40766

N,N-Dimethylmethyleneiminium chloride

≥95.0% (AT)

• Synonym(s): Böhme′s salt, Böhme′s salt, Dimethylformiminium chloride, Methylenedimethylammonium chloride
• Linear Formula: CH₂=N⁺(CH₃)₂Cl^-
• CAS Number: 30354-18-8
• Molecular Weight: 93.56
• Beilstein/REAXYS Number: 505955
• EC Number: 250-142-4
• MDL number: MFCD00011809
• UNSPSC Code: 12352100
• PubChem Substance ID: 57650016
• NACRES: NA.22

Properties

• Quality Level: 100
• 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

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

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 Information

• pictograms: GHS02,GHS07
• signalword: Warning
• hcodes: H228,H315,H319,H335
• pcodes: P210 - P240 - P241 - P261 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Sol. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 4.1B - Flammable solid hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 179.6 °F - closed cup
• flash_point_c: 82 °C - closed cup
• ppe: dust mask type N95 (US), Eyeshields, Gloves