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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:
33797-51-2
Molecular Weight:
185.01
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24852854
EC Number:
251-680-2
Beilstein/REAXYS Number:
1731022
MDL number:
MFCD00011810
Assay:
98%

Key Documents

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InChI key

VVDUZZGYBOWDSQ-UHFFFAOYSA-M

InChI

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

SMILES string

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

assay

98%

mp

219 °C (dec.) (lit.)

solubility

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

functional group

amine

Quality Level

100

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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
GHS07

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCR2489
MKCQ3458
MKCN0560
MKCK4779
MKCH7423

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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)
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
Tetrahedron Asymmetry, 5, 921-921 (1994)
Synthetic Routes to Unsymmetrical Porphyrins.
Nardis S.
Synthesis and Modifications of Porphyrinoids, 203-239 (2014)
Journal of the Chemical Society. Perkin Transactions 1, 3295-3295 (1992)
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