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B91005

Sigma-Aldrich

tert-Butyl carbazate

98%, for peptide synthesis

Synonym(s):

tert-Butoxycarbonyl hydrazide, Boc-hydrazide

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About This Item

Linear Formula:
(CH3)3COCONHNH2
CAS Number:
870-46-2
Molecular Weight:
132.16
Beilstein:
1756967
EC Number:
212-795-3
MDL number:
MFCD00007593
UNSPSC Code:
12352108
PubChem Substance ID:
24892122
NACRES:
NA.22

product name

tert-Butyl carbazate, 98%

Assay

98%

form

crystals

bp

63-65 °C/0.1 mmHg (lit.)

mp

39-42 °C (lit.)

application(s)

peptide synthesis

SMILES string

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

InChI

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

InChI key

DKACXUFSLUYRFU-UHFFFAOYSA-N

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Related Categories

Application

Employed in a palladium-catalyzed cross-coupling with vinyl halides leading to N-Boc-N-alkenylhydrazines.
Reagent used in solid phase peptide synthesis and in α-amino aldehyde optical purity determinations. Condenses with aldehydes to form hydrazones which are intermediates in the synthesis of HIV-1 protease inhibitors.

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H228

Precautionary Statements

P210

Hazard Classifications

Flam. Sol. 1

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

195.8 °F

Flash Point(C)

91 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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Tetrahedron Letters, 34, 5425-5425 (1993)
Journal of the Chemical Society. Chemical Communications, 1052-1052 (1993)
Tetrahedron Letters, 34, 6599-6599 (1993)
José Barluenga et al.
Organic letters, 9(2), 275-278 (2007-01-16)
N-Boc-N-alkenylhydrazines, an almost unknown type of compounds, have been prepared with high to moderate yields via palladium-catalyzed cross-coupling between alkenyl halides and tert-butyl carbazate. The present methodology represents the first general way to access this highly functionalized and unusual type
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