1918-77-0

Basic information

• Product Name: 2-Thiopheneacetic acid
• