Methyl 9-broMononanoate

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Cat Number

INT67878153

CAS Number

67878-15-3

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Product Detail Description Scientific Support Customer Q&A

CAS Number

67878-15-3

Storage

2-8℃

Synonyms

9-Bromo-nonanoic acid methyl ester;Nonanoic acid, 9-bromo-, methyl ester;9-bromonanoic acidmethyl ester

Molecular Formula

C10H19BrO2

Molecular Weight

251.16

Appearance

Clear colorless to yellow liquid

Boiling Point

131℃

Relative Density

1.19

General Description

Methyl 9-bromononanoate is a methyl ester of a nine-carbon fatty acid (nonanoic acid, pelargonic acid) bearing a bromine atom at the terminal C-9 position of the chain. The alpha,omega-difunctional nature of this compound — with the ester at C-1 and the bromine at C-9 — provides two chemically distinct handles for further chain elongation, cyclization, or functional group interconversion. The methyl ester protects the carboxylic acid and provides enhanced lipophilicity.

Mechanism of Action

Methyl 9-bromononoate functions as a versatile fatty acid derivative and chain-elongation building block in pharmaceutical and materials synthesis. The terminal bromine is an excellent leaving group for nucleophilic substitution reactions (to introduce amines, thiols, or other nucleophiles), for intramolecular cyclization to form medium- and large-ring lactones, and for transition-metal-catalyzed cross-coupling reactions. The methyl ester can be hydrolyzed or transesterified to the free acid or other esters.

Application

Methyl 9-bromononoate is used as an intermediate in the synthesis of fatty acid-derived pharmaceuticals, including prostaglandin analogs, leukotriene modifiers, and anti-inflammatory lipid mediators. It is also used in the synthesis of pheromones, fragrances, and natural product derivatives. The alpha,omega-bifunctional nature enables its use in polymer chemistry as a chain-transfer agent and in the synthesis of amphiphilic block copolymers.

Methyl 9-bromononanoate was synthesized as a key intermediate for preparing the C8 spacer in dodecylcarboxybetaine surfactants used to study adsorption at the air-water interface. The synthesis started from decanedioic acid, which was deuterated via PtO-catalyzed exchange in D₂O/Na₂O₂, then esterified with methanol. Monomethyl decanoate was isolated by distillation, followed by bromination using HgO/Br₂ in CCl₄ to yield methyl 9-bromononanoate. This compound was then reacted with dodecyldimethylamine to form the quaternary ammonium salt, which after hydrolysis gave the final betaine with an eight-methylene spacer. Neutron reflection studies revealed that with the long C8 spacer, the carboxylate group projects out of water and likely becomes undissociated in the adsorbed layer, causing unusually early surface saturation at one-tenth of the CMC.

References

Ma K, et al. Unusual adsorption at the air–water interface of a zwitterionic carboxybetaine with a large charge separation. Langmuir, 2016, 32(14): 3340-3347.

What is the recommended storage condition for Methyl 9-broMononanoate?

It should be stored at 2-8°C in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Can we obtain batch-specific analytical data for Methyl 9-broMononanoate?

Batch-specific COA documents are standard with every shipment. Additional analytical reports, including HPLC chromatograms or spectral data, may be provided upon request.

Is Methyl 9-broMononanoate available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

What is the primary synthetic application of Methyl 9-broMononanoate?

It is widely used as a key building block or intermediate in multi-step pharmaceutical synthesis workflows, providing versatile reactivity for constructing target molecular architectures.

What is the minimum order quantity (MOQ) for Methyl 9-broMononanoate?

Flexible MOQ options are available to support both early-stage research and large-scale manufacturing needs. Our team can tailor order quantities to match your specific requirements.