25245-58-3

Basic information

• Product Name: METHYLGLYCERIN
• Synonyms: METHYLGLYCERIN;2-Methyl-Glycerol
• CAS NO: 25245-58-3
• Molecular Formula: C₄H₁₀O₃
• Molecular Weight: 106.1204
• Mol File: 25245-58-3.mol

Chemical Properties

• Boiling Point: 281.8 °C at 760 mmHg
• Flash Point: 145.8 °C
• Appearance: /
• Density: 1.217 g/cm³
• Vapor Pressure: 0.000412mmHg at 25°C
• Refractive Index: 1.489
• PKA: 13.75±0.29(Predicted)
• CAS DataBase Reference: METHYLGLYCERIN(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLGLYCERIN(25245-58-3)
• EPA Substance Registry System: METHYLGLYCERIN(25245-58-3)

Safety Data

• Hazardous Substances Data: 25245-58-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 4626, 1982 DOI: 10.1021/jo00145a004

InChI:InChI=1/C4H10O3/c1-4(7,2-5)3-6/h5-7H,2-3H2,1H3

Upstream product

• 597-32-0 1,3-dichloro-2-methyl-propan-2-ol 
• 597-33-1 3-chloro-2-methyl-propane-1,2-diol 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 77-49-6 2-Methyl-2-nitro-1,3-propanediol 
• 872-30-0 2-methylglycidol 
• 78947-98-5 3-(iodomethyl)-3-methyl-2,5-dioxacyclopentanone 
• 162537-13-5 1,3-bis[tert-butyldimethylsilyloxy]-2-methylpropan-2-ol 

Downstream Products

• 78-85-3 2-methylpropenal 
• 61580-09-4 4-methyl-2,6,7-trioxa-1-phosphabicyclo[2,2,1]heptane 
• 86884-87-9 (4RS)-4-hydroxymethyl-2,2,4-trimethyl-1,3-dioxolane 
• 1375107-95-1 7-bromo-8-fluoroquinoline 
• 1228960-86-8 1,1,1-tris[(pyridine-4-yloxy)methyl]ethane 
• 121363-85-7 2-methyl-1,3-di-O-trityl-1,2,3-propanetriol 

Relevant articles and documents

DXP reductoisomerase: Reaction of the substrate in pieces reveals a catalytic role for the nonreacting phosphodianion group

The role of the nonreacting phosphodianion group of 1-deoxy-d-xylulose-5- phosphate (DXP) in catalysis by DXP reductoisomerase (DXR) was investigated for the reaction of the substrate in pieces . The truncated substrate 1-deoxy-l-erythrulose is converted by DXR to 2-C-methylglycerol with a k cat/Km that is 106-fold lower than that for DXP. Phosphite dianion was found to be a nonessential activator, providing 3.2 kcal/mol of transition state stabilization for the truncated substrate. These results implicate a phosphate-driven conformational change involving loop closure over the DXR active site to generate an environment poised for catalysis.

Molybdenum-Catalyzed Hydroxyl-Directed Anti-Dihydroxylation of Allylic and Homoallylic Alcohols

A catalytic hydroxyl-directed anti-dihydroxylation of allylic and homoallylic alcohols has been developed. This operationally simple method was successfully applied to the direct anti-monodihydroxylation of allylic alcohols containing at least one distal olefinic unit. Under the catalysis of commercially available MoO2(acac)2, an array of hydroxylated dienes were successfully converted into various 1,2,3-triols using hydrogen peroxide as an environmentally benign oxidant under aerobic conditions, notably, in complete regioselectivities and in the most cases in diastereospecific pathway.

The role of phosphate in a multistep enzymatic reaction: Reactions of the substrate and intermediate in pieces

