2-Chlorotrityl chloride
Synonym(s):2-Chlorotrityl chloride;Chloro(2-chlorophenyl)diphenylmethane
- CAS NO.:42074-68-0
- Empirical Formula: C19H14Cl2
- Molecular Weight: 313.22
- MDL number: MFCD00040399
- EINECS: 255-647-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-09-12 21:58:09
What is 2-Chlorotrityl chloride?
Chemical properties
off-white to yellow or brown beads
The Uses of 2-Chlorotrityl chloride
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.
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.
Properties of 2-Chlorotrityl chloride
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 for 2-Chlorotrityl chloride
Signal word | Warning |
Pictogram(s) |
Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H290:Corrosive to Metals H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P234:Keep only in original container. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 2-Chlorotrityl chloride
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SHIVAM PETROCHEM INDUSTRIES
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Horizon Chemicals
Sibram Pharmaceutical
Navone Specialties (OPC) Pvt Ltd
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