Di-tert-butyl azodicarboxylate

• Catalog No.: 11625
• CAS Number: 870-50-8
• M. F.: C10H18N2O4
• M. W.: 230.26092
• Purity: ≥98.0% (GC)

SYNONYMS

• Title: 偶氮二甲酸二叔丁酯
• IUPAC name: N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide
• IUPAC Traditional name: N-[(tert-butoxycarbonyl)imino](tert-butoxy)formamide
• Synonyms: NSC 109889; DBAD; Bis(1,1-dimethylethyl)azodicarboxylate; Di-tert-butyl azodiformate

DATABASE IDS

• CAS Number: 870-50-8
• EC Number: 212-796-9
• Beilstein Number: 1911434
• MDL Number: MFCD00015001

PROPERTIES

• Grade: purum
• Linear Formula: (CH3)3COCON=NCOOC(CH3)3
• Purity: ≥98.0% (GC)
• Melting Point: 89-92 °C(lit.)
• Melting Point: 89-92 °C
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• GHS Precautionary statements: P261-P305 + P351 + P338
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• Storage Temperature: 2-8°C
• German water hazard class: 3

DETAILS

Description (English)

Other Notes
Acid labile reagent for Mitsunobu reactions allowing facile isolation of products 8; Electrophilic amination and hydrazination of enolates and lithium alkyls9,10,11
Application
Reactant for:
• Preparation of hexapeptide key fragments via stereoselective selenocyclization/oxidative deselenylation or hydrazination/cyclization reactions1
• Asymmetric Michael addition reactions2
• Preparation of dipeptidyl peptidase IV dependent water-soluble prodrugs via Mitsunobu reaction3
• Synthesis of pyrroloisoquinoline template via stereoselective N-acyliminium-mediated cyclization and enolate amination for synthesis of peptidomimetic compounds4
• Barbier-type propargylation reactions5
• Synthesis of bacterial peptide deformylase (PDF) inhibitor fumimycin6
• Asymmetric amination of glycine Schiff bases7

Description (简体中文)

Other Notes
酸不稳定试剂，用于温和分离产品的 Mitsunobu 反应8；烯醇化物和烷基锂的亲电氨基化和肼化反应9,10,11
Application
Reactant for:
• Preparation of hexapeptide key fragments via stereoselective selenocyclization/oxidative deselenylation or hydrazination/cyclization reactions1
• Asymmetric Michael addition reactions2
• Preparation of dipeptidyl peptidase IV dependent water-soluble prodrugs via Mitsunobu reaction3
• Synthesis of pyrroloisoquinoline template via stereoselective N-acyliminium-mediated cyclization and enolate amination for synthesis of peptidomimetic compounds4
• Barbier-type propargylation reactions5
• Synthesis of bacterial peptide deformylase (PDF) inhibitor fumimycin6
• Asymmetric amination of glycine Schiff bases7