alpha-2-Chloroisodurene Chemical Properties

Melting point:

87-89 °C(lit.)

Boiling point:

140 °C15 mm Hg(lit.)

Density 

1.0131 (estimate)

refractive index 

1.5162 (estimate)

Flash point:

223 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

Fused Solid, Crystals, and/or Chunks

color 

White

BRN 

386678

Stability:

Air Sensitive, Moisture Sensitive

CAS DataBase Reference

1585-16-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34-20/21/22

Safety Statements 

26-27-28-36/37/39-45-23

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

RTECS 

DP1402000

HazardClass 

8

PackingGroup 

II

HS Code 

29036990

MSDS

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alpha-2-Chloroisodurene Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

2,4,6-Trimethylbenzyl Chloride (cas# 1585-16-6) is a compound useful in organic synthesis.

General Description

α²-Chloroisodurene undergoes coupling reaction with methylmagnesium iodide to yield 1,2-dimesitylethane.

Synthesis

General procedure for the synthesis of 2,4,6-trimethylbenzyl chloride from 2,4,6-trimethylbenzyl alcohol: 2,4,6-trimethylbenzyl alcohol (150 mg, 1.0 mmol) was dissolved in dichloromethane (DCM, 4 mL). Thionyl chloride (87 μL, 1.2 mmol) was added slowly at 0 °C. The reaction mixture was stirred for 1 h at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure to afford the target product 2,4,6-trimethylbenzyl chloride (168 mg, 100% yield) as a white powder. The product was identified by 1H NMR (300 MHz, CDCl3): δ 2.29 (s, 3H), 2.42 (s, 6H), 4.68 (s, 2H), 6.89 (s, 2H). Mass spectrometry analysis showed [M + H]+ peak at 133.

References

[1] Patent: WO2016/16238, 2016, A1. Location in patent: Page/Page column 126
[2] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1397 - 1405
[3] Organic Letters, 2002, vol. 4, # 11, p. 1975 - 1977
[4] Journal of Medicinal Chemistry, 1981, vol. 24, # 4, p. 382 - 389
[5] Synlett, 2014, vol. 25, # 18, p. 2639 - 2643

alpha-2-Chloroisodurene(1585-16-6)Related Product Information

• TRIMETHYLTIN CHLORIDE
• 2-Chloropropane
• Diethylstilbestrol
• 2-Chloro-2-methylpropane
• Trimethoprim
• Thionyl chloride
• tert-Butyldimethylsilyl chloride
• Sodium chloride
• Ammonium chloride
• Polyvinyl chloride
• Calcium chloride
• Triisopropylsilyl chloride
• Choline chloride
• Chloromethyl isopropyl carbonate
• Chlorotriethylsilane
• Pivaloyl chloride
• Potassium chloride
• Methylene Chloride