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Description
TCI D4145 N-(Diphenylmethylene)aminoacetonitrile, CAS 70591-20-7, is a non-heterocyclic building block formed from the condensation of benzophenone imine with aminoacetonitrile. Its structure places a nitrile group at the end of the chain and a diphenyl imine group that acts simultaneously as a protecting and an activating unit on the nitrogen atom. In organic synthesis laboratories, a compound of this type functions as a glycine synthon: a starting material equivalent to the simplest amino acid framework, already equipped with nitrogen protection and therefore ready for alkylation. This role makes it an important reagent for preparing unnatural amino acids and high-value nitrogen derivatives.
The principal advantage of this compound lies in the acidity of the proton located between the imine group and the nitrile group. Both of these electron-withdrawing groups stabilise the carbanion formed after deprotonation, so alkylation can be carried out with bases that are not excessively strong and with a wide range of electrophiles. The bulky benzophenone imine group provides a well-defined steric environment around the reaction centre, a property widely exploited in asymmetric alkylation using chiral phase-transfer catalysts. Once alkylation is complete, the imine group can be removed to reveal the free nitrogen functionality.
In Indonesian laboratories, this building block is typically used in university and institutional synthetic organic chemistry groups, in medicinal chemistry research, and in method development work where amino acid analogues are required. It is handled on the research bench in standard glassware under ordinary synthetic conditions, weighed out in small portions for reaction screening, and stored between campaigns as part of a general building-block inventory alongside other protected glycine equivalents.
Laboratory Applications
Glycine synthon chemistry — the protected nitrogen and activated methylene position let researchers build amino acid frameworks directly without a separate protection step beforehand.
Unnatural amino acid synthesis — alkylation at the acidic centre introduces custom side chains, giving access to amino acid analogues not available from natural sources.
Asymmetric phase-transfer alkylation — the bulky benzophenone imine creates a defined steric environment around the reactive centre, allowing chiral catalysts to control the stereochemical outcome.
Medicinal chemistry building-block work — the nitrile terminus and removable imine protection provide two handles for further elaboration into nitrogen-rich target molecules.
Synthetic methodology development — the moderate base requirement and broad electrophile compatibility make this reagent a convenient substrate for testing and optimising new alkylation conditions.
Specifications
Brand: TCI
CAS number: 70591-20-7
Chemical name: N-(Diphenylmethylene)aminoacetonitrile
Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
Pack sizes: available in standard TCI catalogue pack sizes; confirm the required quantity when ordering
Storage: store according to the manufacturer's stated conditions on the product label and safety data sheet
Handling and Storage
Keep the container tightly closed and store it in a cool, dry, well-ventilated area away from direct sunlight, heat sources, moisture and incompatible materials, following the storage conditions stated by the manufacturer on the label and safety data sheet. Use the original supplier container or an equivalent chemically resistant, clearly labelled vessel, and reseal it promptly after each use. Handle the material in a fume hood with appropriate personal protective equipment, including safety glasses, gloves and a laboratory coat. Weigh and transfer the compound carefully to avoid dust formation, avoid contact with skin and eyes, and consult the safety data sheet before first use and before any waste disposal.
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