2-Bromo-4-methylbenzaldehyde Chemical Properties

Melting point:

30-35 °C (lit.)

Boiling point:

114-115 °C(Press: 5 Torr)

Density 

1.490±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder

color 

Yellow

Sensitive 

Air Sensitive

InChI

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

InChIKey

MUZMDYCVUCMIDC-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(C)C=C1Br

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29124990

MSDS

• Language:English Provider:SigmaAldrich

2-Bromo-4-methylbenzaldehyde Usage And Synthesis

Chemical Properties

White to yellow solid

Uses

2-Bromo-4-methylbenzaldehyde is a useful intermediate for organic synthesis.

Uses

Reactant involved in:

• Carbonylative Stille couplings followed by isomerization and intramolecular Heck reactions
• Knoevenagel condensation
• Cyclization of N-(α-methyl-p-methoxybenzyl)-imino-esters
• Imination and oxidative heterocyclization / carbonylation
• Intramolecular amination
• Intermolecular and intramolecular hydroacylation of alkenes by aromatic aldehydes

Uses

Reactant involved in:• ;Carbonylative Stille couplings followed by isomerization and intramolecular Heck reactions1• ;Knoevenagel condensation2• ;Cyclization of N-(α-methyl-p-methoxybenzyl)-imino-esters3• ;Imination and oxidative heterocyclization / carbonylation4• ;Intramolecular amination5• ;Intermolecular and intramolecular hydroacylation of alkenes by aromatic aldehydes6

Synthesis

General method: benzyl alcohol substrate (2-bromo-4-methylphenyl) methanol (0.2 mmol), FeCl3-6H2O (0.002 mmol, 5.4 mg) and triphenylmethanol (0.2 mmol, 52 mg) were mixed in a dry reaction vessel. Subsequently, the reaction mixture was heated at 55 °C for 1 h under microwave radiation. Upon completion of the reaction, the crude product was purified by fast column chromatography to afford the target product 2-bromo-4-methylbenzaldehyde.

References

[1] New Journal of Chemistry, 2017, vol. 41, # 22, p. 13377 - 13381
[2] Tetrahedron, 2015, vol. 71, # 38, p. 6744 - 6748

2-Bromo-4-methylbenzaldehyde(824-54-4)Related Product Information

• 2-Bromo-4-methylbenzoic acid
• p-Tolualdehyde
• 3-Bromoanisole
• Benzyl bromide
• Bromotrimethylsilane
• 4-Dimethylaminobenzaldehyde
• 3-(Trifluoromethyl)benzaldehyde
• 4-(Trifluoromethyl)benzaldehyde
• BROMOPENTAMETHYLBENZENE
• Cyclohexylmethyl bromide
• Bromine
• TOLUALDEHYDES
• 5-BROMO-2-METHYLBENZALDEHYDE
• 3-BROMO-4-METHYLBENZALDEHYDE DIMETHYL ACETAL
• 2-bromo-5-methylbenzaldehyde
• 2-Bromo-4-methylbenzaldehyde
• 3-BROMO-4-METHYLBENZALDEHYDE