98572-00-0

Basic information

• Product Name: (S)-2-(Hydroxymethyl)-1,4-benzodioxane
• Synonyms: (S)-2-(Hydroxymethyl)-1,4-benzodioxane;(S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol
• CAS NO: 98572-00-0
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• Mol File: 98572-00-0.mol

Chemical Properties

• Melting Point: 74-74.5 °C
• Boiling Point: 281.142 °C at 760 mmHg
• Flash Point: 123.831 °C
• Appearance: /
• Density: 1.214 g/cm³
• Storage Temp.: 2-8°C
• PKA: 13.98±0.10(Predicted)
• CAS DataBase Reference: (S)-2-(Hydroxymethyl)-1,4-benzodioxane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(Hydroxymethyl)-1,4-benzodioxane(98572-00-0)
• EPA Substance Registry System: (S)-2-(Hydroxymethyl)-1,4-benzodioxane(98572-00-0)

Safety Data

• Hazardous Substances Data: 98572-00-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-(Hydroxymethyl)-1,4-benzodioxane is used as a precursor in the synthesis of MDMA, a recreational drug, for its psychoactive effects.
Used in Chemical Industry:
(S)-2-(Hydroxymethyl)-1,4-benzodioxane is used as a starting material in the synthesis of various organic compounds due to its unique chemical structure.
Used in Medicinal Research:
(S)-2-(Hydroxymethyl)-1,4-benzodioxane is studied for its potential medicinal properties, such as its antioxidant and antimicrobial effects, for the development of new therapeutic agents.
However, it is important to note that due to its toxic properties and its use in the illegal drug trade, the use and production of (S)-2-(Hydroxymethyl)-1,4-benzodioxane are heavily regulated in many countries.

Upstream product

• 113826-06-5 (R)-glycidyl tosylate 
• 120-80-9 benzene-1,2-diol 
• 10001-78-2 (S)-2-Butylamino-1-(R)-2,3-dihydro-benzo[1,4]dioxin-2-yl-ethanol 
• 115563-60-5 (R)-1,4-benzodioxane-2-carboxaldehyde 
• 3663-82-9 2-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin 
• 108-05-4 vinyl acetate 
• 177351-41-6 7-methoxy-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylic acid 
• 160657-86-3 7-acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid amide 
• 75280-32-9 7-Acetyl-2,3-dihydro-1,4-benzodioxin-2-carboxylic acid ethyl ester 
• 160657-99-8 7-hydroxy-2,3-dihydrobenzo[1,4]dioxine-2-carboxylic acid 
• 156357-33-4 (2R)-2-Carboxy-7-hydroxy-2,3-dihydro-1,4-benzodioxin 
• 115563-61-6 (S)-1-(R)-2,3-Dihydro-benzo[1,4]dioxin-2-yl-2-propylamino-ethanol 
• 98571-98-3 (2S,3S)-4-(2-benzyloxyphenoxy)-2,3-epoxy-1-(p-toluenesulfonyloxy)-butane 
• 3663-80-7 1,4-benzodioxane-2-carboxylic acid 

Downstream Products

• 62501-73-9 (2S)-2-(hydroxymethyl)-1,4-benzodioxan tosylate 
• 62501-70-6 (R)-(2,3-dihydrobenzo[b][1,4] dioxin-2-yl)methyl 4-methylbenzenesulfonate 
• 115649-80-4 (-)-Spiroxatrine 
• 119746-74-6 (R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-{[(S)-1-(2,3-dihydro-benzo[1,4]dioxin-2-yl)methyl]-methyl-amino}-ethyl) ester 5-methyl ester 
• 119746-78-0 (S)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-{[(S)-1-(2,3-dihydro-benzo[1,4]dioxin-2-yl)methyl]-methyl-amino}-ethyl) ester 5-methyl ester 
• 1142953-55-6 (R)-2-(bromomethyl)-2,3-dihydrobenzo [b][1,4] dioxine 
• 104874-86-4 (S)-doxazosin 
• 70918-53-5 (+)-(2R)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid 
• 1219800-50-6 (R)-tert-butyl 4-(2,3-dihydrobenzo[b][1,4]dioxine-2-carbonyl)piperazine-1-carboxylate 
• 860173-98-4 (R)-N-(1,4-benzodioxan-2-carbonyl)piperazine 
• 104874-86-4 (R)-doxazosin 
• 46049-49-4 (S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanamine 
• 77133-43-8 (S)-WB-4101 
• 187543-59-5 (R)-7-methyl-1,4-benzodioxan-2-ylmethyl 4-toluenesulphonate 

Relevant articles and documents

Lipase-catalyzed kinetic resolution of (±)-2-hydroxymethyl-1,4-benzodioxane

The title compound has been kinetically resolved in a lipase-catalyzed transesterification with vinyl acetae in organic solvents. The influence of the enzyme source as well as the character of the solvent on the enantioselectivity has been studied.

