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40766

Sigma-Aldrich

N,N-Dimethylmethyleneiminium chloride

≥95.0% (AT)

Synonym(s):

Böhme′s salt, Böhme′s salt, Dimethylformiminium chloride, Methylenedimethylammonium chloride

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About This Item

Linear Formula:
CH2=N+(CH3)2Cl-
CAS Number:
Molecular Weight:
93.56
Beilstein:
505955
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥95.0% (AT)

form

powder

reaction suitability

reaction type: C-C Bond Formation

mp

146-148 °C (lit.)

SMILES string

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

InChI

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

InChI key

ZJTROANVDZIEGB-UHFFFAOYSA-M

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Application

N,N-Dimethylmethyleneiminium chloride (Böhme′s salt) is a dimethylaminomethylating agent that can be used as one of the key reagents in the following applications:
  • Electrophilic aminomethylation of aldehydes and ketones to synthesize corresponding Mannich products, also known as Mannich reaction.
  • Preparation of dihydronaphthyridinones as HIV-1 integrase inhibitors.
  • Preparation of cyanotetrahydrooxo-β-carbolines via cyclocondensation of cyanomethyl indole-2-carboxylate with ammonia.
  • Asymmetric synthesis of phalarine via stereospecific Pictet-Spengler cyclocondensation and traceless chirality transfer from L-tryptophan.
  • Synthesis of functionalized diarylpyrrolizines as inhibitors of microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LOX).
  • Synthesis of (±)-phalarine with the rearrangement of an azaspiroindolenine and Gassman oxindole preparation as key steps.

Reacant for:
Preparation of dihydronaphthyridinones as HIV-1 integrase inhibitors
Mannich reactions
Preparation of cyanotetrahydrooxo-ß-carbolines via cyclocondensation reactions
Asymmetric synthesis of phalarine via stereospecific Pictet-Spengler cyclocondensation and traceless chirality transfer from L-tryptophan
Synthesis of functionalized diarylpyrrolizines as inhibitors of microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LOX)
Synthesis of (±)-phalarine with the rearrangement of an azaspiroindolenine and Gassman oxindole preparation as key steps

Other Notes

"Mannich-reagent" for direct use; higher yields of purer products were achieved in shorter times compared with the classical "Mannich reaction"; in-situ preparation of the reactive triflate with TMS-triflate

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °C - closed cup

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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G. Kinast et al.
Angewandte Chemie (International Edition in English), 88, 261-261 (1976)
Total Synthesis of Enantiopure Phalarine via a Stereospecific Pictet? Spengler Reaction: Traceless Transfer of Chirality from l-Tryptophan.
Trzupek J D, et al.
Journal of the American Chemical Society, 132(24), 8506-8512 (2010)
The Mannich reaction-II: derivatization of aldehydes and ketones using dimethyl (methylene) ammonium salts.
Holy N, et al.
Tetrahedron, 35(5), 613-619 (1979)
H. Bohme
Angewandte Chemie (International Edition in English), 88, 772-772 (1976)
H.-U. Reissig et al.
Liebigs Ann. Chem., 1914-1914 (1986)

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