91191-95-6

Basic information

• Product Name: (S)-(+)-2-(METHYLMETHOXY)-1,2-PROPANEDIOL
• Synonyms: (S)-(+)-2-(METHYLMETHOXY)-1,2-PROPANEDIOL;((S)-2-(METHOXYMETHOXY)PROPAN-1-OL;(S)-2-Methoxymethoxy-1-propanol;MOM protected (S)-1,2-Propanediol;(S)-2-Ethoxypropane-1,2-diol
• CAS NO: 91191-95-6
• Molecular Formula: C₅H₁₂O₃
• Molecular Weight: 120.15
• Product Categories: Chiral Compound
• Mol File: 91191-95-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 153.861 °C at 760 mmHg
• Flash Point: 75 °C
• Appearance: /
• Density: 0.998 g/mL at 25 °C
• Vapor Pressure: 1.205mmHg at 25°C
• Refractive Index: 1.411
• CAS DataBase Reference: (S)-(+)-2-(METHYLMETHOXY)-1,2-PROPANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-2-(METHYLMETHOXY)-1,2-PROPANEDIOL(91191-95-6)
• EPA Substance Registry System: (S)-(+)-2-(METHYLMETHOXY)-1,2-PROPANEDIOL(91191-95-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 91191-95-6(Hazardous Substances Data)

Usage

General Description

(S)-(+)-2-(Methylmethoxy)-1,2-propanediol, also known as (S)-MMPD, is a chemical compound with a molecular structure containing a chiral center. It is commonly used as a chiral building block in the synthesis of pharmaceuticals and agrochemicals. (S)-MMPD is known for its ability to selectively generate enantiomerically pure products, making it a valuable tool in the production of chirally pure substances. It is also used in the synthesis of chiral ligands and catalysts for asymmetric synthesis. Additionally, (S)-MMPD has potential applications in the development of new materials and in the field of organic chemistry.

InChI:InChI=1/C5H12O3/c1-5(3-6)8-4-7-2/h5-6H,3-4H2,1-2H3/t5-/m0/s1

Upstream product

• 91191-93-4 (-)-ethyl (S)-2-hydroxypropionate methoxymethyl ether 
• 119650-35-0 (S)-methyl 2-(methoxymethoxy)propanoate 

Downstream Products

• 1311285-22-9 N-[(2Z)-3-butyl[1,3]thiazolo[4,5-c]pyridin-2(3H)-ylidene]-2-{[(2S)-2-(methoxymethoxy)propyl]oxy}-5-(trifluoromethyl)benzamide 
• 1311285-25-2 N-[(2Z)-1-butyl[1,3]thiazolo[5,4-b]pyridin-2(1H)-ylidene]-2-{[(2S)-2-(methoxymethoxy)propyl]oxy}-5-(trifluoromethyl)benzamide 
• 1147133-24-1 C₁₂H₁₅NO₇ 

Relevant articles and documents

Stereoselective synthesis of (-)-synparvolide B

The stereoselective synthesis of (-)-synparvolide B, isolated from Syncolostemon parviflorus, has been accomplished from (S)-ethyl lactate. A 1,2-chelation controlled allylation, Sharpless asymmetric epoxidation, Brown asymmetric allylation and RCM reactions were used as the key steps.

Scope and limitations of ether-directed, metal-catalysed aza-Claisen rearrangements; Improved stereoselectivity using non-coordinating solvents

In an effort to understand and enhance the stereochemical outcome of the MOM-ether directed rearrangement of allylic trichloroacetimidates we have investigated various reaction conditions for this process. A range of Pd(ii) and other metal catalysts have been shown to effectively catalyse the rearrangement providing the subsequent allylic amides in high selectivity (up to 11: 1 ratio of diastereomers). The replacement of THF as a solvent in this reaction with non-coordinating solvents such as toluene has led to an enhancement of the directing effect resulting in a significant increase in the diastereoselective outcome (15: 1 ratio). The reaction was also carried out for the first time, using a highly coordinating ionic solvent which disrupts binding of the Pd(ii)-catalyst to the MOM-ether yielding the allylic amide in only moderate diastereoselectivity. These results provide further evidence for the ether directed aza-Claisen rearrangement of allylic trichloroacetimidates. The Royal Society of Chemistry 2006.

A highly stereoselective ether directed palladium catalysed aza-Claisen rearrangement

A highly stereoselective rearrangement of allylic trichloroacetimidates to allylic trichloroamides has been achieved using adjacent ether groups to direct facial coordination of the palladium(II) catalyst. The Royal Society of Chemistry 2005.