2-Chlorotrityl chloride Chemical Properties

Melting point:

130-135 °C

Boiling point:

421.3±40.0 °C(Predicted)

Density 

1.222±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in Chloroform, methanol and dichloromethane, insoluble in water

form 

Powder

color 

Pale yellow crystalline powder

BRN 

1983914

CAS DataBase Reference

42074-68-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25-22

RIDADR 

3261

WGK Germany 

3

F 

10-21

HS Code 

2903 99 80

HazardClass 

8

PackingGroup 

III

MSDS

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

2-Chlorotrityl chloride Usage And Synthesis

Chemical Properties

off-white to yellow or brown beads

Uses

2-Chlorotrityl chloride is used as an intermediate of clotrimazole. It is also used in the preparation of modified trityl nucleosides as inhibitors of P. falciparum dUTPase. In addition, it serves as a protecting group reagent for carboxylic acids forming esters.

Application

2-Chlorotrityl Chloride is used in convergent peptide synthesis. Extremely acid labile resin for preparing peptide acids and partially protected peptide fragments by the Fmoc strategy. Cleavage can be effected by using AcOH/TFE/DCM or 0.5% TFA.

Preparation

2-Chlorotrityl chloride synthesis: It is esterified with 2-Chlorobenzoic acid and ethanol in the presence of sulfuric acid or p-toluenesulfonic acid to generate Ethyl 2-Chlorobenzoate, which is then condensed with phenylmagnesium bromide (Grignard reaction) to obtain (2-Chlorophenyl)diphenylmethanol magnesium salt is hydrolyzed with sulfuric acid to obtain (2-Chlorophenyl)diphenylmethanol, which is then chlorinated with thionyl chloride to obtain the product.

Biotechnological Applications

The 2-chlorotrityl chloride (2-CTC) resin is one of the most frequently used and most versatile resins for the large-scale manufacture of peptides. It is slightly less acid-labile than Trityl Resin and thus more widely used in solid phase peptide synthesis. Peptides UBI-8 and UBI-9 were synthesized by Fmoc-solid phase chemistry using a 2-chlorotrityl chloride linker-resin. Trityl linkers have certain advantages in comparison to the alkoxybenzyl alcohol (eg. Wang resin), especially in the area of peptide chemistry. First, the problem of racemization during the loading of the first amino acid (using DIPEA) is avoided with trityl linkers. Second, due to steric factors, no diketopiperazine formation is observed.

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