TRIPHENYLCHLOROMETHANE

PRODUCT IDENTIFICATION
CAS NO. 76-83-5

TRIPHENYLCHLOROMETHANE

EINECS NO. 200-986-4
FORMULA (C6H5)3CCl
MOL WT. 278.78

H.S. CODE

 2903.69.0008

TOXICITY

 Mouse LD50 (intravenous):180mg/kg
SYNONYMS

Trityl Chloride; Triphenylmethyl chloride;

alpha-Chlorotriphenylmethane; 1,1',1''-(Chloromethylidyne)trisbenzene; Chlorotriphenylmethane;

SMILES

C(c1ccccc1)(c1ccccc1)(c1ccccc1)Cl

CLASSIFICATION

Protecting and Derivatizing reagent. Tritylation agent

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white to yellow powder
MELTING POINT 110 - 112 C
BOILING POINT

310 C

SPECIFIC GRAVITY

 

SOLUBILITY IN WATER Insoluble
pH  
VAPOR DENSITY

9.6

log Pow 5.25 (Octanol-water)
VAPOR PRESSURE 3.87E-06 (mmHg at 25 C)
HENRY'S LAW 1.36E-05 (atm-m3/mole at 25 C)
OH RATE 1.29E-11 (cm3/molecule-sec at 25 C Atmospheric)

REFRACTIVE INDEX

 

NFPA RATINGS

  

AUTOIGNITION

 

FLASH POINT

 

STABILITY Stable under normal conditions (Moisture sensitive)

GENERAL DESCRIPTION & EXTERNAL LINKS
The term "trityl " refers to a triphenylmethanyl compound in which three phenyl rings are bonded to a single carbon. Trityl anion stabilized by extensive delocalization over three phenyl rings absorbs the visible region of the spectrum and originates brilliant and fluorescent red to violet colors.  Triphenylmethane is the basic skeleton of many dyes. Trityl chloride (an efficient tritylation and subsequent detritylation agent) is an Intermediate for dyes and pharmaceuticals such as zidovudine (also called azidothymidine ), an antiviral drug used in the treatment of AIDS (acquiredimmune deficiency syndrome) and of AIDS-related complex and other organic synthesis.

Wikipedia Linking: http://en.wikipedia.org/wiki/Trityl_chloride

http://www.sigmaaldrich.com/
One of the common difficulties with natural product and other multi-step syntheses is the need to render one functional group inert to a particular reagent while keeping another group open for further chemical elaboration. Despite the great advances made in the involved syntheses of multifunctional products, selectivity in functional group transformations remains a critical issue in organic synthesis. Unfortunately for the synthetic chemist, there is no perfect protecting group applicable to any functional group in any situation. Thus, the need exists for the synthetic chemist to have a handy toolbox of selective and efficient protecting groups that can be applied and easily removed under a variety of conditions....
F-Trityl Alcohol and Chlorides:Several fluorous versions of trityl protecting groups are available from Sigma-Aldrich for the protection of alcohols, amines and carboxylates. These include F-Trt, F-MMT, and F-DMT that are analogous to the conventional trityl, monomethoxy trityl, and dimethoxy trityl groups and react analogously to their non-fluorous counterpart. Each of these groups is acid labile with the relative rate of deprotection being F-Trt < F-MMT < F-DMT. The F-DMT group has recently been used in oligonucleotide synthesis followed by purification through F-SPE. 

http://journals.tubitak.gov.tr/
N-triphenylmethyl and N-4,4'-dimethoxytriphenylmethyl of o-aminophenol, m-aminophenol, and paminophenol compounds were easily prepared from triphenylmethyl chloride and 4,4'-dimethoxytriphenylmethyl chloride. S-triphenylmethyl-2-mercapto ethanol was also selectively synthesized using the triphenylmethyl chloride and 2-mercapto ethanol. The reactivity of nitrogen and sulfur versus oxygen in the protection reactions was compared. In principle, the protection of aminophenols and 2-mercapto ethanol with triarylmethyls (trityls) may take place on the oxygen. However, in this framework, we discuss the di erent reactivities of oxygen, nitrogen and sulfur towards triphenylmethyl chloride (TrCl) and 4,4'-dimethoxytriphenylmethyl chloride (DMTrCl) and  nd that nitrogen and sulfur are more reactive than oxygen......
SALES SPECIFICATION

APPEARANCE

 white to yellow powder

CONTENT

97.5% min

MELTING POINT

 109 C min
LOSS ON DRYING

0.5% max
RESIDUE ON IGNITION

0.2% max
TRANSPORTATION
PACKING
25kgs in  Bag
HAZARD CLASS 8 (Packing Group: III)
UN NO. 3261
OTHER INFORMATION
Hazard Symbols: C, Risk Phrases: 34, Safety Phrases: 24/25