1-[5-(4-Methylphenyl)-2-thienyl]ethanone

Base Information

• Chemical Name: 1-[5-(4-Methylphenyl)-2-thienyl]ethanone
• CAS No.: 51335-91-2
• Molecular Formula: C13H12OS
• Molecular Weight: 216.304
• DSSTox Substance ID: DTXSID30400599
• Wikidata: Q82203614
• Mol file: 51335-91-2.mol

Synonyms:51335-91-2;1-[5-(4-Methylphenyl)-2-thienyl]ethanone;1-[5-(4-methylphenyl)thiophen-2-yl]ethanone;Ethanone, 1-[5-(4-methylphenyl)-2-thienyl]-;SCHEMBL9910293;DTXSID30400599;AKOS004117277;BB 0223062;1-[5-(4-Methylphenyl)thiophen-2-yl]ethan-1-one;A1-35629

Chemical Property of 1-[5-(4-Methylphenyl)-2-thienyl]ethanone

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 216.06088618
• Heavy Atom Count: 15
• Complexity: 231

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C2=CC=C(S2)C(=O)C

Technology Process of 1-[5-(4-Methylphenyl)-2-thienyl]ethanone

There total 12 articles about 1-[5-(4-Methylphenyl)-2-thienyl]ethanone 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: 100.0%

2-Acetylthiophene (88-15-3,97511-16-5) + para-bromotoluene (106-38-7) → 1-[5-(4-methylphenyl)thiophene-2-yl]ethanone (51335-91-2)

Guidance literature:

With dichloro[1-(β-methallyl)-3-(2,3,4,5,6-pentamethyl)benzylbenzimidazole-2-ylidene]pyridine palladium(II); potassium acetate; In N,N-dimethyl acetamide; at 130 ℃; for 1h; Reagent/catalyst; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.jorganchem.2019.121076

Reference yield: 96.0%

para-bromotoluene (106-38-7) + (5-acetylthiophen-2-yl)boronic acid (206551-43-1) → 1-[5-(4-methylphenyl)thiophene-2-yl]ethanone (51335-91-2)

Guidance literature:

With C₂₃H₂₄Cl₂N₄Pd; potassium hydroxide; In ethanol; at 22 ℃; for 24h;

DOI:10.1016/j.ica.2018.06.028

Reference yield: 93.0%

2-acetyl-5-iodothiophene (30955-94-3) + para-methylphenylmagnesium bromide (4294-57-9) → 1-[5-(4-methylphenyl)thiophene-2-yl]ethanone (51335-91-2) + 5,5'-di(1-oxoethyl)-2,2'-bithiophene (18494-73-0) + (4,4'-dimethyl-1,1'-biphenyl) (613-33-2)

Guidance literature:

para-methylphenylmagnesium bromide; With bismuth(III) chloride;

2-acetyl-5-iodothiophene; With potassium phosphate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 90 ℃; for 1h; Inert atmosphere;

DOI:10.1055/s-0030-1260554

upstream raw materials:

2-p-tolylthiophene

acetyl chloride

2-Acetylthiophene

p-methylbenzenediazonium chloride

Downstream raw materials:

C₂₁H₁₄ClNO₂S

C₂₁H₁₄BrNO₂S

2-Methyl-2-[1-(5-p-tolyl-thiophen-2-yl)-eth-(E)-ylideneaminooxy]-propionic acid ethyl ester

2-[1-(5-p-Tolyl-thiophen-2-yl)-eth-(E)-ylideneaminooxy]-propionic acid ethyl ester

Refernces

• 1、 ?zdemir, Ismail,Gürbüz, Nevin,Hamdi, Naceur,Mansour, Lamjed,Slimani, Ichraf. "Synthesis, characterization and catalytic activity of PEPPSI-type palladium–NHC complexes". . . Retrieved 2020/10/12.
• 2、 Kalo?lu, Murat,Kalo?lu, Nazan,?zdemir, Nam?k,?zdemir, ?smail. "The first use of [PdBr2(imidazolidin-2-ylidene)(pyridine)] catalysts in the direct C-H bond arylation of C2-substituted furan and thiophene". . p. 2821 - 2843. Retrieved 2021/04/21.