214475-53-3

Basic information

• Product Name: 4-(FMOC-HYDRAZINO)-BENZOIC ACID
• Synonyms: RARECHEM EM WB 0134;FMOC-4-HYDRAZINOBENZOIC ACID;FMOC-NH-ABZ(4)-OH;4-(2-FMOC-HYDRAZINO)BENZOIC ACID;4-(9-FLUORENYLMETHOXYCARBONYL-HYDRAZINO)-BENZOIC ACID;4-CARBOXYPHENYLHYDRAZINE FMOC;4-(FMOC-HYDRAZINO)-BENZOIC ACID;Fmoc-4-hydrazinobenzoic acid≥ 96% (HPLC)
• CAS NO: 214475-53-3
• Molecular Formula: C₂₂H₁₈N₂O₄
• Molecular Weight: 374.39
• Product Categories: Aromatic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 214475-53-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.363 g/cm³
• Storage Temp.: 2-8°C
• PKA: 4.58±0.10(Predicted)
• BRN: 8082614
• CAS DataBase Reference: 4-(FMOC-HYDRAZINO)-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(FMOC-HYDRAZINO)-BENZOIC ACID(214475-53-3)
• EPA Substance Registry System: 4-(FMOC-HYDRAZINO)-BENZOIC ACID(214475-53-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 214475-53-3(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

Synthetic route

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 4-Hydrazinobenzoic acid (619-67-0) → 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane	75%

(S)-2-Amino-3-(4-chloro-phenyl)-propionic acid benzhydryl ester + 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → (S)-3-(4-Chloro-phenyl)-2-{4-[N'-(9H-fluoren-9-ylmethoxycarbonyl)-hydrazino]-benzoylamino}-propionic acid benzhydryl ester

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide for 48h; Ambient temperature;

4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → (S)-3-(4-Chloro-phenyl)-2-{4-[N'-(9H-fluoren-9-ylmethoxycarbonyl)-hydrazino]-benzoylamino}-propionic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: DCCI, HOBt / dimethylformamide / 48 h / Ambient temperature 2: TFA, anisole / 2.5 h / Ambient temperature View Scheme

taxol (33069-62-4) + 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → C69H67N3O17

Conditions	Yield
With dmap; diisopropyl-carbodiimide In DMF (N,N-dimethyl-formamide)

polyethylene glycol polyamide resin + 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → C22H18N3O3Pol

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 13h; Inert atmosphere; solid phase reaction;

Fmoc-Val-OH (68858-20-8) + Fmoc-Leu-OH (35661-60-0) + N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3) + C26H25N6O5Pol + C50H45NO15 (1571865-26-3) + N-Fmoc L-Phe (35661-40-6) + 4-(Fmoc-hydrazino)-benzoic acid (214475-53-3) → C68H74N7O16Pol

Conditions

Yield

Stage #1: C26H25N6O5Pol With piperidine In N,N-dimethyl-formamide Stage #2: 4-(Fmoc-hydrazino)-benzoic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide TenGel NH2 resin; Stage #3: Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; C50H45NO15; N-Fmoc L-Phe Further stages;

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 619-67-0 4-Hydrazinobenzoic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Relevant articles and documents

Chemoselective Copper-Mediated Modification of Selenocysteines in Peptides and Proteins

Highly valuable bioconjugated molecules must be synthesized through efficient, chemoselective chemical modifications of peptides and proteins. Herein, we report the chemoselective modification of peptides and proteins via a reaction between selenocysteine residues and aryl/alkyl radicals. In situ radical generation from hydrazine substrates and copper ions proceeds rapidly in an aqueous buffer at near neutral pH (5-8), providing a variety of Se-modified linear and cyclic peptides and proteins conjugated to aryl and alkyl molecules, and to affinity label tag (biotin). This chemistry opens a new avenue for chemical protein modifications.