14149-00-9

Usage

Type of compound

Quaternary ammonium salt

Uses

a. Catalyst in organic synthesis
b. Intermediate in the production of pharmaceuticals and dyes
c. Corrosion inhibitor
d. Stabilizer in the production of plastics and rubber

Physical state

White crystalline solid

Solubility

Soluble in water

Melting point

270-275°C

Safety precautions

a. May cause irritation to the skin
b. May cause irritation to the eyes
c. May cause irritation to the respiratory tract

Handling

Handle with caution due to potential irritation and health risks

Upstream product

• 221375-48-0 (N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide 
• 100-44-7 benzyl chloride 
• 3082-58-4 (S)-1,2-diphenylethyl amine 
• 173345-75-0 (S)-N-Boc-1,2-diphenylethylamine 
• 7699-79-8 benzhydrylidene-benzyl-amine 
• 100-39-0 benzyl bromide 
• 100-46-9 benzylamine 
• 126003-99-4 (1R,2R,5R)-3-[(E)-(S)-1,2-Diphenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 

Relevant academic research and scientific papers

One-pot synthesis of chiral nonracemic amines

One-pot five-component reactions of oxathiazolidine-S-oxides with mesitylmagnesium bromide, lithium bis(trimethylsilyl)amide, aldehydes and Grignard reagents afford chiral nonracemic amines or sulfinamides in good yields and high stereoselectivities.

Asymmetric synthesis of chiral amines by highly diastereoselective 1,2- additions of organometallic reagents to N-tert-butanesulfinyl imines

High yielding and highly diastereoselective methods for 1,2-additions of organometallic reagents to N-tert-butanesulfinyl aldimines (2) and N-tert- butanesulfinyl kerimines (3) are described. The additions of alkyl, aryl, alkenyl, and allyl carbanions to a diverse set of imines with different steric and electronic properties are demonstrated. Acidic methanolysis of the sulfinamide products (4 and 6) delivers highly enantioenriched α-branched and α,α-dibranched amines. Since a broad range of sulfinyl imines are easily accessible from aldehydes and ketones, a wide variety of enantioentriched amines may be prepared.

A new asymmetric synthesis of (S)-dolaphenine and its heteroaromatic congeners utilizing (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone as chiral auxiliaries

(+)-2-hydroxy-3-pinanone ((+)-HyPN,(+)-2a) and (-)-3-hydroxy-2-caranone ((-)-2b) were respectively converted to the corresponding Schiff bases 18a and 18b with 1-(2-thiazolyl)methylamine (17). Alkylation followed by removal of the chiral auxiliaries (+)-2a and (-)-2b afforded (S)-dolaphenine (10) as an optically pure form. The method was applied to the asymmetric synthesis of the dolaphenine analogs 27a-d.

Chiral quaternary benzophenone hydrazonium salt derivatives; efficient chiral catalysts for the enantioselective phase-transfer alkylation of imines. Application to synthesis of chiral primary amines

(2S)-1-Methyl-1-[N-(diphenylmethylene)-2-hydroxymethylpyrrolidine hydrazonium iodide I-a has been designed to catalyse the enantioselective phase-transfer alkylation of N-(diphenylmethylene) benzenemethanamine II. Although the weak acidic character of the latter, alkylations have been performed within reasonable reaction times. Optically active primary amines III a-e have been prepared in good chemical yields and up to 94% e.e. using 2-5 mol-% of the chiral catalyst only.