1726-94-9

Usage

Uses

Used in Organic Synthesis:
TRITYL ISOTHIOCYANATE is used as a reagent for the modification of amino acids and peptides, facilitating the creation of new bioactive molecules and materials due to its ability to react with nucleophiles.
Used in Chemical Research:
TRITYL ISOTHIOCYANATE is used as a building block in the synthesis of various organic compounds, contributing to the advancement of chemical knowledge and the development of novel chemical entities.
Used in Pharmaceutical Development:
TRITYL ISOTHIOCYANATE is used in the development of new drugs and pharmaceuticals, leveraging its reactivity to create potential therapeutic agents that could address unmet medical needs.

InChI:InChI=1/C20H15NS/c22-16-21-20(17-10-4-1-5-11-17,18-12-6-2-7-13-18)19-14-8-3-9-15-19/h1-15H

Upstream product

• 5961-98-8 thiocyanatochloride 
• 519-73-3 triphenylmethane 
• 505-14-6 thiocyanogen 
• 7511-40-2 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside 
• 127066-71-1 3,4,6-tri-O-acetyl-2-O-methyl-β-D-glucopyranosyl thiocyanate 
• 76-84-6 triphenylmethyl alcohol 
• 1858-25-9 phosphoryl-isothiocyanate 
• 99337-73-2 1,2,3,6-tetra-O-acetyl-4-O-trityl-β-D-glucopyranose 
• 1701-93-5 silver thiocyanate 
• 540-72-7 sodium thiocyanide 
• 1147550-11-5 ammonium thiocyanate 
• 5824-40-8 Triphenylmethylamin 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 163276-49-1 1-thiocyanatopyrrolidine-2,5-dione 

Downstream Products

• 4172-17-2 N-(N'-Triphenylmethylthiocarbamoyl)morpholin 
• 21198-26-5 4-triphenylmethyl-thiosemicarbazide 
• 21076-56-2 4-Triphenylmethyl-2-methyl-thiosemicarbazid 
• 20922-73-0 N-(diphenylmethyl)-N'-(triphenylmethyl)-thiourea 
• 596-31-6 methoxytriphenylmethane 
• 379-30-6 Trityl trifluoroacetate 
• 17714-77-1 trityl benzoate 
• 1727-16-8 S-trityl benzothioate 
• 6639-43-6 2,2,2-triphenylacetonitrile 
• 14309-25-2 trityl azide 
• 5824-40-8 Triphenylmethylamin 
• 1727-15-7 trityl thioacetic acid 
• 978-86-9 4-tritylphenol 
• 182934-27-6 1-Benzyl-5-(3-trityl-thioureidomethyl)-1H-imidazole-4-carboxylic acid amide 

Relevant academic research and scientific papers

Synthesis methods for isothiocyanate derivative

The invention discloses synthesis methods for an isothiocyanate derivative. The first synthesis method includes reacting raw materials, including primary amine, trifluoromethyltrimethylsilane, potassium fluoride and sulfur, with an organic solvent at the room temperature to obtain the isothiocyanate derivative. The synthetic isothiocyanate derivative has the advantages of simple operation, safety,high efficiency, non-toxicity, low raw material price, mild condition, high yield, wide application range of substrates, high compatibility of functional groups and the like. The second synthesis method includes reacting raw materials, including the primary amine, silver trifluoromethane and potassium bromide, with the organic solvent at the room temperature to obtain the isothiocyanate derivative. The isothiocyanate derivative has the advantages of simple operation, safety, high efficiency, easy availability of the raw materials, nearly quantitative yield, wide application range of the substrates, applicability to selective post-modification of drugs or complex compounds, and the like.

Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines

Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF3SiMe3, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines

The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o-phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one-pot process. Thiocarbonyl fluoride is generated in situ and is rapidly fully converted in one pot under mild conditions; therefore, no special safety precautions are needed.

2,4,4,6-Tetrabromo-2,5-cyclohexadienone as an efficient reagent for phosphine-free electrophilic transformation of alcohols and epoxides

In this study, 2,4,4,6-tetrabromo-2,5-cyclohexadienone (TABCO) was prepared and used successfully as a stable phosphine-free reagent for the conversion of alcohols into alkyl thiocyanates and epoxides into 2-hydroxythiocyanates. The reactions seem to proceed via in situ generation of electrophilic sulfur species by reaction of NH4SCN and TABCO. This combined reagent worked well with both alcohols and epoxides in acetonitrile solvent and under solvent-free conditions.

Facile and versatile synthesis of alkyl and aryl isothiocyanates by using triphosgene and cosolvent

A mild and efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH 3)2CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Phosphine-free conversion of alcohols into alkyl thiocyanates using trichloroisocyanuric acid/NH4SCN

A convenient and efficient phosphine-free procedure for the one-pot conversion of primary, secondary and tertiary alcohols into the corresponding alkyl thiocyanates or alkyl isothiocyanates is described using trichloroisocyanuric acid/NH4SCN.

In situ-generated N-thiocyanatosuccinimide (NTS) as a highly efficient reagent for the one-pot thiocyanation or isothiocyanation of alcohols

The first application of in situ-generated N-thiocyanatosuccinimide (NTS) for the thiocyanation of alcohols is described. This method can be easily applied for the facile conversion of primary, secondary and tertiary alcohols into the corresponding alkyl thiocyanates or alkyl isothiocyanates in good to excellent yields.

Oxalic acid-catalyzed reaction of alcohols with NaSCN: The effects of additives NaI and i2

Oxalic acid-mediated conversion of alcohols to thiocyante and/or isothiocyanate is described. Aliphatic tertiary alcohols give isothiocyanate by the reaction with NaSCN in the presence of I2, whereas they give thiocyanate without it. Copyright

Kinetic studies on the reactivity of triphenylmethyl cations adsorbed on silica, alumina, and aluminosilicate

The apparent rate constants ka?2 of different surface-mediated reactions of three nucleophiles 1,4-cyclohexadiene, triethylsilane, and isobutylvinyl ether with triphenylmethylium ions have been determined for three different solid acid catalysts and various triphenylmethylium precursors (R1R2R3C-X, X = SCN, OH, Cl, or Br). Generation of triphenylmethylium ions [R1R2R3C+] was used for kinetic measurements when R1R2R3C-X derivates are chemisorbed to the solid acid catalysts. The catalysis of those surface-mediated reactions by a silica, an alumina, and an aluminosilicate has been studied in a slurry of dichloromethane at ambient temperature. The value of ka?2 increases in the order OH- - - - and silica s of the corresponding HX from R1R2R3C-X or the acidity of the solid acid (Adolph, S.; Spange, S.; Zimmermann, Y. J. Phys. Chem. B 2000, 104, 6429-6438) indicating the importance of the effective surface concentration of [R1R2R3C+] on the apparent rate constant. It is also shown that the specific rate constant of the surface-mediated reaction can be interpreted in terms of Mayr's nucleophilicity parameters of the ??-nucleophile (N) and the pKR+ values of the carbenium ion derived from polar reactions in homogeneous solution.

A Convenient Synthesis of Tertiary Isothiocyanates and Acyl Isothiocyanates Using Phosphoryl Isothiocyanate.

Phosphoryl iosthiocyanate, PO(NCS)3, reacts readily with tertiary alcohols and carboxylic acids, giving the respective tertiary isothiocyanates and acyl isothiocyanates in good yields and purity.