1522-13-0

Basic information

• Product Name: 1,1,3-Triphenylpropargyl alcohol
• Synonyms: RARECHEM AM UC 0715;TIMTEC-BB SBB009045;1,1,3-TRIPHENYL-2-PROPYN-1-OL;1,1,3-TRIPHENYL-PROP-2-YN-1-OL;1,1,3-TRIPHENYLPROPARGYL ALCOHOL;LABOTEST-BB LT00159755;2-Propyn-1-ol, 1,1,3-triphenyl-;Benzenemethanol, alpha-phenyl-alpha-(phenylethynyl)-
• CAS NO: 1522-13-0
• Molecular Formula: C₂₁H₁₆O
• Molecular Weight: 284.35
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives
• Mol File: 1522-13-0.mol
• Article Data: 51

Chemical Properties

• Melting Point: 80-82 °C(lit.)
• Boiling Point: 220 °C / 1mmHg
• Flash Point: 215.473 °C
• Appearance: Slightly yellow powder
• Density: 1.183 g/cm³
• Vapor Pressure: 1.15E-09mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 11.31±0.29(Predicted)
• CAS DataBase Reference: 1,1,3-Triphenylpropargyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,3-Triphenylpropargyl alcohol(1522-13-0)
• EPA Substance Registry System: 1,1,3-Triphenylpropargyl alcohol(1522-13-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39-36/37/39-22
• WGK Germany: 3
• Hazardous Substances Data: 1522-13-0(Hazardous Substances Data)

Usage

Chemical Properties

Slightly yellow powder

Uses

1,1,3-Triphenylpropargyl Alcohol is used as a reagent in the chemical synthesis of several organic compounds including that of polysubstituted 4H-thiopyrans from β-oxodithioesters and the one-pot synthesis of pyrazoles via a four-step cascade sequence.

General Description

1,1,3-Triphenylpropargyl alcohol can be used in the synthesis of a single isomer of a naphthalene compound.

InChI:InChI=1/C21H16O/c22-21(19-12-6-2-7-13-19,20-14-8-3-9-15-20)17-16-18-10-4-1-5-11-18/h1-15,22H

Upstream product

• 2216-94-6 phenylpropynoic acid ethyl ester 
• 119-61-9 benzophenone 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 59738-55-5 trimethyl-(1,1,3-triphenylprop-2-ynyloxy)silane 
• 101-48-4 phenylacetaldehyde dimethyl acetal 
• 536-74-3 phenylacetylene 
• 932-88-7 1-iodo-2-phenylethyne 
• 91-01-0 1,1-Diphenylmethanol 
• 675825-21-5 Lithium enolate of the acetaldehyde 
• 90-99-3 diphenylchloromethane 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 6607-46-1 (1,2-dibromovinyl)benzene 
• 56024-62-5 3-acetoxy-1,3,3-triphenylpropyne 
• 67-64-1 acetone 

Downstream Products

• 849-01-4 1,3,3-triphenylprop-2-en-1-one 
• 6880-25-7 1,1,3-triphenylpropan-1-ol 
• 2115-19-7 ethyl 1,1,3-triphenyl-2-propynyl ether 
• 871877-19-9 hexaphenyl-hexa-1,5-diyne 
• 90496-59-6 1,1-Dimethyl-3-phenyl-2-((Z)-1-phenyl-propenyl)-1H-indene 
• 90496-60-9 1,1-Dimethyl-2-(2-methyl-1-phenyl-propenyl)-3-phenyl-1H-indene 
• 116607-64-8 2-(p-nitrophenyl)-4-phenyl-3-benzoylchromane 
• 90496-61-0 1-Methyl-1,3-diphenyl-2-(1-phenyl-vinyl)-1H-indene 
• 117552-48-4 E-5-phenyl-pent-2-en-4-ynoic acid ethyl ester 
• 99203-88-0 C₄₂H₃₀ 
• 517-51-1 5,6,11,12-tetraphenylnaphthacene 
• 1018449-86-9 1-(2-chloroethoxy)-1,1,3-triphenylprop-1-yne 
• 1018449-87-0 3-(benzyloxy)-1,3,3-triphenylprop-1-yne 
• 1160855-17-3 C₂₉H₃₂OSi 

Relevant articles and documents

Triaryl methane derivatives as antiproliferative agents

Clotrimazole (CLT) 1, a synthetic anti-fungal imidazole derivative, inhibits tumor cell proliferation and angiogenesis. In the current study, flow cytometric analysis demonstrated that the decrease in tumor cell growth by CLT 1 was associated with inhibition of cell cycle progression at the G 1-S phase transition, resulting in G0-G1 arrest. A series of CLT 1 analogues has been generated in order to develop CLT 1 derivatives that are devoid of the imidazole moiety which is responsible for the hepatoxicity associated with CLT 1 while retaining CLT 1 efficacy. The majority of these analogues demonstrate in vitro antiproliferative activity ranging from submicromolar to micromolar concentrations.

Bimetal Cooperatively Catalyzed Arylalkynylation of Alkynylsilanes

An unprecedented Pd/Rh cooperatively catalyzed arylalkynylation of alkynylsilanes was developed to merge an alkynylidene moiety with benzosilacycle. These silaarenes possess a particular aggregation-induced emission behavior. Mechanistic investigations demonstrate that the relay trimetallic transmetalation plays a pivotal role in governing this transformation.

Calcium-Catalyzed Intramolecular Hydroamination-Deacylation Reaction of in situ formed β-Amino Allenes

We have developed a simple, One-Pot, three-component reaction of tert-propargyl alcohols, primary amines and acyl ketones to synthesize fully substituted pyrroles and pyridine derivatives in good to excellent yields with large substrate diversity. An eco-friendly calcium catalyst catalyzes the reaction to form the key intermediate β-amino allene that undergoes subsequent Thorpe-Ingold effect assisted hydroamination and aromaticity driven deacylation reaction to yield fully substituted five and six-membered azacyclic compounds. (Figure presented.).

Synthesis of 1H-Pyrrolo[1,2-a]indoles via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with 2-Ethynylanilines

A novel highly efficient, environmentally benign Lewis acid-catalyzed, and protection-free protocol for the construction of valuable polycyclic products bearing a 1H-pyrrolo[1,2-a]indole scaffold is described, starting from readily available propargylic alcohols and 2-ethynylanilines. The one-pot transformation entails the cleavage of one C?O bond, and the construction of two C?N bonds and one C?C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.