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

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
• 6-β-(thiophen-2′-yl)acetamidomorphine

Uses

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.

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°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%.

References

[1] Patent: CN107011319, 2017, A. Location in patent: Paragraph 0010; 0018-0025
[2] Patent: CN105601502, 2016, A. Location in patent: Paragraph 0076; 0077; 0078
[3] Patent: CN105585478, 2016, A. Location in patent: Paragraph 0064; 0065
[4] Bulletin de la Societe Chimique de France, 1949, p. 847,851
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 500