ESCHENMOSER'S SALT Property

Melting point:

146-148 °C(lit.)

Flash point:

180 °F

storage temp. 

Store below +30°C.

solubility 

Chloroform (Very Slightly, Heated), DMSO (Sparingly, Heated, Sonicated)

form 

Solid

color 

White to Off-White

BRN 

505955

Stability:

Hygroscopic, Unstable in Protic Solvent

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 1325 4.1/PG 3

WGK Germany 

3

F 

3-10-21

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H228Flammable solid

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

ESCHENMOSER'S SALT Chemical Properties,Usage,Production

Uses

N,N-Dimethylmethyleneiminium chloride (B?hme′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.