1,9-Decadiyne

Base Information

• Chemical Name: 1,9-Decadiyne
• CAS No.: 1720-38-3
• Molecular Formula: C10H14
• Molecular Weight: 134.221
• Hs Code.: 29012900
• European Community (EC) Number: 217-012-9
• UNII: H6VZJ7LN6L
• DSSTox Substance ID: DTXSID4061913
• Nikkaji Number: J150.548C
• Wikidata: Q27117282
• Metabolomics Workbench ID: 55693
• Mol file: 1720-38-3.mol

Synonyms:1,9-Decadiyne;deca-1,9-diyne;1720-38-3;H6VZJ7LN6L;EINECS 217-012-9;UNII-H6VZJ7LN6L;DTXSID4061913;CHEBI:37823;BAA72038;MFCD00014926;AKOS006223687;CS-0215756;D1326;FT-0607063;D89835;EN300-298553;Q27117282

Chemical Property of 1,9-Decadiyne

Chemical Property:

• Appearance/Colour: Clear yellow liquid
• Vapor Pressure: 1.04mmHg at 25°C
• Melting Point: -6.35°C (estimate)
• Refractive Index: 1.449-1.453
• Boiling Point: 183.7 °C at 760 mmHg
• Flash Point: 56.9 °C
• PSA: 0.00000
• Density: 0.832 g/cm³
• LogP: 2.59340
• Storage Temp.: Flammables area
• Water Solubility.: Insoluble in water.
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 134.109550447
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

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

1,9-Decadiyne >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.
• Hazard Codes: R10:Flammable.
• Statements: 10
• Safety Statements: 16

MSDS Files:

Useful:

• Canonical SMILES: C#CCCCCCCC#C
• Uses: One-step synthesis of carbametacyclophane 3 from 1,9-decadiyne and diethyl acetylenedicarboxylate is described. The use of 1,9-decadiyne as a nucleophile led only to the monoalkynylation product, a selectivity that would be difficult to achieve with a catalytic in situ metalation process. 1,9-decadiyne reacts with iodobenzene (excess) to afford the bis-Sonogashira coupling product in excellent yield. 1,9-Decadiyne was dihydrated and gave 2,9-decanedione in 92% yield.

Technology Process of 1,9-Decadiyne

There total 8 articles about 1,9-Decadiyne 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: 52.0%

1 ,6-dibromohexane (629-03-8) + lithium acetylide-ethylenediamine complex (1216963-74-4) → 1,9-decadiyne (1720-38-3)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 2h;

DOI:10.1055/s-2003-42421

Reference yield:

1,10-bis(trimethylsilyl)-1,9-decadiyne (88736-98-5) → 1,9-decadiyne (1720-38-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol070904q

Reference yield:

C10H18Br4 → 1,9-decadiyne (1720-38-3)

Guidance literature:

With n-butyllithium; N,N-diethylethylenediamine; In 2-methyltetrahydrofuran; hexane; at -30 - 5 ℃;

DOI:10.1021/acs.orglett.7b02867

upstream raw materials:

1 ,6-dibromohexane

sodium acetylide

1,4-dibromo-butane

propargyl bromide

Downstream raw materials:

1,6-bis-(3-phenyl-isoxazol-5-yl)-hexane

1,10-decadiene

1,10-diphenyl-1,9-decadiyne

decanedial

Refernces

• 1、 Xu, Feng,Zhong, Yong-Li,Li, Hongming,Qi, Ji,Desmond, Richard,Song, Zhiguo J.,Park, Jeonghan,Wang, Tao,Truppo, Matthew,Humphrey, Guy R.,Ruck, Rebecca T.. "Asymmetric Synthesis of Functionalized trans-Cyclopropoxy Building Block for Grazoprevir". . p. 5880 - 5883. Retrieved 2017/11/10.