CAS 870-50-8|NSC 109889|Di-tert-butyl azodicarboxylate|Bis(1,1-dimethylethyl)azodicarboxylate|Di-tert-butyl azodiformate|N-[(tert-butoxycarbonyl)imino](tert-butoxy)formamide|DBAD|偶氮二甲酸二叔丁酯|...

General Information

Structure

Molecular Formula

C₁₀H₁₈N₂O₄

Molecular Mass

230.26092

Exact Mass

230.12665707

Charge

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

Canonic Smiles

O=C(OC(C)(C)C)/N=N/C(=O)OC(C)(C)C

Isomeric Smiles

O(C(=O)/N=N/C(=O)OC(C)(C)C)C(C)(C)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

2.1676028

LogD (pH = 7.4)

2.1676028

Log P

2.1676028

Molar Refractivity

56.5902

Polarizability

22.475769

Polar Surface Area

77.32

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

NSC 109889Bis(1,1-dimethylethyl)azodicarboxylateDi-tert-butyl azodicarboxylateDi-tert-butyl azodiformateDBAD偶氮二甲酸二叔丁酯偶氮二羧酸二叔丁酯DTADAzodicarboxylic acid di-tert-butyl esterDi-tert-butyl azodicarboxylate 98%Di-tert-butyl diazene-1,2-dicarboxylate

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

Names and Identifiers

Registration numbers

MDL Number

CAS Number

Beilstein Number

EC Number

PubChem CID

PubChem SID

Registration numbers

Properties

Physical Property

Melting Point

89-92°C

89-92 °C(lit.)

89-92 °C

89-92°C

Product Information

Purity

98%

≥98.0% (GC)

Linear Formula

(CH3)3COCON=NCOOC(CH3)3

Grade

purum

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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

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

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

Molecule Details

References

PubChem Literature

From Data Sources

• Useful "NH₂⁺" synthon for enantioselective amination reactions: J. Am. Chem. Soc., 108, 6394, 6395, 6397 (1986); Tetrahedron Lett., 29, 6765 (1988).

• Aza-dienophile. The ester groups are readily removed from adducts by acid: J. Org. Chem., 26, 4336 (1961); 38, 2043 (1973); 40, 563 (1975).

• Mitsunobu reaction with alcohols gives a direct route to the corresponding N,N'-di-Boc protected hydrazine derivatives: Tetrahedron Lett., 37, 4327 (1996).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

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

Registration numbers

MDL Number

CAS Number

Beilstein Number

EC Number

PubChem CID

PubChem SID

Properties

Physical Property

Melting Point

89-92°C

89-92 °C(lit.)

89-92 °C

89-92°C

Product Information

Purity

98%

≥98.0% (GC)

Linear Formula

(CH3)3COCON=NCOOC(CH3)3

Grade

purum

Molecule Details

Sigma Aldrich

D1516

135992

11625

References

PubChem Literature

From Data Sources

• Useful "NH₂⁺" synthon for enantioselective amination reactions: J. Am. Chem. Soc., 108, 6394, 6395, 6397 (1986); Tetrahedron Lett., 29, 6765 (1988).

• Aza-dienophile. The ester groups are readily removed from adducts by acid: J. Org. Chem., 26, 4336 (1961); 38, 2043 (1973); 40, 563 (1975).

• Mitsunobu reaction with alcohols gives a direct route to the corresponding N,N'-di-Boc protected hydrazine derivatives: Tetrahedron Lett., 37, 4327 (1996).

Bioactivity

PubChem BioAssay

Molecule

ID:89999