| Identification | More | [Name]
2-Thenaldehyde | [CAS]
98-03-3 | [Synonyms]
2-FORMYL THIOPHENE
2-THENALDEHYDE
2-THIOPHENALDEHYDE
2-THIOPHENEALDEHYDE
2-THIOPHENECARBALDEHYDE
2-THIOPHENECARBOXALDEHYDE
AKOS BBS-00003201
THENALDEHYDE
THIENYL-2-ALDEHYDE
THIOPHENE-2-ALDEHYDE
THIOPHENE-2-CARBALDEHYDE
THIOPHENE-2-CARBOXALDEHYDE
TIMTEC-BB SBB004321
2-Thienal
2-thienaldehyde
2-Thienylaldehyde
2-Thienylcarboxaldehyde
2-thiophenaldeyde(stabilizedwithhq)
2-thiophencarboxaldehyde
2-thiophene carboxyaldehyde | [EINECS(EC#)]
202-629-8 | [Molecular Formula]
C5H4OS | [MDL Number]
MFCD00005429 | [Molecular Weight]
112.15 | [MOL File]
98-03-3.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow to light brown liquid | [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)
| [color ]
clear yellow
| [Specific Gravity]
1.2 | [Odor]
sulfurous | [Odor Type]
sulfurous | [Water Solubility ]
insoluble | [Sensitive ]
Air Sensitive | [Detection Methods]
GC | [BRN ]
105819 | [InChIKey]
CNUDBTRUORMMPA-UHFFFAOYSA-N | [LogP]
1.020 | [Uses]
Thiophene derivatives, introducing thenyl
group into organic compounds. | [CAS DataBase Reference]
98-03-3(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Thiophenecarboxaldehyde(98-03-3) | [Storage Precautions]
Store under nitrogen | [EPA Substance Registry System]
98-03-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37:Wear suitable gloves .
S24:Avoid contact with skin .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 2810 | [WGK Germany ]
3
| [RTECS ]
XM8135000
| [F ]
9 | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Description]
2-Thiophenecarboxaldehyde(98-03-3), 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 Properties]
clear yellow to light brown liquid | [Application]
2-Thenaldehyde(T2A,98-03-3) 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.
| [Definition]
ChEBI: An aldehyde that is thiphene substituted by a formyl group at position 2. | [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 Description]
Pharmaceutical 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 | [Synthesis]
2-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).
 | [Purification Methods]
Wash 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 |
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