3-Bromo-4-methylbenzaldehyde

3-Bromo-4-methylbenzaldehyde Property

Melting point:

47-52℃

Boiling point:

79-86 °C(Press: 0.5 Torr)

Density 

1.490±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C8H7BrO/c1-6-2-3-7(5-10)4-8(6)9/h2-5H,1H3

InChIKey

WTXXUAHMTVAQHW-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(C)C(Br)=C1

CAS DataBase Reference

36276-24-1

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37/38-43

Safety Statements 

26-36/37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2913000090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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-Bromo-4-methylbenzaldehyde Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 3-bromo-4-methylbenzaldehyde from 3-bromo-4-methylbenzyl alcohol: To a solution of 3-bromo-4-methylbenzyl alcohol (4.5 g, 22.4 mmol) in chloroform (100 mL) was added manganese dioxide (15 g, 172 mmol). The reaction mixture was refluxed under stirring in an oil bath at 70°C for 18 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the solvent was removed under vacuum to give the crude product. The crude product was purified by column chromatography (150 mL SiO2, eluent was a mixture of ethyl acetate and hexane, 1:9, v/v) to afford 3-bromo-4-methylbenzaldehyde (3.2974 g, 74% yield) as a white crystalline solid. The product characterization data were as follows: 1H NMR (400 MHz, CDCl3) δ 9.91 (s, 1H), 8.02 (d, J = 1.6 Hz, 1H), 7.70 (dd, J = 7.6, 1.6 Hz, 1H), 7.39 (d, J = 8.0 Hz, 1H), 2.47 (s, 3H); 13C NMR (100.6 MHz CDCl3) δ 190.4, 145.1, 135.8, 133.4, 131.3, 128.3, 125.6, 23.4; GC-MS (M)+ C8H7OBr calculated value 197.9680, measured value 197.9665.

References

[1] Patent: WO2013/40227, 2013, A2. Location in patent: Page/Page column 37; 38
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8432 - 8454
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 3973 - 4001
[4] Patent: US2003/195259, 2003, A1