1708-39-0

Basic information

• Product Name: 2-PHENYL-1.3-DIOXOLANE-4-METHANOL
• Synonyms: 2-phenyl-3-dioxolane-4-methanol;2-phenyl-m-dioxan-5-ol;BENZALDEHYDEGLYCERALACETAL;2-Phenyl-4-hydroxymethyl-1,3-dioxolane 95%;(2-Phenyl-1,3-dioxolane-4-yl)methanol;(2-phenyl-1,3-dioxolan-4-yl)methanol;1,2-BENZYLIDENEGLYCEROL
• CAS NO: 1708-39-0
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20048
• EINECS: 216-962-1
• Mol File: 1708-39-0.mol

Chemical Properties

• Melting Point: 84 °C
• Boiling Point: 280 °C(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 1.185 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000253mmHg at 25°C
• Refractive Index: n20/D 1.538(lit.)
• PKA: 14.20±0.10(Predicted)
• CAS DataBase Reference: 2-PHENYL-1.3-DIOXOLANE-4-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PHENYL-1.3-DIOXOLANE-4-METHANOL(1708-39-0)
• EPA Substance Registry System: 2-PHENYL-1.3-DIOXOLANE-4-METHANOL(1708-39-0)

Safety Data

• RTECS: JI3325000
• Hazardous Substances Data: 1708-39-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-PHENYL-1.3-DIOXOLANE-4-METHANOL is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
2-PHENYL-1.3-DIOXOLANE-4-METHANOL is used as a building block in the synthesis of complex organic molecules. Its reactive functional groups enable the formation of a wide range of chemical products, including specialty chemicals and advanced materials.
Used in Preparation of Glycerol Benzaldehyde:
2-PHENYL-1.3-DIOXOLANE-4-METHANOL is used as a starting material for the preparation of Glycerol Benzaldehyde with high specific selectivity. This process highlights the compound's utility in the synthesis of valuable chemical intermediates.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Mildly toxic by skin contact. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C10H12O3/c11-6-9-7-12-10(13-9)8-4-2-1-3-5-8/h1-5,9-11H,6-7H2

Upstream product

• 100-52-7 benzaldehyde 
• 56-81-5 glycerol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 98-88-4 benzoyl chloride 
• 108826-60-4 2-Phenyl-[1,3]dioxolane-4-carbaldehyde 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 15719-64-9 methylammonium carbonate 
• 96-24-2 3-monochloro-1,2-propanediol 
• 62999-50-2 1,2-benzylidene-3-buten-1,2-diol 
• 500021-11-4 (R)-1,2-O-benzylideneglyceraldehyde 

Downstream Products

• 101597-44-8 (2-phenyl-1,3-dioxolan-4-yl)methyl benzoate 
• 1708-40-3 2-phenyl-[1,3]dioxan-5-ol 
• 90904-26-0 4-(1-methoxymethyl)-2-phenyl-1,3-dioxolane 
• 18418-22-9 palmitic acid (2-phenyl-1,3-dioxolan-4-yl)methyl ester 
• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 3376-49-6 2-benzoyloxypropane-1,3-diol 
• 3376-59-8 2,3-dihydroxypropyl benzoate 
• 103160-49-2 1,2-O,O'-bisdecanoyl-3-O-benzyl-rac-glycerol 
• 6972-79-8 dibenzyl glycerol 
• 59991-89-8 1,2-dibenzylpropanetriol 
• 51164-00-2 4-Benzyloxymethyl-2-phenyl-[1,3]dioxolane 
• 1390617-16-9 C₁₉H₂₀BrF₃O₄ 
• 1390617-12-5 C₂₀H₂₆O₄ 
• 1390617-17-0 C₁₈H₂₄O₄ 

Relevant articles and documents

Microwave rehydrated Mg-Al-LDH as base catalyst for the acetalization of glycerol

Acetalization of glycerol with aldehydes to form cyclic acetals is an industrially important reaction and is generally carried out using acid catalysts. Base catalysts such as LDH can bring about microwave-assisted acetalization of glycerol and aldehydes to form 5-membered and 6-membered cyclic acetals. Among the different LDHs used, Mg-Al-LDH was found to exhibit maximum conversion of glycerol into 5-membered cyclic acetal. Modification of Mg-Al-LDH involving calcination at 450°C and subsequent microwave-assisted rehydration showed improved glycerol conversion rate under similar reaction conditions. Rehydration of calcined Mg-Al-LDH by microwave irradiation was found to result in LDH regaining its layered structure with higher basicity possibly exposing more hydroxyl ions responsible for basicity. Multiple use of methanol washed spent catalyst showed good repeatability for conversion up to three cycles which subsequently showed a marginal decrease in the conversion. Further dehydration followed by rehydration of the spent LDH catalyst under microwave irradiation was found to rejuvenate the catalytic activity to its initial level.

