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Sigma-Aldrich

tert-Butyl carbamate

98%

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Synonym(s):
Boc-amide
Linear Formula:
NH2COOC(CH3)3
CAS Number:
4248-19-5
Molecular Weight:
117.15
Beilstein:
1744500
EC Number:
224-209-3
MDL number:
MFCD00007962
PubChem Substance ID:
24850207
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

mp

105-108 °C (lit.)

SMILES string

CC(C)(C)OC(N)=O

InChI

1S/C5H11NO2/c1-5(2,3)8-4(6)7/h1-3H3,(H2,6,7)

InChI key

LFKDJXLFVYVEFG-UHFFFAOYSA-N

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General description

Palladium-catalyzed cross-coupling reaction of tert-butyl carbamate with various aryl(Het) halides with Cs2CO3 as base in 1,4-dioxane (solvent) has been investigated.

Application

tert-Butyl carbamate was used in palladium-catalyzed synthesis of N-Boc-protected anilines. It was used in the synthesis of tetrasubstituted pyrroles, functionalized with ester or ketone groups at C-3 position.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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One-Pot Three-Component Synthesis of Tetrasubstituted NH Pyrroles from Secondary Propargylic Alcohols, 1, 3-Dicarbonyl Compounds and tert-Butyl Carbamate.
Cadierno V, et al.
Journal of Heterocyclic Chemistry, 47(1), 233-236 (2010)
Swapna Bhagwanth et al.
The Journal of organic chemistry, 74(12), 4634-4637 (2009-06-13)
The scope of Pd-catalyzed synthesis of N-Boc-protected anilines from aryl bromides and commercially available tert-butyl carbamate is described. For the first time, this process can be conducted at room temperature (17-22 degrees C) using a combination of Pd(2)dba(3).CHCl(3) and a
Pd-catalyzed amidation of aryl (Het) halides with< i> tert</i>-butyl carbamate.
Qin L, et al.
Tetrahedron Letters, 51(33), 4446-4448 (2010)
Maximilian Tromayer et al.
Polymer chemistry, 8(2), 451-460 (2017-03-07)
The possibility of the direct encapsulation of living cells
Zeljko M Svedružić et al.
PloS one, 7(3), e32293-e32293 (2012-04-06)
We describe molecular processes that can facilitate pathogenesis of Alzheimer's disease (AD) by analyzing the catalytic cycle of a membrane-imbedded protease γ-secretase, from the initial interaction with its C99 substrate to the final release of toxic Aβ peptides. The C-terminal
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