3-Methyl-2-thiophenecarboxaldehyde

Base Information

• Chemical Name: 3-Methyl-2-thiophenecarboxaldehyde
• CAS No.: 5834-16-2
• Molecular Formula: C6H6OS
• Molecular Weight: 126.179
• Hs Code.: 29349990
• European Community (EC) Number: 227-418-8
• UNII: ZHC9WE8PS0
• DSSTox Substance ID: DTXSID80207070
• Nikkaji Number: J37.033I
• Wikidata: Q72491477
• Mol file: 5834-16-2.mol

Synonyms:3-Methyl-2-thiophenecarboxaldehyde;5834-16-2;3-Methylthiophene-2-carboxaldehyde;3-Methylthiophene-2-carbaldehyde;2-formyl-3-methylthiophene;3-Methylthiophene-2-aldehyde;3-Methyl-2-formylthiophene;2-Thiophenecarboxaldehyde, 3-methyl-;3-Methyl-2-thiophenecarboxaldehyde ,tech;3-Methyl-2-thiophene carboxaldehyde;MFCD00005430;ZHC9WE8PS0;3-Methyl-2-thiophenecarbaldehyde;3-Methyl-2-thiophenecarboxaldehyde, tech grade;EINECS 227-418-8;3-Methylthiophene-2-Aldehyde (3-M-T-2-A);UNII-ZHC9WE8PS0;BIDD:GT0155;SCHEMBL447131;3-methylthiophene carboxaldehyde;3-METHYL-2-THENALDEHYDE;thiophene, 3-Methyl, 2-formyl;3-methyl-2-thiophencarboxaldehyde;3-methylthiophene-2-carboaldehyde;DTXSID80207070;3-methyl-thiophene-2-carbaldehyde;3-Methylthiophen-2-carboxaldehyde;3-methyl-thiophene-2-carboxaldehyde;3-Methyl-2-carboxaldehyde-thiophene;GEO-01955;STK801368;AKOS000119473;PS-3269;SY008987;AM20100422;CS-0071758;FT-0616189;M0899;EN300-20132;W-105398;F2190-0652;Z104477012;3-Methyl-2-thiophenecarboxaldehyde, 90%, technical grade;MORANTEL HYDROGEN TARTRATE IMPURITY E [EP IMPURITY]

Chemical Property of 3-Methyl-2-thiophenecarboxaldehyde

Chemical Property:

• Appearance/Colour: clear yellow to brown liquid
• Vapor Pressure: 0.144mmHg at 25°C
• Melting Point: 260-262 °C
• Refractive Index: n20/D 1.587(lit.)
• Boiling Point: 216 °C at 760 mmHg
• Flash Point: 85.2 °C
• PSA: 45.31000
• Density: 1.18 g/cm³
• LogP: 1.86900
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Water Solubility.: insoluble
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 126.01393598
• Heavy Atom Count: 8
• Complexity: 92.5

Purity/Quality:

99% ^*data from raw suppliers

3-Methyl-2-thiophenecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36/37/39-26-36-7/9-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC=C1)C=O
• General Description: 3-Methyl-2-thiophenecarboxaldehyde serves as a key starting material in the synthesis of thieno[2,3-c]pyrroles via a retro-malonate addition reaction, demonstrating its utility in constructing heterocyclic frameworks. Its reactivity enables further transformations, such as Diels-Alder cycloadditions, highlighting its importance in the preparation of complex organic compounds with potential applications in pharmaceuticals and materials science.

Technology Process of 3-Methyl-2-thiophenecarboxaldehyde

There total 30 articles about 3-Methyl-2-thiophenecarboxaldehyde 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%

morpholine (110-91-8,99108-56-2) + S2 Cl2 + sulfuric acid (7664-93-9) → 3-methyl-2-thiophenecarboxaldehdye (5834-16-2,699531-50-5)

Guidance literature:

With manganese dioxide; acetic acid; In acetone;

Reference yield: 89.0%

2,3-dimethylthiophene (632-16-6) → 3-methyl-2-thiophenecarboxaldehdye (5834-16-2,699531-50-5)

Guidance literature:

With trichlorophosphate; In N,N-dimethyl-formamide; at 100 ℃; for 8h; Cooling with ice;

DOI:10.3390/molecules23020252

Reference yield: 75.0%

3-methylthiophene-2-carbonitrile (55406-13-8) → 3-methyl-2-thiophenecarboxaldehdye (5834-16-2,699531-50-5)

Guidance literature:

With diisobutylaluminium hydride; In hexane; chlorobenzene; at 0 ℃; for 1.33333h; Inert atmosphere;

DOI:10.1039/c5cc06095h

upstream raw materials:

3-Methylthiophene

N,N-dimethyl-formamide

N-methyl-N-phenylformamide

thiophene-2-carbaldehyde

Downstream raw materials:

3-methyl-2-(2-nitroethenyl)thiophene

(E)-3-(3-methyl-thien-2-yl)-2-propenoic acid

3-methyl-thiophene-2-carbaldehyde semicarbazone

(E)-2-((3-methylthiophen-2-yl)methylene)hydrazinecarbothioamide

Refernces

Thieno<2,3-c>pyrroles: Synthesis, Diels-ALder Reaction, and Synthetic Utility

10.1021/jo00295a038

The research focuses on the synthesis and chemical reactions of thieno[2,3-c]pyrroles. The authors developed a novel method for synthesizing these compounds through a retro-malonate addition reaction, starting from 3-methyl-2-thiophenecarboxaldehyde and diethyl malonate. They also explored the Diels-Alder reactions of thieno[2,3-c]pyrroles with reactive dienophiles such as N-phenylmaleimide and dimethyl acetylenedicarboxylate, leading to the formation of cycloadducts. The study includes the synthesis of various N-substituted thieno[2,3-c]pyrroles and their subsequent reactions to produce compounds like benzo[b]thiophene. The research also investigates the free-energy barriers of inversion of the imine nitrogens in the cycloadducts using variable-temperature 'H NMR spectroscopy. The study provides valuable insights into the synthetic utility and reactivity of thieno[2,3-c]pyrroles, contributing to the field of organic chemistry and potentially to the development of new pharmaceuticals and electroconducting polymers.