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870-46-2 molecular structure
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(tert-butoxy)carbohydrazide

ChemBase ID: 69919
Molecular Formular: C5H12N2O2
Molecular Mass: 132.16098
Monoisotopic Mass: 132.08987763
SMILES and InChIs

SMILES:
C(=O)(NN)OC(C)(C)C
Canonical SMILES:
NNC(=O)OC(C)(C)C
InChI:
InChI=1S/C5H12N2O2/c1-5(2,3)9-4(8)7-6/h6H2,1-3H3,(H,7,8)
InChIKey:
DKACXUFSLUYRFU-UHFFFAOYSA-N

Cite this record

CBID:69919 http://www.chembase.cn/molecule-69919.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(tert-butoxy)carbohydrazide
IUPAC Traditional name
tert-butoxycarbohydrazide
Synonyms
tert-Butoxycarbonyl hydrazide
Boc-hydrazide
tert-Butyl carbazate
tert-butyl hydrazinecarboxylate
tert-Butyl carbazate
Boc-hydrazine
tert-Butoxycarbonylhydrazine
Boc-肼
叔丁氧羰基肼
肼基甲酸叔丁酯
CAS Number
870-46-2
3346-63-2
EC Number
212-795-3
MDL Number
MFCD00007593
Beilstein Number
1756967
PubChem SID
24851826
24892122
162035644
PubChem CID
70091

CALCULATED PROPERTIES

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 cm3 Polarizability 13.3093605 Å3
Polar Surface Area 64.35 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
37-41°C expand Show data source
38-42 °C expand Show data source
39-42 °C(lit.) expand Show data source
Boiling Point
63-65 °C/0.1 mmHg(lit.) expand Show data source
63-65°C/0.1mm expand Show data source
Flash Point
197.6 °F expand Show data source
91°C(195°F) expand Show data source
92 °C expand Show data source
Storage Warning
IRRITANT expand Show data source
Moisture Sensitive expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
UN Number
UN1325 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
4.1 expand Show data source
Packing Group
III expand Show data source
Risk Statements
11 expand Show data source
Safety Statements
33 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS Hazard statements
H228 expand Show data source
GHS Precautionary statements
P210-P241-P280-P240-P370+P378A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥98.0% (GC) expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
purum expand Show data source
Linear Formula
(CH3)3COCONHNH2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B91005 external link
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
Sigma Aldrich - 19740 external link
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

REFERENCES

REFERENCES

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

PATENTS

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INTERNET

INTERNET

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