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Triphenylmethyl Chloride

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Triphenylmethyl Chloride Basic information

Product Name:
Triphenylmethyl Chloride
Synonyms:
  • [Chloro(diphenyl)methyl]benzene
  • 1,1’,1’’-(chloromethylidyne)tris-benzen
  • 1,1’,1’’(-Chloromethylidyne)trisben-zene
  • chlorotriphenyl-methan
  • Methane, chlorotriphenyl-
  • CHLOROTRIPHENYLMETHANE
  • BENZENE, 1,1',1''-(CHLOROMETHYLIDYNE)TRIS-
  • TRT-CL
CAS:
76-83-5
MF:
C19H15Cl
MW:
278.78
EINECS:
200-986-4
Product Categories:
  • Regant series
  • Starting Raw Materials & Intermediates
  • Amino Acid Derivatives
  • Organics
  • N-Protecting Reagents
  • Biochemistry
  • Nucleosides, Nucleotides & Related Reagents
  • Protecting Agents for Hydroxyl and Amino Groups
  • Protecting Agents, Phosphorylating Agents & Condensing Agents
  • Protection & Derivatization Reagents (for Synthesis)
  • Synthetic Organic Chemistry
  • OLED materials,pharm chemical,electronic
  • API Intermediate
  • 1
  • bc0001
  • TOP2
  • 76-83-5
Mol File:
76-83-5.mol
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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)
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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
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

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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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