N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide

• ChemBase ID: 89999
• Molecular Formular: C10H18N2O4
• Molecular Mass: 230.26092
• Monoisotopic Mass: 230.12665707
• SMILES: O(C(=O)/N=N/C(=O)OC(C)(C)C)C(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)/N=N/C(=O)OC(C)(C)C
• InChI: InChI=1S/C10H18N2O4/c1-9(2,3)15-7(13)11-12-8(14)16-10(4,5)6/h1-6H3
• InChIKey: QKSQWQOAUQFORH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide; (E)-N-{[(tert-butoxy)carbonyl]imino}(tert-butoxy)formamide
• IUPAC Traditional name: N-[(tert-butoxycarbonyl)imino](tert-butoxy)formamide; (E)-N-[(tert-butoxycarbonyl)imino](tert-butoxy)formamide
• Synonyms: Di-tert-butyl azodicarboxylate 98%; Bis(1,1-dimethylethyl)azodicarboxylate; DBAD; Di-tert-butyl azodiformate; NSC 109889; Di-tert-butyl azodicarboxylate; Azodicarboxylic acid di-tert-butyl ester; DTAD; Di-tert-butyl diazene-1,2-dicarboxylate; 偶氮二甲酸二叔丁酯; 偶氮二羧酸二叔丁酯

Database IDs

• CAS Number: 870-50-8
• EC Number: 212-796-9
• MDL Number: MFCD00015001
• Beilstein Number: 1911434
• PubChem SID: 24848251; 162076854
• PubChem CID: 6034084

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 2.1676028
• LogD (pH = 7.4): 2.1676028
• Log P: 2.1676028
• Molar Refractivity: 56.5902 cm^3
• Polarizability: 22.475769 Å^3
• Polar Surface Area: 77.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 89-92 °C; 89-92 °C(lit.); 89-92°C; 89-92°C

Safety Information

• Storage Warning: Irritant/Light Sensitive/Keep Cold/Store under Argon; Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Linear Formula: (CH3)3COCON=NCOOC(CH3)3

DETAILS

Sigma Aldrich - D1516

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

Sigma Aldrich - 135992

Application
Reagent employed in the electrophilic amination of β-keto esters catalyzed by an axially chiral guanidine.8 Building block in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such a L-proline or (S)-2-pyrrolidinyl tetrazole.9
Utilized in the asymmetric Friedel-Crafts amination via a chiral organocatalyst.
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
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 11625

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

REFERENCES

• Aza-dienophile. The ester groups are readily removed from adducts by acid: J. Org. Chem., 26, 4336 (1961); 38, 2043 (1973); 40, 563 (1975).
• Useful "NH₂⁺" synthon for enantioselective amination reactions: J. Am. Chem. Soc., 108, 6394, 6395, 6397 (1986); Tetrahedron Lett., 29, 6765 (1988).
• Mitsunobu reaction with alcohols gives a direct route to the corresponding N,N'-di-Boc protected hydrazine derivatives: Tetrahedron Lett., 37, 4327 (1996).