5-Methoxythiophene-2-carbaldehyde

Base Information

• Chemical Name: 5-Methoxythiophene-2-carbaldehyde
• CAS No.: 35087-46-8
• Molecular Formula: C6H6O2S
• Molecular Weight: 142.178
• Hs Code.: 2934999090
• European Community (EC) Number: 865-822-1
• DSSTox Substance ID: DTXSID80579885
• Nikkaji Number: J2.480.790H
• Wikidata: Q82470530
• Mol file: 35087-46-8.mol

Synonyms:5-Methoxythiophene-2-carbaldehyde;35087-46-8;5-methoxy-2-thiophenecarbaldehyde;5-methoxy-thiophene-2-carbaldehyde;2-Thiophenecarboxaldehyde, 5-methoxy-;5-methoxy-2-thiophenecarboxaldehyde;SCHEMBL125451;DTXSID80579885;NVDZOPRKCPVWOS-UHFFFAOYSA-N;AKOS000278537;SY019673;CS-0451512;EN300-110076;F53534;A874784;Z1255429054

Chemical Property of 5-Methoxythiophene-2-carbaldehyde

Chemical Property:

• Melting Point: 24-26 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• Boiling Point: 79-81 °C(Press: 0.9 Torr)
• PSA: 54.54000
• Density: 1.240±0.06 g/cm3(Predicted)
• LogP: 1.56920
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 142.00885060
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

95+% ^*data from raw suppliers

5-Methoxy-2-thiophenecarbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(S1)C=O
• Uses: 5-Methoxy-2-thiophenecarbaldehyde is an impurity of Prasugrel (P701150, HCl); an antiplatelet agent.

Technology Process of 5-Methoxythiophene-2-carbaldehyde

There total 8 articles about 5-Methoxythiophene-2-carbaldehyde 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: 95.0%

2-methoxythiophene (16839-97-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-methoxythiophene-5-carbaldehyde (35087-46-8)

Guidance literature:

2-methoxythiophene; With n-butyllithium; In diethyl ether; hexane; at 0 ℃; for 1h;

N,N-dimethyl-formamide; In diethyl ether; hexane; for 1h; Further stages.; Heating;

DOI:10.1016/j.tet.2008.07.043

Reference yield: 90.0%

5-bromo-2-methoxythiophene (57070-77-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-methoxythiophene-5-carbaldehyde (35087-46-8)

Guidance literature:

5-bromo-2-methoxythiophene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; at -78 - 20 ℃; for 2.33333h; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.11.010

Reference yield: 71.0%

2-methoxythiophene (16839-97-7) + bromodichloromethane (75-27-4) → 2-methoxythiophene-5-carbaldehyde (35087-46-8)

Guidance literature:

2-methoxythiophene; bromodichloromethane; With 1,1'-bis-(diphenylphosphino)ferrocene; potassium phosphate; palladium diacetate; acetic anhydride; silver carbonate; In acetonitrile; at 60 ℃; for 24h; Schlenk technique; Inert atmosphere;

With hydrogenchloride; In dichloromethane; at 30 ℃;

DOI:10.1016/j.tetlet.2018.07.013

upstream raw materials:

N-methyl-N-phenylformamide

2-methoxythiophene

N,N-dimethyl-formamide

5-bromo-2-methoxythiophene

Downstream raw materials:

4-(5-methoxy-thiophen-2-ylmethylene)-2-phenyl-4H-oxazol-5-one

(E)-p-nitrophenyl 3-(5-methoxy-2-thienyl)acrylate

N-[2-(5-methoxy-[2]thienyl)-ethyl]-benzamide

2-Benzamino-7-methoxy-heptansaeure

Refernces

• 1、 Faouzi, Abdelfattah,Arnaud, Alexandre,Bancet, Alexandre,Barette, Caroline,Preto, Jordane,Do, Cong Viet,Jordheim, Lars Petter,Bousfiha, Zineb,Nguyen, Thi Thanh Binh,Verrière, Marion,Farce, Amaury,Fauvarque, Marie-Odile,Barret, Roland,Lomberget, Thierry. "Combretastatin A-4 sulfur-containing heterocyclic derivatives: Synthesis, antiproliferative activities and molecular docking studies". . . Retrieved 2021/02/27.
• 2、 Bao, Yan,Wang, Jian-Yong,Zhang, Ya-Xuan,Li, Yan,Wang, Xi-Sheng. "Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation". supporting information. p. 3147 - 3150. Retrieved 2018/07/13.