(Z)-9-Tetradecenal

Base Information

• Chemical Name: (Z)-9-Tetradecenal
• CAS No.: 53939-27-8
• Molecular Formula: C14H26 O
• Molecular Weight: 210.36
• Hs Code.: 2912190090
• European Community (EC) Number: 258-875-1
• UNII: 24Y7I2IU6D
• DSSTox Substance ID: DTXSID5041196
• Nikkaji Number: J705F
• Wikidata: Q27253883
• Metabolomics Workbench ID: 3575
• Mol file: 53939-27-8.mol

Synonyms:Z-9-Tetradecenal;(Z)-9-Tetradecenal;(Z)-Tetradec-9-enal;53939-27-8;9-Tetradecenal, (Z)-;9Z-Tetradecenal;9-Tetradecenal, (9Z)-;(Z)-9-Tetradecen-1-al;Caswell No. 934A;BRN 1937971;(9Z)-9-Tetradecenal;EINECS 258-875-1;UNII-24Y7I2IU6D;AI3-35584;24Y7I2IU6D;CIS-9-TETRADECENAL;(9Z)-tetradec-9-enal;SCHEMBL811890;DTXSID5041196;TETRADECENAL, (Z)-9-;ANJAOCICJSRZSR-WAYWQWQTSA-N;CHEBI:179485;Z9-14:AL;LMFA06000181;LS-148924;Q27253883

Chemical Property of (Z)-9-Tetradecenal

Chemical Property:

• Vapor Pressure: 0.00135mmHg at 25°C
• Boiling Point: 297.4°Cat760mmHg
• Flash Point: 137.9°C
• PSA: 17.07000
• Density: 0.839g/cm³
• LogP: 4.66240
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 11
• Exact Mass: 210.198365449
• Heavy Atom Count: 15
• Complexity: 149

Purity/Quality:

93% ^*data from raw suppliers

CIS-9-TETRADECENAL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Low toxicity by ingestion.
• Hazard Codes: Low toxicity by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCCC=O
• Isomeric SMILES: CCCC/C=C\CCCCCCCC=O

Technology Process of (Z)-9-Tetradecenal

There total 25 articles about (Z)-9-Tetradecenal 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: 91.0%

1-cyano-8Z-tridecene (72025-22-0) → (Z)-9-tetradecenal (53939-27-8)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1007/BF00949490

Reference yield: 89.0%

(Z)-9-tetradecen-1-ol (35153-15-2) → (Z)-9-tetradecenal (53939-27-8)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 1.5h;

Reference yield:

1,1,9-trichloro-1-nonene (3930-10-7) → (Z)-9-tetradecenal (53939-27-8)

Guidance literature:

Multi-step reaction with 4 steps

1: n-PrLi / diethyl ether; tetrahydrofuran; benzene / -20 -> 20 deg C, 1.5 h

2: 1.) HMPA / 1.) ether, THF, benzene, 20 deg C, 12 h, 2.) DMSO, 100-110 deg C, 5 h

3: 6 g / hydrogen / Lindlar catalyst / hexane / 20 °C

4: 91 percent / (i-Bu)2AlH / diethyl ether / 1 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; hydrogen; propyllithium; diisobutylaluminium hydride; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; hexane; benzene;

DOI:10.1007/BF00949490

upstream raw materials:

(Z)-9-tetradecen-1-ol

1-cyano-8Z-tridecene

1,1,9-trichloro-1-nonene

C₉H₁₄ClLi

Refernces

• 1、 Majee. "Simple syntheses of (Z)-7-dodecen-1-ol, (Z)-7-tetradecen-1-yl acetate, (Z)-9-tetradecenal and (Z)-9-hexadecen-1-yl acetate from aleuritic acid". . p. 1435 - 1438. Retrieved 2013/02/23.
• 2、 Trehan,Vig,Singh,Sharma,Kad. "Stereospecific syntheses of a few Lepidoptera pheromones containing (Z)-alkene moiety". . p. 518 - 520. Retrieved 2007/10/02.