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214914

Sigma-Aldrich

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
Beilstein:
1731022
EC Number:
251-680-2
MDL number:
MFCD00011810
UNSPSC Code:
12352100
PubChem Substance ID:
24852854
NACRES:
NA.22

Assay

98%

mp

219 °C (dec.) (lit.)

solubility

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

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

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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
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)
J. Prakt. Chem./Chem.-Ztg., 336, 91-91 (1994)
Synthetic Routes to Unsymmetrical Porphyrins.
Nardis S.
Synthesis and Modifications of Porphyrinoids, 203-239 (2014)
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