40766
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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
250-142-4
Beilstein/REAXYS Number:
505955
MDL number:
Assay:
≥95.0% (AT)
Form:
powder
Quality Level
assay
≥95.0% (AT)
form
powder
reaction suitability
reaction type: C-C Bond Formation
mp
146-148 °C (lit.)
functional group
amine
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
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-β-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
Preparation of dihydronaphthyridinones as HIV-1 integrase inhibitors
Mannich reactions
Preparation of cyanotetrahydrooxo-β-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
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signalword
Warning
hcodes
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
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
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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)
G. Kinast et al.
Angewandte Chemie (International Edition in English), 88, 261-261 (1976)
N. Holy et al.
Tetrahedron, 35, 613-613 (1979)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 40766-5G | 04061833355404 |
| 40766-25G | 04061838349224 |