Method for synthesizing optically pure 2-hydroxymethyl-1,4-benzodioxin and derivatives of optically pure 2-hydroxymethyl-1,4-benzodioxin

The invention discloses a method for synthesizing optically pure 2-hydroxymethyl-1,4-benzodioxin and derivatives of the optically pure 2-hydroxymethyl-1,4-benzodioxin. The method comprises the steps that cheap 2-bromophenol or derivatives of the 2-bromoph

Aromatic propionic acid derivative, preparation method and uses thereof

The present invention discloses a compound represented by a general formula I or a tautomer, a racemate, an enantiomer, a diastereomer, a mixture and a pharmaceutically acceptable salt thereof, wherein each substituent is defined in the specification and claims. According to the present invention, the compound has obvious agonistic activity and selectivity to a GPR40 receptor in vitro, and the oral administration of the compound can significantly reduce the blood glucose concentration of rats after oral administration of glucose and increase the glucose tolerance capacity of rats in a dose-dependent manner so as to provide the good in vivo glucose lowering effect and achieve excellent pharmacokinetic properties and excellent drug-forming properties, such that the compound of the present invention can be used for the preparation of drugs for treating metabolic diseases such as diabetes and the like.

Palladium-Catalyzed Asymmetric Dihydroxylation of 1,3-Dienes with Catechols

A palladium-catalyzed asymmetric dihydroxylation of 1,3-dienes with catechols is developed using chiral pyridinebis(oxazoline) ligands. Various chiral 2-substituted 1,4-benzodioxanes could be synthesized with moderate to high yields and enantioselectivities from readily available starting materials. The reaction is proposed to proceed through a cascade Wacker-type hydroxypalladation/asymmetric allylation process.

Enantioselective Access to Chiral 2-Substituted 2,3-Dihydrobenzo[1,4]dioxane Derivatives through Rh-Catalyzed Asymmetric Hydrogenation

Rh-catalyzed asymmetric hydrogenation of various benzo[b][1,4]dioxine derivatives was successfully developed to prepare chiral 2-substituted 2,3-dihydrobenzo[1,4]dioxane derivatives using ZhaoPhos and N-methylation of ZhaoPhos ligands with high yields and excellent enantioselectivities (up to 99% yield, >99% enantiomeric excess (ee), turnover number (TON) = 24 000). Moreover, this asymmetric hydrogenation methodology, as the key step with up to 10 000 TON, was successfully applied to develop highly efficient synthetic routes for the construction of some important biologically active molecules, such as MKC-242, WB4101, BSF-190555, and (R)-doxazosin·HCl.

Preparation method of 1,4-benzdioxan-2-formic acid

The invention provides a preparation method of 1,4-benzdioxan-2-formic acid. The preparation method comprises the following steps: by taking benzylodiglycidyl ether and o-halogen phenol as raw materials, performing cyclization reaction, debenzylation reaction and oxidization reaction to obtain the 1,4-benzdioxan-2-formic acid. The preparation method provided by the invention is simple in reactionprocess; as the benzylodiglycidyl ether and the o-halogen phenol are used as the raw materials for reaction, no pollutants are produced, and no-irritative and no-allergic objects are produced; compared with other existing lines, the preparation method is environmentally friendly, high in total yield and favorable for mass production; the ee value of the finally prepared 1,4-benzdioxan-2-formic acid is more than or equal to 99 percent, and the chiral purity is high.

Design and optimization of 2,3-dihydrobenzo[b][1,4]dioxine propanoic acids as novel GPR40 agonists with improved pharmacokinetic and safety profiles

GPR40 has become a new potential therapeutic target for the treatment of diabetes due to its role in mediating the enhancement of glucose-stimulated insulin secretion in pancreatic β cells with a low risk of hypoglycemia. As an effort to extend the chemical space and identify structurally distinct GPR40 agonists with improved liver safety, a novel series of fused-ring phenyl propanoic acid analogues were designed. Comprehensive structure-activity relationship studies around novel scaffolds were conducted and led to several analogues exhibited potent GPR40 agonistic activities and high selectivity against other fatty acid receptors. Further evaluation of pharmacokinetic (PK) profiles and in vivo efficacy identified compound 40a with excellent PK properties and significant glucose-lowering efficacy during an oral glucose tolerance test. In addition, compound 40a displayed lower hepatobiliary transporter inhibition and favorable druggability. All results indicate that compound 40a is a promising candidate for further development.

Enantioselective Synthesis of Chiral Oxygen-Containing Heterocycles Using Copper-Catalyzed Aryl C-O Coupling Reactions via Asymmetric Desymmetrization

An enantioselective desymmetric aryl C-O coupling reaction was demonstrated under the catalysis of CuI and a chiral cyclic diamine ligand. A series of chiral oxygen-containing heterocyclic units such as 2,3-dihydrobenzofurans, chromans, and 1,4-benzodioxanes with tertiary or quaternary stereocarbon centers were synthesized with this method. DFT calculations were also carried out for a better understanding of the model for enantiocontrol.

DOPAMINE D2 RECEPTOR LIGANDS

The present invention relates to novel dopamine D2 receptor ligands. The invention further relates to functionally-biased dopamine D2 receptor ligands and the use of these compounds for treating or preventing central nervous system and systemic disorders associated with dysregulation of dopaminergic activity. The present invention relates to novel compounds that modulate dopamine D2 receptors. In particular, compounds of the present invention show functional selectivity at the dopamine D2 receptors and exhibit selectivity downstream of the D2 receptors, on the 0- arrestin pathway and/or on the cAMP pathway.

Method for synthesizing asymmetric C-O coupled compound and application of asymmetric C-O coupled compound

The invention discloses a method for synthesizing an asymmetric C-O coupled compound and application of the asymmetric C-O coupled compound and belongs to the technical field of chemical synthesis. According to the method, a compound represented by a form