ChemicalBook Product Catalog Organic Chemistry Hydrocarbons and derivatives Hydrocarbon halides 1-Bromo-4-tert-butylbenzene

1-Bromo-4-tert-butylbenzene

Product Name1-Bromo-4-tert-butylbenzene
CAS3972-65-4
MFC10H13Br
MW213.11
EINECS223-599-2
MOL File3972-65-4.mol

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
Storage Class	10 - Combustible liquids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2

MSDS

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

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

253185-03-4

3972-65-4

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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