137588-59-1

Basic information

• Product Name: (-)-(5R,3R,2R)-5-(1-HYDROXY-1-METHYLETHYL)-3-CYANO-2-METHYLCYLOHEXANONE
• Synonyms: (-)-(5R,3R,2R)-5-(1-HYDROXY-1-METHYLETHYL)-3-CYANO-2-METHYLCYLOHEXANONE;(-)-(5R,3R,2R)-5-(1-Hydroxy-1-methylethyl)-3-cyano-2-methylcylohexanone
• CAS NO: 137588-59-1
• Molecular Formula: C₁₁H₁₇NO₂
• Molecular Weight: 195.26
• Mol File: 137588-59-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 351.7°Cat760mmHg
• Flash Point: 166.5°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 2.38E-06mmHg at 25°C
• Refractive Index: 1.486
• PKA: 14.90±0.29(Predicted)
• CAS DataBase Reference: (-)-(5R,3R,2R)-5-(1-HYDROXY-1-METHYLETHYL)-3-CYANO-2-METHYLCYLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(5R,3R,2R)-5-(1-HYDROXY-1-METHYLETHYL)-3-CYANO-2-METHYLCYLOHEXANONE(137588-59-1)
• EPA Substance Registry System: (-)-(5R,3R,2R)-5-(1-HYDROXY-1-METHYLETHYL)-3-CYANO-2-METHYLCYLOHEXANONE(137588-59-1)

Safety Data

• Hazardous Substances Data: 137588-59-1(Hazardous Substances Data)

Usage

General Description

(-)-(5R,3R,2R)-5-(1-hydroxy-1-methylethyl)-3-cyano-2-methylcyclohexanone, also known as Ropivacaine, is a local anesthetic medication belonging to the amino amide group. It is used to numb a specific area without causing unconsciousness. Ropivacaine works by blocking the sodium channels in the nerve fibers, which prevents the transmission of pain signals to the brain. It is commonly used for epidural anesthesia during labor and surgery, as well as for nerve block procedures to manage pain. Ropivacaine has a higher safety profile compared to other local anesthetics, as it is less likely to cause systemic toxicity and is less cardiotoxic. However, it can still cause adverse effects such as dizziness, headache, and nerve damage if not used properly.

InChI:InChI=1/C11H17NO2/c1-7-8(6-12)4-9(5-10(7)13)11(2,3)14/h7-9,14H,4-5H2,1-3H3/t7-,8+,9-/m1/s1

Upstream product

• 137625-67-3 (-)-(1R,2R,5R)-2-methyl-5-(1-methylethenyl)-3-oxocyclohexanecarbonitrile 

Downstream Products

• 67413-30-3 (S)-Aziridin-2-carbonsaeureamid 
• 143023-76-1 (+)-5R-(1-Hydroxy-1-methyl ethyl)-3S-(N-acryloylaminomethyl)-2-methylcyclohexanone 
• 143023-78-3 (+)-5R-(1-Hydroxy-1-methyl ethyl)-3S-(N-acetylaminomethyl)-2-methylcyclohexanone 
• 1037268-15-7 (1R,2R,3R,5R)-1-amino-2-methyl-5-(1-hydroxy-1-methyl-ethyl)cyclohexane-1,3-dicarbonitrile 

Relevant articles and documents

A recyclable chiral auxiliary for the asymmetric syntheses of α-aminonitriles and α-aminophosphinic derivatives

Optically active α-aminonitriles and α-aminophosphinic derivatives have been prepared in high yield and high ee using an easy route by extending our previously developed method involving the following sequence: (i) stereoselective Strecker condensation of

Influence of a Hydroalcoholic Solvent on the Enantioselectivity of α-Amino nitrile Hydration Catalysed by Chiral Ketones

The enantioselective hydration of α-aminonitriles 1, RCH(CN)NH2 i; 1c: R = Ph> has been achieved in an alkaline hydroalcoholic medium in the presence of chiral ketonic catalysts.Of the different ketones used, (-)-(5R,3R,2R)-5-(methylethenyl)-3-cyano-2-methylcyclohexanone (8) gives rise to significant enantioselectivity D/kL = 2.1; T = 10 deg C; solvent, water-propan-2-ol (45:55,v/v)>.Although the structure of the catalyst could probably be improved, we show in this paper that the efficiency and especiallythe enantioselectivity of the catalyst are not only under steric control but also depend on the nature and composition of the hydroalcoholic solvent.Thus, for the three aminonitriles studied in the presence of the catalyst 8, the increase in percentage of propan-2-ol favours the hydration of the D α-aminonitrile as shown for the hydration of 1c for which the ratio kD/kL increases threefold when the percentage of propan-2-ol increases from 10 to 95percent.