10-Bromodecanoic Acid: Properties, Handling & Lab Use Guide

10-Bromodecanoic acid is an omega-bromine-substituted medium-chain fatty acid that serves as a versatile bifunctional building block in organic synthesis, surface functionalization, and materials science research.

CAS Number

50782-69-9

Molecular Formula

C10H19BrO2

Molecular Weight

251.16 g/mol

Appearance

White to off-white crystalline solid

Functional Groups

Terminal alkyl bromide (C-10) and carboxylic acid (C-1)

Key Application

Bifunctional linker for SAM formation, polymer synthesis, and surface modification

Recommended Storage

Store in a cool, dry, well-ventilated area away from light and moisture

Chemical Identity and Physical Properties

10-Bromodecanoic acid (CAS 50782-69-9) is a ten-carbon, straight-chain fatty acid derivative bearing a bromine atom at the terminal omega (C-10) position and a free carboxylic acid at the alpha (C-1) end. Its molecular formula is C₁₀H₁₉BrO₂ with a molecular weight of 251.16 g/mol.

At room temperature the compound presents as a white to off-white crystalline solid. The two distinct reactive termini — a nucleofugal alkyl bromide susceptible to S_N2 displacement and an ionisable carboxylic acid — define its utility as a bifunctional linker. The medium alkyl chain (ten carbons) confers sufficient hydrophobicity for ordered monolayer packing while maintaining practical solubility in common polar aprotic solvents such as DMF, DMSO, and dichloromethane.

Note: Melting point and exact solubility data should be confirmed against the certificate of analysis supplied with each lot.

Key Laboratory Applications

The orthogonal reactivity of the carboxylic acid and the terminal alkyl bromide makes 10-Bromodecanoic acid valuable across several research domains:

• Self-Assembled Monolayers (SAMs): The compound is widely used to generate omega-carboxy-terminated or omega-bromo-terminated SAMs on gold, silver, and other metal substrates. The carboxylate head group anchors to the surface, exposing the reactive bromide terminus for subsequent derivatisation, or vice versa depending on orientation.
• Polymer and Macromolecular Chemistry: The alkyl bromide terminus is suitable for atom-transfer radical polymerisation (ATRP) initiation or as a point of attachment in step-growth polymer architectures.
• Bioconjugation and Linker Chemistry: The carboxylic acid can be activated (e.g., NHS ester formation) for conjugation to amine-bearing biomolecules, while the bromide end allows thiol or amine displacement, enabling construction of heterobifunctional crosslinkers.
• Organic Synthesis Intermediates: It serves as a precursor to omega-functionalised decanoic acid derivatives including azido, amino, thiol, and cyano analogues via nucleophilic substitution.

Researchers should select reaction conditions appropriate to the functional group being targeted to avoid unintended side reactions at the alternative terminus.

Safe Handling and Storage Guidelines

10-Bromodecanoic acid is an irritant and should be handled with appropriate personal protective equipment (PPE) including chemical-resistant gloves, safety goggles, and a laboratory coat. All operations should be performed in a well-ventilated fume hood to minimise inhalation exposure to dust or vapour.

Storage recommendations:

• Store in a tightly sealed container in a cool (typically 2–8 °C or room temperature per CoA specification), dry, and well-ventilated location.
• Protect from light and moisture, which can promote hydrolysis or oxidative degradation.
• Keep away from strong bases, strong oxidising agents, and reactive nucleophiles to prevent uncontrolled reactions.
• Follow local regulations for storage and disposal of organobromine compounds.

Spill and disposal: Contain spills with inert absorbent material and dispose of as halogenated organic waste in accordance with institutional and local environmental regulations. Consult the Safety Data Sheet (SDS) supplied by Aladdin Scientific for full hazard and first-aid information.

Review flag: Specific GHS hazard classification codes should be confirmed from the current SDS for lot-specific data.

Purity, Quality Specifications and Analytical Verification

For research applications, particularly surface chemistry and polymer synthesis where trace impurities can disrupt monolayer order or polymerisation kinetics, reagent purity is critical. Aladdin Scientific's 10-Bromodecanoic acid (SKU C118560) is offered at research-grade purity; consult the product page and accompanying Certificate of Analysis (CoA) for the lot-specific purity value and analytical method (typically GC or HPLC).

