4-Chloro-2-butyn-1-ol

Base Information

• Chemical Name: 4-Chloro-2-butyn-1-ol
• CAS No.: 13280-07-4
• Molecular Formula: C4H5 Cl O
• Molecular Weight: 104.536
• Hs Code.: 2905590090
• European Community (EC) Number: 641-314-3
• DSSTox Substance ID: DTXSID80157804
• Nikkaji Number: J50.241C
• Wikidata: Q83025964
• Mol file: 13280-07-4.mol

Synonyms:4-Chloro-2-butyn-1-ol;13280-07-4;4-chlorobut-2-yn-1-ol;2-Butyn-1-ol, 4-chloro-;1-Chloro-2-butyn-4-ol;1-chloro-4-hydroxy-2-butyne;BRN 1098382;4-01-00-02220 (Beilstein Handbook Reference);4-chloro-but-2-yn-1-ol;SCHEMBL500202;DTXSID80157804;MFCD01656722;AKOS005257737;LS-47489;CS-0262802;FT-0692461;EN300-83765;4-Chloro-2-butyn-1-ol, >=95.0% (GC);F83383

Chemical Property of 4-Chloro-2-butyn-1-ol

Chemical Property:

• Vapor Pressure: 0.0866mmHg at 25°C
• Refractive Index: 1.5004
• Boiling Point: 199.2°Cat760mmHg
• PKA: 12.92±0.10(Predicted)
• Flash Point: 74.3°C
• PSA: 20.23000
• Density: 1.204g/cm³
• LogP: 0.22090
• Storage Temp.: ?20°C
• Solubility.: Miscible with diethyl ether.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 104.0028925
• Heavy Atom Count: 6
• Complexity: 76

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-2-butyn-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.; R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.; R34:Causes burns.
• Hazard Codes: Xn
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C#CCCl)O
• Uses: 4-Chloro-2-butyn-1-ol is used in preparatiion of allenes.

Technology Process of 4-Chloro-2-butyn-1-ol

There total 5 articles about 4-Chloro-2-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: 75.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-propynyl chloride (624-65-7) → 4-chlorobut-2-yn-1-ol (13280-07-4)

Guidance literature:

2-propynyl chloride; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 0.25h;

formaldehyd; In diethyl ether; hexane; at -78 - -20 ℃;

DOI:10.1021/ja043097o

Reference yield: 65.0%

1,4-dihydroxybut-2-yne (110-65-6) → 4-chlorobut-2-yn-1-ol (13280-07-4)

Guidance literature:

With pyridine; thionyl chloride; In diethyl ether; at 10 - 20 ℃; for 16h;

Reference yield: 60.5%

Dioctadecylamine (112-99-2) + 1,4-Dichloro-2-butyne (821-10-3) → 4-chlorobut-2-yn-1-ol (13280-07-4) + N-(4-chlorobut-2-yn-1-yl)-N-octadecyloctadecan-1-amine (1428580-29-3) + N,N,N’,N’-tetraoctadecylbut-2-yne-1,4-diamine (1428580-30-6) + di-N,N-(4-chlorobut-2-ynyl)-N,N-dioctadecylammonium chloride

Guidance literature:

With sodium carbonate; In benzene; at 65 - 70 ℃; for 16h; Inert atmosphere;

DOI:10.1002/hlca.201100410

upstream raw materials:

1,4-dihydroxybut-2-yne

formaldehyd

2-propynyl chloride

Dioctadecylamine

Downstream raw materials:

(3-nitro-phenyl)-carbamic acid-(4-chloro-but-2-ynyl ester)

hex-2-yn-1-ol

4-phenyl-2-butyn-1-ol

2,3-butadien-1-ol

Refernces

• 1、 Esselman, Brian J.,Hyland, Grace E.,Knezz, Stephanie N.,Kougias, Samuel M.,Lee, Daniel J.,McMahon, Robert J.,Owen, Andrew N.,Patel, Aatmik R.,Sanchez, Rodrigo A.,Woods, R. Claude. "Synthesis and Characterization of Cyanobutadiene Isomers-Molecules of Astrochemical Significance". . . Retrieved 2020.
• 2、 Grugel, Christian P.,Breit, Bernhard. "Rhodium-Catalyzed Enantioselective Cyclization of 3-Allenyl-indoles: Access to Functionalized Tetrahydrocarbazoles". . p. 5798 - 5802. Retrieved 2019.
• 3、 Grugel, Christian P.,Breit, Bernhard. "Rhodium-Catalyzed Diastereo- And Enantioselective Tandem Spirocyclization/Reduction of 3-Allenylindoles: Access to Functionalized Vinylic Spiroindolines". supporting information. p. 9672 - 9676. Retrieved 2019/12/24.