Triphenylmethyl chloride
[CAS# 76-83-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Benzylpyridine
• Name: Triphenylmethyl chloride
• Synonyms: alpha-Chlorotriphenylmethane; Triphenylchloromethane; Trityl chloride
• Molecular Formula: C₁₉H₁₅Cl
• Molecular Weight: 278.78
• CAS Registry Number: 76-83-5
• EC Number: 200-986-4
• SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl

Properties

• Solubility: 0.1 g/mL (chloroform) (Expl.)
• Density: 1.1±0.1 g/mL, Calc.^*
• Melting point: 109-113 °C (Expl.)
• Index of Refraction: 1.608, Calc.^*
• Boiling Point: 374.3 °C (760 mmHg), Calc.^*, 387.8-404.3 °C (Expl.)
• Flash Point: 177.9±12.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H314-H315-H335-H400-H410
• Safety Statements: P260-P261-P264-P271-P273-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P319-P321-P332+P317-P362+P364-P363-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1C	H314

• Transport Information: UN 3261

Discovery and Applications

Triphenylmethyl chloride, also known as trityl chloride, is an organic compound with the formula C19H15Cl. It is classified as a chlorinated derivative of triphenylmethane. The substance is primarily used in organic synthesis and has found applications in the preparation of various compounds in both laboratory and industrial settings.

Triphenylmethyl chloride was first synthesized in the late 19th century as part of research into the chemistry of triphenylmethane derivatives. It is most commonly utilized as a reagent in the formation of triphenylmethyl (trityl) derivatives. These derivatives are important in the synthesis of a variety of organic compounds, particularly in the field of pharmaceuticals and fine chemicals.

The primary application of triphenylmethyl chloride is in the introduction of the trityl group (C6H5)3C− to other organic molecules. The trityl group is a bulky, non-polar group that is often used to protect sensitive functional groups, particularly in the synthesis of complex organic molecules. For example, in carbohydrate chemistry, tritylation is frequently used to protect hydroxyl groups during multi-step synthetic procedures. The bulky trityl group prevents unwanted reactions at the protected position, which can be removed later when desired, typically through acidic conditions.

Another significant use of triphenylmethyl chloride is in the synthesis of various triphenylmethyl derivatives, which are employed as reagents or intermediates in organic synthesis. These derivatives have applications in the development of pharmaceutical compounds, as well as in the production of dyes and other specialty chemicals. Additionally, triphenylmethyl chloride has been employed in the preparation of stable radical species, which have been used in studies of chemical reactions and mechanisms.

Triphenylmethyl chloride has also been used in the preparation of certain ion-exchange resins, where it can react with amines or other nucleophiles to create functionalized resins for separation and purification applications. Furthermore, the compound has been studied for its potential role in the preparation of certain metal-organic frameworks, which are of interest in the field of materials science.

The use of triphenylmethyl chloride in organic synthesis has made it an important tool in the development of complex chemical compounds. Despite its utility, safety precautions must be observed when handling the compound, as triphenylmethyl chloride can be hazardous, especially in high concentrations or in closed systems.

In conclusion, triphenylmethyl chloride is a versatile reagent in organic synthesis, primarily used for the introduction of the trityl group in various chemical transformations. Its applications in protecting functional groups and preparing organic derivatives have made it valuable in pharmaceutical, chemical, and materials science.

References

2024. Synthesis of tert-Butyl N-(2-{[({1-Methyl-5-[(triphenylmethyl)amino]-1H-pyrazol-4-yl}amino)carbonyl]amino}ethyl)carbamate. Russian Journal of Organic Chemistry, 60(1).
DOI: 10.1134/s1070428024010160

2024. Evolution of Electronic Properties along the Path from a Covalent to a Tetrel Bond in the Synthesis of Tetraphenyl Substituted Compounds. Moscow University Chemistry Bulletin, 79(4).
DOI: 10.3103/s0027131424700275

2023. Carbocation Catalysis in the Synthesis of Heterocyclic Compounds. Chemistry of Heterocyclic Compounds, 59(1-2).
DOI: 10.1007/s10593-023-03157-3