39098-97-0 Usage
Description
2-Thiopheneacetyl chloride is used as a reagent to synthesize diamide derivatives of (S)-BINOL. These derivatives display potential anti-inflammatory and anti-arthritis effects. 2-Thiopheneacetyl chloride is also used in the synthesis of Nitrocefin (N493815), a chromogenic substrate that changes colour in the presence of β-lactamases and penicillin-binding proteins.
Chemical Properties
CLEAR BROWN LIQUID
Uses
Different sources of media describe the Uses of 39098-97-0 differently. You can refer to the following data:
1. 2-Thiopheneacetyl chloride was used in the synthesis of (S)-ethyl-1-(2-thiopheneacetyl)-3-piperidinecarboxylate, nipecotate-containing immunopotentiator, 5-fluorouracil-cephalosporin prodrug, series of new N,N?-di(thiopheneacetyl)diamines derivatives and 6-β-(thiophen-2?-yl)acetamidomorphine. Also used in the synthesis of Nitrocefin.
2. 2-Thiopheneacetyl chloride was used in the synthesis of:(S)-ethyl-1-(2-thiopheneacetyl)-3-piperidinecarboxylate, nipecotate-containing immunopotentiator5-fluorouracil-cephalosporin prodrugseries of new N,N′-di(thiopheneacetyl)diamines derivatives6-β-(thiophen-2′-yl)acetamidomorphine
General Description
A clear yellow to dark brown liquid. Insoluble in water and denser than water. Corrosive to skin, and eyes. Vapors severely irritate respiratory tract.
Air & Water Reactions
Insoluble in water. Decomposes exothermically in water yielding fumes of toxic hydrogen chloride.
Reactivity Profile
THIOPHENE-2-ACETYL CHLORIDE is incompatible with water, bases (including amines), with strong oxidizing agents, and with alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Health Hazard
TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
Fire Hazard
Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
Synthesis
In the four-hole boiling flask with mechanical stirring, thermometer, air guide outlet, add 100g 2-thiophene acetic acid; 350g methylene dichloride, stirs and is warming up to 37 DEG C, starts to drip 250g sulfur oxychloride under the protection of nitrogen; within 1.5 hours, drip off insulation reaction 2.5 hours at this temperature.The methylene dichloride of underpressure distillation remnants, continues to distill obtaining 2-thiophen acetyl chloride 102.5g, and yield reaches 91.5%.
Check Digit Verification of cas no
The CAS Registry Mumber 39098-97-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,9,0,9 and 8 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 39098-97:
(7*3)+(6*9)+(5*0)+(4*9)+(3*8)+(2*9)+(1*7)=160
160 % 10 = 0
So 39098-97-0 is a valid CAS Registry Number.
InChI:InChI=1/C6H5ClOS/c7-6(8)4-5-2-1-3-9-5/h1-3H,4H2
39098-97-0Relevant articles and documents
Intramolecular carbenoid insertions into thiophene: Reactions of 1-diazo-3-(2-thienyl)-2-propanone and 1-diazo-3-(3-thienyl)-2-propanone
Frampton, Christopher S.,Pole, David L.,Yong, Kelvin,Capretta, Alfredo
, p. 5081 - 5084 (1997)
Treatment of 1-diazo-3-(2-thienyl)-2-propanone with catalytic rhodium (II) acetate results in cyclopropanation followed by acid-catalyzed ring opening and tautomerization to yield 5,6-dihydro-4H-cyclopenta[b]thiophen-5-one. Under the same conditions, however, the isomecic 1-diazo-3-(3-thienyl)-2-propanone generates a cyclopropane intermediate which undergoes [4+2] cycloreversion, isomerization and Diels-Alder dimerization to give a complex spiro-disulphide. While the 2-substituted thiophene behaves like other homologous members of the thienyl series, the isomeric 3-substituted thiophene undergoes chemistry seen previously with analogous furanyl compounds. The insight into the mechanistic underpinnings provided by preliminary molecular modeling at a PM3 level is discussed.
A Simple and Efficient Synthesis of Fused Benzo[ b ]thiophene Derivatives
Ulyankin, Evgeny B.,Kostyuchenko, Anastasia S.,Chernenko, Sergey A.,Bystrushkin, Mikhail O.,Samsonenko, Anna L.,Shatsauskas, Anton L.,Fisyuk, Alexander S.
, p. 2422 - 2434 (2021/04/21)
A new approach to the synthesis of fused benzothiophene derivatives was developed based on iodine-promoted photocyclization of 4,5-diaryl-substituted thiophenes obtained in three steps from commercially available compounds. Comparative analysis showed that photochemical cyclization is a more efficient method for the preparation of fused benzo[ b ]thiophene derivatives, compared to oxidative coupling of 4,5-diaryl-substituted thiophenes in the presence of iron(III) chloride and palladium-catalyzed intramolecular arylation. This new approach provides an efficient synthesis of functionally substituted naphtho[2,1- b:3,4- b ′]dithiophenes, phenanthro[9,10- b ]thiophenes, benzo[1,2- b:3,4- b ′:6,5- b ′′]trithiophenes, as well as new fused heterocycles containing a pyridine ring and/or a carbazole moiety.
One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
Bobal, Pavel,Otevrel, Jan,Svestka, David
, p. 25029 - 25045 (2020/07/14)
We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is
