5-Chloro-1-pentyne

Base Information

• Chemical Name: 5-Chloro-1-pentyne
• CAS No.: 14267-92-6
• Molecular Formula: C5H7Cl
• Molecular Weight: 102.564
• Hs Code.: 29032900
• European Community (EC) Number: 238-159-5
• DSSTox Substance ID: DTXSID3065742
• Nikkaji Number: J216.932K
• Wikidata: Q72456331
• Mol file: 14267-92-6.mol

Synonyms:5-Chloro-1-pentyne;14267-92-6;5-Chloropent-1-yne;1-Pentyne, 5-chloro-;5-chloro-pent-1-yne;EINECS 238-159-5;5-Chloro-1-pentyne, 98%;5-chloropentyne;4-Pentynyl Chloride;MFCD00001014;1-chloro-4-pentine;1-chloro-4-pentyne;Pent-4-yn-1-yl chloride;SCHEMBL103284;DTXSID3065742;BCP33456;AKOS009156964;CS-W009550;CS-17333;FT-0600990;EN300-93546;5-Chloropent-1-yne pound>>1-Pentyne, 5-chloro-;A807943;J-802149

Chemical Property of 5-Chloro-1-pentyne

Chemical Property:

• Appearance/Colour: clear, colorless clear liquid
• Vapor Pressure: 20.4mmHg at 25°C
• Melting Point: -61°C (estimate)
• Refractive Index: n20/D 1.444(lit.)
• Boiling Point: 117.888 °C at 760 mmHg
• Flash Point: 15.556 °C
• PSA: 0.00000
• Density: 0.966 g/cm³
• LogP: 1.63860
• Storage Temp.: −20°C
• Water Solubility.: Not miscible in water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 102.0236279
• Heavy Atom Count: 6
• Complexity: 57.6

Purity/Quality:

99% ^*data from raw suppliers

5-Chloropent-1-yne ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-38-36/37/38
• Safety Statements: 23-24/25-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C#CCCCCl
• Uses: 5-Chloro-1-pentyne is used with α-diazoesters in a copper-catalyzed synthesis of pyrazoles. It is also used in the synthesis of 5-chloro-2-trimethylstannyl-1-pentene by reacting with Me3SnCu.Me2S. 5-Chloro-1-pentyne was used in the synthesis of 5-chloro-2-trimethylstannyl-1-pentene by reacting with Me3SnCu.Me2S. It was also used with α-diazoesters in a copper-catalyzed synthesis of pyrazoles.

Technology Process of 5-Chloro-1-pentyne

There total 9 articles about 5-Chloro-1-pentyne 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: 98.4%

pent-1-yn-5-ol (5390-04-5) → 1-chloro-4-pentyne (14267-92-6)

Guidance literature:

With methanesulfonyl chloride; triethylamine; at 15 - 20 ℃; for 2.5h; Temperature;

Reference yield: 78.0%

sodium acetylide (1066-26-8) + 1.3-chlorobromopropane (109-70-6) → 1-chloro-4-pentyne (14267-92-6)

Guidance literature:

With ammonia; at -40 ℃; for 3h;

DOI:10.1002/ejoc.200600556

Reference yield:

→ 1-chloro-4-pentyne (14267-92-6) + Cyclopropylacetylene (6746-94-7)

Guidance literature:

upstream raw materials:

pent-1-yn-5-ol

sodium acetylide

1.3-chlorobromopropane

acetylene

Downstream raw materials:

5-iodopent-1-yne

6-chloro-1,1-diphenylhex-2-yn-1-ol

1-chloro-6,6-dimethylhept-4-yne

vinyltriethylsilane

Refernces

• 1、 Mutlib,Chen,Shockcor,Espina,Chen,Cao,Du,Nemeth,Prakash,Gan. "Characterization of novel glutathione adducts of a non-nucleoside reverse transcriptase inhibitor, (S)-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-3,4-dihyd ro-2(1h)-quinazolinone (DPC 961), in rats. Possible formation of an oxirene metabolic intermediate from a disubstituted alkyne". . p. 775 - 784. Retrieved 2000.
• 2、 Lambert,J.B. et al.. "-". . p. 633 - 636. Retrieved 1975.
• 3、 Qiu, Sheng-Qi,Ahmad, Tanveer,Xu, Yun-He,Loh, Teck-Peng. "Palladium-Catalyzed Cascade Intramolecular Cyclization and Allylation of Enynoates with Allylic Alcohols". . p. 6729 - 6736. Retrieved 2019/06/14.
• 4、 Borukhova, Svetlana,Nol, Timothy,Hessel, Volker. "Continuous-Flow Multistep Synthesis of Cinnarizine, Cyclizine, and a Buclizine Derivative from Bulk Alcohols". . p. 67 - 74. Retrieved 2016/01/16.