Thiophene-2-carbaldehyde

Base Information

• Chemical Name: Thiophene-2-carbaldehyde
• CAS No.: 98-03-3
• Molecular Formula: C5H4OS
• Molecular Weight: 112.152
• Hs Code.: Oral rat: LD50: 915 mg/kg
• European Community (EC) Number: 202-629-8
• NSC Number: 2162
• UNII: IW05BB9XBM
• DSSTox Substance ID: DTXSID7052656
• Nikkaji Number: J37.032K
• Wikipedia: Thiophene-2-carboxaldehyde
• Wikidata: Q27159509
• Metabolomics Workbench ID: 44007
• ChEMBL ID: CHEMBL328441
• Mol file: 98-03-3.mol

Synonyms:2-thiophene carboxaldehyde;2-thiophenecarboxaldehyde

Chemical Property of Thiophene-2-carbaldehyde

Chemical Property:

• Appearance/Colour: clear yellow to light brown liquid
• Vapor Pressure: 0.368mmHg at 25°C
• Melting Point: <10 °C
• Refractive Index: n20/D 1.591(lit.)
• Boiling Point: 198 °C at 760 mmHg
• Flash Point: 77.8 °C
• PSA: 45.31000
• Density: 1.238 g/cm³
• LogP: 1.56060
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: insoluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 111.99828592
• Heavy Atom Count: 7
• Complexity: 72.5

Purity/Quality:

99% min. ^*data from raw suppliers

2-Thiophenecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-43
• Safety Statements: 36/37/39-37-24-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: C1=CSC(=C1)C=O
• Uses: Thiophene derivatives, introducing thenyl group into organic compounds. 2-Thiophenecarboxaldehyde is used in the synthesis of β-aryl-β-amino acids, urea derivatives. Arylation reagent. Also used to synthesize unsaturated ketones as antiviral and cytotoxic agents.

Technology Process of Thiophene-2-carbaldehyde

There total 170 articles about Thiophene-2-carbaldehyde 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: 60.0%

thiophene-2-carbonitrile (1003-31-2) → thiophene-2-carbaldehyde (98-03-3) + 2-Aminomethylthiophene (27757-85-3)

Guidance literature:

thiophene-2-carbonitrile; With diisobutylaluminium hydride; In toluene; at 20 ℃; for 0.222222h; Flow reactor;

With water; sodium L-tartrate; In toluene; at 0 ℃; chemoselective reaction;

DOI:10.1016/j.tetlet.2011.08.144

Reference yield: 59.0%

2-thienyl chloride (96-43-5) + Trimethyl borate (121-43-7,63156-11-6) → thiophene (188290-36-0,8014-23-1,25233-34-5) + thiophene-2-carbaldehyde (98-03-3) + thiophene boronic acid (6165-68-0)

Guidance literature:

With aluminium; In N,N-dimethyl-formamide; byproducts: Al(3+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), dried over sodium or magnesium sulfate and concentrated undervacuum, side product phenol formation avoided by work-up under inert at mosphere, recrystallized in CH2Cl2;

DOI:10.1039/b200744b

Reference yield: 57.0%

2-bromothiophene (1003-09-4) + Trimethyl borate (121-43-7,63156-11-6) → thiophene (188290-36-0,8014-23-1,25233-34-5) + thiophene-2-carbaldehyde (98-03-3) + thiophene boronic acid (6165-68-0)

Guidance literature:

With magnesium; In N,N-dimethyl-formamide; byproducts: Mg(2+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), dried over sodium or magnesium sulfate and concentrated undervacuum, side product phenol formation avoided by work-up under inert at mosphere, recrystallized in CH2Cl2;

DOI:10.1039/b200744b

upstream raw materials:

orthoformic acid triethyl ester

diazomethane

2-Iodothiophene

carbon monoxide

Downstream raw materials:

2-<(2-thienylmethyl)amino>pyridine

3,3'-(thiophen-2-ylmethylene)bis(indole)

(Z)-3-(thiophen-2-yl)-2-(p-tolyl)acrylonitrile

(E)-2-(2-phenylethenyl)thiophene

Refernces

• 1、 Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang. "Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal". . . Retrieved 2021/09/28.
• 2、 Bartling, Stephan,Beller, Matthias,Chandrashekhar, Vishwas G.,Jagadeesh, Rajenahally V.,Rabeah, Jabor,Rockstroh, Nils,Senthamarai, Thirusangumurugan. "A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides". supporting information. p. 508 - 531. Retrieved 2022/02/11.