9-Tetradecen-1-ol

Base Information

• Chemical Name: 9-Tetradecen-1-ol
• CAS No.: 52957-16-1
• Molecular Formula: C14H28 O
• Molecular Weight: 212.376
• Hs Code.: 2905290000
• DSSTox Substance ID: DTXSID50880834
• Nikkaji Number: J1.015.719F,J429.199I
• Wikidata: Q82862218
• Metabolomics Workbench ID: 3267
• Mol file: 52957-16-1.mol

Synonyms:9,10-tetradecenol;9,10-tetradecenol, (Z)-isomer;9-tetradecen-1-ol;cis,trans-9,10-tetradecenol;myristoleyl alcohol

Chemical Property of 9-Tetradecen-1-ol

Chemical Property:

• Vapor Pressure: 6.83E-05mmHg at 25°C
• Boiling Point: 307.1°C at 760 mmHg
• Flash Point: 108.6°C
• PSA: 20.23000
• Density: 0.846g/cm³
• LogP: 4.45580
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 11
• Exact Mass: 212.214015512
• Heavy Atom Count: 15
• Complexity: 129

Purity/Quality:

98.5% ^*data from raw suppliers

(9E)-Tetradecen-1-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCCCO
• Isomeric SMILES: CCCC/C=C/CCCCCCCCO
• Uses: (9E)-Tetradecen-1-ol is found in flowers of Tibetan medicinal plants of three Gentiana species and may have various pharmacological activity.

Technology Process of 9-Tetradecen-1-ol

There total 3 articles about 9-Tetradecen-1-ol 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:

9-bromononan-1-ol (55362-80-6) → 9-tetradecenyl alcohol (52957-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / acetonitrile

2: DMSO, NaH / tetrahydrofuran / 0.5 h

With sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; acetonitrile;

DOI:10.1271/bbb1961.44.257

Reference yield:

1-hexene (592-41-6,25067-06-5) + oleoyl alcohol (143-28-2,593-47-5,84286-21-5) → (Z)-9-tetradecen-1-ol (35153-15-2) + 9-tetradecenyl alcohol (52957-16-1)

Guidance literature:

With C₃₂H₄₃N₃O₄Ru; In tetrahydrofuran; for 5h; Overall yield = 77 %; Overall yield = 0.73 g; diastereoselective reaction;

Reference yield:

pentanal (110-62-3) + (9-hydroxynonyl)(triphenyl)phosphonium bromide (73945-70-7) → (Z)-9-tetradecen-1-ol (35153-15-2) + 9-tetradecenyl alcohol (52957-16-1)

Guidance literature:

With sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1271/bbb1961.44.257

upstream raw materials:

pentanal

(9-hydroxynonyl)(triphenyl)phosphonium bromide

9-bromononan-1-ol

1-hexene

Downstream raw materials:

(E)-tetradec-9-en-1-yl acetate

3(Z),13(E)-octadecadien-1-yl acetate

C₂₃H₄₂O₂

tetradec-9-enoic acid

Refernces

• 1、 Horiike,Tanouchi,Hirano. "A convenient method for synthesizing (Z)-alkenols and their acetates". . p. 257 - 261. Retrieved 2007/10/02.