3-Acetyl-2,5-dichlorothiophene

Base Information

• Chemical Name: 3-Acetyl-2,5-dichlorothiophene
• CAS No.: 36157-40-1
• Molecular Formula: C6H4Cl2OS
• Molecular Weight: 195.069
• Hs Code.: 29349990
• European Community (EC) Number: 252-893-3
• UNII: QRT2T98QV7
• DSSTox Substance ID: DTXSID60189724
• Nikkaji Number: J254.880A
• Wikidata: Q72435066
• Mol file: 36157-40-1.mol

Synonyms:3-Acetyl-2,5-dichlorothiophene;36157-40-1;1-(2,5-dichlorothiophen-3-yl)ethanone;1-(2,5-Dichloro-3-thienyl)ethan-1-one;1-(2,5-dichlorothiophen-3-yl)ethan-1-one;1-(2,5-Dichloro-3-thienyl)ethanone;Ethanone, 1-(2,5-dichloro-3-thienyl)-;C6H4Cl2OS;MFCD00014522;2,5-Dichloro-3-thienyl methyl ketone;1-(2,5-Dichloro-thiophen-3-yl)-ethanone;EINECS 252-893-3;1-(2,5-dichlorothien-3-yl)ethan-1-one;QRT2T98QV7;BIDD:GT0097;SCHEMBL542159;GYFDNIRENHZKGR-UHFFFAOYSA-;DTXSID60189724;CHEBI:194727;AMY23244;STK427054;AKOS000276629;AC-6966;CS-W010632;PB47335;3-Acetyl-2,5-dichlorothiophene, 98%;1-(2,5-Dichloro-3-thienyl)ethanone #;SY034796;1-(2,5-dichloro-3-thienyl)-1-ethanone;A1182;A6273;FT-0614876;EN300-13118;7M-751;P10027;Z89265801;F0001-2738

Chemical Property of 3-Acetyl-2,5-dichlorothiophene

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.0543mmHg at 25°C
• Melting Point: 37-40 °C(lit.)
• Refractive Index: 1.575
• Boiling Point: 233.9 °C at 760 mmHg
• Flash Point: 95.3 °C
• PSA: 45.31000
• Density: 1.452 g/cm³
• LogP: 3.25750
• Storage Temp.: Refrigerator
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 193.9359913
• Heavy Atom Count: 10
• Complexity: 151

Purity/Quality:

99% ^*data from raw suppliers

3-Acetyl-2,5-dichlorothiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37/39-22-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(SC(=C1)Cl)Cl
• Uses: 3-Acetyl-2,5-dichlorothiophene may be used in the following syntheses:substituted chalconesAL-4623A and AL-4862 (brinzolamide), inhibitors of topical carbonic anhydrase2,5-dichlorothiophene-3-carboxylic acid, which is the starting reagent required for the synthesis of 2,5-dichloro-N-(substituted amino-carbonothioyl)thiophene-3-carboxamides and 2-(substituted amino)-4H-thieno[3,2-e]-1,3-thiazin-4-ones

Technology Process of 3-Acetyl-2,5-dichlorothiophene

There total 2 articles about 3-Acetyl-2,5-dichlorothiophene 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: 90.0%

2,5-diclorothiophene (3172-52-9,173777-89-4) + acetyl chloride (75-36-5) → 3-acetyl-2,5-dichlorothiophene (36157-40-1)

Guidance literature:

With aluminum (III) chloride; In carbon disulfide; at 20 ℃; for 25h;

DOI:10.1007/s10870-016-0661-z

Reference yield:

1-methyl-4-chlorobutenal (61170-81-8) + thioacetyl chloride (16911-84-5) → 3-acetyl-2,5-dichlorothiophene (36157-40-1)

Guidance literature:

1-methyl-4-chlorobutenal; With sodium hydrogencarbonate; In acetone; at -15 - 10 ℃; for 1h;

thioacetyl chloride; In acetone; at 75 ℃; for 4h; Solvent; Temperature; Reagent/catalyst;

Reference yield: 97.0%

3-acetyl-2,5-dichlorothiophene (36157-40-1) + benzyl chloride (100-44-7) → 3-Acetyl-2-(phenylmethyl)thio-5-chlorothiophene (160982-09-2)

Guidance literature:

benzyl chloride; With thiourea; In ethanol; water; for 2h; Reflux; Large scale;

3-acetyl-2,5-dichlorothiophene; With sodium hydroxide; In ethanol; water; for 3h; regioselective reaction; Reflux; Large scale;

DOI:10.1021/op9802125

upstream raw materials:

2,5-diclorothiophene

acetyl chloride

1-methyl-4-chlorobutenal

thioacetyl chloride

Downstream raw materials:

2,5-dichlorothiophene-3-carboxylic acid

1-(thiophen-3-yl)-ethanone

1-(5-Chlor-3-thienyl)-ethanon

3-acetyl-2-chlorothiophene

Refernces

• 1、 Delgado,Henao,Quintana,Al-Maqtari,Jamalis,Sirat. "Structural Characterization of a New Chalcone Compound Containing a Thiophene Moiety: (E)-3-(5-Bromothiophen-2-YL)-1- (2,5-Dichlorothiophen-3-YL)-2-Propen-1-One". . p. 1440 - 1445. Retrieved 2018.
• 2、 Al-Refai, Mahmoud,Ibrahim, Mohammad M.,Geyer, Armin,Marsch, Michael,Ali, Basem F.. "Synthesis, Spectroscopic Characterization and X-ray Structure Analysis of 6-(2,5-Dichlorothiophen-3-yl)-2-methoxy-4-(4-methoxyphenyl)pyridine-3-carbonitrile". . p. 331 - 340. Retrieved 2016.
• 3、 Al-Refai, Mahmoud,Ibrahim, Mohammad M.,Azmi, Mohamad Nurul,Osman, Hasnah,Bakar, Mohamad Hafizi Abu,Geyer, Armin. "The synthesis, characterization, cytotoxic activity assessment and structure-activity relationship of 4-aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles". . . Retrieved 2019/11/20.