36815
1-(Diethoxymethyl)imidazole
≥97.0%
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About This Item
Empirical Formula (Hill Notation):
C8H14N2O2
CAS Number:
Molecular Weight:
170.21
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
908482
Assay:
≥97.0%
Form:
liquid
InChI
1S/C8H14N2O2/c1-3-11-8(12-4-2)10-6-5-9-7-10/h5-8H,3-4H2,1-2H3
SMILES string
CCOC(OCC)n1ccnc1
InChI key
NNQBAGFIYBBAFL-UHFFFAOYSA-N
assay
≥97.0%
form
liquid
refractive index
n20/D 1.464
density
1.041 g/mL at 20 °C (lit.)
functional group
ether
storage temp.
2-8°C
Quality Level
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.
signalword
Warning
hcodes
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
WGK 3
flash_point_f
233.6 °F
flash_point_c
112.0 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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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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