5-Bromovaleric Acid (also known as 5-Bromopentanoic acid) CAS 2067-33-6 is a versatile halogenated carboxylic acid widely used as a key intermediate in organic synthesis. This bifunctional compound features a terminal bromine atom and a carboxylic acid group, enabling nucleophilic substitution, esterification, amidation, and chain extension reactions, making it valuable in pharmaceutical, agrochemical, and fine chemical manufacturing.

5-Bromovaleric acid Key Specifications

  • Chemical Name: 5-Bromovaleric acid / 5-Bromopentanoic acid
  • CAS Number: 2067-33-6
  • Molecular Formula: C₅H₉BrO₂
  • Molecular Weight: 181.03 g/mol
  • Appearance: White to light yellow to light beige crystalline solid or powder (may appear as low-melting solid)
  • Purity: Typically ≥97% (GC or titration; higher grades available)
  • Melting Point: Approximately 38–40 °C
  • Boiling Point: 142–145 °C at 13 mmHg
  • Synonyms: δ-Bromovaleric acid, 5-Bromo-n-valeric acid, Pentanoic acid 5-bromo-, 5-Bromopentanoic acid

How 5-Bromovaleric Acid Works in Synthesis

The bromine at the ω-position (gamma to the carboxyl) is highly reactive toward nucleophiles (SN2 displacement), while the carboxylic acid allows for easy derivatization into esters, amides, acid chlorides, or reduction products. This dual functionality supports multi-step syntheses, including:

  • Formation of long-chain amines, thiols, or azides via substitution
  • Preparation of lactones or cyclic compounds through intramolecular reactions
  • Chain elongation for API intermediates

It is stable under standard storage but should be handled with care due to its corrosive nature.

5-Bromovaleric acid Primary Applications

  • Intermediate in pharmaceutical synthesis (e.g., related to anticoagulants like apixaban derivatives and other APIs)
  • Building block for agrochemicals and pesticides
  • Synthesis of specialty chemicals, surfactants, and polymer modifiers
  • Preparation of aminoglycoside resistance inhibitors and other bioactive molecules
  • Research use in organic chemistry for ω-functionalized carboxylic acids
  • Precursor for radiolabeled compounds or probes

5-Bromovaleric acid is particularly favored when a five-carbon spacer with a reactive bromide is required in target molecules.

Benefits

  • High reactivity of the primary bromide for clean substitutions
  • Straightforward purification due to its solid form at room temperature
  • Cost-effective route to ω-substituted pentanoic acid derivatives
  • Broad compatibility in multi-step synthetic sequences
  • Reliable availability in research and bulk quantities

Frequently Asked Questions (FAQs)

What is it primarily used for?

It serves as a key synthetic intermediate for introducing a five-carbon chain with a terminal functional group, especially in pharmaceutical intermediates, agrochemicals, and fine chemical production.

Why choose 5-Bromovaleric acid over shorter or longer bromoalkanoic acids?

The five-carbon chain provides an optimal spacer length for many biologically active molecules, balancing flexibility and steric considerations in drug design and linker applications.

Is it hazardous?

Yes, it is corrosive to skin, eyes, and mucous membranes (similar to other haloacids). Handle with appropriate PPE, in a fume hood, and avoid contact or inhalation.

Can it be used to make esters or amides directly?

Yes, the carboxylic acid group readily undergoes esterification (e.g., with alcohols under acid catalysis) or amidation (e.g., via acid chloride or coupling agents), while preserving the bromide for later functionalization.

What solvents are suitable for reactions with 5-Bromovaleric acid?

Common solvents include dichloromethane, THF, DMF, acetonitrile, and toluene. Avoid strong bases or nucleophilic solvents that may displace the bromide prematurely.

Is high-purity it available for scale-up?

Yes, ≥97–99% purity grades are standard for research, process development, and commercial production.

How should it be stored?

Store in a cool, dry place under inert atmosphere if possible, tightly sealed to prevent moisture absorption or bromine loss. Shelf life is good under proper conditions.

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