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

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

Uses

Used in Chemical Synthesis:
1,1,3-Triphenylpropargyl alcohol is used as a reagent for the chemical synthesis of several organic compounds. Its application is particularly notable in the synthesis of polysubstituted 4H-thiopyrans from β-oxodithioesters and the one-pot synthesis of pyrazoles via a four-step cascade sequence. This versatility in synthesis makes it a valuable tool for creating complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,1,3-Triphenylpropargyl alcohol is used as a key intermediate in the synthesis of various drug molecules. Its ability to participate in multiple reaction pathways allows for the creation of a wide range of pharmaceutical compounds, contributing to the development of new medications and therapies.
Used in Research and Development:
1,1,3-Triphenylpropargyl alcohol is also utilized in research and development settings, where it aids in the exploration of new chemical reactions and the synthesis of novel compounds. Its unique properties and reactivity make it an essential component in the advancement of organic chemistry and related fields.
Used in Material Science:
Within the material science industry, 1,1,3-Triphenylpropargyl alcohol can be employed in the development of new materials with specific properties. Its role in the synthesis of naphthalene compounds and other complex molecules can lead to the creation of advanced materials with applications in various industries, such as electronics, aerospace, and automotive.

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

• 109-72-8 n-butyllithium 
• 622-25-3 1-(2-chlorovinyl)benzene 
• 119-61-9 benzophenone 
• 1004-22-4 (phenylethynyl)sodium 
• 101-48-4 phenylacetaldehyde dimethyl acetal 
• 536-74-3 phenylacetylene 
• 56024-62-5 3-acetoxy-1,3,3-triphenylpropyne 
• 675825-21-5 Lithium enolate of the acetaldehyde 
• 932-88-7 1-iodo-2-phenylethyne 
• 91-01-0 1,1-Diphenylmethanol 
• 4440-01-1 lithium phenylacetylide 
• 591-50-4 iodobenzene 
• 3923-52-2 1,1-diphenyl-2-propyn-1-ol 
• 90-99-3 diphenylchloromethane 

Downstream Products

• 62155-40-2 propyl-(triphenyl-prop-2-ynyl)-ether 
• 90496-62-1 7-Benzhydrylidene-6-methyl-8-phenyl-bicyclo[4.2.0]oct-1⁽⁸⁾-ene 
• 116607-65-9 2,2-cyclohexyl-4-phenyl-3-benzoylchromane 
• 116575-91-8 2-methyl-2-vinyl-4-phenyl-3-benzoylchromane 
• 116575-89-4 2,2-dimethyl-4-phenyl-3-benzoylchromane 
• 90496-57-4 C₂₅H₂₂ 
• 90496-61-0 1-Methyl-1,3-diphenyl-2-(1-phenyl-vinyl)-1H-indene 
• 121507-64-0 phenyl-(triphenyl-prop-2-ynyl)-ether 
• 97924-55-5 5-chloro-5,6,11,12-tetraphenyl-5,12-dihydro-naphthacene 
• 2115-19-7 ethyl 1,1,3-triphenyl-2-propynyl ether 
• 2115-13-1 1-chloro-1,3,3-triphenylallene 
• 2115-14-2 bromo-triphenyl-allene 
• 849-01-4 1,3,3-triphenylprop-2-en-1-one 
• 850-65-7 3-methoxy-1,3,3-triphenylprop-1-yne 

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.

Gold-catalyzed tandem annulations of pyridylhomopropargylic alcohols with propargyl alcohols

A gold-catalyzed tandem annulation of propargylic alcohols and pyridylhomopropargylic alcohols is achieved, providing an atom-economical approach to a diverse set of polycyclic dihydrobenzofurans in good yields. The reaction proceeds via the 5-endo-dig cyclization/Meyer?Schuster rearrangement/Friedel?Crafts-type pathway. In this way, three C?C bonds and one C? O bond form to give a polycyclic skeleton in a one-pot process. Moreover, the products exhibit unique optical properties, which reveal their potential application value.

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.).

Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols

A new method for the efficient synthesis of hexahydro-1H-fluorene and octahydrobenzo[a]azulene derivatives through a ring-expansion strategy is reported. With an appropriate combination of thulium(III) trifluoromethanesulfonate and 13X molecular sieves, a range of unsaturated polycyclic compounds were obtained in good yields. Mechanism studies reveal that the reaction is more likely to undergo Meyer–Schuster rearrangement, ring expansion, and Friedel–Crafts-type pathways, which provide a conceptually different strategy for the ring opening of tertiary cycloalkanols.

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.

Br?nsted Acid Promoted Thermal-Ring-Rearrangement of Fluorenopyrans to 2-(1H-Inden-3-yl)-9H-fluoren-3-ols Bearing Two All-Carbon-Quaternary Centres

4-Aryl-fluorenopyrans bearing quaternary centre at C2 and C6 positions underwent a thermal-ring-rearrangement with a catalytic amount of pTsOH to furnish 2-(1H-inden-3-yl)-9H-fluoren-3-ols with two all carbon-quaternary centres, in which one is retained a

In Situ Generation of Allenes and their Application to One-Pot Assembly of Functionalized Fluoreno[3,2-b]furans by Calcium-Catalyzed, Regioselective, 3-Component Reactions

We have developed a novel synthetic methodology for the preparation of tetra-annulated fluorenofurans and fluorenopyrans using calcium(II)-catalyzed one-pot, three-component reaction. In this reaction, tert-propargyl alcohols react with 1,3-dicarbonyls to form tetra-substituted allenes, which are subsequently undergoing regiodivergent annulation with sec-propargyl alcohols to produce the fluorene-fused furan compounds. Broad substrate scope, regioselectivity, gram-scale synthesis, and benzylic functionalization of products are some of the highlights of this protocol.

Bi(OTf)3 catalyzed synthesis of acyclic β-sulfanyl ketones via a tandem Meyer-Schuster rearrangement/conjugate addition reaction

A new strategy to prepare acyclic β-carbonyl thioethers from propargyl alcohols and sulfur nucleophiles is reported. The investigation of the reaction substrates scope indicated that primary 3-aryl propargyl alcohols and thiols underwent the transformation smoothly. The reaction probably proceeded a Bi(OTf)3-catalyzed tandem Meyer-Schuster rearrangement of 3-aryl propargyl alcohol, followed by a thiol Michael conjugate addition of thiols to in situ generated α, β-unsaturated ketones. The method was 100% atom economic, high-yielding, and easy to handle, making it a valuable method for the construction of β-carbonyl sulfides.

Regiospecific formal [3 + 2] annulation of: Tert -propargyl alcohols with acyclic 1,3-diketones via the cycloisomerization of homoallenyl ketones

A one-pot, regiospecific synthesis of dihydrofurans bearing a quaternary centre and tetrasubstituted furans is developed from the formal [3 + 2] annulation of tert-propargyl alcohols and 1,3-diketones under Ca(ii)/DBU conditions. The reaction proceeds through the SN2I mechanism to form homoallenyl ketone and a subsequent cycloisomerization to yield novel and new chemical entities of privileged scaffolds.