1,9-Decadiene

Base Information

• Chemical Name: 1,9-Decadiene
• CAS No.: 1647-16-1
• Deprecated CAS: 143000-98-0
• Molecular Formula: C10H18
• Molecular Weight: 138.253
• Hs Code.: 2901299090
• European Community (EC) Number: 216-711-6
• NSC Number: 102789
• UNII: 2KWZ01G244
• DSSTox Substance ID: DTXSID4022159
• Nikkaji Number: J80.271I
• Wikidata: Q19885565
• RXCUI: 1729153
• Metabolomics Workbench ID: 130295
• ChEMBL ID: CHEMBL31020
• Mol file: 1647-16-1.mol

Synonyms:1,9-decadiene

Chemical Property of 1,9-Decadiene

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 2.09mmHg at 25°C
• Melting Point: -69.6°C (estimate)
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 169 °C at 760 mmHg
• Flash Point: 41.7 °C
• PSA: 0.00000
• Density: 0.752 g/cm³
• LogP: 3.69900
• Storage Temp.: Flammables area
• Solubility.: It is soluble in organic solvents.
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 138.140850574
• Heavy Atom Count: 10
• Complexity: 70

Purity/Quality:

97% ^*data from raw suppliers

1,?9-?Decadiene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCCCCCCC=C
• Uses: It is widely used in the manufacturers and suppliers of pharmaceuticals and intermediates in the preparation of fine chemicals. 1,9-decadiene is also used as a starting material in ADMET polymerizations .

Technology Process of 1,9-Decadiene

There total 49 articles about 1,9-Decadiene 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: 90.0%

ethene (74-85-1) + 1,2-cyclooctene (931-88-4,22770-27-0,3958-30-3,25267-51-0) → 1,10-decadiene (1647-16-1)

Guidance literature:

Mo(NC₆H₃(CH(CH₃)2)2)(CHC(CH₃)2C₆H₅)(NC₄H₂(CH₃)2)(OC₁₀H₉BrC₁₀H₉BrOSi(CH₃)2C(CH₃)3); In 1,3,5-trimethyl-benzene; for 16h; under 7600.51 Torr; Product distribution / selectivity; Inert atmosphere; Sealed system;

Reference yield: 88.0%

1,10-Decanediol (112-47-0) → 1,10-decadiene (1647-16-1) + 9-Decen-1-ol (13019-22-2)

Guidance literature:

With 1-hexadecylcarboxylic acid; at 340 ℃; for 6h; Molecular sieve;

Reference yield: 88.0%

1,12-dodecandiol (5675-51-4) → 1,10-decadiene (1647-16-1)

Guidance literature:

With methoxy(cyclooctadiene)rhodium(I) dimer; N,N-Dimethylacrylamide; 3-Methoxybenzoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 90 ℃; for 24h; chemoselective reaction; Inert atmosphere; Glovebox; Sealed tube;

DOI:10.1021/jacs.8b06069

upstream raw materials:

1,4-Diiodobutane

1,9-decadiyne

1,10-decanediol diacetate

2,13-dioxa-tetradecanedioic acid diethyl ester

Downstream raw materials:

rac/meso-1,2,9,10-diepoxydecane

1.10-Bis--decan

2-pentylcyclohexanone

1,10-Decanediol

Refernces

Tandem 1,3-Dipolar Cycloaddition and Electrophilic Cyclization Reactions: Cyclic Ether Subunits of Polyether Antibiotics from Unsaturated Isoxazolines

10.1021/jo00288a047

The research focuses on the development of a new strategy for the construction of polyether antibiotic substructural units, such as spiroketals, tetrahydrofurans, and tetrahydropyrans. The strategy involves a tandem 1,3-dipolar cycloaddition and electrophilic cyclization sequence, which proceeds via the intermediacy of an isoxazoline. The method was found to be versatile and provided a unique exploitation of the control elements in dipolar cycloaddition and electrophilic cyclization chemistry. Key chemicals used in the process include various isoxazolines (e.g., la, lb, lc, Id, le, lg, lh), triphenylacetonitrile oxide, iodine, and different dienes such as 1,5-hexadiene, 1,7-octadiene, and 1,9-decadiene, among others. The research concluded that this approach could be a general and versatile route to the cyclic ether substructural units common to polyether antibiotics, with the ability to control stereoselectivity in the electrophilic cyclization step.