5,9-dimethylheptadecane

Base Information

• Chemical Name: 5,9-dimethylheptadecane
• CAS No.: 108195-53-5
• Molecular Formula: C₁₉H₄₀
• Molecular Weight: 268.527

Synonyms:

Chemical Property of 5,9-dimethylheptadecane

Chemical Property:

• Boiling Point: 83 °C(Press: 0.8 Torr)
• Density: 0.783±0.06 g/cm3(Predicted)

Purity/Quality:

5,9-Dimethylheptadecane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• General Description: 5,9-Dimethylheptadecane is a branched alkane that exists as a mixture of stereoisomers, primarily (5S,9S)- and (5R,9S)-forms, and serves as the main sex-pheromone component of *Leucoptera scitella*. It can be synthesized from (R)-citronellal via a baker's yeast-mediated reduction and subsequent steps, demonstrating its role in insect chemical communication. 5,9-dimethylheptadecane is structurally characterized by two methyl groups at the 5th and 9th carbon positions of a heptadecane backbone. No other common names for 5,9-dimethylheptadecane were mentioned in the provided literature.

Technology Process of 5,9-dimethylheptadecane

There total 59 articles about 5,9-dimethylheptadecane 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: 83.0%

(3E,5E,11E)-(R)-5,9-Dimethyl-heptadeca-3,5,11-triene (135461-16-4,135461-17-5,135461-18-6,135557-80-1) → (5SR,9S)-5,9-dimethyl-heptadecane (108195-53-5,121723-03-3,121723-04-4,121723-05-5,121723-06-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1016/S0040-4039(00)78807-1

Reference yield: 81.0%

propyl bromide (106-94-5) + (2R,6S)-2,6-dimethyltetradecyl tosylate (299430-29-8) → (5S,9S)-5,9-Dimethylheptadecane (108195-53-5,121723-03-3,121723-04-4,121723-05-5,121723-06-6)

Guidance literature:

propyl bromide; With magnesium; In tetrahydrofuran; at 20 ℃; for 1h;

(2R,6S)-2,6-dimethyltetradecyl tosylate; With dilithium tetrachlorocuprate; In tetrahydrofuran; at -78 - 0 ℃; for 24h;

DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield: 76.0%

(5S,7RS,9S)-5,9-Dimethyl-7-(phenylsulfonyl)heptadecane (131906-84-8,132015-49-7) → (5S,9S)-5,9-Dimethylheptadecane (108195-53-5,121723-03-3,121723-04-4,121723-05-5,121723-06-6)

Guidance literature:

With sodium amalgam; In ethanol; for 40h; Ambient temperature;

upstream raw materials:

(3E,5E,11E)-(R)-5,9-Dimethyl-heptadeca-3,5,11-triene

3,7-dimethyl-oct-6-enal

(R)-Citronellal

(R)-2,6-dimethyltetradeca-2,8-diene

Refernces

Stereospecific inversion of secondary tosylates to yield chiral methyl-branched building blocks, applied to the asymmetric synthesis of leafminer sex pheromones

10.1016/j.tetasy.2012.05.023

The research aims to synthesize all four possible stereoisomers of 5,9-dimethylheptadecane, a major sex pheromone component secreted by female moths of the mountain-ash bentwing (Leucoptera scitella). The study aimed to develop a method for creating chiral building blocks with high enantiomeric excess, which could be used for the systematic synthesis of dimethyl hydrocarbons. The researchers utilized (R)- and (S)-propylene oxide as starting materials, converting them into secondary tosylates. These tosylates underwent stereospecific inversion via SN2 reactions with nucleophiles like the enolate of dimethyl malonate and the anion of methyl sulfone, yielding chiral blocks A and B with methyl branches at the 3- and 2-positions, respectively. The enantiopurities of these blocks were confirmed by chiral HPLC analysis. The chiral building blocks were then coupled to synthesize all stereoisomers of 5,9-dimethylheptadecane. The study concluded that the stereospecific conversion of chiral secondary tosylates via SN2 reactions is a viable strategy for synthesizing chiral methyl-branched compounds with high enantiomeric purity, which can be applied to the synthesis of other dimethyl hydrocarbons and potentially used in pest control and pheromone identification.

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