Triphenylmethyl Chloride Chemical Properties

Melting point:

109-112 °C(lit.)

Boiling point:

230-235 °C20 mm Hg(lit.)

Density 

1.1088 (rough estimate)

refractive index 

1.6281 (estimate)

Flash point:

230-235°C/20mm

storage temp. 

Store below +30°C.

solubility 

chloroform: 0.1 g/mL, clear

form 

Powder or Crystals

color 

White to off-white or light yellow-beige

Water Solubility 

Insoluble in water. Soluble in chloroform, hexane, benzene, ether, acetone and tetrahydrofuran.

Sensitive 

Lachrymatory

BRN 

397363

CAS DataBase Reference

76-83-5(CAS DataBase Reference)

NIST Chemistry Reference

Triphenylmethyl chloride(76-83-5)

EPA Substance Registry System

Chlorotriphenylmethane (76-83-5)

Safety Information

Hazard Codes 

C,N

Risk Statements 

34-50/53-14-36/37

Safety Statements 

26-36/37/39-45-61-27

RIDADR 

UN 3261 8/PG 3

WGK Germany 

3

RTECS 

PA6450000

F 

10-19-21

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29036990

Hazardous Substances Data

76-83-5(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 5000 mg/kg

MSDS

• Language:English Provider:alpha-Chlorotriphenylmethane
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Triphenylmethyl Chloride Usage And Synthesis

Chemical Properties

Triphenylmethyl chloride or trityl chloride (TrCl) is a white to yellow solid. Insoluble in water, easily soluble in benzene, carbon disulfide, petroleum ether, slightly soluble in alcohol and ether, and becomes trityl alcohol after absorbing water. It is an alkyl halide, sometimes used to introduce the trityl protecting group.

Uses

Trityl Chloride is an alkyl halide commonly used in organic synthesis to introduce the trityl protecting group. Trityl Chloride is used in the preparation of S-trityl-L-cysteine (STLC), a tight-bindin g inhibitor of Eg5 that prevents mitotic progression.

Application

Triphenylmethyl Chloride acts as a protecting reagent for amines, alcohols, and thiols. It can be used as a catalyst:
Efficient method of tritylation of sensitive compounds and their subsequent detritylation.
In Ritter type synthesis of 1-amidoalkyl-2-naphtols through a one-pot three-component reaction of naphthol, aryl aldehydes and acetonitrile.
In the synthesis of 1,2,4,5-tetrasubstituted imidazoles via a one-pot multi-component reaction of benzil with aldehydes, primary amines, and ammonium acetate.
In the preparation of amido alkyl phenols via one-pot, multi-component reaction of phenols, aromatic aldehydes, and amides under solvent-free conditions.
In one-pot, multi-component synthesis of substituted piperidines using aromatic aldehydes, amines, and β-ketoesters.

Preparation

Triphenylmethyl Chloride may be prepared by the reaction of triphenylmethanol with acetyl chloride, or by the Friedel–Crafts alkylation of benzene with carbon tetrachloride to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed.

Purification Methods

Crystallise trityl chloride from iso-octane. Also crystallise it from 5 parts of pet ether (b 90-100o) and 1 part of acetyl chloride using 1.8g of solvent per g of chloride. Dry it in a desiccator over soda lime and paraffin wax. [Bachman Org Synth Coll Vol III 841 1955, Thomas & Rochow J Am Chem Soc 79 1843 1957, Moisel et al. J Am Chem Soc 108 4706 1986, Beilstein 5 H 750, 5 I 346, 5 II 615, 5 III 2315, 5 IV 2497.] It is moisture sensitive and LACHRYMATORY,

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