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Sigma-Aldrich

1-(Diethoxymethyl)imidazole

≥97.0%

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About This Item

Empirical Formula (Hill Notation):
C8H14N2O2
CAS Number:
61278-81-7
Molecular Weight:
170.21
Beilstein/REAXYS Number:
908482
MDL number:
MFCD00956331
UNSPSC Code:
12352100
PubChem Substance ID:
57649666
NACRES:
NA.22

assay

≥97.0%

form

liquid

refractive index

n20/D 1.464

density

1.041 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC(OCC)n1ccnc1

InChI

1S/C8H14N2O2/c1-3-11-8(12-4-2)10-6-5-9-7-10/h5-8H,3-4H2,1-2H3

InChI key

NNQBAGFIYBBAFL-UHFFFAOYSA-N

Related Categories

General description

1-(Diethoxymethyl)imidazole is an orthoamide protected imidazole. The dianion reacts selectively at the 2 position 1-(Diethoxymethyl)imidazole is a 1-substituted imidazoles. Isoprene-mediated lithiation of 1-(diethoxymethyl)imidazole, leads to the preparation of the corresponding 2-lithio intermediate, which reacts with different electrophiles to afford 2-functionalised imidazoles.

Application

1-(Diethoxymethyl)imidazole may be used in the preparation of various hydroxy- and amino-functionalized imidazoles, via isoprene-mediated lithiation followed by reaction with an electrophile.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

233.6 °F

flash_point_c

112.0 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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1, 2-Functionalized Imidazoles as Palladium Ligands: An Efficient and Robust Catalytic System for the Fluorine-Free Hiyama Reaction.
Martinez R, et al.
European Journal of Organic Chemistry, 4, 872-877 (2014)
N.J. Curtis et al.
The Journal of Organic Chemistry, 45, 4038-4038 (1980)
Isoprene-catalysed lithiation: deprotection and functionalisation of imidazole derivatives.
Torregrosa R, et al.
Tetrahedron, 63(4), 947-952 (2007)
L.N. Pridgen et al.
Tetrahedron Letters, 38, 1275-1275 (1997)

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