19131-99-8

Basic information

• Product Name: (S)-(-)-N,ALPHA-DIMETHYLBENZYLAMINE
• Synonyms: (S)-N-METHYL-1-PHENYLETHANAMINE;S(-)-N-METHYL-1-PHENYLETHYLAMINE;(S)(-)-N-METHYL-ALPHA-PHENETHYLAMINE;(S)-N-METHYL-ALPHA-PHENYLETHYLAMINE;(S)-(-)-N-METHYL A-METHYLBENZYLAMINE;(S)-(-)-N,ALPHA-DIMETHYLBENZYLAMINE;(S)-(-0-N,α-DIMETHYLBENZYLAMINE;(s)-(-)-n,α-dimethylbenzylamine
• CAS NO: 19131-99-8
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• Product Categories: Chiral Compound
• Mol File: 19131-99-8.mol
• Article Data: 28

Chemical Properties

• Melting Point: 116°C (estimate)
• Boiling Point: 74-76 °C11 mm Hg(lit.)
• Flash Point: 143 °F
• Appearance: /
• Density: 0.928 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00238mmHg at 25°C
• Refractive Index: n20/D 1.512(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.77±0.10(Predicted)
• BRN: 1446867
• CAS DataBase Reference: (S)-(-)-N,ALPHA-DIMETHYLBENZYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-N,ALPHA-DIMETHYLBENZYLAMINE(19131-99-8)
• EPA Substance Registry System: (S)-(-)-N,ALPHA-DIMETHYLBENZYLAMINE(19131-99-8)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 26-36-45
• RIDADR: UN 2619 8/PG 2
• WGK Germany: 3
• F: 10-23
• HazardClass: IRRITANT
• Hazardous Substances Data: 19131-99-8(Hazardous Substances Data)

Usage

Uses

Used to make asymmetric organometallic catalysts (e.g., for conjugate additions to enones).

General Description

(S)-(-)-N,a-Dimethylbenzylamine may be used along with benzaldehyde in the Mannich-type aminoalkylation of 2-naphthol to form 1-((S)-phenyl(((1′S)-1′-phenylethyl)methylamino)methyl)-2-naphthol. This optically active tertiary aminonaphthol can catalyze the enantioselective alkenylation of various aldehyde to generate chiral (E)- allyl alcohols.

InChI:InChI=1/C10H11NS/c1-7-4-9(3)10(11-6-12)5-8(7)2/h4-5H,1-3H3

Upstream product

• 10557-01-4 (E)-N-(α-methylbenzylidene)methylamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 79-22-1 methyl chloroformate 
• 6907-71-7 N-(1-phenylethylidene)methanamine 
• 6948-01-2 N-formyl-(-)-α-phenylethylamine 
• 98-86-2 acetophenone 
• 74-89-5 methylamine 
• 118762-10-0 N-chloro-N,α-dimethylbenzylamine 
• 42882-26-8 N-methyl-N-(1-phenylethyl)amine 
• 67-56-1 methanol 
• 74-88-4 methyl iodide 
• 173278-25-6 tert-butyl (S)-methyl(1-phenylethyl)carbamate 
• 14185-42-3 (S)-methyl (1-phenylethyl)carbamate 
• 33290-12-9 (1S)-N-1-Phenethyl-3-hydroxy-2,2-dimethylpropanamide 

Downstream Products

• 90504-13-5 (S)(-)-N-methyl-N-(pyridin-2-yl)-α-phenylethylamine 
• 82297-07-2 Acetic acid 1-methyl-2-[methyl-(1-phenyl-ethyl)-amino]-propyl ester 
• 82297-08-3 Acetic acid 2-[methyl-(1-phenyl-ethyl)-amino]-1-phenoxymethyl-ethyl ester 
• 126745-09-3 N'-[(S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-methyl-propyl]-N-methyl-N-((S)-1-phenyl-ethyl)-formamidine 
• 122873-90-9 (S_p,S_c)-O-2-(trimethylsilyl)ethyl N,P-dimethyl-N-(1-phenylethyl)phosphonamidothioate 
• 122873-91-0 (R_p,S_c)-O-2-(trimethylsiyl)ethyl N,P-dimethyl-N-(1-phenylethyl)phosphonamidothioate 
• 89362-14-1 Methyl-penta-2,3-dienyl-((S)-1-phenyl-ethyl)-amine 
• 75263-10-4 [(Ethyl-{[methyl-((R)-1-phenyl-ethyl)-amino]-methyl}-phosphanyl)-methyl]-methyl-((R)-1-phenyl-ethyl)-amine 
• 134295-63-9 (S)-N-Methyl-N-(1-phenylethyl)benzenesulfonamide 
• 17683-36-2 (-)-methyl(2-hydroxyethyl)(1-phenylethyl)amine 
• 79349-06-7 N-methyl-N-<(-)-α-phenylethyl>-o-hydroxybenzamide 
• 75263-12-6 Methyl-[({[methyl-((S)-1-phenyl-ethyl)-amino]-methyl}-phenyl-phosphanyl)-methyl]-((S)-1-phenyl-ethyl)-amine 
• 155795-38-3 (S)-N-methyl-N-(1-phenylethyl)chloroacetamide 
• 167933-96-2 N-Methyl-N-nitroso-1(S)-phenylethylamine 

Relevant articles and documents

Solid-phase supported chiral lithium amides used in deprotonation reactions

The lithium salt of polymer supported phenylethyl amine showed surprisingly high enantioselectivity in the asymmetric deprotonation reaction of cyclohexene oxide. The polymer supported chiral lithium amide base also proved to be more reactive compared to the free chiral lithium amide base. This is a new insight in the development and mechanism of chiral lithium amide bases used in asymmetric reactions.

CHIRALITY SENSING WITH MOLECULAR CLICK CHEMISTRY PROBES

The present invention relates to an analytical method that includes providing a sample potentially containing a chiral analyte that can exist in stereoisomeric forms, and providing a probe selected from the group consisting of coumarin-derived Michael acceptors, dinitrofluoroarenes and analogs thereof, arylsulfonyl chlorides and analogs thereof, arylchlorophosphines and analogs thereof, aryl halophosphites, and halodiazaphosphites. The sample is contacted with the probe under conditions to permit covalent binding of the probe to the analyte, if present in the sample; and, based on any binding that occurs, the absolute configuration of the analyte in the sample, and/or the concentration of the analyte in the sample, and/or the enantiomeric composition of the analyte in the sample is/are determined. The probe may be a coumarin-derived Michael acceptor, a di nitrofluoroarene or analog thereof, an arylsulfonyl chloride or analog thereof, an arylchlorophosphine or analog thereof, an aryl halophosphite, or a halodiazaphosphite.

A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines

Chloramines are an important class of reagents, providing a convenient source of chlorine or electrophilic nitrogen. However, the instability of these compounds is a problem which makes their isolation and handling difficult. To overcome these hazards, a continuous-flow approach is reported which generates and immediately reacts N-chloramines directly, avoiding purification and isolation steps. 2-Chloramines were produced from the reaction of styrenes with N-alkyl-N-sulfonyl-N-chloramines, whilst N-alkyl or N,N’-dialkyl-N-chloramines reacted with anisaldehyde in the presence of t-BuO2H oxidant to afford amides. Primary and secondary imines were produced under continuous conditions from the reaction of N-chloramines with base, with one example subsequently reduced under asymmetric conditions to produce a chiral amine in 94% ee.