TCI
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Description
TCI D4171 2,2-Dimethylvaleronitrile (CAS 20654-47-1) is an aliphatic nitrile built on a five-carbon chain carrying two methyl groups at the second carbon, which places the cyano function directly on a quaternary carbon centre. The compound is supplied by TCI as a non-heterocyclic building block, and its role in the laboratory is that of a compact starting material for the construction of branched molecules. Because the skeleton already carries built-in steric hindrance, researchers can move straight into functional group transformation work rather than assembling a quaternary carbon centre themselves, a step that normally demands specialised reaction conditions and additional synthetic operations.
The characteristics that make this material a frequent choice begin with the versatility of the nitrile group itself, which serves as an entry point toward amines, carboxylic acids, amides, ketones and tetrazole rings. This reactivity is combined with a pentyl chain that is shorter than that of the corresponding hexyl analogue. The more compact chain gives the molecule slightly lower lipophilicity, so the compound is often used alongside its longer-chain counterpart to trace the influence of chain length on both activity and solubility. The geminal methyl groups also lock the alpha position against deprotonation, which delivers cleaner reaction pathways and simpler product profiles.
In Indonesian laboratories, a building block of this type is typically drawn on in synthetic organic and medicinal chemistry research groups, in university research units and in industrial development laboratories where branched aliphatic fragments are needed. It is generally handled at bench scale for exploratory synthesis, for preparing small sets of related analogues, and for method development work in which a sterically hindered nitrile is required as a reliable and predictable point of departure.
Laboratory Applications
- Nitrile reduction to primary amines: the cyano group provides a direct route to a branched neopentyl-type amine without the need to construct the hindered quaternary carbon separately.
- Hydrolysis to carboxylic acids and amides: the nitrile converts cleanly into acid or amide derivatives, giving access to sterically shielded carbonyl compounds for further coupling chemistry.
- Tetrazole ring formation: the nitrile function serves as the precursor for tetrazole synthesis, a heterocycle widely applied as a bioisosteric replacement in medicinal chemistry programmes.
- Ketone synthesis via organometallic addition: addition of organometallic reagents to the nitrile carbon delivers hindered ketones, with the geminal methyl groups suppressing competing alpha deprotonation side reactions.
- Chain length structure–activity studies: paired with its longer-chain hexyl analogue, this pentyl compound allows researchers to probe how chain length affects biological activity and solubility behaviour.
Specifications
- Brand: TCI
- CAS number: 20654-47-1
- Chemical name: 2,2-Dimethylvaleronitrile
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research and laboratory pack sizes; please confirm the current packaging option when ordering
- Storage: keep in the closed original container under the storage conditions stated on the manufacturer label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry and well-ventilated area, away from heat, ignition sources and incompatible materials, and follow the specific storage conditions printed on the TCI label and safety data sheet. Keep the material in its original supplier container, or in a chemically compatible and clearly labelled alternative, and reseal it promptly after each use to limit exposure to air and moisture. All handling should take place in a fume hood with appropriate personal protective equipment, including safety glasses, gloves and a laboratory coat. Consult the manufacturer safety data sheet before use, and dispose of residues and contaminated materials in accordance with applicable laboratory chemical waste procedures.
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