Sustainable valorisation of glycerol via acetalization as well as carboxylation reactions over silicotungstates anchored to zeolite Hβ

A simple, green and effective pathway towards valorisation of glycerol to value added products has been demonstrated. In this context, catalysts comprising parent as well as lacunary silicotungstates anchored to large pore zeolite Hβ have been synthesized and characterized by various physicochemical methods. Parent silicotungstic acid based catalyst proved to be better catalyst in terms of conversion of glycerol showing 73% conversion for carboxylation reaction and 97% conversion of glycerol towards acetalization reaction. The better activity of the catalyst was correlated with its strong acidic character. It was observed that by tuning the acidity of parent silicotungstate by formation of lacunary silicotungstate leads to the increase in the selectivity of 5-membered dioxolane from 68% to 78% and selectivity of glycerol carbonate from 72% to 75%. Both the catalysts were reusable up to four cycles under the investigated reaction conditions. The probable mechanisms for both the reactions are also discussed.

Glycerol acetals and ketals as bio-based solvents: Positioning in Hansen and COSMO-RS spaces, volatility and stability towards hydrolysis and autoxidation

Four recently launched cyclic glycerol acetals or ketals are evaluated as bio-based solvents. Three of them are industrially available and result from the condensation of glycerol with formaldehyde, acetone and isobutyl methyl ketone. The fourth is under development and is prepared by the reaction of glycerol with benzaldehyde under heterogeneous acidic catalysis. Their solvent properties are evaluated through Hansen and COSMO-RS (COnductor-like Screening MOdel for Real Solvents) approaches, in comparison with traditional petrochemical solvents. Dioxolane- and dioxane-type isomers have close solubility parameters; however the nature of the starting aldehyde/ketone significantly impacts the solvency properties. The stability to hydrolysis depends heavily on both the aldehyde/ketone part and on the size of the ring. In acidic medium, acetals are found to be more stable than ketals and glycerol-based ketals are more stable than ethylene glycol-based ketals. In the case of benzaldehyde glycerol acetal, it is shown that the 6-membered ring isomer (dioxane-type) is approximately 8 times more stable than the 5-membered ring counterpart (dioxolane-type) at low pH. Stability towards autoxidation by O2 is high for formaldehyde and acetone-derived acetals and drops for the other two compounds. Glycerol acetals and ketals are promising potential alternatives to some harmful solvents such as glycol ethers and aniline. This journal is

One-step synthesis of solid sulfonic acid catalyst and its application in the acetalization of glycerol: Crystal structure of cis-5-hydroxy-2-phenyl-1,3- dioxane trimer

A one-pot method was employed to immobilize sulfonic acid onto silica obtained from rice husk ash using 3-(mercaptopropyl)trimethoxysilane to form a solid catalyst denoted as RHASO3H. BET measurements of the catalyst showed the surface area to be 340 m2 g-1 with the average pore volume of 0.24 mL g-1 and the pore diameter of 2.9 nm. Acidity test of cation exchange capacity and pyridine adsorption studies revealed the presence of Bronsted acid sites on the catalyst surface. The catalyst was used in the acetalization reaction of glycerol with benzaldehyde. Under optimized conditions, the reaction showed the maximum conversion of 78 % after 8 h with 67 % selectivity towards the five membered ring isomer. Variation in the glycerol concentration had a significant effect on the reactants conversion. A single crystal X-ray study of one of the products proved the existence of a unique trimer formed by hydrogen bonding by the six-membered cis-isomer. The catalyst was several times recycled without any loss of its catalytic activity.

Low temperature synthesis of bio-fuel additives via valorisation of glycerol with benzaldehyde as well as furfural over a novel sustainable catalyst, 12-tungstosilicic acid anchored to ordered cubic nano-porous MCM-48

The present article demonstrates designing of novel catalyst, 12-tungstosilicic acid (TSA) anchored to ordered nano-porous MCM-48 (nMCM-48); TSA/nMCM-48, characterization and evaluation for synthesis of bio-fuel additives via glycerol valorisation with aromatic aldehydes. The nanopores of support were confirmed by BET and TEM while the interaction between TSA and nMCM-48 was confirmed by decrease in the surface area and pore volume of the catalysts. Assessment of vital reaction parameters (% loading of active species, mole ratio of reactants, catalyst amount, temperature and time) were performed to achieve maximum conversion of glycerol. The catalyst showed noteworthy performance at 30 °C towards conversion (>85 %) and thermodynamically stable dioxane derivative (>60 %) with remarkable TON (5945 for benzaldehyde and 7355 for furfural). The catalyst was regenerated and used for successive four catalytic runs with almost same activity. The superiority of novel catalyst is because of its geometry and nano porosity.

