Nonyl 8-bromooctanoate

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Cat Number

INT2089253381

CAS Number

2089253-38-1

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Product Detail Description Scientific Support Customer Q&A

CAS Number

2089253-38-1

Synonyms

8-Bromo-octanoic acid nonyl ester

Molecular Formula

C17H33BrO2

Molecular Weight

349.35

General Description

Nonyl 8-bromooctanoate is an ester formed from 8-bromooctanoic acid and nonan-1-ol (nonyl alcohol), creating an alpha,omega-difunctional molecule with a bromine at the C-8 terminal position of the octanoate chain and a nonyl alkoxy group at the carboxylate terminus. This asymmetric, doubly functional ester is a versatile intermediate for the synthesis of macrolides, pheromones, and other bioactive lipophilic compounds.

Mechanism of Action

Nonyl 8-bromooctanoate functions as a bifunctional building block with two orthogonal reactive sites. The terminal bromine at C-8 undergoes nucleophilic substitution (SN2) with soft nucleophiles (thiols, malonate, azide) and can be converted to other functional groups via SN2 or used in intramolecular cyclization. The ester linkage can be hydrolyzed or reduced to reveal the carboxylic acid or primary alcohol, respectively, providing additional synthetic handles.

Application

Nonyl 8-bromooctanoate is used as an intermediate in the synthesis of macrolide antibiotics, pheromones, and bioactive lipid derivatives. Its nonyl ester group mimics the natural lipophilicity of bioactive fatty acids, making it useful in the synthesis of prostaglandin analogs, leukotriene derivatives, and anti-inflammatory lipid mediators. It is also used in the synthesis of surfactants and plasticizers.

A novel amino lipid series was developed for mRNA delivery using lipid nanoparticles (LNPs). Key synthetic intermediate nonyl 8-bromooctanoate was prepared by esterification of 8-bromooctanoic acid with nonan-1-ol using EDC/DMAP. This intermediate was then reacted with 2-aminoethan-1-ol to form nonyl 8-((2-hydroxyethyl)amino)octanoate, which subsequently underwent alkylation with heptadecan-9-yl 8-bromooctanoate to yield the final lipid 5. This lipid demonstrated high mRNA encapsulation efficiency (97.5%), optimal particle size (86.2 nm), and surface pKa 6.56. In vivo studies showed lipid 5 enabled 5-fold higher protein expression than MC3 in non-human primates, with rapid tissue clearance and no toxicity after 5 weekly doses. Endosomal escape efficiency was 6-fold higher than MC3.

References

Sabnis S, et al. A novel amino lipid series for mRNA delivery: improved endosomal escape and sustained pharmacology and safety in non-human primates. Molecular Therapy, 2018, 26(6): 1509-1519.

What is the recommended storage condition for Nonyl 8-bromooctanoate?

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

What documentation is provided with each batch of Nonyl 8-bromooctanoate?

Each batch is accompanied by a Certificate of Analysis (COA) covering identity, potency, and relevant purity tests. Safety Data Sheets (SDS) are available upon request.

What is the primary synthetic application of Nonyl 8-bromooctanoate?

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 analytical characterization data is available for Nonyl 8-bromooctanoate?

Standard analytical data including HPLC purity profile, NMR confirmation, and physical specifications are included in the COA. Additional characterization data can be arranged upon request.

Is Nonyl 8-bromooctanoate suitable for use in regulated pharmaceutical processes?

Yes, it is manufactured under quality standards consistent with regulated pharmaceutical applications, including in-process controls and release testing aligned with industry requirements.