5834-16-2

Basic information

• Product Name: 3-Methyl-2-thiophenecarboxaldehyde
• Synonyms: 2-FORMYL-3-METHYLTHIOPHENE;AKOS BBS-00003151;3-METHYL-2-THIENALDEHYDE;3-METHYL-2-THIOPHENECARBOXALDEHYDE;3-METHYL-2-THIOPHENECARBALDEHYDE;3-METHYLTHIOPHENE-2-FORMALDEHYDE;3-METHYLTHIOPHENE-2-ALDEHYDE;3-METHYLTHIOPHENE-2-CARBOXALDEHYDE
• CAS NO: 5834-16-2
• Molecular Formula: C₆H₆OS
• Molecular Weight: 126.18
• EINECS: 227-418-8
• Product Categories: Thiophene&Benzothiophene;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Thiophenes
• Mol File: 5834-16-2.mol
• Article Data: 20

Chemical Properties

• Melting Point: 260-262 °C
• Boiling Point: 78-80 °C (15 mmHg)
• Flash Point: 180 °F
• Appearance: Clear yellow to brown/Liquid
• Density: 1.17 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.144mmHg at 25°C
• Refractive Index: n20/D 1.587(lit.)
• Storage Temp.: Store below +30°C.
• Water Solubility: insoluble
• Sensitive: Air Sensitive
• BRN: 107874
• CAS DataBase Reference: 3-Methyl-2-thiophenecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-thiophenecarboxaldehyde(5834-16-2)
• EPA Substance Registry System: 3-Methyl-2-thiophenecarboxaldehyde(5834-16-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36/37/39-26-36-7/9-37
• WGK Germany: 3
• HazardClass: IRRITANT, AIR SENSITIVE
• Hazardous Substances Data: 5834-16-2(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to brown liquid

Uses

Different sources of media describe the Uses of 5834-16-2 differently. You can refer to the following data:
1. 3-Methyl-2-thiophenecarboxaldehyde is used in the synthesis of 2,3-dimethyl-5-(2,6,10-trimethylundecyl)thiophene. It is also used to investigate versatile bioconversion capacity of baker′s yeast for the generation of thiols from cysteine-aldehyde conjugates.
2. 3-Methyl-2-thiophenecarboxaldehyde was used in the synthesis of 2,3-dimethyl-5-(2,6,10-trimethylundecyl)thiophene. It was used to investigate versatile bioconversion capacity of baker′s yeast for the generation of thiols from cysteine-aldehyde conjugates.

InChI:InChI=1/C6H6OS/c1-5-2-3-8-6(5)4-7/h2-4H,1H3

Upstream product

• 616-44-4 3-Methylthiophene 
• 75-27-4 bromodichloromethane 
• 23806-24-8 3-methyl-2-thiophenecarboxylic acid 
• 632-16-6 2,3-dimethylthiophene 
• 110-91-8 morpholine 
• 7664-93-9 sulfuric acid 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 
• 35340-18-2 N-Methyl-2,6-diisopropyl-formanilid 
• 22699-63-4 N,N-dicyclohexylformamide 
• 35517-66-9 N-(2,6-Dimethylphenyl)-N-methylformamide 
• 4885-02-3 Dichloromethyl methyl ether 
• 2700-30-3 N,N-diisorpopylformamide 
• 2861-59-8 N-formylindoline 

Downstream Products

• 946113-22-0 C₁₁H₁₇NOS 
• 119198-72-0 5-Isopropyl-5H-thieno[2,3-c]pyrrole 
• 119198-75-3 5-Phenyl-5H-thieno[2,3-c]pyrrole 
• 119198-74-2 5-Benzyl-5H-thieno[2,3-c]pyrrole 
• 125302-60-5 5-Cyclohexyl-5H-thieno[2,3-c]pyrrole 
• 125302-64-9 5-(p-aminophenyl)thieno<2,3-c>pyrrole 
• 125329-33-1 dimethyl 4,7-dihydro-8-cyclohexylbenzothiophen-4,7-imine-5,6-dicarboxylate 
• 125302-72-9 dimethyl 4,7-dihydro-8-phenylbenzothiophen-4,7-imine-5,6-dicarboxylate 
• 125302-71-8 dimethyl 4,7-dihydro-8-benzylbenzothiophen-4,7-imine-5,6-dicarboxylate 
• 125409-07-6 exo-N-phenyl-4,5,6,7-tetrahydro-8-methylbenzothiophen-4,7-imine-5,6-dicarboximide 
• 125302-67-2 endo-N-phenyl-4,5,6,7-tetrahydro-8-methylbenzothiophen-4,7-imine-5,6-dicarboximide 
• 55406-13-8 3-methylthiophene-2-carbonitrile 
• 224-07-7 phenanthro<2,3-b>thiophene 

Relevant articles and documents

Regioselective electrophilic formylation - 3-substituted thiophenes as a case study

A variety of methods for regioselective formylation have been examined and exemplified with 3-methylthiophene. Optimal yields and regioselectivity for 2-formylation were obtained with N-formylpyrrolidine (11:1) although up to a 46:1 ratio could be obtained with MeOCHCl2:TiCl4, albeit in lower yield. Optimal 5-formylation (1:1.5) was obtained when using N- formylindoline:(COCl)2. (C) 2000 Elsevier Science Ltd.

Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation

A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.

Systematic structure-activity relationship (SAR) exploration of diarylmethane backbone and discovery of a highly potent novel uric acid transporter 1 (URAT1) inhibitor

In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.