26447-85-8

Basic information

• Product Name: Methyl 2,2-dithienylglycolate
• Synonyms: 2-HYDROXY-2,2-BIS(2-THIENYL)ACETIC ACID METHYL ESTER;METHYL 2,2-DITHIENYL GLYCOLATE;Methyl di(2-thienyl)glycolate;methyl hydroxy(di-2-thienyl)acetate;2,2-Di(2-thienyl)glycolic acid methyl ester;Di-2-thienyl-glycolic Acid Methyl Ester;Hydroxydithien-2-ylacetic Acid Methyl Ester;α-Hydroxy-α-2-thienyl-2-thiopheneacetic Acid Methyl Ester
• CAS NO: 26447-85-8
• Molecular Formula: C₁₁H₁₀O₃S₂
• Molecular Weight: 254.33
• EINECS: 1308068-626-2
• Product Categories: Sulphur Derivatives;(intermediate of tiotropium bromide);Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;api;Tiotropium Bromide Intermediates
• Mol File: 26447-85-8.mol

Chemical Properties

• Boiling Point: 406.5 °C at 760 mmHg
• Flash Point: 199.6 °C
• Appearance: /
• Density: 1.392 g/cm³
• Vapor Pressure: 2.46E-07mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 10.43±0.29(Predicted)
• CAS DataBase Reference: Methyl 2,2-dithienylglycolate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,2-dithienylglycolate(26447-85-8)
• EPA Substance Registry System: Methyl 2,2-dithienylglycolate(26447-85-8)

Safety Data

• Hazardous Substances Data: 26447-85-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2,2-dithienylglycolate is used as an intermediate in the synthesis of Tiotropium Bromide, a long-acting bronchodilator. This medication is utilized for the treatment of chronic obstructive pulmonary disease (COPD) and asthma, as it helps to relax and widen the airways, improving breathing capacity and reducing symptoms.

InChI:InChI=1/C11H10O3S2/c1-14-10(12)11(13,8-4-2-6-15-8)9-5-3-7-16-9/h2-7,13H,1H3

Upstream product

• 553-90-2 Dimethyl oxalate 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 1003-09-4 2-bromothiophene 
• 26878-13-7 methyl 2-thienylglyoxylate 
• 64-19-7 acetic acid 

Downstream Products

• 136310-66-2 (1R,3S,5S)-2'-hydroxy-2',2'-di(thiophen-2''-yl)acetic acid 8-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl ester 
• 136310-64-0 N-demethyltiotropium 
• 320347-97-5 hydroxydithien-2-ylacetic acid 1-aza-bicyclo[2.2.2]oct-3(R)-yl ester 
• 139404-48-1 tiotropium bromide 
• 320345-99-1 aclidinium bromide 
• 646530-82-7 scopoline 
• 1346762-49-9 trans-4-[(tert-butoxycarbonyl)(methyl)amino]cyclohexyl hydroxy(di-2-thienyl)-acetate 
• 616866-05-8 2-hydroxy-2,2-dithien-2-ylacetic acid (3R)-1-(2-phenoxyethyl)pyrrolidin-3-yl ester 

Relevant articles and documents

Selective synthesis of methyl dithienyl-glycolates

An efficient selective synthesis of methyl dithienyl-glycolates has been developed. The interest of this two steps protocol resides in the possibility of synthesized either methyl 2,2-dithienyl glycolate – the target intermediate for the preparation of an

PROCESS FOR THE PURIFICATION OF METHYL-2,2-DITHIENYLGLYCOLATE

The present invention relates to a purification process for obtaining methyl-2,2-dithienylglycolate, with a reduced content of methyl-2- (thiophene-2-yl)-2-(thiophene-3-yl) glycolate, for use in the pharmaceutical industry.

Novel method for synthesis and purification of aclidinium bromide

The invention discloses a novel method for synthesis and purification of aclidinium bromide. According to the method, tetrahydrofuran is used, haloalkane is used as an initiator, and a finished product is obtained through solvent extraction and recrystall

Discovery of novel quaternary ammonium derivatives of (3R)-quinuclidinol esters as potent and long-acting muscarinic antagonists with potential for minimal systemic exposure after inhaled administration: Identification of (3R)-3-{[hydroxy(di-2-thienyl)acetyl]oxy}-1-(3-phenoxypropyl)-1-azoniabicyclo[2. 2.2]octane bromide (aclidinium bromide)

The objective of this work was to discover a novel, long-acting muscarinicM3 antagonist for the inhaled treatment of chronic obstructive pulmonary disease (COPD), with a potentially improved risk-benefit profile compared with current antimuscarinic agents. A series of novel quaternary ammonium derivatives of (3R)-quinuclidinol esters were synthesized and evaluated. On the basis of its overall profile, (3R)-3-{[hydroxy(di-2-thienyl) acetyl]oxy}-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide (aclidiniumbromide) emerged as a candidate for once-daily maintenance treatment of COPD. This compound is a potent muscarinic antagonist, with long duration of action in vivo, and was found to have a rapid hydrolysis in human plasma, minimizing the potential to induce class-related systemic side effects. Aclidinium bromide is currently in phase III development for maintenance treatment of patients with COPD.

TROPAN COMPOUND

The conventional anticholinergic drugs for administration through inhalation have been considered to have the possibility of aggravating dysuria associated with prostatic hyperplasia mediated by blood, and it has been demanded that the conventional anticholinergic drugs for administration through inhalation will have to show reduced side effects or adverse ractions. The present invention relates to a compound represented by the general formula (I): (wherein A represents; and R1, R2, R3 and R1 each a hydrogen atom or a substituent; R5 is a substituent; X- is an anion;the symbol: denotes an exo-form or endo-form, or their mixture), its salt or solvation product thereof. They are useful as a prophylactic and/or therapeutic agent with reduced side effects or adverse reactions for the diseases mediated by the muscarinic receptor.

ORGANIC COMPOUNDS

Compounds of formula (I), in salt or zwitterionic form wherein, wherein R1, R2, R3, and R4 have the meanings as indicated in the specification, are useful for treating conditions that are mediated by the muscarinic M3 receptor. Pharmaceutical compositions that contain the compounds and a process for preparing the compounds are also described.

Azabicycloalkane compounds

This invention provides compounds of formula I: wherein R1, R2, R3, R4, R5, R6 and R7 are as defined in the specification, or a pharmaceutically acceptable salt or solvate or stereoisomer thereof. The compounds of this invention possess both β2 adrenergic receptor agonist and muscarinic receptor antagonist activity. Such compounds are useful for treating pulmonary disorders, such as chronic obstructive pulmonary disease and asthma.