3-Butyn-1-OL

Base Information

• Chemical Name: 3-Butyn-1-OL
• CAS No.: 927-74-2
• Molecular Formula: C4H6O
• Molecular Weight: 70.091
• Hs Code.: 29052990
• European Community (EC) Number: 213-161-9
• NSC Number: 9708
• UNII: P74L430293
• DSSTox Substance ID: DTXSID1022136
• Nikkaji Number: J1.744B
• Wikidata: Q223060
• Metabolomics Workbench ID: 51319
• Mol file: 927-74-2.mol

Synonyms:3-butyn-1-ol

Chemical Property of 3-Butyn-1-OL

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 4.41mmHg at 25°C
• Melting Point: - 63.6 °C(lit.)
• Refractive Index: n20/D 1.441(lit.)
• Boiling Point: 130.125 °C at 760 mmHg
• PKA: 14.22±0.10(Predicted)
• Flash Point: 36.111 °C
• PSA: 20.23000
• Density: 0.924 g/cm³
• LogP: 0.00200
• Storage Temp.: Flammables area
• Solubility.: Miscible with alcohols and organic solvents. Immiscible with ali
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 70.041864811
• Heavy Atom Count: 5
• Complexity: 47.9

Purity/Quality:

99% ^*data from raw suppliers

3-Butyn-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 26-36-37/39-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C#CCCO
• Uses: (3-Butyn-1-ol) Alkynyl substrate used in a study of a palladium-catalyzed coupling with β-tetrionic acid bromide leading to alkynyl substituted furanones in good yield.1 3-butyn-1-ol is used in the study of a palladium-catalyzed coupling with beta-tetrionic acid bromide to prepare alkynyl substituted furanones. It is also used to prepare Markovnikov addition product. Further, it is used as an intermediate of an active pharmaceutical ingredient such as fexofenadine. Synthon for preparation of oxygen-containing heterocycles and protected esters of s-Hydroxy-L-isoleucine

Technology Process of 3-Butyn-1-OL

There total 22 articles about 3-Butyn-1-OL which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-(but-3-yn-1-yloxy)tetrahydropyran (40365-61-5) → 2-methoxytetrahydropyran (6581-66-4) + 3-Butyn-1-ol (927-74-2)

Guidance literature:

With methanol; DOWEX 50 W-X₂ cation exchange resin; at 40 ℃; for 1h;

Reference yield: 97.0%

pyridine-2-carboxylic acid but-3-ynyl ester → 3-Butyn-1-ol (927-74-2)

Guidance literature:

With zinc diacetate; In methanol; dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2005.05.125

Reference yield: 93.0%

4-<(triphenylmethyl)oxy>-1-butyne (75014-48-1) → 3-Butyn-1-ol (927-74-2)

Guidance literature:

With indium(III) chloride; water; In acetonitrile; for 2h; Heating;

upstream raw materials:

oxirane

sodium acetylide

2,3-butadien-1-ol

3-bromobut-3-en-1-ol

Downstream raw materials:

but-3-yn-1-yl acetate

terephthalic acid di-but-3-ynyl ester

3-butyn-1-yl p-toluenesulfonate

3,3-dimethoxybutan-1-ol

Refernces

Chemistry of enediynyl azides: Activation through a novel pathway

10.1039/b612114d

The research focuses on the chemistry of enediynyl azides, specifically the spontaneous activation of a nonaromatic enediynyl azide under ambient conditions. The study explores the synthesis and reactivity of enediyne scaffolds 1–4, which contain alkene and azide functionalities. The experiments involved coupling bromoalkenes with 3-butyn-1-ol under Sonogashira conditions, followed by mesylation and conversion to azides. The synthesized compounds were analyzed using techniques such as FTIR, 1H-NMR, 13C-NMR, and ESI mass spectrometry to monitor the disappearance of azide peaks, the presence of specific functional groups, and the formation of new products. The research also observed the intramolecular cycloaddition of the aromatic enediyne 3 and the nonaromatic enediyne 4, leading to the formation of triazoline fused enediyne 22 and benzotriazine derivative 27, respectively. The study suggests that the mechanism involves initial dipolar cycloaddition with the alkyne, followed by rearrangement and cyclization, ultimately leading to the formation of diradicals that can cleave DNA under ambient conditions. This research contributes to the understanding of enediyne reactivity and has implications for the development of potential DNA-cleaving agents.

One-pot, three-component synthesis of 4-Aryl-5,6-dihydropyran via prins-friedel-crafts reaction

10.1055/s-0029-1219779

The research focuses on the development of an efficient method for the synthesis of 4-aryl-5,6-dihydropyrans, which are heterocyclic compounds found in many biologically active natural products and pharmaceuticals. The purpose of this study was to create a one-pot, three-component synthesis via Prins-Friedel-Crafts reaction, utilizing aldehydes or epoxides, homopropargylic alcohols, and arenes, all promoted by boron trifluoride etherate as a Lewis acid catalyst. The conclusions drawn from the research indicate that this method is effective for synthesizing 4-aryl-dihydropyrans with good to moderate yields, without the formation of 4-halosubstituted side products, and can be extended to epoxides when aldehydes are not readily accessible. The chemicals used in the process include a range of aldehydes, homopropargylic alcohols, various arenes, and boron trifluoride etherate as the catalyst.