Methyl 2,2-dithienylglycolate

Base Information

• Chemical Name: Methyl 2,2-dithienylglycolate
• CAS No.: 26447-85-8
• Molecular Formula: C11H10O3S2
• Molecular Weight: 254.331
• Hs Code.: 2934999090
• European Community (EC) Number: 607-936-4
• UNII: J997BSP5GL
• DSSTox Substance ID: DTXSID10465166
• Nikkaji Number: J25.398G
• Wikidata: Q72490363
• Mol file: 26447-85-8.mol

Synonyms:26447-85-8;Methyl 2,2-dithienylglycolate;Methyl 2,2-dithienyl glycolate;Methyl 2-hydroxy-2,2-di(thiophen-2-yl)acetate;methyl 2-hydroxy-2,2-dithiophen-2-ylacetate;Methyl Di(2-thienylglycolate);2-Thiopheneacetic acid, alpha-hydroxy-alpha-2-thienyl-, methyl ester;methyl hydroxy(di-2-thienyl)acetate;MFCD08458380;Methyl di(2-thienyl)glycolate;Methyl 2-Hydroxy-2,2-di(2-thienyl)acetate;Tiotropium Bromide Monohydrate Imp. E (EP);Tiotropium Bromide Imp. E (EP);Methyl 2-Hydroxy-2,2-dithiophen-2-ylacetate;Tiotropium Bromide Monohydrate Impurity E;Tiotropium Impurity E;AC-607;EC 607-936-4;J997BSP5GL;Hydroxy-di-thiophen-2-yl-acetic acid methyl ester;methyl 2-hydroxy-2,2-bis(thiophen-2-yl)acetate;SCHEMBL826276;2-hydroxy-2,2-dithiophen-2-ylacetic acid methyl ester;methyl di-(2-thienyl)glycolate;Methyl-2,2-dithienyl Glycolate;DTXSID10465166;SYHWYWHVEQQDMO-UHFFFAOYSA-N;BCP12268;Methyl 2,2-di(2-thienyl)glycolate;methyl hydroxy[di(2-thienyl)]acetate;AKOS015850983;CS-W020702;GS-3211;Methyl hydroxy[di(thiophen-2-yl)]acetate;SY021325;Hydroxydithien-2-ylacetic Acid Methyl Ester;FT-0645043;NS00006952;Methyl2-hydroxy-2,2-di(thiophen-2-yl)acetate;methyl 2-oxidanyl-2,2-dithiophen-2-yl-ethanoate;A818447;2-Hydroxy-2,2-dithien-2-ylacetic acid methyl ester;J-016429;J-521885;2-hydroxy-2,2-bis(2-thienyl)acetic acid methyl ester;Methyl alpha-hydroxy-alpha-2-thienyl-2-thiopheneacetate;TIOTROPIUM BROMIDE MONOHYDRATE IMPURITY E [EP IMPURITY];2-Thiopheneacetic acid, .alpha.-hydroxy-.alpha.-2-thienyl-, methyl ester

Chemical Property of Methyl 2,2-dithienylglycolate

Chemical Property:

• Vapor Pressure: 2.46E-07mmHg at 25°C
• Refractive Index: 1.623
• Boiling Point: 406.5 °C at 760 mmHg
• PKA: 10.43±0.29(Predicted)
• Flash Point: 199.6 °C
• PSA: 103.01000
• Density: 1.392 g/cm³
• LogP: 2.21850
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 254.00713652
• Heavy Atom Count: 16
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

Methyl 2,2-dithienylglycolate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1=CC=CS1)(C2=CC=CS2)O
• Uses: Methyl Di(2-thienylglycolate) (Tiotropium EP Impurity E) is an intermediate in the production of Tiotropium Bromide, a long-acting bronchodilator. Intermediate in the production of Tiotropium Bromide, a long-acting bronchodilator.

Technology Process of Methyl 2,2-dithienylglycolate

There total 6 articles about Methyl 2,2-dithienylglycolate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

2-bromothiophene (1003-09-4) + methyl 2-thienylglyoxylate (26878-13-7) → hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8)

Guidance literature:

2-bromothiophene; With n-butyllithium; In tetrahydrofuran; for 0.333333h; Inert atmosphere; Cooling;

methyl 2-thienylglyoxylate; In tetrahydrofuran; for 0.5h; Inert atmosphere; Cooling;

DOI:10.24820/ark.5550190.p010.717

Reference yield: 60.0%

Dimethyl oxalate (553-90-2) → hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8)

Guidance literature:

2-bromothiophene; With magnesium; In diethyl ether; at 0 - 35 ℃; for 3h;

Dimethyl oxalate; In diethyl ether; at 45 ℃; for 0.75h; Heating / reflux;

With sulfuric acid; at 20 ℃; for 1h;

Reference yield: 58.0%

2-bromothiophene (1003-09-4) + Dimethyl oxalate (553-90-2) → hydroxy-di-thiophen-2-yl-acetic acid methyl ester (26447-85-8)

Guidance literature:

2-bromothiophene; With iodine; magnesium; In tetrahydrofuran; ethyl bromide; for 1h; Reflux;

Dimethyl oxalate; In tetrahydrofuran; ethyl bromide; at -4 - 20 ℃; for 8h; Temperature;

upstream raw materials:

Dimethyl oxalate

acetic acid

thiophen-2-yl magnesium bromide

2-bromothiophene

Downstream raw materials:

hydroxydithien-2-ylacetic acid 1-aza-bicyclo[2.2.2]oct-3(R)-yl ester

N-demethyltiotropium

tiotropium bromide

aclidinium bromide

Refernces

• 1、 -. "PROCESS FOR THE PURIFICATION OF METHYL-2,2-DITHIENYLGLYCOLATE". Page/Page column 13-14. . Retrieved 2019/07/17.
• 2、 Prat, María,Fernández, Dolors,Buil, M. Antonia,Crespo, María I.,Casals, Gaspar,Ferrer, Manuel,Tort, Laia,Castro, Jordi,Monleón, Juan M.,Gavaldà, Amadeu,Miralpeix, Montserrat,Ramos, Israel,Doménech, Teresa,Vilella, Dolors,Antón, Francisca,Huerta, Josep M.,Espinosa, Sonia,López, Manuel,Sentellas, Sonia,González, Marisa,Albertí, Joan,Segarra, Victor,Cárdenas, Alvaro,Beleta, Jorge,Ryder, Hamish. "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)". supporting information; experimental part. p. 5076 - 5092. Retrieved 2010/03/01.