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761052

Sigma-Aldrich

1H-Imidazole-1-carboxylic acid-3-butenyl ester

97%

Synonym(s):

Heller-Sarpong Reagent-Homoallyl

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About This Item

Empirical Formula (Hill Notation):
C8H10N2O2
CAS Number:
202523-13-5
Molecular Weight:
166.18
MDL number:
MFCD22666440
UNSPSC Code:
12352005
PubChem Substance ID:
329766902
NACRES:
NA.22

assay

97%

form

liquid

refractive index

n20/D 1.488

density

1.107 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

O=C(OCCC=C)N1C=CN=C1

InChI

1S/C8H10N2O2/c1-2-3-6-12-8(11)10-5-4-9-7-10/h2,4-5,7H,1,3,6H2

InChI key

BNGLJMQCDKTXTL-UHFFFAOYSA-N

Application

1H-Imidazole-1-carboxylic acid-3-butenyl ester can be used:
  • To prepare bis-naphthyridine derived cyclic mismatch binding ligands (CMBLs) which exhibit DNA repeat binding properties.
  • As a reagent in the chemoselective esterification of carboxylic acids.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

230.0 °F

flash_point_c

110 °C

Certificates of Analysis (COA)

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Design and synthesis of cyclic Mismatch-Binding Ligands (CMBLs) with variable linkers by Ring-Closing metathesis and their photophysical and DNA repeat binding properties
Mukherjee S, et al.
Chemistry?A European Journal , 23, 11385-11396 (2017)
Chemoselective esterification and amidation of carboxylic acids with imidazole carbamates and ureas
Heller ST and Sarpong R
Organic Letters, 12(20), 4572-4575 (2010)

Related Content

Heller Group – Professor Product Portal

Professor Heller and coworkers are engaged in the development of mild and chemoselective acylation reactions using carbonylazole-derived reagents. To that end, they have developed a suite of carbonylimidazole derivatives for facile and chemoselective esterification (MImC, etc.) and amidation (WImC) of carboxylic acids, in collaboration with Professor Richmond Sarpong.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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