10,12-Hexadecadienal

Base Information

• Chemical Name: 10,12-Hexadecadienal
• CAS No.: 69977-24-8
• Molecular Formula: C16H28 O
• Molecular Weight: 236.39
• Nikkaji Number: J760I,J761G
• Metabolomics Workbench ID: 3492
• Mol file: 69977-24-8.mol

Synonyms:10,12-hexadecadienal;bombykal;bombykal, (E,E)-isomer;bombykal, (E,Z)-isomer;bombykal, (Z,Z)-isomer

Chemical Property of 10,12-Hexadecadienal

Chemical Property:

• Vapor Pressure: 8.89E-05mmHg at 25°C
• Boiling Point: 339.9°C at 760 mmHg
• Flash Point: 167.9°C
• PSA: 17.07000
• Density: 0.852g/cm³
• LogP: 5.21860
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 12
• Exact Mass: 236.214015512
• Heavy Atom Count: 17
• Complexity: 204

Purity/Quality:

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

(10E,12E)-10,12-Hexadecadienal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC=CC=CCCCCCCCCC=O
• Isomeric SMILES: CCC/C=C/C=C/CCCCCCCCC=O
• Uses: The sex pheromone of Maruca vitrata.

Technology Process of 10,12-Hexadecadienal

There total 13 articles about 10,12-Hexadecadienal 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: 99.0%

(10E,12E)-hexadeca-10,12-dien-1-ol (765-19-5) → (E,E)-10,12-hexadecadienal (69977-24-8)

Guidance literature:

With dipyridinium dichromate; In dichloromethane; at 20 ℃; for 2h; Molecular sieve;

DOI:10.1021/ol702982x

Reference yield:

1-Bromo-2E,4E-octadiene (60388-62-7) → (E,E)-10,12-hexadecadienal (69977-24-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Mg / 2) Li₂CuCl₄ / 1) THF, 2) THF a) 1 h, b) -10 deg C, 3 h

2: 81.2 percent / pTsOH / methanol / 6 h / Ambient temperature

3: 62 percent / PCC / CH₂Cl₂ / 1 h / Ambient temperature

With toluene-4-sulfonic acid; magnesium; pyridinium chlorochromate; dilithium tetrachlorocuprate; In methanol; dichloromethane;

Reference yield:

(E,E)-octa-2,4-dien-1-ol (56904-85-9,69668-94-6,119518-99-9,119519-00-5,18409-20-6) → (E,E)-10,12-hexadecadienal (69977-24-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 71.8 percent / PBr₃, pyridine / diethyl ether / 1) overnight, 2) reflux, 0.5 h

2: 1) Mg / 2) Li₂CuCl₄ / 1) THF, 2) THF a) 1 h, b) -10 deg C, 3 h

3: 81.2 percent / pTsOH / methanol / 6 h / Ambient temperature

4: 62 percent / PCC / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; phosphorus tribromide; toluene-4-sulfonic acid; magnesium; pyridinium chlorochromate; dilithium tetrachlorocuprate; In methanol; diethyl ether; dichloromethane;

upstream raw materials:

(10E,12E)-hexadeca-10,12-dien-1-ol

8-ethoxycarbonyloctanoyl chloride

2-(9-bromononyloxy)tetrahydropyran

(E)-2-penten-4-yn-1-ol

Refernces

• 1、 Vig,Sharma,Gupta. "Syntheses of sex pheromone components of sphingid moths". . p. 37 - 38. Retrieved 2007/10/02.
• 2、 Yadav, J. S.,Balakrishnan, Kamalam,Sivadasan, Latha. "Synthesis of (E,E)-10,12-hexadecadienal and (Z)-11-octadecenal". . p. 297 - 302. Retrieved 2007/10/02.