94991-72-7

Basic information

• Product Name: S-(+)-Mexiletine
• Synonyms: (S)-Mexiletine;2-Propanamine, 1-(2,6-dimethylphenoxy)-, (2S)- (9CI);2-Propanamine, 1-(2,6-dimethylphenoxy)-, (S)-;d-Mexiletine;S-(+)-Mexiletine;(S)-1-(2,6-DiMethylphenoxy)propan-2-aMine
• CAS NO: 94991-72-7
• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.25878
• Mol File: 94991-72-7.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 271.5°C at 760 mmHg
• Flash Point: 112.2°C
• Appearance: /
• Density: 0.979g/cm³
• Vapor Pressure: 0.00642mmHg at 25°C
• Refractive Index: 1.516
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: S-(+)-Mexiletine(CAS DataBase Reference)
• NIST Chemistry Reference: S-(+)-Mexiletine(94991-72-7)
• EPA Substance Registry System: S-(+)-Mexiletine(94991-72-7)

Safety Data

• Hazardous Substances Data: 94991-72-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H17NO/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6,10H,7,12H2,1-3H3/t10-/m0/s1

Upstream product

• 252049-72-2 (2S)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-(R)-mandelamide 
• 31828-71-4 RS-mexiletine 
• 265994-90-9 (+)-(S)-2-[2-(2,6-dimethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione 
• 141-78-6 ethyl acetate 
• 143-07-7 lauric acid 
• 576-26-1 2.6-dimethylphenol 
• 61102-09-8 (RS)-1-(2,6-dimethylphenoxy)propan-2-ol 
• 72806-53-2 1-(2,6-Dimethylphenoxy)-2-azido-propan 
• 68164-74-9 1-(2,6-Dimethylphenoxy)-2-methansulfonyloxy-propan 
• 252049-70-0 (2RS)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-tetrahydropyranyl-(R)-mandelamide 
• 1051392-84-7 (E)-1-(2,6-dimethyl-phenoxy)-propan-2-one O-benzyl oxime 
• 1093278-37-5 (2S)-[(2,6-dimethylphenoxy)methyl]-1-[(R)-1-phenylethyl]aziridine 
• 5370-01-4 (rac)-mexiletine hydrochloride 
• 252049-71-1 (2R)-N-(1-(2',6'-dimethylphenoxy)-2-propyl)-(R)-mandelamide 

Downstream Products

• 1100754-02-6 tert-butyl (R)-1-(2,6-dimethylphenoxy)propan-2-ylcarbamate 
• 53012-41-2 (2,6-dimethylphenoxy)-2-propanone 

Relevant articles and documents

Enantiodivergent syntheses of (+)- and (?)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (?)-mexiletine from D-(+)-mannitol

Chiron approach was used to acquire optically pure (R)- and (S)-1-(2,6-dimethylphenoxy)propan-2-ol, immediate precursors of (S)- and (R)-mexiletines, respectively. Two different routes were followed from a D-mannitol-derived optically pure common precursor to get the enantiomeric alcohols separately. Comparison of their specific rotation values with the corresponding literature values as well as exact mirror-image relationship between their CD curves proved their high enantiopurity. These alcohols were then transformed to the corresponding amine-drugs in an efficient one-step process instead of two steps described in the literature.

Chiral aziridine ring opening: facile synthesis of (R)-mexiletine and (R)-phenoxybenzamine hydrochloride

Abstract A simple and efficient synthesis of chiral drugs (R)-mexiletine 1, an anti-arrhythmic drug and (R)-phenoxybenzamine hydrochloride 2, an anti-hypertensive drug has been described via controlled reductive ring opening of chiral aziridine as a key step. The target compounds 1 and 2 were obtained in overall yields of 34% and 10.5%, respectively.

Liquid chromatographic resolution of mexiletine and its analogs on crown ether-based chiral stationary phases

Mexiletine, an effective class IB antiarrhythmic agent, and its analogs were resolved on three different crown ether-based chiral stationary phases (CSPs), one (CSP 1) of which is based on (+)-(18-crown-6)-2,3,11,12- tetracarboxylic acid and the other two (CSP 2 and CSP 3) are based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6. Mexiletine was resolved with a resolution (RS) of greater than 1.00 on CSP 1 and CSP 3 containing residual silanol group-protecting n-octyl groups on the silica surface, but with a resolution (RS) of less than 1.00 on CSP 2. The chromatographic behaviors for the resolution of mexiletine analogs containing a substituted phenyl group at the chiral center on the three CSPs were quite dependent on the phenoxy group of analytes. Namely, mexiletine analogs containing 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3-methylphenoxy, 4-methylphenoxy, and a simple phenoxy group were resolved very well on the three CSPs even though the chiral recognition efficiencies vary with the CSPs. However, mexiletine analogs containing 2-methylphenoxy group were not resolved at all or only slightly resolved. Among the three CSPs, CSP 3 was found to show the highest chiral recognition efficiencies for the resolution of mexiletine and its analogs, especially in terms of resolution (RS). Chirality 26:272-278, 2014. 2014 Wiley Periodicals, Inc.