1-Bromo-4-tert-butylbenzene Chemical Properties

Melting point:

13-16 °C(lit.)

Boiling point:

80-81 °C2 mm Hg(lit.)

Density 

1.229 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.533(lit.)

Flash point:

97 °C

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

color 

Clear colorless to slightly yellow

Specific Gravity

1.229

Water Solubility 

Insoluble in water.

BRN 

1859117

InChI

InChI=1S/C10H13Br/c1-10(2,3)8-4-6-9(11)7-5-8/h4-7H,1-3H3

InChIKey

XHCAGOVGSDHHNP-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

3972-65-4(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1-bromo-4-(1,1-dimethylethyl)-(3972-65-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-24/25-37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29036990

MSDS

• Language:English Provider:1-Bromo-4-(1,1-dimethylethyl)benzene
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1-Bromo-4-tert-butylbenzene Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid

Uses

1-Bromo-4-tert-butylbenzene was used in the synthesis of 4-tert-butyl-phenylboronic acid1, 1-deoxy analogs of CP-47,497 (n = 0 to 7) and 1-deoxy analogs of CP-55,940 (n = 0 to 7). It undergoes lithium-bromide exchange reactions with n-butyllithium and tert-butyllithium at 0°C in various solvents.

General Description

1-Bromo-4-tert-butylbenzene undergoes lithium-bromide exchange reactions with n-butyllithium and tert-butyllithium at 0°C in various solvents.

Synthesis

Iron powder (0.03 mmol) was added to a solution of tert-butylbenzene (1.0 mmol) in dichloromethane (0.15 mL) at 0°C and under argon protection. Bromine (1.05 mmol) was added slowly and the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was washed with 1 M NaOH solution and subsequently extracted with dichloromethane (3×). The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by distillation under reduced pressure (about 100 °C, 120 Pa) to give a colorless oily liquid in 80% yield.

References

[1] Tetrahedron Letters, 2003, vol. 44, # 30, p. 5747 - 5750
[2] RSC Advances, 2014, vol. 4, # 92, p. 51016 - 51021
[3] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443
[4] Journal of Organic Chemistry, 1988, vol. 53, # 23, p. 5545 - 5547
[5] Russian Journal of General Chemistry, 2010, vol. 80, # 3, p. 451 - 454

1-Bromo-4-tert-butylbenzene(3972-65-4)Related Product Information

• tert-Butyldimethylsilyl chloride
• 2-Bromo-2-methylpropane
• Methyl 4-tert-butylbenzoate
• Ethylbenzene
• tert-Butylhydroquinone
• tert-Butyl hydroperoxide
• 4-tert-Butylaniline
• 4-tert-Butylcatechol
• tert-Butyl methyl ether
• 2-tert-Butylphenol
• tert-Butylbenzene
• Allylbenzene
• 4-tert-Butylphenol
• 4-tert-Butylcyclohexyl acetate
• 3-Bromoanisole
• Benzene
• DI-TERT-BUTYL ETHER
• 4-tert-Butylbenzaldehyde