CAS 870-46-2|CAS 3346-63-2|tert-Butyl carbazate|(tert-butoxy)carbohydrazide|tert-butoxycarbohydrazide|tert-butyl hydrazinecarboxylate|tert-Butoxycarbonyl hydrazide|肼基甲酸叔丁酯|tert-Butyl carbazat...

General Information

Structure

Molecular Formula

C₅H₁₂N₂O₂

Molecular Mass

132.16098

Exact Mass

132.08987763

Charge

InChI

InChI=1S/C5H12N2O2/c1-5(2,3)9-4(8)7-6/h6H2,1-3H3,(H,7,8)

InChIKey

DKACXUFSLUYRFU-UHFFFAOYSA-N

Canonic Smiles

NNC(=O)OC(C)(C)C

Isomeric Smiles

C(=O)(NN)OC(C)(C)C

Calculated Properties

JChem

Acid pKa

13.11165

H Acceptors

H Donor

LogD (pH = 5.5)

0.3457911

LogD (pH = 7.4)

0.34647724

Log P

0.34648678

Molar Refractivity

34.3792

Polarizability

13.3093605

Polar Surface Area

64.35

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

tert-Butyl carbazatetert-butyl hydrazinecarboxylatetert-Butoxycarbonyl hydrazide肼基甲酸叔丁酯tert-Butyl carbazate叔丁氧羰基肼Boc-肼Boc-hydrazidetert-ButoxycarbonylhydrazineBoc-hydrazine

IUPAC name

(tert-butoxy)carbohydrazide

IUPAC Traditional name

tert-butoxycarbohydrazide

Names and Identifiers

Registration numbers

CAS Number

870-46-23346-63-2

MDL Number

MFCD00007593

PubChem SID

2489212216203564424851826

EC Number

212-795-3

Beilstein Number

1756967

PubChem CID

70091

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

B91005

Packaging
5, 25, 100, 500 g in poly bottle
Application
Employed in a palladium-catalyzed cross-coupling with vinyl halides leading to N-Boc-N-alkenylhydrazines.1Reagent used in solid phase peptide synthesis2 and in α-amino aldehyde optical purity determinations.3 Condenses with aldehydes to form hydrazones which are intermediates in the synthesis of HIV-1 protease inhibitors.4

19740

Other Notes
Starting material for preparing BOC-azide, a reagent to introduce the BOC amino protection; E. Wünsch in Houben-Weyl, Vol. 15/1, Synthese von grossen Peptiden, p. 112.; Reagent for the synthesis of sulfonic and carboxylic hydrazides1

Molecule Details

References

PubChem Literature

From Data Sources

• Protected hydrazine derivative, permitting selective reaction at one N atom, followed by mild acidic cleavage of the Boc group. For preparation of, e.g. N-aminosuccinimide, free from the cyclic hydrazide, see: J. Org. Chem., 37, 2040 (1972). Similarly, reaction with carbonyl or sulfonyl halides, followed by cleavage with HCl, provides a route to monoacyl hydrazides: Synthesis, 244 (1980). It is also commonly used in the synthesis of aza-amino acids; see, for example: Synthesis, 141 (1991) and references therein.

• Precursor of the somewhat unstable tert-butyl azidoformate, useful for introduction of the Boc protecting group, see: Org. Synth. Coll., 5, 157 (1973). Caution! Possible violent decomposition of this azide on heating.

• Monoalkylhydrazines can be prepared via reduction of Boc-hydrazones with borane-THF, and cleavage with HCl: J. Org. Chem., 46, 5413 (1981).

References

Bioactivity

PubChem BioAssay

Bioactivity