8-Hexadecenal, 14-methyl-, (8Z)-

Base Information

• Chemical Name: 8-Hexadecenal, 14-methyl-, (8Z)-
• CAS No.: 60609-53-2
• Molecular Formula: C17H32 O
• Molecular Weight: 252.44
• Hs Code.: 2912190090
• European Community (EC) Number: 262-326-1
• Mol file: 60609-53-2.mol

Synonyms:14-methylhexadec-8-enal;8-Hexadecenal, 14-methyl-, (8Z)-;60609-53-2;14-Methyl-8-hexadecen-1-AL;FT-0640705

Chemical Property of 8-Hexadecenal, 14-methyl-, (8Z)-

Chemical Property:

• Vapor Pressure: 7.47E-05mmHg at 25°C
• Refractive Index: 1.4540 (25℃)
• Boiling Point: 342.5°C at 760 mmHg
• Flash Point: 169.7°C
• PSA: 17.07000
• Density: 0.840±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 5.68860
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 13
• Exact Mass: 252.245315640
• Heavy Atom Count: 18
• Complexity: 196

Purity/Quality:

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

14-METHYL-Z-8-HEXA-DECEN-1-AL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)CCCCC=CCCCCCCC=O
• Uses: (Z)-14-Methyl-8-hexadecenal is a female sex pheromone.

Technology Process of 8-Hexadecenal, 14-methyl-, (8Z)-

There total 11 articles about 8-Hexadecenal, 14-methyl-, (8Z)- 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: 79.0%

(Z)-14-Methyl-8-Hexadecen-1-ol (30689-78-2) → (Z)-14-Methyl-8-Hexadecenal (60609-53-2,60609-52-1)

Guidance literature:

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; at 0 - 20 ℃; for 2.5h; Reagent/catalyst; Temperature;

Reference yield:

5-methylhept-1-ene (13151-04-7) → (Z)-14-Methyl-8-Hexadecenal (60609-53-2,60609-52-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaBH₄, BF₃-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H₂O₂ / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h

2: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C

3: 66 percent / liquid ammonia / 6 h

4: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h

5: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol

6: pyridinium chlorochromate / CH₂Cl₂ / 7 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; lithium amide; boron trifluoride diethyl etherate; dihydrogen peroxide; phosphorus tribromide; ethylenediamine; pyridinium chlorochromate; nickel diacetate; In ethanol; dichloromethane; ammonia;

Reference yield:

1-bromo-2-methyl-butane (10422-35-2,99032-67-4,534-00-9,5973-11-5) → (Z)-14-Methyl-8-Hexadecenal (60609-53-2,60609-52-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Mg / 1.) ether, 2.) ether, reflux, 16 h

2: 1.) NaBH₄, BF₃-etherate, 2.) 3 N aq. NaOH, 3.) 30percent aq. H₂O₂ / 1.) THF, 20-25 deg C, 20-25 min, 3.) THF, 30-35 deg C, 2 h

3: 76 percent / phosphorus tribromide / 20 h / 55 - 60 °C

4: 66 percent / liquid ammonia / 6 h

5: 1.) lithium amide, hexamethylphosphorotriamide / 1.) 20 deg C, 1 h, 2.) 40-45 deg C, 10 h

6: sodium borohydride, ethylenediamine / nickel acetate / aq. ethanol

7: pyridinium chlorochromate / CH₂Cl₂ / 7 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; lithium amide; boron trifluoride diethyl etherate; dihydrogen peroxide; phosphorus tribromide; magnesium; ethylenediamine; pyridinium chlorochromate; nickel diacetate; In ethanol; dichloromethane; ammonia;

upstream raw materials:

(Z)-14-Methyl-8-Hexadecen-1-ol

5-methylhept-1-ene

1-bromo-2-methyl-butane

5-methyl-1-heptanol

Refernces

• 1、 Kovalev, B. G.,Rastegaeva, V. M.. "SYNTHETIC INVESTIGATIONS INTO INSECT-ATTRACTING SUBSTANCES (SEX ATTRACTANTS). IV. SYNTHESIS OF 14-METHYL-8-cis-HEXADECENAL AND 14-METHYL-8-trans-HEXADECENAL, COMPONENTS OF THE SEX PHEROMONE OF THE DERMESTID BEETLE Trogoderma granarium EVERTS". . p. 44 - 47. Retrieved 2007/10/02.