Modified boehmite: A choice of catalyst for the selective conversion of glycerol to five-membered dioxolane

The choice of the active site and support matrix decides the activity of a catalyst. Any modifications on these will have a significant impact on the reactivity and selectivity of the catalyst. Here, we have synthesised WO3-loaded boehmite and applied it for the acetalization of a biomass-derived bulk chemical, glycerol. The well-characterized acid catalyst exhibits a selective acetalization of glycerol with good conversions into a five-membered dioxolane product. The cyclability of the catalyst up to six times along with the retention of the catalytic activity ensures the heterogeneity of the material.

The Chiral Target of Daptomycin Is the 2R,2′S Stereoisomer of Phosphatidylglycerol

Daptomycin (dap) is an important antibiotic that interacts with the bacterial membrane lipid phosphatidylglycerol (PG) in a calcium-dependent manner. The enantiomer of dap (ent-dap) was synthesized and was found to be 85-fold less active than dap against

Preparation method of glycerol formal

The invention discloses a preparation method of benzaldehyde glycerol acetal. The method adopts a solid catalyst composed of phosphomolybdic acid anions and polymeric ionic liquid cations to catalyzethe reaction of benzaldehyde and glycerol, and due to the fine adjustment of acid-base sites, the yield of benzaldehyde glycerol acetal prepared through the method reaches 95%, and meanwhile, the six-membered ring acetal has specific selectivity.

High-efficacy glycerol acetalization with silica gel immobilized Br?nsted acid ionic liquid catalysts - Preparation and comprehending the counter-anion effect on the catalytic activity

Imidazolium sulfonate zwitterions (ZIs) with unconventional counter-anions were used to fabricate a series of mesoporous silica-gel-immobilized Br?nsted acid ionic liquid (SG@BAIL) nanocatalysts. In comparison to traditional heterogeneous catalysts, these immobilised heterogeneous catalysts have the advantage of ionic-liquid acidic sites and the advantage of solid silica gel as a support, increasing their catalytic activities. The catalysts were analysed using a series of physicochemical techniques and their catalytic efficiencies were evaluated during the acetalization of glycerol (G) with benzaldehyde (B). The influence of the counter-anions present in the SG@BAIL catalysts was initially investigated in terms of the percentage conversion vs. the reaction time at a particular temperature. Furthermore, different parametric studies relating to the acetalization reaction were carried out based on the catalyst with the maximum activity. SG-[C3ImC3SO3H][OTf] was observed to have the highest catalytic performance and durability during ecofriendly acetal synthesis, with the highest selectivity for 1,3-dioxane. Parametric studies of the acetalization reaction were carried out, and the catalyst showed noteworthy performance at 90 °C, showing 94% conversion in an equimolar reactant mixture under solvent-free conditions with 0.03 wt% catalyst loading in a short time span of 75 min. In addition, kinetics modelling was performed using reversible second-order kinetics to calculate the forward rate constants at various temperatures. The activation energy of the reaction was determined using the Arrhenius equation, and the overall activation energy was 69.33 kJ mol-1. These investigations have demonstrated the excellent potential of SG@BAIL catalysts for practical application in the glycerol acetalization process.

Structure–Activity Relationships of WOx-Promoted TiO2–ZrO2 Solid Acid Catalyst for Acetalization and Ketalization of Glycerol towards Biofuel Additives

Abstract: WOx-promoted TiO2–ZrO2 solid acid catalyst was prepared and applied in the catalytic acetalization and ketalization of glycerol with carbonyl compounds to produce biofuel additives. The presence of WOx promoter and TiO2 remarkably improved the catalytic activity of ZrO2. Approximately, 100% glycerol conversion was evidenced with non-bulky aliphatic aldehydes and ketones like, propanol and cyclohexanone. The physical characterization of WOx-promoted TiO2–ZrO2, revealed a higher formation of tetragonal crystalline phase of ZrO2, over monoclinic. The total surface acidity and the ratio of Br?nsted to Lewis acidic site concentrations were determined by NH3-TPD and pyridine-chemisorbed FTIR spectroscopy, respectively. A considerably higher concentration of Lewis acidic sites, ~ 213.29?μmol/gm, was evidenced on the WOx-promoted TiO2–ZrO2 catalyst surface. Catalytic activity study revealed a direct correlation between the surface Lewis acidic site concentration and the activity of catalyst. This significant observation indicated the key role of Lewis acidic sites in this catalytic process. The WOx-promoted TiO2–ZrO2 catalyst was also considerably stable and showed good performance in the acetalization/ketalization of glycerol with other substituted carbonyl compounds. Graphic Abstract: The WOx-promoted TiO2–ZrO2 solid acid catalyst exhibits superior catalytic performance for acetalization and ketalization of glycerol with carbonyl compounds to produce biofuel additives. [Figure not available: see fulltext.].