1,1'-(Thiophene-2,5-diyl)bisethan-1-one

Base Information

• Chemical Name: 1,1'-(Thiophene-2,5-diyl)bisethan-1-one
• CAS No.: 4927-10-0
• Molecular Formula: C8H8O2S
• Molecular Weight: 168.216
• European Community (EC) Number: 225-556-3
• DSSTox Substance ID: DTXSID00197747
• Nikkaji Number: J25.417G
• Wikidata: Q72462586
• Mol file: 4927-10-0.mol

Synonyms:2,5-diacetylthiophene;4927-10-0;1-(5-acetylthiophen-2-yl)ethanone;1,1'-(Thiophene-2,5-diyl)bisethan-1-one;EINECS 225-556-3;SCHEMBL2872059;DTXSID00197747;AKOS022505063;1-(5-acetylthiophen-2-yl)ethan-1-one;1-(5-ACETYL-THIOPHEN-2-YL)-ETHANONE;SR-01000511030;SR-01000511030-1

Chemical Property of 1,1'-(Thiophene-2,5-diyl)bisethan-1-one

Chemical Property:

• Melting Point: 171-173oC
• Boiling Point: 306.2°Cat760mmHg
• Flash Point: 139°C
• PSA: 62.38000
• Density: 1.184g/cm³
• LogP: 2.15330
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 168.02450067
• Heavy Atom Count: 11
• Complexity: 169

Purity/Quality:

98%Min ^*data from raw suppliers

1-(5-ACETYL-THIOPHEN-2-YL)-ETHANONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC=C(S1)C(=O)C
• General Description: 1,1'-(Thiophene-2,5-diyl)bisethan-1-one (also known as 2,5-diacetylthiophene) is a symmetrical diacetylaromatic compound that can be enantioselectively reduced by baker's yeast (Saccharomyces cerevisiae) to yield optically active secondary alcohols with high enantiomeric purity. 1,1'-(thiophene-2,5-diyl)bisethan-1-one, along with other diacetylaromatic substrates, demonstrates the utility of biocatalytic reduction under mild conditions, providing an efficient alternative to conventional chemical methods for asymmetric synthesis.

Technology Process of 1,1'-(Thiophene-2,5-diyl)bisethan-1-one

There total 13 articles about 1,1'-(Thiophene-2,5-diyl)bisethan-1-one 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: 86.0%

5-acetyl-2-(α-methoxyimino)ethylthiophene (114774-08-2) → 2,5-diacetylthiophene (4927-10-0)

Guidance literature:

With hydrogenchloride; at 70 ℃; for 8h;

DOI:10.1055/s-1992-26245

Reference yield: 43.0%

methyl ethynyl ketone (1423-60-5) → 2,5-diacetylthiophene (4927-10-0) + 2,4-diacetylthiophene (22176-00-7) + 1,3,5-triacetylbenzene (779-90-8)

Guidance literature:

With sulfur; In benzene; at 205 - 215 ℃; for 14h;

DOI:10.3987/R-1987-08-2215

Reference yield: 39.0%

2,5-dibromothiophen (3141-27-3) + N,N-dimethyl acetamide (127-19-5,116057-81-9) → 2,5-diacetylthiophene (4927-10-0)

Guidance literature:

2,5-dibromothiophen; With n-butyllithium; In diethyl ether; hexane; at -70 ℃; for 0.5h;

N,N-dimethyl acetamide; In diethyl ether; hexane;

DOI:10.1016/j.tetlet.2008.11.061

upstream raw materials:

2-Acetylthiophene

acetic anhydride

diazomethane

diethyl ether

Downstream raw materials:

(S)-(-)-2-acetyl-5-(1-hydroxyethyl)thiophene

Refernces

Highly enantioselective reduction of symmetrical diacetylaromatics with baker's yeast

10.1016/S0957-4166(97)00462-X

The research investigates the asymmetric reduction of various symmetrical diacetylaromatic compounds using baker's yeast (Saccharomyces cerevisiae) to obtain optically active secondary alcohols with high enantiomeric purity. The study explores the reduction of compounds such as 2,6-diacetylpyridine (la), 2,6-diacetylpyridine 1-oxide (lb), 1,2-diacetylb°enzene (lc), 1,3-diacetylbenzene (ld), 1,4-diacetylbenzene (le), 2,5-diacetylfuran (If), 2,5-diacetylthiophene (lg), and 2,5-diacetylpyrrole (lh). The researchers optimized reaction conditions to selectively produce monoalcohols over diols, achieving excellent yields and enantiomeric purities. Key chemicals involved in the research include the diacetylaromatic substrates, baker's yeast, sucrose, and various reagents used in the synthesis and analysis of the compounds, such as methoxymethoxyethyl groups, maleic acid, hydrogen peroxide, oxalyl chloride, dimethyl sulfoxide, and triethylamine. The study highlights the effectiveness of baker's yeast as a biocatalyst for enantioselective reductions under mild conditions, offering a valuable alternative to traditional chemical methods.