3-Acetyl-5-chlorothiophene

Base Information

• Chemical Name: 3-Acetyl-5-chlorothiophene
• CAS No.: 58119-67-8
• Molecular Formula: C6H5ClOS
• Molecular Weight: 160.624
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID00574110
• Wikidata: Q82463029
• Mol file: 58119-67-8.mol

Synonyms:3-ACETYL-5-CHLOROTHIOPHENE;58119-67-8;1-(5-chlorothiophen-3-yl)ethanone;1-(5-CHLOROTHIOPHEN-3-YL)ETHAN-1-ONE;2-chloro-4-acetylthiophene;SCHEMBL3187535;DTXSID00574110;MFCD00082792;AKOS000280449;GS-5828;PB18443;3-Acetyl-5-chlorothiophene, AldrichCPR;CS-0052862;A22180;EN300-160233

Chemical Property of 3-Acetyl-5-chlorothiophene

Chemical Property:

• Boiling Point: 237.1±25.0 °C(Predicted)
• PSA: 45.31000
• Density: 1.312±0.06 g/cm3(Predicted)
• LogP: 2.60410
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 159.9749636
• Heavy Atom Count: 9
• Complexity: 126

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Acetyl-5-chlorothiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CSC(=C1)Cl

Technology Process of 3-Acetyl-5-chlorothiophene

There total 1 articles about 3-Acetyl-5-chlorothiophene 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:

3-acetyl-2,5-dichlorothiophene (36157-40-1) → 1-(thiophen-3-yl)-ethanone (1468-83-3) + 1-(5-Chlor-3-thienyl)-ethanon (58119-67-8) + 3-acetyl-2-chlorothiophene (81557-66-6)

Guidance literature:

With sodium tetrahydroborate; hydrogen; calcium oxide; palladium; In ethanol; at 20 ℃; under 760 Torr; Rate constant; other temperature, other solvent, other acceptor;

DOI:10.1007/BF00512953

Reference yield:

1-(5-Chlor-3-thienyl)-ethanon (58119-67-8) → 5-(5-chloro-thiophen-3-yl)-5-methyl-4-oxo-4,5-dihydro-furan-2-carboxylic acid (1-phenyl-ethyl)-amide

Guidance literature:

Multi-step reaction with 6 steps

1.1: KOtBu / tetrahydrofuran / 20 °C

1.2: tetrahydrofuran / -78 - 20 °C

2.1: N-methylmorpholine oxide; OsO₄ / acetone; H₂O / 20 °C

3.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -50 - 20 °C

4.1: NaH / tetrahydrofuran / 65 °C

4.2: aq. HCl / dioxane / 20 °C

5.1: aq. HCl / dioxane / 12 h / 50 °C

6.1: Et₃N; mesyl chloride / CH₂Cl₂ / 20 °C

6.2: CH₂Cl₂ / 20 °C

With hydrogenchloride; osmium(VIII) oxide; oxalyl dichloride; potassium tert-butylate; sodium hydride; dimethyl sulfoxide; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; 3.1: Swern oxidation;

DOI:10.1021/jm070022x

Reference yield:

1-(5-Chlor-3-thienyl)-ethanon (58119-67-8) → 5-(5-chloro-thiophen-3-yl)-5-methyl-4-oxo-4,5-dihydro-furan-2-carboxylic acid (1-phenyl-ethyl)-amide

Guidance literature:

Multi-step reaction with 6 steps

1.1: KOtBu / tetrahydrofuran / 20 °C

1.2: tetrahydrofuran / -78 - 20 °C

2.1: N-methylmorpholine oxide; OsO₄ / acetone; H₂O / 20 °C

3.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -50 - 20 °C

4.1: NaH / tetrahydrofuran / 65 °C

4.2: aq. HCl / dioxane / 20 °C

5.1: aq. HCl / dioxane / 12 h / 50 °C

6.1: Et₃N; mesyl chloride / CH₂Cl₂ / 20 °C

6.2: CH₂Cl₂ / 20 °C

With hydrogenchloride; osmium(VIII) oxide; oxalyl dichloride; potassium tert-butylate; sodium hydride; dimethyl sulfoxide; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone; 3.1: Swern oxidation;

DOI:10.1021/jm070022x

upstream raw materials:

3-acetyl-2,5-dichlorothiophene

Downstream raw materials:

2-chlorothiophene-4-carboxylic acid

4,5-Dichlor-thiophen-3-carbonsaeure

Refernces