650597-66-3

Basic information

• Product Name: 1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, Methyl ester, (2S)-
• Synonyms: 1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, Methyl ester, (2S)-
• CAS NO: 650597-66-3
• Molecular Formula: C10H10O4
• Molecular Weight: 194.184
• Mol File: 650597-66-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, Methyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, Methyl ester, (2S)-(650597-66-3)
• EPA Substance Registry System: 1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, Methyl ester, (2S)-(650597-66-3)

Safety Data

• Hazardous Substances Data: 650597-66-3(Hazardous Substances Data)

Usage

Description

1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, methyl ester, (2S)is an organic compound with a molecular structure that features a benzene ring with two oxygen atoms forming a dioxin ring fused to it. The 2,3-dihydro indicates the presence of a saturated carbon-carbon bond between the 2nd and 3rd carbon atoms. The (2S)configuration denotes the stereochemistry of the molecule, with the methyl ester group attached to the 2nd carbon atom in an S-configuration.

Uses

1. Used in Pharmaceutical Industry:
1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, methyl ester, (2S)is used as a reactant for the preparation of benzo-fused heterocycle sulfamide derivatives from chroman-2-carboxylic acid. These derivatives are synthesized through amination and condensation reactions and are utilized for the treatment of pain.
2. Used in Chemical Synthesis:
1,4-Benzodioxin-2-carboxylic acid, 2,3-dihydro-, methyl ester, (2S)can also be used as an intermediate in the synthesis of various other organic compounds, particularly those with benzo-fused heterocycles. Its unique structure and functional groups make it a valuable building block for creating novel molecules with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 67-56-1 methanol 
• 3663-80-7 1,4-benzodioxane-2-carboxylic acid 
• 1008-92-0 2-cyano-1,4-benzodioxane 
• 120-80-9 benzene-1,2-diol 
• 1729-67-5 Methyl 2,3-dibromopropionate 
• 4442-59-5 (2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl)amine 
• 1492478-58-6 C₁₀H₁₁NO₃ 
• 1616377-88-8 rac-2-N,N-dichloroaminomethyl-1,4-benzodioxane 
• 70918-54-6 (S)‐1,4‐benzodioxane‐2‐carboxylic acid 
• 3663-79-4 methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate 
• 46049-48-3 (R)-2-((amino)methyl)-1,4-benzodioxane 
• 1616377-82-2 (R)-2-N,N-dichloroaminomethyl-1,4-benzodioxane 
• 70918-53-5 (+)-(2R)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid 
• 1616377-89-9 C₁₀H₁₁NO₃ 

Relevant articles and documents

A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes

We report the synthesis of enantiomerically enriched 1,4-benzodioxanes containing alkyl, aryl, heteroaryl, and/or carbonyl substituents at the 2-position. The starting 1,4-benzodioxines were readily synthesized via ring closing metathesis using an efficient nitro-Grela catalyst at ppm levels. Excellent enantioselectivities of up to 99:1 er were obtained by using the versatile catalyst system [Ir(cod)Cl]2/BIDIME-dimer in the asymmetric hydrogenation of 2-substituted 1,4-benzodioxines. Furthermore, DFT calculations reveal that the selectivity of the process is controlled by the protonation step; and coordinating groups on the substrate may alter the interaction with the catalyst, resulting in a change in the facial selectivity.

From 2-aminomethyl-1,4-benzodioxane enantiomers to unichiral 2-cyano- and 2-carbonyl-substituted benzodioxanes via dichloroamine

2-Substituted 1,4-benzodioxanes, such as 2-cyano-, 2-methoxycarbonyl-, 2-aminocarbonyl-, and 2-formyl-1,4-benzodioxane, are key synthons that for the most part are never described as enantiomers or are inadequately characterized for enantiomeric purity. They were prepared by quantitative N,N-dichlorination of (R)- and (S)-2-aminomethyl-1,4-benzodioxane and successive functional group conversions in high yields without any racemization of the stereogenic benzodioxane C(2).

Chemoenzymatic synthesis of piperoxan, prosympal, dibozane, and doxazosin

The synthesis of both enantiomers of 1,4-benzodioxan-2-carboxylic acid 1, a key synthetic intermediate for the therapeutic agents piperoxan, prosympal, dibozane, and doxazosin was achieved with good yields and high enantioselectivities via the Arthrobacter sp. lipase catalyzed kinetic resolution of ester (±)-17a. The influence of the co-solvents and the immobilization of the lipase upon kinetic resolution demonstrated that immobilized whole cells, in the presence of n-butanol as a co-solvent, resulted in the optimal resolution of the substrate (ee ～99%, E = 535) at 258 mmol (50 g/L) substrate concentration.