromo-5-chlorophenol
• 4,4'-[(3H-2,1-Benzoxathiole 2,2-dioxide)-3-ylidene]bis(2-bromo-6-chlorophenol),4,4'-(3H-2,1-benzoxathiol-3-ylidene)bis[2-bromo-6-chlorophenol] S,S-dioxide
• 2,2’-methylenebis(6-bromo-4-chlorophenol
• 4-BROMO-3-CHLOROPHENOL
• 4-BROMO-2-CHLOROPHENOL,4-Bromo-2-chlorophenol,98%
• 5-BROMO-2-CHLOROANISOLE