38401-69-3

Basic information

• Product Name: 5-M-TOLYL-THIOPHENE-2-CARBALDEHYDE
• Synonyms: AKOS BAR-0532;5-M-TOLYL-THIOPHENE-2-CARBALDEHYDE;5-(3-METHYLPHENYL)THIOPHENE-2-CARBALDEHYDE;5-(3-METHYLPHENYL)-2-THIOPHENECARBALDEHYDE
• CAS NO: 38401-69-3
• Molecular Formula: C₁₂H₁₀OS
• Molecular Weight: 202.27
• Mol File: 38401-69-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 343.9±30.0 °C(Predicted)
• Appearance: /
• Density: 1.175±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 5-M-TOLYL-THIOPHENE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-M-TOLYL-THIOPHENE-2-CARBALDEHYDE(38401-69-3)
• EPA Substance Registry System: 5-M-TOLYL-THIOPHENE-2-CARBALDEHYDE(38401-69-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 38401-69-3(Hazardous Substances Data)

Upstream product

• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 17933-03-8 m-tolylboronic acid 
• 98-03-3 thiophene-2-carbaldehyde 
• 591-17-3 meta-bromotoluene 
• 85553-43-1 2-(3-methylphenyl)thiophene 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 166591-62-4 5-(3-methylphenyl)-2-thiophenecarboxylic acid 
• 1025871-45-7 5-(3-methylphenyl)-2-thiophenecarboxylic acid, N-tert-butylamide 
• 1027426-80-7 5-m-Tolyl-thiophene-2-carbonyl chloride 

Relevant articles and documents

Bis(imino)acenaphthene (BIAN)-Supported N-Heterocyclic Carbene Palladium Complexes with Ancillary Ligands: Readily Activated Precatalysts for Direct C-H Arylation of Thiophenes

We report herein a highly efficient direct C-H arylation of thiophenes with (hetero)aryl bromides by bulky bis(imino)acenaphthene (BIAN)-supported N-heterocyclic carbene palladium complexes. The relationship between the structure of palladium complexes with ancillary ligands and catalytic properties was discussed. Upon a low palladium loading of 0.01-0.05 mol %, the bulky palladium complex was successfully used to catalyze the cross-coupling of a variety of thiophens with (hetero)aryl bromides under aerobic conditions. Furthermore, it provides a practical and straightforward access to poly(3-hexylthiophenes) with high molecular weight and high HT value under aerobic reaction conditions. To access the mechanistic of the transformation, experiment investigation and DFT calculations on the direct arylation were performed, which supported the involvement of a Pd(0)/Pd(II)CMD process.

Substituted hexahydrobenzo[f]thieno[c]quinolines as dopamine D1- selective agonists: Synthesis and biological evaluation in vitro and in vivo

A series of substituted 9,10- dihydroxyhexahydrobenzo[f]thieno[c]quinolines (TB[f]Q), varying with respect to the position of the thiophene relative to the benzo[f]quinoline core and the nature and position of the substituent on the thiophene, were prepared and evaluated for their affinity and selectivity for the dopamine D1-like receptor. The thieno[3,2-c]B[f]Q regioisomers bearing a small alkyl (C1-C3) substituent at the 2 position were potent (K(i) 50) D1 agonists with close to full agonist activity (IA > 85%). The compounds were resolved and found to exhibit a high level of enantiospecificity in their interaction with the D1 receptor. Selected compounds were tested in vivo in the 6-OHDA rodent model of Parkinson's disease and for their liability to produce seizure-like activities in mice. (5aR)-trans-2-Propyl-4,5,5a,6,7,11b-hexahydro-3-thia-5-azacyclopent-1- ena[c]phenanthrene-9,10-diol (5) emerged as the compound with the best overall in vivo profile in terms of potency (ED50 = 0.04 μmol/kg) and safety.