(5-bromo-2-nitrophenyl)methanol

(5-bromo-2-nitrophenyl)methanol Property

storage temp. 

Sealed in dry,Room Temperature

form 

wooly crystalline solid

color 

Cream (hint of peach)

Safety

HS Code 

2909498090

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.

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

(5-bromo-2-nitrophenyl)methanol Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of (5-bromo-2-nitrophenyl)methanol from 5-bromo-2-nitrobenzoic acid: to a solution of 5-bromo-2-nitrobenzoic acid (280 g, 1.14 mol, 1.0 eq.) in tetrahydrofuran (THF, 1.5 L) was slowly added dropwise a THF solution of 10 M borane-dimethyl sulfide (BH3-Me2S) (119.7 mL, 1.05 equivalent) for 30 min. After dropwise addition, the reaction mixture was heated to 70 °C and maintained at this temperature for 3 hours. Upon completion of the reaction, the mixture was cooled to 0 °C and methanol (MeOH, 100 mL) was slowly added to quench the reaction, followed by concentration under reduced pressure. To the concentrated residue was added a mixed petroleum ether/ethyl acetate solvent (1000 mL, 10:1 volume ratio) and stirred for 1 hour. The precipitate precipitated was collected by filtration to afford the target product (5-bromo-2-nitrophenyl)methanol (160 g, 689 mmol, 60.49% yield) as a white solid. The product was confirmed by 1H NMR (400 MHz, chloroform-d): δ=7.98-7.91 (m, 2H), 7.55 (dd, J=1.8,8.8 Hz, 1H), 4.97 (br.s., 2H), 2.77 (br.s., 1H). The mass spectrum (ESI) showed [M+H]+ peaks of 232.2/234.2.

References

[1] Patent: WO2018/68017, 2018, A1. Location in patent: Page/Page column 154; 156; 157
[2] Patent: US2017/190713, 2017, A1. Location in patent: Paragraph 0189
[3] Chemistry - A European Journal, 2012, vol. 18, # 12, p. 3706 - 3720
[4] Small, 2015, vol. 11, # 33, p. 4090 - 4096