2,4-Hexadiyne-1,6-diol

Base Information

• Chemical Name: 2,4-Hexadiyne-1,6-diol
• CAS No.: 3031-68-3
• Molecular Formula: C6H6O2
• Molecular Weight: 110.112
• Hs Code.: 29052900
• European Community (EC) Number: 221-210-0
• NSC Number: 11686
• UNII: 37EGG3KXZ3
• DSSTox Substance ID: DTXSID50184400
• Nikkaji Number: J205.341A
• Wikidata: Q83055321
• Mol file: 3031-68-3.mol

Synonyms:2,4-Hexadiyne-1,6-diol;Hexa-2,4-diyne-1,6-diol;3031-68-3;Diacetylene glycol;2,4-Hexadiynediol;2,4-Hexadiyn-1,6-diol;37EGG3KXZ3;1,6-Dihydroxy-2,4-hexadiyne;EINECS 221-210-0;NSC 11686;NSC-11686;MFCD00020619;NSC11686;2,6-diol;UNII-37EGG3KXZ3;HOCH2C=C-C=CCH2OH;SCHEMBL302049;hexa-2, 4-diyne-1, 6-diol;JXMQYKBAZRDVTC-UHFFFAOYSA-;DTXSID50184400;AKOS015837596;BS-43974;2,4-HEXADIYN-1,6-DIOL, 97%,;CS-0313228;FT-0610230;FT-0610232;H0619;T72262;2,4-Hexadiyne-1,6-diol, >=98.0% (GC);J-017906

Chemical Property of 2,4-Hexadiyne-1,6-diol

Chemical Property:

• Vapor Pressure: 0.0002mmHg at 25°C
• Melting Point: 109-112 °C
• Refractive Index: 1.561
• Boiling Point: 292.1 °C at 760 mmHg
• PKA: 12.26±0.10(Predicted)
• Flash Point: 151 °C
• PSA: 40.46000
• Density: 1.234 g/cm³
• LogP: -1.02220
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 110.036779430
• Heavy Atom Count: 8
• Complexity: 146

Purity/Quality:

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

2,4-Hexadiyne-1,6-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 16-22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C#CC#CCO)O
• Uses: 2,4-Hexadiyne-1,6-diol may be used as a starting material in the synthesis of thiarubrine A (an antibiotic). It may also be used to synthesize disodium salt of 2,4-hexadiyne 1,6-disulfate (HDDS).

Technology Process of 2,4-Hexadiyne-1,6-diol

There total 27 articles about 2,4-Hexadiyne-1,6-diol 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%

propargyl alcohol (107-19-7) → Hexa-2,4-diyne-1,6-diol (3031-68-3)

Guidance literature:

With copper(l) iodide; triethylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride; In acetonitrile; at 25 ℃; for 24h;

DOI:10.1039/b212430k

Reference yield: 88.0%

3-iodo-2-propyn-1-ol (1725-82-2) + propargyl alcohol (107-19-7) → Hexa-2,4-diyne-1,6-diol (3031-68-3)

Guidance literature:

With pyrrolidine; copper(l) iodide; at 0 - 20 ℃; for 0.5h;

Reference yield: 80.0%

3-iodo-2-propyn-1-ol (1725-82-2) + phenylacetylene (536-74-3) + benzyl azide (622-79-7) → 1-benzyl-4-phenyl-5-iodo-1,2,3-triazole (860002-66-0) + 1-benzyl-4-(hydroxymethyl)-5-iodo-1H-1,2,3-triazole (1418018-19-5) + Hexa-2,4-diyne-1,6-diol (3031-68-3)

Guidance literature:

With copper(l) iodide; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); potassium acetate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; In tetrahydrofuran; at 20 ℃; for 4h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00975

upstream raw materials:

formaldehyd

Butadiyne

propargyl alcohol

1,6-bis-(1-butoxy-ethoxy)-hexa-2,4-diyne

Downstream raw materials:

1,6-bis(p-toluenesulfonyloxy)-2,4-hexadiyne

5,5'-bis-hydroxymethyl-1,1'-diphenyl-1H,1'H-[4,4']bi[1,2,3]triazolyl

1,6-hexanediol

(2E,4E)-hexa-2,4-diene-1,6-diol

Refernces

• 1、 Fedenok, Lidiya G.,Shvartsberg, Mark S.. "Features of the mechanism of oxidative dehydrodimerization of propynol". . p. 3776 - 3778. Retrieved 2011.
• 2、 Gupta, Neeraj,Shallu,Kad, Goverdhan Lal,Singh, Jasvinder. "First total synthesis of acetylenic alcohol 15-methyltricosa-2,4-diyne-1, 6-diol (strongylodiol-G) derived from marine sponge". . p. 424 - 430. Retrieved 2014.
• 3、 Shergina,S.I. et al.. "-". . . Retrieved 1973.
• 4、 Gonzalez-Arellano, Camino,Balu, Alina Mariana,Luque, Rafael,MacQuarrie, Duncan J.. "Catalytically active self-assembled silica-based nanostructures containing supported nanoparticles". . p. 1995 - 2002. Retrieved 2010.
• 5、 Gao, Lingfeng,Wang, Bin,Zheng, Gengxiu. "Leaf-like CuO nanosheets on rGO as an efficient heterogeneous catalyst for Csp-Csp homocoupling of terminal alkynes". . . Retrieved 2020/12/21.
• 6、 Wang, Gongbao,Lindeboom, Erik-Jan,Van Heerewaarden, Chris,Minnaard, Adriaan J.. "Synthesis of ene-yne-enes by nickel-catalyzed double SN2′ substitution of 1,6-dichlorohexa-2,4-diyne". . p. 2347 - 2355. Retrieved 2017/07/22.