4-tert-Butylbenzyl bromide Chemical Properties

Melting point:

8-12 °C (lit.)

Boiling point:

93-94 °C/1.5 mmHg (lit.)

Density 

1.236 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.545(lit.)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Liquid

color 

Clear light yellow

Specific Gravity

1.236

BRN 

471674

InChI

InChI=1S/C11H15Br/c1-11(2,3)10-6-4-9(8-12)5-7-10/h4-7H,8H2,1-3H3

InChIKey

QZNQSIHCDAGZIA-UHFFFAOYSA-N

SMILES

C1(CBr)=CC=C(C(C)(C)C)C=C1

CAS DataBase Reference

18880-00-7(CAS DataBase Reference)

NIST Chemistry Reference

p-tert-Butylbenzyl bromide(18880-00-7)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

19

HazardClass 

8

PackingGroup 

II

HS Code 

29036990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4-tert-Butylbenzyl bromide Usage And Synthesis

Chemical Properties

colorless to light yellow liquid

Uses

4-tert-Butylbenzyl bromide, a hydrophobic reactant, was used to keep the loaded mesoporous material particles under continuous stirring.

General Description

The nucleophilic substitution reaction of 4-tert-butylbenzyl bromide and potassium iodide was carried out in oil-in-water microemulsions based on various surfactants.

Synthesis

General procedure for the synthesis of 4-tert-butylbenzyl bromide from 4-tert-butyltoluene: Referring to Example 19 Preparation of N-(4-tert-butylbenzyl)methanamine (Alternative method), 4-tert-butyltoluene (14.8 g, 0.10 mol) was dissolved in carbon tetrachloride, and N-bromosuccinimide (17.8 g, 0.10 mol) and benzoyl peroxide (200 mg) were added . The reaction mixture was refluxed for 2 h and subsequently cooled to room temperature. The insoluble material was removed by filtration and the filtrate was washed with carbon tetrachloride. The filtrate was concentrated under reduced pressure and the resulting residue was dissolved in hexane and dried with magnesium sulfate. Finally, the solvent was evaporated under reduced pressure to give 22.7 g of 4-tert-butylbenzyl bromide (yield: 100%).

References

[1] Patent: US6586633, 2003, B1
[2] Patent: CN105315127, 2016, A. Location in patent: Paragraph 0044-0050
[3] Tetrahedron Letters, 2009, vol. 50, # 16, p. 1861 - 1865
[4] Synthesis, 2009, # 11, p. 1807 - 1810
[5] Synthetic Communications, 2010, vol. 40, # 7, p. 998 - 1003

4-tert-Butylbenzyl bromide(18880-00-7)Related Product Information

• tert-Butyl hydroperoxide
• 4-tert-Butylbenzylamine
• tert-Butylhydroquinone
• Methyl 4-tert-butylbenzoate
• Xylene
• 4-tert-Butylphenol
• Benzyl bromide
• tert-Butyl methyl ether
• tert-Butanol
• 4-tert-Butylcatechol
• Sodium bromate
• Ethidium bromide
• Allyl bromide
• Rocuronium bromide
• Benzene
• 4'-tert-Butyl-4-chlorobutyrophenone
• 4-tert-Butylbenzyl chloride
• 4-TERT-BUTYLPHENYLACETIC ACID