(Z)-9-Tetradecenyl acetate

Base Information

• Chemical Name: (Z)-9-Tetradecenyl acetate
• CAS No.: 16725-53-4
• Deprecated CAS: 105421-23-6
• Molecular Formula: C16H30 O2
• Molecular Weight: 254.413
• Hs Code.: 29161900
• European Community (EC) Number: 240-780-1
• UNII: TN9973W29F
• DSSTox Substance ID: DTXSID50894976
• Nikkaji Number: J650E
• Wikidata: Q27290039
• Metabolomics Workbench ID: 3961
• Mol file: 16725-53-4.mol

Synonyms:(Z)-9-tetradecenyl acetate;9-tetradecenyl acetate

Chemical Property of (Z)-9-Tetradecenyl acetate

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 0.000136mmHg at 25°C
• Melting Point: 12 - 14 ºC
• Refractive Index: 1.4455-1.4475
• Boiling Point: 135 ºC(0.5 mmHg)
• Flash Point: 98.5ºC
• PSA: 26.30000
• Density: 0.878 g/cm³
• LogP: 5.02660
• Storage Temp.: -20°C
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 254.224580195
• Heavy Atom Count: 18
• Complexity: 209

Purity/Quality:

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

(Z)-9-TetradecenylAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Low toxicity by ingestion.
• Hazard Codes: Low toxicity by ingestion.
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC=CCCCCCCCCOC(=O)C
• Isomeric SMILES: CCCC/C=C\CCCCCCCCOC(=O)C
• Uses: (Z)-9-Tetradecenyl Acetate is one of the sex pheromone components of Ostrinia genus in Japan.

Technology Process of (Z)-9-Tetradecenyl acetate

There total 114 articles about (Z)-9-Tetradecenyl acetate 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: 96.0%

(Z)-9-tetradecen-1-ol (35153-15-2) + acetic anhydride (108-24-7) → (Z)-9-tetradecen-1-yl acetate (16725-53-4)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere; Schlenk technique; Cooling with ice;

Reference yield: 80.0%

(Z)-1-(2-Tetrahydropyranyloxy)-9-tetradecene (71612-09-4,61405-40-1) → (Z)-9-tetradecen-1-yl acetate (16725-53-4)

Guidance literature:

With acetic acid; acetyl chloride; at 35 - 40 ℃;

Reference yield: 74.0%

acetic anhydride (108-24-7) + (Z)-14-Methoxymethoxy-tetradec-5-ene → (Z)-9-tetradecen-1-yl acetate (16725-53-4) + Acetic acid ((Z)-tetradec-9-enyl)oxymethyl ester

Guidance literature:

With iron(III) chloride; In dichloromethane; at -30 ℃; for 4h;

DOI:10.1055/s-2000-6258

upstream raw materials:

9-acetoxynonal

pentyltriphenylphosphonium bromide

(Z)-1-chlorotetradec-9-ene

potassium acetate

Downstream raw materials:

(Z)-9-tetradecen-1-ol

(Z)-9-tetradecenal

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

cis-9,10-epoxytetradecyl acetate

Refernces

• 1、 Ishmuratov,Kharisov,Yakovleva,Botsman,Galeeva,Ishmuratova,Tolstikov. "A versatile approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid". . p. 1595 - 1597. Retrieved 1998.
• 2、 Warthen. "". . p. 371. Retrieved 1968.
• 3、 Browne, Duncan L.,Colombel-Rouen, Sophie,Crévisy, Christophe,Curbet, Idriss,Mauduit, Marc,McBride, Tom,Morvan, Jennifer,Roisnel, Thierry. "Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**". supporting information. p. 19685 - 19690. Retrieved 2021/08/06.
• 4、 -. "Method for synthesizing grassland spodoptera litura sex pheromone active ingredients". Paragraph 0047-0049. . Retrieved 2020/07/02.