35900-26-6

Basic information

• Product Name: 4-METHYL-5-NONANONE
• Synonyms: 4-METHYL-5-NONANONE;4-Methyl-5-nonanone, 99+%;4-Methylnonan-5-one;4- Methyl-5-nononone;4-Methyl-5-nonanone, GC 98%
• CAS NO: 35900-26-6
• Molecular Formula: C₁₀H₂₀O
• Molecular Weight: 156.27
• Product Categories: insect pheromone
• Mol File: 35900-26-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: -3.45°C (estimate)
• Boiling Point: 189-190°C
• Flash Point: 189-190°C
• Appearance: /
• Density: 0.817±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.345mmHg at 25°C
• Refractive Index: 1.4215 (estimate)
• Storage Temp.: Room Temperature, Under inert atmosphere
• Solubility: Chloroform (Soluble), DMSO (Slightly)
• CAS DataBase Reference: 4-METHYL-5-NONANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-5-NONANONE(35900-26-6)
• EPA Substance Registry System: 4-METHYL-5-NONANONE(35900-26-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• TSCA: Yes
• Hazardous Substances Data: 35900-26-6(Hazardous Substances Data)

Usage

Uses

4-Methyl-5-nonanone is a pheromone produced by male West Indian sugarcane borer (WISB).

Synthesis Reference(s)

Journal of the American Chemical Society, 114, p. 4422, 1992 DOI: 10.1021/ja00037a070Tetrahedron Letters, 35, p. 3065, 1994 DOI: 10.1016/S0040-4039(00)76829-8

InChI:InChI=1/C10H20O/c1-4-6-8-10(11)9(3)7-5-2/h9H,4-8H2,1-3H3/t9-/m1/s1

Upstream product

• 109-69-3 n-Butyl chloride 
• 63169-61-9 2-methylpentanoyl 2-methylpentanoate 
• 625-29-6 2-methyl-1-chlorobutane 
• 2082-59-9 pentanoic anhydride 
• 154170-44-2 (+/-)-4-Methyl-5-nonanol 
• 67-56-1 methanol 
• 502-56-7 nonanone-5 
• 74-88-4 methyl iodide 
• 62183-32-8 (1-butyl-pent-1-enyloxy)-trimethyl-silane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 77-78-1 dimethyl sulfate 
• 542-69-8 1-iodo-butane 
• 78428-09-8 2-Methyl-pentanoic acid pyridin-2-yl ester 
• 3473-24-3 4,6-dibromo-nonan-5-one 

Downstream Products

• 154170-44-2 (+/-)-syn-4-Methyl-5-nonanol 
• 154170-44-2 (+/-)-anti-4-Methyl-5-nonanol 
• 154170-44-2 (+/-)-4-Methyl-5-nonanol 

Relevant articles and documents

Synthesis of β-Methyl Alcohols: Influence of Alkyl Chain Length on Diastereoselectivity and New Attractants of Rhynchophorus ferrugineus

The diastereoselectivity of adducts in the addition reaction via the Felkin-Anh model is affected significantly by the steric effect of bulky groups. However, the influence of steric alkyl chain length has not been studied for the diastereoselectivity. In this work, we present a new strategy for the racemic synthesis of β-methyl alcohols to obtain various diastereomer ratios using the Felkin-Anh model. The addition of alkyl Grignard reagents to α-methyl aldehydes afforded diastereomer ratios of threo/erythro ≈ 2:1, while the reduction in structurally related ketones using LiAlH4 afforded ratios of threo/erythro ≈ 1:1. The experimental data showed no effect of alkyl chain length on either side on the stereoselectivity of adducts. All synthesized analogues were evaluated for attractiveness to Rhynchophorus ferrugineus weevils in the field. Five novel derivatives, including two alcohols and three ketones, were found to attract weevils in the field trials. Among them, 3-methyldecan-4-one (5b) and 4-methyldecan-5-ol (11a) were found to be the most attractive to the insects.

PROCESSES FOR PREPARING 4-METHYL-5-NONANONE AND 4-METHYL-5-NONANOL

The present invention provides a process for preparing 4-methyl-5-nonanone of the following formula (3): the process comprising at least a step of subjecting 2-methylpentanoic anhydride of the following formula (1) and an n-butyl nucleophilic reagent of the following general formula (2) in which M represents Li, MgZ1, or ZnZ1, wherein Z1 represents a halogen atom or an n-butyl group, to a nucleophilic substitution. reaction Coproduce 4-methyl-5-nonanone (3), as well as a process for preparing 4-methyl-5-nonanol of the following formula (5), the process comprising at least steps of preparing 4-methyl-5-nonanone; and subjecting the obtained 4-methyl-5-nonanone and a reducing agent to a reduction reaction to produce 4-methyl-5-nonanol (5).

Highly Regioselective Monoalkylation of Ketones via Manganese Enolates Prepared from Manganese Amides.

Ketones are regioselectively converted to Mn-enolates by treatment with Mn-amides such as Ph(Me)NMnCl in THF at 20 deg C.Mn-enolates can then be regioselectively monoalkylated in good yields.The formation of di or polyalkylated products is never observed ( 1percent).