4-(Fmoc-hydrazino)-benzoic acid is a substituted aromatic amino acid derivative featuring a benzoic acid core bearing a hydrazino substituent and an Fmoc (9H-fluoren-9-ylmethoxycarbonyl) group on the hydrazine nitrogen. The molecule contains a carboxylic acid functional group and a protected hydrazine motif, with the Fmoc carbamate serving to mask the nucleophilicity of the hydrazino nitrogen and to support chemoselective handling during stepwise assembly of more complex structures. It is used as a building block in peptide and hydrazide/amide-related synthetic routes where an Fmoc-protected hydrazino handle enables controlled coupling, as well as in chemical biology and analytical workflows that require a protected nitrogen functionality for subsequent derivatization or conjugation.
CAT No: CP26776
CAS No:214475-53-3
Synonyms/Alias:4-(2-Fmoc-hydrazino)benzoicacid;214475-53-3;Fmoc-4-hydrazinobenzoicacid;ST51036376;AC1MBSX9;ACMC-1CBO6;17336_ALDRICH;SCHEMBL178731;4-(fmoc-hydrazinyl)benzoicacid;17336_FLUKA;4-(fmoc-hydrazino)-benzoicacid;CTK4E6815;MolPort-003-725-700;ZINC2577890;6772AH;AKOS024385668;MCULE-5924128085;AK186289;PL007428;KB-238999;RT-012899;TC-169392;4-{[(fluoren-9-ylmethoxy)carbonylamino]amino}benzoicacid;4-[2-(9H-fluoren-9-ylmethoxycarbonyl)hydrazinyl]benzoicacid;4-[({[(9H-FLUOREN-9-YL)METHOXY]CARBONYL}AMINO)AMINO]BENZOICACID
4-(Fmoc-hydrazino)-benzoic acid is an aromatic, Fmoc-protected hydrazine building block featuring a benzoic acid functionality and an Fmoc group suitable for stepwise assembly in peptide and amide-forming workflows. The hydrazino side functionality provides a reactive handle for derivatization and conjugation strategies, while the benzoic acid moiety supports downstream coupling chemistry to generate functionalized linkers, tags, and hydrazide-containing intermediates. In research settings, this compound is used to introduce a hydrazine-bearing aromatic element into larger constructs where controlled reactivity and orthogonal functional-group management are required.
1. Peptide And Linker Synthesis
4-(Fmoc-hydrazino)-benzoic acid is used by peptide chemistry groups to incorporate an Fmoc-protected aromatic hydrazine motif into peptide-like sequences and modular linker segments during protected-building-block assembly. The combination of an Fmoc group with a benzoic acid functionality enables the preparation of hydrazine-functionalized intermediates that can be carried forward into custom peptide synthesis workflows, including the generation of peptide conjugation precursors. Researchers commonly select this reagent when they need a stable, isolable building block that preserves the hydrazine functionality for later derivatization rather than exposing it directly during chain assembly.
2. Hydrazide And Conjugation Chemistry
4-(Fmoc-hydrazino)-benzoic acid is applied in chemical biology and bioconjugation development as a hydrazine-bearing aromatic precursor for constructing hydrazide-containing linkages and functional tags. The hydrazino group enables subsequent derivatization steps that are used to attach the aromatic motif to larger molecules such as peptides, small-molecule probes, or polymeric materials through hydrazine-reactive coupling strategies. This product is particularly useful in workflows where a protected, Fmoc-bearing scaffold is first assembled or handled under controlled conditions, then converted into a reactive hydrazine/hydrazide functionality for downstream conjugate formation.
3. Probe And Tag Intermediate Development
4-(Fmoc-hydrazino)-benzoic acid supports the preparation of labeled or affinity-tagged intermediates used in probe construction and analytical reagent development. The aromatic benzoic acid core provides a rigid scaffold that can be carried into probe molecules as a structural element, while the hydrazino functionality offers a chemically addressable site for incorporation into detection or enrichment formats. Teams developing chemical probes, diagnostic research reagents, or assay components often use this building block to introduce a defined hydrazine handle into their synthesis plan, enabling later attachment of reporter groups or capture moieties under conditions compatible with their overall conjugation strategy.
4. Pharmaceutical Intermediate Building Block
4-(Fmoc-hydrazino)-benzoic acid is used in medicinal chemistry and pharmaceutical intermediate development as a functionalized aromatic hydrazine building block for constructing hydrazine-derived motifs within larger synthetic sequences. The presence of both an Fmoc group and a benzoic acid functionality supports its role as a protected, modular intermediate that can be transformed into downstream coupling partners and functional groups used in SAR (structure-activity relationship) exploration. Process and R&D chemists commonly select this reagent when they need a defined hydrazine-containing aromatic unit that can be integrated into multi-step synthesis while maintaining manageable reactivity until the appropriate stage in the workflow.
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