29021-82-7

Basic information

• Product Name: 1-phenylbut-2-yne-1,4-diol
• Synonyms: 1-phenylbut-2-yne-1,4-diol
• CAS NO: 29021-82-7
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• Mol File: 29021-82-7.mol
• Article Data: 19

Chemical Properties

• Melting Point: 83 °C
• Boiling Point: 349.7°Cat760mmHg
• Flash Point: 176°C
• Appearance: /
• Density: 1.207g/cm³
• Vapor Pressure: 1.73E-05mmHg at 25°C
• Refractive Index: 1.603
• PKA: 12.21±0.20(Predicted)
• CAS DataBase Reference: 1-phenylbut-2-yne-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenylbut-2-yne-1,4-diol(29021-82-7)
• EPA Substance Registry System: 1-phenylbut-2-yne-1,4-diol(29021-82-7)

Safety Data

• Hazardous Substances Data: 29021-82-7(Hazardous Substances Data)

Usage

Appearance

Colorless to light yellow solid The compound's physical form is a solid, with colors ranging from colorless to light yellow.

Solubility

Soluble in water and organic solvents 1-phenylbut-2-yne-1,4-diol can dissolve in both water and various organic solvents, making it suitable for use in different chemical reactions and processes.

Use as a reactant

Organic synthesis The compound is often used as a starting material in the synthesis of various substituted benzene derivatives, which are important intermediates in the production of pharmaceuticals and agrochemicals.

Building block

Pharmaceutical and agrochemical production 1-phenylbut-2-yne-1,4-diol serves as a key building block in the synthesis of pharmaceuticals and agrochemicals, highlighting its importance in these industries.

Potential properties

Anti-inflammatory and antioxidant Research has shown that 1-phenylbut-2-yne-1,4-diol possesses potential anti-inflammatory and antioxidant properties, making it a compound of interest for medical and pharmaceutical research.

Safety precautions

Handle with care and use by trained professionals Due to its potential health hazards, 1-phenylbut-2-yne-1,4-diol should be handled and used with caution, and only by trained professionals in controlled laboratory settings.

InChI:InChI=1/C10H10O2/c11-8-4-7-10(12)9-5-2-1-3-6-9/h1-3,5-6,10-12H,8H2

Upstream product

• 107-19-7 propargyl alcohol 
• 100-51-6 benzyl alcohol 
• 50-00-0 formaldehyd 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 100-52-7 benzaldehyde 
• 32833-64-0 4-Allyloxy-1-phenyl-but-2-yn-1-ol 
• 167107-72-4 4-(tert-butyldiphenylsilyloxy)-1-phenylbut-2-yn-1-ol 
• 52547-82-7 1-hydroxy-1-phenyl-4-(tetrahydropyran-2'-yloxy)but-2-yne 
• 925-90-6 ethylmagnesium bromide 
• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 

Downstream Products

• 61955-85-9 1-acetoxy-4-phenyl-but-3-en-2-one 
• 74141-11-0 trans-1-Phenyl-2-buten-1,4-diol 
• 1597429-28-1 C₁₀H₁₁IO₂ 

Relevant articles and documents

Synthesis and in vitro evaluation of (R), (S) and (R/S)-2-hexyne-1,4-diol, a natural product produced by fungus Clitocybe catinus, and related analogs as potential anticancer agents

The search for natural products and related analogs as potential anticancer agents has seen a significant growth worldwide. Since small sized propargylic diols can be found in nature and chemically synthesized, their evaluation against cancer cells has been of great interest, being a topic of relevance to be investigated. For this purpose, a scalable approach aiming at the synthesis of several propargylic diols and their bioactivity against seven tumor cell lines were evaluated. Interestingly, when the compound 1a, a natural product produced by fungus Clitocybe catinus, was tested in its racemic mixture a more effective activity was observed if compared when enantiopure R-1a or S-1a were tested separately.

Enantioselective Isothiourea-Catalysed Michael-Michael-Lactonisation Cascade Reaction for the Synthesis of δ-Lactones and 1,2,3,4-Substituted Cyclopentanes

This manuscript describes the application of α,β-unsaturated acyl ammonium intermediates in a Michael-Michael-lactonisation cascade process to furnish δ-lactones. Generation of α,β-unsaturated acyl ammonium intermediates was achieved upon addition of isothiourea catalyst HyperBTM into α,β-unsaturated acid chlorides. Subsequent reaction with enone-malonates gave access to δ-lactones in 20-64% yield, 72.5:27.5 to 95:5 er and 81:19 to >95:5 dr. Additionally, application of a ring-opening protocol yielded 1,2,3,4-substituted cyclopentanes in 28-77% yield, 76:24 to 98:2 er and 86:14 to >95:5 dr. Interestingly, the highest er was observed at high reaction temperatures, with 70°C proving optimal. This effect was investigated by conducting an Eyring analysis, which indicated that differential activation entropy rather than differential activation enthalpy is responsible for enantiodiscrimination in this process.

Palladium-catalyzed [4 + 2] cycloaddition of aldimines and 1,4-dipolar equivalents via amphiphilic allylation

The combination of Pd catalyst and diethylzinc with triethylborane promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine rings are applicable for the synthesis of isoquinoline derivatives via the Diels-Alder reaction followed by an oxidation reaction with DDQ.