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Merck
CN

214914

N,N-Dimethylmethyleneiminium iodide

98%

Synonym(s):

N,N-Dimethylmethyleneammonium iodide, Eschenmoser’s salt

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About This Item

Linear Formula:
CH2=N+(CH3)2I-
CAS Number:
Molecular Weight:
185.01
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
251-680-2
Beilstein/REAXYS Number:
1731022
MDL number:
Assay:
98%
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Quality Level

assay

98%

mp

219 °C (dec.) (lit.)

solubility

water: soluble 50 mg/mL, clear to slightly hazy, colorless to yellow

functional group

amine

SMILES string

[I-].C[N+](C)=C

InChI

1S/C3H8N.HI/c1-4(2)3;/h1H2,2-3H3;1H/q+1;/p-1

InChI key

VVDUZZGYBOWDSQ-UHFFFAOYSA-M

General description

N,N-Dimethylmethyleneiminium iodide is useful reagent for many synthetic applications, especially aminomethylation and conversion of ketones to α,β−unsaturated enones.


pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves



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A new method using 2-chloro-4, 6-dimethoxy-1, 3, 5-triazine for facile elimination of dimethylamino group in Eschenmoser's methylenation for synthesis of a, ?-unsaturated esters.
Yamada K, et al.
Tetrahedron Letters, 54(13), 1753-1760 (2013)
Tetrahedron Asymmetry, 5, 921-921 (1994)
Masayuki Inoue et al.
The Journal of organic chemistry, 72(8), 3065-3075 (2007-03-16)
(-)-Merrilactone A [(-)-1], isolated from Illicium merrillianum in 2000, possesses neurite outgrowth activity in cultures of fetal rat cortical neurons, and, therefore, is expected to show therapeutic potential for the treatment of neurodegeneration associated with Alzheimer's and Parkinson's diseases. Apart



Global Trade Item Number

SKUGTIN
214914-10G04061838773234
214914-50G04061832763217