Thiophene-2,4-dicarbaldehyde

Base Information

• Chemical Name: Thiophene-2,4-dicarbaldehyde
• CAS No.: 932-93-4
• Molecular Formula: C6H4O2S
• Molecular Weight: 140.163
• Hs Code.: 2934999090
• European Community (EC) Number: 861-727-4
• DSSTox Substance ID: DTXSID00362852
• Nikkaji Number: J3.071.048G
• Wikidata: Q82146333
• Mol file: 932-93-4.mol

Synonyms:thiophene-2,4-dicarbaldehyde;932-93-4;Thiophene-2,4-dicarboxaldehyde;2,4-thiophenecarboxaldehyde;3,5-Thiophenedicarbaldehyde;SCHEMBL346857;DTXSID00362852;MFCD03990651;AKOS006344011;AS-50361;CS-0157345;O12151;EN300-1179753

Chemical Property of Thiophene-2,4-dicarbaldehyde

Chemical Property:

• PSA: 62.38000
• LogP: 1.37310
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 139.99320054
• Heavy Atom Count: 9
• Complexity: 124

Purity/Quality:

95% ^*data from raw suppliers

Thiophene-2,4-dicarbaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=C(SC=C1C=O)C=O

Technology Process of Thiophene-2,4-dicarbaldehyde

There total 4 articles about Thiophene-2,4-dicarbaldehyde 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: 22.0%

2,4-dibromothiophene (3140-92-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → thiophene-2,4-dicarbaldehyde (932-93-4)

Guidance literature:

2,4-dibromothiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.5h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Inert atmosphere;

With tert.-butyl lithium; In tetrahydrofuran; hexane; pentane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.03.084

Reference yield:

4-bromo-2-thiophenecarboxaldehyde diethyl acetal (1487-22-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → thiophene-2,4-dicarbaldehyde (932-93-4)

Guidance literature:

With n-butyllithium; Acidic conditions;

DOI:10.1021/acs.orglett.7b02317

Reference yield:

diiodo-2,4 thiophene (19259-06-4) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → thiophene-2,4-dicarbaldehyde (932-93-4)

Guidance literature:

Multistep reaction; (i) nBuLi, (ii) /BRN= 605365/;

upstream raw materials:

diiodo-2,4 thiophene

N,N-dimethyl-formamide

2,4-dibromothiophene

4-bromo-2-thiophenecarboxaldehyde diethyl acetal

Downstream raw materials:

2,4-bis{(E)-2-[4-(tert-butylsulfanyl)phenyl]ethenyl}thiophene

2,4-dimethylthiophene

Refernces

• 1、 Panchal, Santosh P.,Anand, Venkataramanarao G.. "Oxidative Transformation of a Tetrathia S-Confused Isophlorin into Porphyrin Cation". supporting information. p. 4854 - 4857. Retrieved 2017/09/23.