6418-47-9

Basic information

• Product Name: 3-Methylheneicosane
• Synonyms: 3-Methylheneicosane;Heneicosane, 3-methyl-
• CAS NO: 6418-47-9
• Molecular Formula: C₂₂H₄₆
• Molecular Weight: 310.60064
• Mol File: 6418-47-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 29°C (estimate)
• Boiling Point: 358.08°C (estimate)
• Flash Point: 145°C
• Appearance: /
• Density: 0.7823 (estimate)
• Vapor Pressure: 1.01E-05mmHg at 25°C
• Refractive Index: 1.4384 (estimate)
• CAS DataBase Reference: 3-Methylheneicosane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylheneicosane(6418-47-9)
• EPA Substance Registry System: 3-Methylheneicosane(6418-47-9)

Safety Data

• Hazardous Substances Data: 6418-47-9(Hazardous Substances Data)

Usage

General Description

3-Methylheneicosane is a linear alkane with the chemical formula C24H50. It is a hydrocarbon, meaning it consists entirely of hydrogen and carbon atoms. This chemical is also known as 3-Methylheneicosane and has a molecular weight of 338.66 g/mol. It is a colorless, waxy solid that is insoluble in water. 3-Methylheneicosane is commonly used in the production of various industrial lubricants and fuels due to its high boiling point and thermal stability. It is also known to exhibit surfactant properties and may be utilized as an emulsifier or dispersant in various industrial applications.

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 
• 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 
• 75-01-4 chloroethylene 
• 3452-07-1 1-Eicosene 

Relevant articles and documents

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.