6418-47-9

Usage

Uses

Used in Lubricant Production:
3-Methylheneicosane is used as a base oil in the production of industrial lubricants due to its high boiling point and thermal stability. Its properties provide excellent lubrication and reduce wear and tear in machinery.
Used in Fuel Production:
As a hydrocarbon, 3-Methylheneicosane is used in the production of various fuels. Its high energy content and compatibility with other fuel components make it a valuable component in fuel formulations.
Used as a Surfactant in Industrial Applications:
3-Methylheneicosane exhibits surfactant properties, making it suitable for use as an emulsifier or dispersant in various industrial processes. Its ability to reduce surface tension and stabilize mixtures of immiscible liquids contributes to improved process efficiency and product quality.
Used in Chemical Synthesis:
3-Methylheneicosane can be used as a starting material or intermediate in the synthesis of various organic compounds. Its unique structure and properties make it a valuable building block in the production of specialty chemicals and materials.

InChI:InChI=1/C22H46/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(3)5-2/h22H,4-21H2,1-3H3

Synthetic route

1-octadecylmagnesium bromide (92206-73-0) + butanone (78-93-3) → 3-methylheneicosane (6418-47-9)

Conditions	Yield
With diethyl ether und Erhitzen des Reaktionsprodukts mit Naphthalin-2-sulfonsaeure auf 110grad und Hydrieren des erhaltenen Olefin-Gemisches an Raney-Nickel bei 100grad/100 at;

chloroethylene (75-01-4) + 1-Eicosene (3452-07-1) → 3-methylheneicosane (6418-47-9) + 3-Methylene-henicosane + 3-Methyl-henicos-1-ene

Conditions	Yield
With bis(acetylacetonate)nickel(II); zirconocene dichloride; triethylaluminum; diisobutylaluminium hydride; triphenylphosphine 1.) RT, 10 h, 2.) RT, 10 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

10-Undecen-1-ol (112-43-6) → 3-methylheneicosane (6418-47-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / 12 h / 0 °C 2: NaI / acetone / 1.) reflux, 1.5 h, 2.) 20 deg C, 48 h 3: 1.) CuI, 2,2'-biphenyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) 20 deg C, 12 h 4: 1.) AlEt3, Cp2ZrCl2, 2.) Ni(acac)2, PPh3, i-Bu2AlH / 1.) RT, 10 h, 2.) RT, 10 h View Scheme

1-iodo-10-undecene (7766-49-6) → 3-methylheneicosane (6418-47-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) CuI, 2,2'-biphenyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) 20 deg C, 12 h 2: 1.) AlEt3, Cp2ZrCl2, 2.) Ni(acac)2, PPh3, i-Bu2AlH / 1.) RT, 10 h, 2.) RT, 10 h View Scheme

10-undecen-1-yl p-toluenesulfonate (51148-67-5) → 3-methylheneicosane (6418-47-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: NaI / acetone / 1.) reflux, 1.5 h, 2.) 20 deg C, 48 h 2: 1.) CuI, 2,2'-biphenyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) 20 deg C, 12 h 3: 1.) AlEt3, Cp2ZrCl2, 2.) Ni(acac)2, PPh3, i-Bu2AlH / 1.) RT, 10 h, 2.) RT, 10 h View Scheme

nonylmagnesium bromide (39691-62-8) → 3-methylheneicosane (6418-47-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) CuI, 2,2'-biphenyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) 20 deg C, 12 h 2: 1.) AlEt3, Cp2ZrCl2, 2.) Ni(acac)2, PPh3, i-Bu2AlH / 1.) RT, 10 h, 2.) RT, 10 h View Scheme

Upstream product

• 92206-73-0 1-octadecylmagnesium bromide 
• 78-93-3 butanone 
• 75-01-4 chloroethylene 
• 3452-07-1 1-Eicosene 
• 39691-62-8 nonylmagnesium bromide 
• 51148-67-5 10-undecen-1-yl p-toluenesulfonate 
• 7766-49-6 1-iodo-10-undecene 
• 112-43-6 10-Undecen-1-ol 

Relevant academic research and scientific papers

INSECT PHEROMONES AND THEIR ANALOGUES. XXXVIII. SYNTHESIS OF (+/-)-3-METHYLHENEICOSAN-2-ONE AND (+/-)-2-ACETOXY-3,7-DIMETHYLPENTADECANE USING THE REDUCTIVE β-VINYLATION OF α-OLEFINS

Schemes are proposed for the synthesis of (+/-)-3-methylheneicosan-2-one and (+/-)-2-acetoxy-3,7-dimethylpentadecane - racemic analogues of the sex pheromones of the common cockroach (Blatella germanica) and of plane sawflies of the genera Diprion and Neodiprion, respectively, using the reductive β-vinylation of α-olefins.