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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:
4248-19-5
Molecular Weight:
117.15
Beilstein:
1744500
EC Number:
224-209-3
MDL number:
MFCD00007962
UNSPSC Code:
12352100
PubChem Substance ID:
24850207
NACRES:
NA.22

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

167398-BULK:
167398-5G:
167398-100G:
167398-1KG:
167398-1G:
167398-VAR:
167398-25G:

Certificates of Analysis (COA)

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Maximilian Tromayer et al.
Polymer chemistry, 8(2), 451-460 (2017-03-07)
The possibility of the direct encapsulation of living cells
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)
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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