Several mechanistically unrelated enzymes utilize the binding energy of their substrate's nonreacting phosphoryl group to accelerate catalysis. Evidence for the involvement of the phosphodianion in transition state formation has come from reactions of the substrate in pieces, in which reaction of a truncated substrate lacking its phosphorylmethyl group is activated by inorganic phosphite. What has remained unknown until now is how the phosphodianion group influences the reaction energetics at different points along the reaction coordinate. 1-Deoxy-d-xylulose-5-phosphate (DXP) reductoisomerase (DXR), which catalyzes the isomerization of DXP to 2-C-methyl-d-erythrose 4-phosphate (MEsP) and subsequent NADPH-dependent reduction, presents a unique opportunity to address this concern. Previously, we have reported the effect of covalently linked phosphate on the energetics of DXP turnover. Through the use of chemically synthesized MEsP and its phosphate-truncated analogue, 2-C-methyl-d-glyceraldehyde, the current study revealed a loss of 6.1 kcal/mol of kinetic barrier stabilization upon truncation, of which 4.4 kcal/mol was regained in the presence of phosphite dianion. The activating effect of phosphite was accompanied by apparent tightening of its interactions within the active site at the intermediate stage of the reaction, suggesting a role of the phosphodianion in disfavoring intermediate release and in modulation of the on-enzyme isomerization equilibrium. The results of kinetic isotope effect and structural studies indicate rate limitation by physical steps when the covalent linkage is severed. These striking differences in the energetics of the natural reaction and the reactions in pieces provide a deeper insight into the contribution of enzyme-phosphodianion interactions to the reaction coordinate.

Chemoenzymatic enantioselective synthesis of 2-substituted glycerol derivatives

2-Substituted glycerol derivatives 4a-g were resolved by acylation with vinyl butyrate in the presence of lipases in organic media. The reverse reaction, the enzymatic hydrolysis of the corresponding butyrates 5a-g, was also highly stereoselective and pro

Development of a multikilogram synthesis of a chiral epoxide precursor to a CCR1 antagonist. Use of in situ monitoring for informed optimisation via fragile intermediates

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USE OF INTERMEDIATES ((R ) -2,2, 4-TRIMETHYL-L, 3-DIOXOLANE-4-YL) METHANOL (A), 3-F LUORO-4-NITRO-PHENOL (B) AND 1- (4-CHLORO- BENZYL) -PIPERIDIN-4-YLAMINE (C)

The present invention relates to novel processes for the preparation of intermediate compounds which can be used to prepare therapeutic agents. The present invention also relates to novel intermediate compounds which can be used to prepare therapeutic agents. More specifically, the invention relates to the use of intermediates ((R) -2,2,4-trimethyl-l, 3- dioxolane-4 -yl) methanol (A), 3-f luoro-4-nitro-phenol (B) and 1- (4-chloro-benZyl) -piperidin-4-ylamine (C).

Enantioselective synthesis of tertiary alcohols by the desymmetrizing benzoylation of 2-substituted glycerols

(Chemical Equation Presented) Complementary catalysts have been found for the enantioselective desymmetrization of 2-substituted glycerols by monobenzoylation with benzoyl chloride and Et3N to give chiral tertiary alcohols with 80 to 94% ee (se

Facile synthesis of C2-symmetric chiral crown ethers with two reactive hydroxymethyl groups

Two C2-symmetric chiral crown ethers, (2S,12S)-2,12- bis(hydroxymethyl)-2,12-dimethyl-18-crown-6 and (2R,9R)-2,9-bis(hydroxymethyl)- 2,9-dimethyl-18-crown-6 were synthesized from a chiral subunit, [(45)-2,2,4-trirnethyl-1,3-dioxolane-4-yl]methanol, at high enantiomeric purity over several steps. This synthetic method offers the potential to construct a variety of C2-symmetric chiral crown ethers using diverse combinations of building blocks. Georg Thieme Verlag Stuttgart.

Sterically Hindered Triacylglycerol Analogues as Potent Inhibitors of Human Digestive Lipases

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Enantioselective hydrolysis of functionalized 2,2-disubstituted oxiranes with bacterial epoxide hydrolases

The biohydrolysis of 2,2-disubstituted oxiranes bearing various oxygen functional groups was investigated using the epoxide hydrolase activity of 11 bacterial strains. The results show that the activity and the selectivity strongly depend on the substrate structure and the biocatalyst. Whereas substrates possessing free hydroxyl groups were not transformed, their analogs, protected as ethers, were well accepted. This allowed the convenient modulation of the enantioselectivity by proper choice of the ether group according to size and polarity. It was found that the distance of the ether-oxygen to the stereogenic quaternary carbon center of the oxirane ring had a profound influence on the enantioselectivity, and several oxiranes were resolved with good to excellent selectivities. The enantiomerically enriched epoxides and vicinal diols thus obtained contain a useful 'synthetic handle' in their side chain, which allows their use as building blocks in asymmetric synthesis.