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40766 Sigma-Aldrich

N,N-Dimethylmethyleneiminium chloride

≥95.0% (AT)

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

  • CAS Number 30354-18-8

  • Linear Formula CH2=N+(CH3)2Cl-

  • Molecular Weight 93.56

  •  Beilstein/REAXYS Number 505955

  •  EC Number 250-142-4

  •  MDL number MFCD00011809

  •  PubChem Substance ID 57650016

  •  NACRES NA.22

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Properties

Related Categories C-C Bond Formation, Chemical Synthesis, Other Synthetic Reagents for C-C Bond Formation, Synthetic Reagents
Quality Level   100
assay   ≥95.0% (AT)
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

Description

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

Packaging

5, 25 g in glass bottle

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
UN1325 - class 4.1 - PG 3 - Flammable solids, organic, n.o.s., HI: all
WGK Germany 
WGK 3
Flash Point(F) 
179.6 °F - closed cup
Flash Point(C) 
82 °C - closed cup

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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