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Description
TCI D3833 N-(Diphenylmethylene)glycine Ethyl Ester, CAS 69555-14-2, is a glycine ethyl ester whose amino group is protected as a benzophenone imine. The compound is one of the most iconic building blocks in peptide chemistry and in the synthesis of unnatural amino acids, because its structure combines two functions at once: the ester group serves as the carboxyl anchor, while the diphenylmethylene imine protects the nitrogen. In the laboratory, this compound acts as an activated glycine precursor — a source of glycine units whose alpha carbon can be deprotonated and functionalised in a controlled manner to install new side chains.
The main characteristic that makes this reagent a preferred choice is the increased acidity of the alpha proton, a consequence of conjugation with both the imine and the ester. The anion that forms is therefore relatively stable and readily alkylated. The two phenyl rings on the imine group provide substantial steric hindrance, and that bulk is the key to asymmetric induction when the reaction is run together with a chiral phase-transfer catalyst. In addition, the imine protecting group can be removed easily under mild acidic hydrolysis conditions, restoring the free amino group without damaging the product. The combination of reactivity and storage stability is what keeps it in routine use.
In Indonesian laboratories, this material is typically found in academic and institutional research settings working on peptide chemistry, amino acid synthesis, and asymmetric catalysis — university organic chemistry groups, medicinal chemistry programmes, and research institutes preparing non-proteinogenic amino acid building blocks. It is generally ordered as a research-scale reagent for bench synthesis and method development rather than for production volumes, and is handled by trained personnel within a standard synthetic organic chemistry workflow.
Laboratory Applications
- Unnatural amino acid synthesis — the protected glycine skeleton allows a new side chain to be installed directly at the alpha carbon, giving access to non-proteinogenic amino acids that are not available from natural sources.
- Asymmetric alkylation under chiral phase-transfer catalysis — the bulky diphenylmethylene imine creates the steric environment needed for effective asymmetric induction, so enantioenriched products can be obtained with a chiral catalyst.
- Peptide chemistry building block preparation — the reagent supplies glycine units in a form where the nitrogen is already protected and the carboxyl is already an ester, matching standard peptide chemistry sequences.
- Alpha-carbon functionalisation methodology development — conjugation with the imine and ester raises alpha-proton acidity, producing a comparatively stable anion that is convenient for screening new alkylation and coupling conditions.
- Deprotection and free amino acid liberation studies — the benzophenone imine is cleaved under mild acidic hydrolysis, letting researchers recover the free amino group without degrading the newly built product.
Specifications
- Brand: TCI
- CAS number: 69555-14-2
- Chemical name: N-(Diphenylmethylene)glycine Ethyl Ester
- Product code: D3833
- Category: Chemistry > Chemical Biology > Peptide Chemistry
- Pack sizes: available in standard TCI research-scale packaging; please refer to the catalogue listing for currently offered sizes
- Storage: store as indicated on the manufacturer's label and product documentation
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area, away from heat, direct sunlight, moisture, and incompatible reagents such as strong acids and strong oxidising agents. Keep the material in its original manufacturer packaging wherever possible; where transfer is necessary, use clean, dry, chemically compatible glass containers with secure closures and clear labelling. Because the imine protecting group is sensitive to acidic hydrolysis, avoid unintended contact with moisture and acidic residues during weighing and transfer. Handle in a fume hood using appropriate personal protective equipment — safety glasses, gloves, and a laboratory coat — and always consult the manufacturer's Safety Data Sheet before use, storage, or disposal.
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