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167398

Sigma-Aldrich

tert-Butyl carbamate

98%

Synonym(s):

Boc-amide

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About This Item

Linear Formula:
NH2COOC(CH3)3
CAS Number:
Molecular Weight:
117.15
Beilstein/REAXYS Number:
1744500
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Maximilian Tromayer et al.
Polymer chemistry, 8(2), 451-460 (2017-03-07)
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Pd-catalyzed amidation of aryl (Het) halides with< i> tert</i>-butyl carbamate.
Qin L, et al.
Tetrahedron Letters, 51(33), 4446-4448 (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
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)
Tetsuo Cai et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 39(43), 8600-8610 (2019-09-19)
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