112211-88-8

Basic information

• Product Name: (S)-2-Isopropylamino-3-methyl-1-butanol
• Synonyms: (S)-2-Isopropylamino-3-methyl-1-butanol;(S)-2-Isopropylamino-3-methyl;(S)-2-(IsopropylaMino)-3-Methylbutan-1-ol
• CAS NO: 112211-88-8
• Molecular Formula: C₈H₁₉NO
• Molecular Weight: 145.24
• Product Categories: Asymmetric Synthesis;Synthetic Organic Chemistry
• Mol File: 112211-88-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 218.4oC at 760 mmHg
• Flash Point: 61oC
• Appearance: /
• Density: 0.88
• Vapor Pressure: 0.0267mmHg at 25°C
• Refractive Index: -3 ° (C=1, EtOH)
• PKA: 14.70±0.10(Predicted)
• CAS DataBase Reference: (S)-2-Isopropylamino-3-methyl-1-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Isopropylamino-3-methyl-1-butanol(112211-88-8)
• EPA Substance Registry System: (S)-2-Isopropylamino-3-methyl-1-butanol(112211-88-8)

Safety Data

• Hazardous Substances Data: 112211-88-8(Hazardous Substances Data)

Usage

General Description

(S)-2-Isopropylamino-3-methyl-1-butanol, also known as levomethadone, is a synthetic opioid analgesic and sedative that is commonly used for pain management and treatment of opioid addiction. It functions by binding to and activating opioid receptors in the central nervous system, resulting in a decrease in the perception of pain and a feeling of relaxation and euphoria. Levomethadone is known for its long duration of action and its ability to produce strong analgesic effects, making it valuable for chronic pain management. However, it is also associated with a potential for abuse and dependence, as well as a risk of respiratory depression and overdose. Therefore, it is strictly regulated and prescribed only under close medical supervision.

InChI:InChI=1/C8H19NO/c1-6(2)8(5-10)9-7(3)4/h6-10H,5H2,1-4H3/t8-/m1/s1

Upstream product

• 219639-09-5 methyl (S)-N-iso-propyl-2-amino-3-methylbutanoate 
• 90600-09-2 N-isopropyl-L-valine 
• 693-04-9 butyl magnesium bromide 
• 140424-74-4 2-((S)-3,4-Diisopropyl-oxazolidin-2-yl)-benzaldehyde 
• 557-20-0 diethylzinc 
• 925-90-6 ethylmagnesium bromide 
• 75-16-1 methylmagnesium bromide 
• 4070-48-8 L-Valine methyl ester 
• 72-18-4 L-valine 
• 2026-48-4 (S)-valinol 

Downstream Products

• 143490-20-4 (2R,4S)-2-(2-bromophenyl)-3,4-diisopropyl-1,3-oxazolidine 
• 143490-20-4 (2S,4S)-2-(2-bromophenyl)-3,4-diisopropyl-1,3-oxazolidine 
• 140424-75-5 (2R,4S)-o-<2-(4,N-diisopropyl-1,3-oxazolidinyl)>benzaldehyde 
• 140424-74-4 (2S,4S)-o-<2-(4,N-diisopropyl-1,3-oxazolidinyl)>benzaldehyde 
• 790196-81-5 N-isopropyl-O-triisopropyl silyl valinol 

Relevant articles and documents

Mixed aggregates containing n-butyl, sec-butyl-, or tert-butyllithium and a chiral lithium amide derived from N-isopropl-O-methyl valinol

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Asymmetric Synthesis using Chiral Bases: Enantioselective α-Alkylation of Carboxylic Acids

Enantioselective alkylation of carboxylic acids (1) and (2) at the α-position can be performed using the chiral lithium isopropylamides (3) or (4), which function as both a strong base and a chiral auxiliary.

Asymmetric addition of n-butyllithium to aldehydes: New insights into the reactivity and enantioselectivity of the chiral amino ether accelerated reaction

Enantioselective butylation of benzaldehyde with n-butyllithium was mediated by a series of chiral lithium amide analogues to give 1-phenylpentanol in good to moderate enantioselectivities. In order to achieve high enantiomeric excess in the reaction, the lithium amide must have a substituent larger than methyl on both the carbon at the stereogenic center and the nitrogen. Computational studies, using semi-empirical (PM3) and density functional (B3LYP) methods, show that the stabilities of the transition states for the chiral lithium amide accelerated butylation of isobutyraldehyde are in agreement with experiments.