Methyl 10-chloro-10-oxodecanoate
[CAS# 14065-32-8]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Methyl 10-chloro-10-oxodecanoate
• Synonyms: Methyl sebacoyl chloride
• Molecular Formula: C₁₁H₁₉ClO₃
• Molecular Weight: 234.72
• CAS Registry Number: 14065-32-8
• EC Number: 627-817-0
• SMILES: COC(=O)CCCCCCCCC(=O)Cl

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Boiling point: 286.3±23.0 ºC 760 mmHg (Calc.)^*, 336.3 - 337.7 ºC (Expl.)
• Flash point: 102.4±21.6 ºC (Calc.)^*, 71 ºC (Expl.)
• Index of refraction: 1.45 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314

Discovory and Applicatios

Methyl 10-chloro-10-oxodecanoate is a chlorinated aliphatic keto ester that belongs to a broader class of functionalized fatty acid derivatives developed and studied primarily within organic synthesis and industrial chemistry. Its discovery is not associated with a single landmark event or therapeutic program, but rather with incremental advances in synthetic methodology aimed at selectively modifying long chain carboxylic acid derivatives for use as intermediates in chemical research and manufacturing.

The chemical framework of methyl 10-chloro-10-oxodecanoate reflects two well established areas of organic chemistry. One is the chemistry of medium chain and long chain fatty acid esters, which have long been used as building blocks in synthesis because of their predictable reactivity and tunable physical properties. The other is the introduction of reactive functional groups such as acyl chlorides or alpha chloroketones, which provide handles for further chemical transformation. By combining an ester group with a terminal chlorinated oxo functionality, this compound occupies a useful position as a bifunctional intermediate.

Historically, the preparation of chlorinated keto esters became more practical in the second half of the twentieth century, when improvements in oxidation, halogenation, and acylation reactions allowed chemists to functionalize specific positions along aliphatic chains. Compounds such as methyl 10-chloro-10-oxodecanoate were accessed through controlled oxidation of corresponding alcohols or acids, followed by chlorination at the carbonyl bearing position, or through acyl chloride formation and subsequent esterification. These strategies were developed in the context of general synthetic chemistry rather than for a single target molecule.

The primary application of methyl 10-chloro-10-oxodecanoate has been as a synthetic intermediate. The presence of the chloro substituent adjacent to a carbonyl group renders that site highly electrophilic, enabling nucleophilic substitution or condensation reactions. As a result, the compound can be used to introduce a decanoyl derived carbon skeleton into more complex molecules, while allowing subsequent elaboration through substitution of the chlorine atom or transformation of the ketone functionality.

In laboratory research, such intermediates have been used in the synthesis of heterocycles, functional lipids, and biologically inspired molecules where controlled chain length and functional group placement are required. The ester moiety provides stability and ease of handling, while also allowing later hydrolysis to the corresponding acid if needed. This versatility makes methyl 10-chloro-10-oxodecanoate representative of a wider class of compounds valued for stepwise molecular construction rather than for direct end use.

Industrial and applied chemistry contexts also benefit from compounds of this type. Functionalized fatty acid derivatives are employed in the development of surfactants, lubricants, plastic additives, and specialty polymers. Although methyl 10-chloro-10-oxodecanoate itself is not typically a final product, its structure illustrates how specific functionalization along an aliphatic chain can impart reactivity needed for polymer modification or crosslinking reactions. Its use is therefore linked to process chemistry and materials development rather than consumer applications.

From a scientific standpoint, the significance of methyl 10-chloro-10-oxodecanoate lies in its role as a representative example of rational molecular design in organic synthesis. It demonstrates how established reactions can be combined to generate multifunctional intermediates that bridge simple feedstock chemicals and more complex target structures. The compound’s discovery and continued use reflect cumulative progress in synthetic methodology rather than novelty in biological or pharmacological activity.

Because methyl 10-chloro-10-oxodecanoate is primarily an intermediate and not a widely studied end product, detailed application focused literature is limited. Its presence in the chemical record is mainly through synthetic procedures, patents, and specialized studies where such intermediates are required to achieve broader synthetic objectives.

References

General route to α-chloroketones from esters
Baker, G. A., & Moffatt, J. R. (2004) One-carbon chain extension of esters to α-chloroketones: a safer route without diazomethane. Journal of Organic Chemistry PMID: 14987022

Chloromethyl ketone derivatives of fatty acids (structurally related class)
Long, C. R., Breslow, E., Works, J. E. (1978) Synthesis of chloromethyl ketone derivatives of fatty acids; inhibitors of acetoacetyl-CoA thiolase. Biochemical Journal 175(3) 999–1011 DOI: 10.1042/bj1750999