3-Fluoro-5-bromophenol

3-Fluoro-5-bromophenol Property

Melting point:

42 °C

Boiling point:

52-55 °C(Press: 9.98e-2 Torr)

Density 

1.764±0.06 g/cm3(Predicted)

Flash point:

110 °C

storage temp. 

2-8°C

form 

powder to crystal

pka

8.01±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C6H4BrFO/c7-4-1-5(8)3-6(9)2-4/h1-3,9H

InChIKey

JCPJGUPQZDEZQH-UHFFFAOYSA-N

SMILES

C1(O)=CC(F)=CC(Br)=C1

CAS DataBase Reference

433939-27-6(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29081990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Fluoro-5-bromophenol Chemical Properties,Usage,Production

Chemical Properties

light yellow crystalline

Uses

3-Fluoro-5-bromophenol is mainly used as an intermediate in organic synthesis, especially in the fields of medicine, pesticides and materials science.

Synthesis

General procedure for the synthesis of 3-bromo-5-fluorophenol from 3,5-difluorobromobenzene: potassium tert-butoxide (76.6 g, 0.682 mol) was added to a solution of 1-bromo-3,5-difluorobenzene (30.6 mL, 0.266 mol) and 2-(methanesulfonyl)ethanol (66 g, 0.531 mol) in dimethylsulfoxide (DMSO, 240 mL) and the reaction was carried out at 0 °C. The reaction mixture was stirred at room temperature for 3 h, followed by slow quenching with 4 N hydrochloric acid to pH < 1. The reaction mixture was extracted several times with ether (Et2O, 12 L) until no product was detected in the aqueous phase. The ether phase was concentrated under reduced pressure to one-third of the original volume and then washed with 1N sodium hydroxide (NaOH, 12 L). After adjusting the sodium hydroxide solution to pH=3, it was again extracted with ether until no product was detected in the aqueous phase. The ether phases were combined, the solvents were evaporated under reduced pressure, and the residue was purified by alumina (Al2O3) column chromatography using ether as eluent to afford 3-bromo-5-fluorophenol as a colorless oil (48 g, 94% yield). The product was analyzed by LC-MS showing the molecular ion peak m/z 190.33 ([M+H]+); the analytical HPLC retention time was 2.26 min (mobile phase: 0-100% acetonitrile/water with 0.1% trifluoroacetic acid, run time 4 min); 1H NMR (400 MHz, CD3OD) δ ppm 6.88-6.64 (m, 2H), and 6.58-6.30 (m, 1H), 4.99 (s, 1H).

References

[1] Patent: WO2007/62308, 2007, A2. Location in patent: Page/Page column 220-221
[2] Synlett, 2009, # 4, p. 633 - 637
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 22, p. 9010 - 9026
[4] Patent: WO2007/62342, 2007, A1. Location in patent: Page/Page column 176; 205
[5] Patent: US2007/161685, 2007, A1. Location in patent: Page/Page column 115