27519-02-4

Basic information

• Product Name: cis-9-Tricosene
• Synonyms: FLYBAIT;CIS-9-TRICOSENE;9-TRICOSENE;(9Z)-9-Tricosene;(9Z)-Tricosene;(z)-9-tricosen;ai3-35349;ent35349
• CAS NO: 27519-02-4
• Molecular Formula: C₂₃H₄₆
• Molecular Weight: 322.61
• EINECS: 248-505-7
• Product Categories: Pharmaceutical Intermediates;pharmacetical;INSECT HORMONE
• Mol File: 27519-02-4.mol
• Article Data: 41

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 300 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear colourless to slightly yellow liquid
• Density: 0.806 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.16E-06mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Storage Temp.: -20°C
• Water Solubility: Miscible with water and hexane. Immiscible with alcohol.
• Merck: 14,6309
• BRN: 1841622
• CAS DataBase Reference: cis-9-Tricosene(CAS DataBase Reference)
• NIST Chemistry Reference: cis-9-Tricosene(27519-02-4)
• EPA Substance Registry System: cis-9-Tricosene(27519-02-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-20/21
• Safety Statements: 24/25-36-26
• WGK Germany: 2
• RTECS: YD0807000
• TSCA: Yes
• Hazardous Substances Data: 27519-02-4(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

Uses

Different sources of media describe the Uses of 27519-02-4 differently. You can refer to the following data:
1. Insect attractant.
2. Muscalure is used to control houseflies (Musca domestica).
3. Muscalure is a molecule with potential for biochemical research.

General Description

Muscalure is an insect pheromone utilized to attract houseflies. It is generally used as a coactive ingredient in fly-bait products.

Safety Profile

Moderately toxic by skin contact.When heated to decomposition it emits acrid smoke andirritating vapors.

Metabolic pathway

Muscalure is a long chain mono-unsaturated hydrocarbon and the 9,lO-double bond is a reactive site towards biologrcal and non-biological oxidative agents.

Degradation

Muscalure is stable to light and temperatures up to 50 °C for one year.

InChI:InChI=1/C23H46/c1-3-5-7-9-11-13-15-17-19-21-23-22-20-18-16-14-12-10-8-6-4-2/h17,19H,3-16,18,20-23H2,1-2H3/b19-17+

Upstream product

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Downstream Products

• 124-19-6 nonan-1-al 
• 124-25-4 myristylaldehyde 
• 35857-62-6 trans-9-tricosene 

Relevant articles and documents

The synthesis of long chain dialkylalkynes, dialkyldiynes and their hydrogenation to monoenes and dienes

Long methylenic chain dialkylalkynes have been synthesised in high yield by an improved procedure. The methodology has been extended to nonconjugated diynes. Catalytic hydrogenation with a poisoned palladium catalyst affords cis-monoenes and cis, cis-dienes respectively. An improved synthesis of cis- 9-tricosene is described.

INSECT PHEROMONES AND THEIR ANALOGS. XIV. SYNTHESIS OF MUSCALURE - THE SEX PHEROMONE OF Musca domestica

A new route to the synthesis of tricos-9Z-one - the sex pheromone of the house fly - has been developed.

REGIOSELECTION IN THE ALKYLATION OF TRIMETHYLSILYLALLYL ANION- STEREOSELECTIVE SYNTHESIS OF DISUBSTITUTED ALKENES.

The regioselection in the alkylation of trimethylsilylallyl anion can be controlled by the use of Schlosser's base to give predominately γ-product with trans geometry at the double bond.Application of this approach to the synthesis of Z-9-tricosene and the Gypsy month sex pheromone is demonstrated.

New simple synthesis of the housefly sex attractant

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A NEW STEREOSELECTIVE SYNTHESIS OF (Z)-9-TRICOSENE, THE SEX ATTRACTANT OF THE COMMON HOUSEFLY

"Muscalure" (9-tricosene) was prepared very readily by an instant-ylid reaction in a highly cis-selective manner although it was found difficult to assess the (Z/E)-ratio with accuracy.

A synthesis of muscalure, the housefly sex attractant

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Stereoselective Alkyne Hydrogenation by using a Simple Iron Catalyst

The stereoselective hydrogenation of alkynes constitutes one of the key approaches for the construction of stereodefined alkenes. The majority of conventional methods utilize noble and toxic metal catalysts. This study concerns a simple catalyst comprised of the commercial chemicals iron(II) acetylacetonate and diisobutylaluminum hydride, which enables the Z-selective semihydrogenation of alkynes under near ambient conditions (1–3 bar H2, 30 °C, 5 mol % [Fe]). Neither an elaborate catalyst preparation nor addition of ligands is required. Mechanistic studies (kinetic poisoning, X-ray absorption spectroscopy, TEM) strongly indicate the operation of small iron clusters and particle catalysts.

Stereoselective cometathesis of 1,5-cyclooctadiene with ethylene as an efficient pathway to Z-ene biologically active natural products

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