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2-Thiophenecarboxaldehyde

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CAS:98-03-3
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2-Thiophenecarboxaldehyde Basic information
Product Name:2-Thiophenecarboxaldehyde
Synonyms:2-Thiophenecarboxaldehyde (stabilized with HQ);2-Formylthiophene, 2-Thenaldehyde;2-Thiophenecarboxaldehyde, 98% 100ML;2-Thiophenecarboxaldehyde ,98%;THIOPHENE-2-CARBALDEHYDE FOR SYNTHESIS;2-Thiophenecarboxaldehyde,Thenaldehyde;2-Thiophenecarboxald;2-Thienylcarboxaldehyde
CAS:98-03-3
MF:C5H4OS
MW:112.15
EINECS:202-629-8
Product Categories:aldehyde;Building Blocks;C1 to C6;C4 to C6;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;Thiophenes & Benzothiophenes;Thiophen;Thiophenes;Aromatic Aldehydes & Derivatives (substituted);Aldehydes;Thiophenes & Benzothiophenes;Thiophene&Benzothiophene;Teniposide Ketotifen;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);bc0001
Mol File:98-03-3.mol
2-Thiophenecarboxaldehyde Structure
2-Thiophenecarboxaldehyde Chemical Properties
Melting point <10°C
Boiling point 198 °C (lit.) 75-77 °C/11 mmHg (lit.)
density 1.2 g/mL at 25 °C (lit.)
refractive index n20/D 1.591(lit.)
Fp 172 °F
storage temp. 2-8°C
solubility Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
form liquid (clear)
Specific Gravity1.2
color clear yellow
Odorsulfurous
Odor Typesulfurous
Water Solubility insoluble
Sensitive Air Sensitive
BRN 105819
InChIKeyCNUDBTRUORMMPA-UHFFFAOYSA-N
LogP1.020
CAS DataBase Reference98-03-3(CAS DataBase Reference)
NIST Chemistry Reference2-Thiophenecarboxaldehyde(98-03-3)
EPA Substance Registry System2-Thiophenecarboxaldehyde (98-03-3)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-43
Safety Statements 36/37/39-37-24-36-26
RIDADR UN 2810
WGK Germany 3
RTECS XM8135000
9
Hazard Note Irritant
TSCA Yes
HS Code 29349990
MSDS Information
ProviderLanguage
2-Formylthiophene English
SigmaAldrich English
ACROS English
ALFA English
2-Thiophenecarboxaldehyde Usage And Synthesis
Description2-Thiophenecarboxaldehyde, also known as alpha-formylthiophene or 2-thienylaldehyde, belongs to the class of organic compounds known as aryl-aldehydes. Aryl-aldehydes are compounds containing an aldehyde group directly attached to an aromatic ring. 2-Thiophenecarboxaldehyde is a sulfurous tasting compound. 2-Thiophenecarboxaldehyde has been detected, but not quantified in, asparagus (Asparagus officinalis). This could make 2-thiophenecarboxaldehyde a potential biomarker for the consumption of these foods. 2-Thiophenecarboxaldehyde is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites.
Chemical Propertiesclear yellow to light brown liquid
Uses2-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.
UsesThiophene derivatives, introducing thenyl group into organic compounds.
Application2-Thenaldehyde(T2A) was originally used to produce a range of antihistamines, including methapyrilene, methaphenilene, and thenalidine. However, this usage has practically disappeared. The anthelmintic pyrantel is an important outlet for T2A, enhanced by new formulations and the development of the medicinal use of pyrantel beyond the original veterinary market. An important T2A derivative is the antihypertensive eprosartan (2-thiophenepropionic acid methyl ester), which acts as a selective angiotensin II receptor antagonist. ?Other pharmaceuticals containing T2A are azosemide a diuretic, and teniposide an antineoplastic.
DefinitionChEBI: 2-Thiophenecarboxaldehyde is an aldehyde that is thiophene substituted by a formyl group at position 2. It has a role as a metabolite. It is a member of thiophenes and an aldehyde.
Synthesis Reference(s)Synthesis, p. 757, 1976 DOI: 10.1055/s-1976-24193
Tetrahedron Letters, 36, p. 455, 1995 DOI: 10.1016/0040-4039(94)02284-I
General DescriptionPharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards
Synthesis2-Thiophenecarboxaldehyde is prepared by the reaction of 2-Iodothiophene and carbon monoxide. The specific synthesis steps are as follows:
General procedure: A flask was charged with aryl iodide 1 (0.5 mmol), Pd(OAc)2 (2.4 mg, 0.01mmol), Na2CO3 (53.1 mg. 0.5 mmol), NaHCO3 (42.0 mg, 0.5 mmol), and PEG-400 (2 g) beforestandard cycles evacuation and backfilling with dry and pure carbon monoxide. Triethylsilane(162.8 μl, 1.0 mmol) was added successively. Then, the mixture was stirred at room temperaturefor the indicated time. At the end of the reaction, the reaction mixture was extracted with diethylether (3 × 10 mL). The organic phases were combined, and the volatile components wereevaporated under reduced pressure. The crude product was purified by column chromatography onsilica gel (petroleum ether / diethyl ether).
2-Thiophenecarboxaldehyde synthesis
Purification MethodsWash it with 50% HCl and distil it under reduced pressure just before use. It has UV: 234nm (hexane). The Z-oxime has m 144o, 136-138o and 142o (H2O). [Beilstein
Tag:2-Thiophenecarboxaldehyde(98-03-3) Related Product Information
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