(Z)-9-Tricosene

Base Information

• Chemical Name: (Z)-9-Tricosene
• CAS No.: 27519-02-4
• Deprecated CAS: 69319-46-6
• Molecular Formula: C23H46
• Molecular Weight: 322.618
• Hs Code.: 29012990
• European Community (EC) Number: 248-505-7
• UNII: 6BSP6HFW73
• DSSTox Substance ID: DTXSID0032653
• Nikkaji Number: J308E
• Wikipedia: (Z)-9-Tricosene
• Wikidata: Q135445
• Metabolomics Workbench ID: 4818
• ChEMBL ID: CHEMBL1894305
• Mol file: 27519-02-4.mol

Synonyms:cis-9-tricosene;muscalure;muscalure, (E)-isomer;muscalure, (Z)-isomer

Chemical Property of (Z)-9-Tricosene

Chemical Property:

• Appearance/Colour: clear colourless to slightly yellow liquid
• Vapor Pressure: 3.16E-06mmHg at 25°C
• Melting Point: 0°C
• Refractive Index: n20/D 1.453(lit.)
• Boiling Point: 399.4 °C at 760 mmHg
• Flash Point: 208.9 °C
• PSA: 0.00000
• Density: 0.802 g/cm³
• LogP: 8.99430
• Storage Temp.: -20°C
• Water Solubility.: Miscible with water and hexane. Immiscible with alcohol.
• XLogP3: 11.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 19
• Exact Mass: 322.359951467
• Heavy Atom Count: 23
• Complexity: 216

Purity/Quality:

90% ^*data from raw suppliers

Muscalure ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-20/21
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Insect Attractants
• Canonical SMILES: CCCCCCCCCCCCCC=CCCCCCCCC
• Isomeric SMILES: CCCCCCCCCCCCC/C=C\CCCCCCCC
• Uses: Insect attractant. Muscalure is used to control houseflies (Musca domestica). Muscalure is a molecule with potential for biochemical research.

Technology Process of (Z)-9-Tricosene

There total 129 articles about (Z)-9-Tricosene 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%

Methanesulfonic acid (Z)-1-octyl-pentadec-6-enyl ester (125043-73-4) → (Z)-tricos-9-ene (27519-02-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; 1) 0 deg C, 0.5 h; 2) 30 deg C, 1 h;

Reference yield: 95.0%

10-tosyl-10-tricos-14Z-enyl isocyanide (93662-71-6) → (Z)-tricos-9-ene (27519-02-4)

Guidance literature:

With lithium; In diethyl ether; ethanol; ammonia; at -32 ℃; for 2h;

DOI:10.1016/0040-4039(84)80057-X

Reference yield: 95.0%

1-tosyltricos-14Z-enyl isocyanide (123363-82-6) → (Z)-tricos-9-ene (27519-02-4)

Guidance literature:

With lithium; In diethyl ether; ethanol; ammonia; at -33 ℃; for 2h;

DOI:10.1016/S0040-4020(01)86095-6

upstream raw materials:

tricos-9-yne

1-decyne

1-tridecene

nonan-1-al

Downstream raw materials:

trans-9-tricosene

nonan-1-al

myristylaldehyde

Refernces

• 1、 Carlson et al.. "". . p. 194,195. Retrieved 1974.
• 2、 Amouroux, Roger,Ejjiyar, Soumeya. "A stereospecific route to functionalized alkenes from tetrahydrofurfurylic acetates, synthesis of pheromones". . p. 3059 - 3062. Retrieved 1991.
• 3、 Abe et al.. "". . p. 2792. Retrieved 1977.
• 4、 Cargill,Rosenblum. "Synthesis of the housefly sex attractant.". . p. 3971 - 3971. Retrieved 1972.
• 5、 Yadav,Tissot. "Electrochemical synthesis of the sex attractant pheromone of the housefly: (Z)-9-tricosene". . p. 1698 - 1701. Retrieved 1984.
• 6、 Eiter,Joop. "Synthesis of tricosen-(9-cis), Muscalure, a housefly attractant". . p. 468 - 469. Retrieved 1972.
• 7、 Wang, Ze-Zhong,Wang, Guang-Zu,Zhao, Bin,Shang, Rui,Fu, Yao. "Cobalt-Catalyzed Decarboxylative Methylation and Ethylation of Aliphatic N-(Acyloxy)phthalimides with Organoaluminum Reagents". supporting information. p. 1221 - 1225. Retrieved 2020/08/17.
• 8、 Kim, Miri,Pitchaiah, Arigala,Park, No-Joong,Hwang, In Taek,Lee, Kee-In. "Practical and scalable synthesis of (Z)-9-Tricosene, the housefly sex pheromone". . p. 628 - 631. Retrieved 2013/02/23.