1,5-Hexadiyne

Base Information

• Chemical Name: 1,5-Hexadiyne
• CAS No.: 628-16-0
• Molecular Formula: C6H6
• Molecular Weight: 78.1136
• Hs Code.: 2901299090
• European Community (EC) Number: 211-029-5
• NSC Number: 155174
• UNII: Z4BAA98LQQ
• DSSTox Substance ID: DTXSID6060848
• Nikkaji Number: J6.875F
• Wikidata: Q27117280
• Metabolomics Workbench ID: 55691
• Mol file: 628-16-0.mol

Synonyms:1,5-Hexadiyne;hexa-1,5-diyne;628-16-0;Bipropargyl;Dipropargyl;HC#CCH2CH2C#CH;Z4BAA98LQQ;EINECS 211-029-5;1,5-Hexadiyne (stabilized with BHT);NSC 155174;NSC-155174;NSC155174;HCCCH2CH2CCH;UNII-Z4BAA98LQQ;1,5-Hexadiyne, stabilized;DTXSID6060848;CHEBI:37821;MFCD00014924;AKOS022623515;FT-0606980;T72733;Q27117280

Chemical Property of 1,5-Hexadiyne

Chemical Property:

• Vapor Pressure: 75.3mmHg at 25°C
• Melting Point: -6°C
• Refractive Index: 1.4400 to 1.4440
• Boiling Point: 86.2°C at 760 mmHg
• Flash Point: -7°C
• PSA: 0.00000
• Density: 0,805 g/cm3
• LogP: 1.03300
• Water Solubility.: Immiscible with water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 78.0469501914
• Heavy Atom Count: 6
• Complexity: 86.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,5-Hexadiyne (stabilized with BHT) >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Statements: 12
• Safety Statements: 9-16-29-33

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: C#CCCC#C
• Uses: 1,5-Hexadiyne is used in the preparation of bisdehydro[12]annulene and biphenylene. It is also used as an important starting material in the preparation of (5Z,9Z)-5,9-hexadecadienoic acid. Further, it is involved in the preparation of linear organotin polymers by reaction with organotin dihydrides.

Technology Process of 1,5-Hexadiyne

There total 25 articles about 1,5-Hexadiyne 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: 60.0%

2-propynyl chloride (624-65-7) → 1,2-hexadiene-5-yne (33142-15-3) + hexa-1,5-diyne (628-16-0)

Guidance literature:

at 20 ℃; under 50 Torr; Kinetics; Photolysis;

DOI:10.1002/(SICI)1097-4601(2000)32:2<118::AID-KIN8>3.0.CO;2-F

Reference yield:

propargyl iodide (659-86-9) → tetramethyl-2,2,3,3 butane (594-82-1) + 4,4-Dimethyl-1-pentyne (13361-63-2) + t-butylallene (26981-77-1) + tert-Butyl iodide (558-17-8) + hexa-1,5-diyne (628-16-0) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With (t-Bu)2CuLi; In diethyl ether; at -78 ℃; Mechanism; Product distribution; also at 0 deg C;

DOI:10.1021/ja00195a054

Reference yield:

1,2,5,6-tetrabromohexane (58443-86-0) → hexa-1,5-diyne (628-16-0)

Guidance literature:

With diethyl ether; ammonia; sodium amide;

DOI:10.1039/jr9500000115

upstream raw materials:

1,2,5,6-tetrabromohexane

2-bromo-hex-1-en-5-yne

sodium acetylide

ethylene dibromide

Downstream raw materials:

Deca-3,7-diin

octa-1,5-diyne

dimethylacetylene

hexane

Refernces

• 1、 Huntsman,Wristers. "-". . p. 342,345. Retrieved 1967.
• 2、 Zakrzewski,Huras,Sas,Zelechowski,Bombinska. "Removal of water - a factor influencing the synthesis of alkynes in a phase-transfer catalyzed β-elimination reaction". . p. 1051 - 1057. Retrieved 2008/09/21.
• 3、 Howe, Pui-Teng,Fahr, Askar. "Pressure and Temperature Effects on Product Channels of the Propargyl (HC≡CCH2) Combination Reaction and the Formation of the First Ring ". . p. 9603 - 9610. Retrieved 2007/10/03.