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T83801

Sigma-Aldrich

Trityl chloride

97%

Synonym(s):

Chlorotriphenylmethane, Triphenylchloromethane, Triphenylmethyl chloride

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About This Item

Linear Formula:
(C6H5)3CCl
CAS Number:
76-83-5
Molecular Weight:
278.78
Beilstein:
397363
EC Number:
200-986-4
MDL number:
MFCD00000813
UNSPSC Code:
12352101
PubChem Substance ID:
24900525
NACRES:
NA.22
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Assay

97%

bp

230-235 °C/20 mmHg (lit.)

mp

109-112 °C (lit.)

SMILES string

ClC(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C19H15Cl/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

InChI key

JBWKIWSBJXDJDT-UHFFFAOYSA-N

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Application

Protecting reagent for amines, alcohols, and thiols.[1][2]
Trityl chloride can be used as a catalyst:
  • In Ritter type synthesis of 1-amidoalkyl-2-naphtols through a one-pot three-component reaction of naphthol, aryl aldehydes and acetonitrile.[3]
  • 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.[4]
  • In the preparation of amido alkyl phenols via one-pot, multi-component reaction of phenols, aromatic aldehydes, and amides under solvent-free conditions.[5]
  • In one-pot, multi-component synthesis of substituted piperidines using aromatic aldehydes, amines, and β-ketoesters.[6]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF4297V
WXBD9072V
WXBD2015V
WXBD6336V
WXBD6165V

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Trityl chloride as an efficient organic catalyst for one-pot, five-component and diastereoselective synthesis of highly substituted piperidines
Sajadikhah SS, et al.
Research on Chemical Intermediates, 40(2), 723-736 (2014)
Trityl chloride as an efficient organic catalyst for the synthesis of 1-amidoalkyl-2-naphtols in neutral media at room temperature
Khazaei A, et al.
Applied Catalysis A: General, 386(1-2), 179-187 (2010)
Tetrahedron Letters, 48, 5017-5017 (2007)
One pot synthesis of 1, 2, 4, 5-tetrasubstituted-imidazoles catalyzed by trityl chloride in neutral media
Moosavi-Zare AR, et al.
Royal Society of Chemistry Advances, 4(105), 60636-60639 (2014)
J S Davidson et al.
Biochimica et biophysica acta, 847(1), 1-7 (1985-10-30)
Intercellular junctional communication was measured using [14C]citrulline incorporation in co-cultures of argininosuccinate synthetase-deficient and argininosuccinate lyase-deficient human fibroblasts. Triphenylmethane, triphenylmethylchloride and tetraphenylboron inhibited communication at concentrations at least 12-fold lower than cytotoxic concentrations. This inhibition was of rapid onset and
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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