Key quality parameters to verify from the CoA:

• Purity (%) by GC or HPLC
• Melting point range
• Water content (Karl Fischer)
• Residual solvent levels if applicable
• Appearance confirmation

If the compound will be used in ultra-sensitive assays, researchers may wish to perform additional characterisation by ¹H NMR to confirm structural integrity and the absence of dehydrohalogenation or hydrolysis by-products (e.g., 9-decenoic acid or sebacic acid derivatives).

Recommended Reaction Protocols and Practical Tips

The following practical guidelines apply to the most common uses of 10-Bromodecanoic acid in the laboratory:

1. Nucleophilic substitution at the C-10 bromide: Reactions with sodium azide, potassium thioacetate, or primary amines in DMF at 50–80 °C typically proceed cleanly. Use of a phase-transfer catalyst can improve yields in biphasic systems. Monitor conversion by TLC or GC.

2. Carboxylic acid activation for amide coupling: Standard carbodiimide (EDC/DCC) or active ester (NHS, pentafluorophenol) protocols are compatible. Protect the alkyl bromide terminus from strong nucleophilic amine excess to minimise competitive displacement.

3. SAM preparation on gold substrates: Dissolve the compound in absolute ethanol (typical concentration 1–5 mM). Immerse clean gold substrates for 12–24 hours under inert atmosphere or nitrogen blanket. Rinse with ethanol and dry under nitrogen before characterisation by contact angle, XPS, or FTIR-ATR.

4. Solvent selection: DMF, DMSO, acetonitrile, and dichloromethane are preferred. Avoid prolonged contact with aqueous base (risk of hydrolysis of the C–Br bond to alcohol) or protic nucleophiles at elevated temperature.

Note: These are general guidance protocols. Optimisation for specific substrates and experimental conditions is the responsibility of the end user. Specific yields and conditions have not been independently verified by Aladdin Scientific for every application.

Frequently asked questions

What solvents are recommended for dissolving 10-Bromodecanoic acid?

10-Bromodecanoic acid dissolves well in polar aprotic solvents such as DMF, DMSO, acetonitrile, and dichloromethane. It also dissolves in absolute ethanol at low concentrations (1–5 mM), which is the typical solvent for SAM preparation. Aqueous and strongly basic solvents should be avoided due to the risk of C–Br hydrolysis.

Can 10-Bromodecanoic acid be used as an ATRP initiator?

Yes, the terminal alkyl bromide group is structurally compatible with ATRP initiation in the presence of appropriate copper-based catalyst systems. However, the free carboxylic acid may require protection or careful selection of ligand and solvent to avoid interference with the catalyst. Researchers should consult the ATRP literature for specific protocol optimisation.

How should 10-Bromodecanoic acid be stored to prevent degradation?

Store the compound in a tightly sealed container, protected from light and moisture, in a cool and well-ventilated area. Exposure to moisture can promote hydrolysis of the C–Br bond, while light exposure may facilitate radical-mediated side reactions. Always check the lot-specific CoA and SDS for any storage temperature requirements.

What are common by-products to watch for when working with 10-Bromodecanoic acid?

The most likely degradation or side-reaction products include 10-hydroxydecanoic acid (from C–Br hydrolysis in the presence of water), 9-decenoic acid (from elimination/dehydrohalogenation under basic conditions), and disubstitution products if excess nucleophile is present. Monitoring reactions by TLC or GC-MS and using anhydrous, inert conditions helps minimise these issues.

Is 10-Bromodecanoic acid suitable for bioconjugation applications?

Yes, its carboxylic acid terminus can be activated using NHS/EDC chemistry for conjugation to amine-containing biomolecules such as antibodies, peptides, or proteins. The terminal bromide can also be displaced by thiol or amine groups present in biomolecules. Care should be taken to control reaction stoichiometry and pH to achieve selective, single-terminus conjugation.

References

1. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology. Chemical Reviews 2005, 105 (4), 1103–1169. doi:10.1021/cr0300789
2. Matyjaszewski, K.; Xia, J. Atom Transfer Radical Polymerization. Chemical Reviews 2001, 101 (9), 2921–2990. doi:10.1021/cr940534g
3. Ulman, A. Formation and Structure of Self-Assembled Monolayers. Chemical Reviews 1996, 96 (4), 1533–1554. doi:10.1021/cr9502357

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