4-Bromo-3-methylphenol Chemical Properties

Melting point:

59-61 °C (lit.)

Boiling point:

142-145 °C/23 mmHg (lit.)

Density 

1.3839 (rough estimate)

refractive index 

1.5772 (estimate)

Flash point:

142-145°C/23mm

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

form 

Crystalline Powder or Chunks

pka

9.51±0.18(Predicted)

color 

White to off-white

BRN 

1859122

InChI

InChI=1S/C7H7BrO/c1-5-4-6(9)2-3-7(5)8/h2-4,9H,1H3

InChIKey

GPOQODYGMUTOQL-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

14472-14-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

29081990

MSDS

• Language:English Provider:4-Bromo-m-cresol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Bromo-3-methylphenol Usage And Synthesis

Chemical Properties

white to off-white crystalline powder or chunks

Uses

4-Bromo-3-methylphenol may be used in the synthesis of bromo[2-methyl-4-[2-(t-butyldimethylsilyloxy)ethyloxy]phenyl]bis(triphenylphopshine)nickel(II) (protected alcohol-functionalized initiator) and bromo-[2-methyl-4-[6-(t-butyldimethylsilyloxy)hexyloxy]phenyl] bis(triphenylphosphine) nickel.

General Description

4-Bromo-3-methylphenol is a brominated phenol. It participates in the total synthesis of 3-methylcalix[4]arene.

Synthesis

General procedure for the synthesis of 4-bromo-3-methylphenol from m-cresol: (a) Preparation of 4-bromo-3-methylphenol: 80.0 g (740 mmol) of m-cresol and 400 mL of glacial acetic acid were added to a 2 L three-neck flask under nitrogen protection. The reaction mixture was cooled to 15 °C, 38 mL (742 mmol) of bromine was added slowly dropwise, and the reaction was stirred for 3 h at 15 °C maintaining the temperature. After completion of the reaction, the reaction solution was poured into 1 L of water and extracted with ether. The organic phase was separated and washed with water to neutral pH and subsequently dried with magnesium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was ground in heptane, filtered and dried to give 70 g (50% yield) of a white powdery product with a melting point of 55-56 °C.

References

[1] Letters in Organic Chemistry, 2018, vol. 15, # 8, p. 682 - 687
[2] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 11, p. 4187 - 4189
[3] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4267 - 4271
[4] Synlett, 2011, # 15, p. 2265 - 2269
[5] Journal of Chemical Research - Part S, 2003, # 9, p. 597 - 598

4-Bromo-3-methylphenol(14472-14-1)Related Product Information

• 3-Ethylphenol
• Xylenol
• o-Cresol
• 3-Trifluoromethylphenol
• 4-Bromophenol
• 3-Bromophenol
• Cresol
• m-Cresol
• p-Cresol
• 4-Bromo-2,6-dimethylaniline
• 4-Bromo-3-fluorobenzonitrile
• 4-Bromo-3-fluorobenzaldehyde
• 4-Bromo-2-chlorobenzonitrile
• 4-BROMO-2-METHYLANISOLE
• 4-Bromo-3-fluorobenzoic acid
• 4-Bromo-2-fluorobenzotrifluoride
• 4-Bromo-2-methyl-benzaldehyde
• 4-Bromo-2-fluoroanisole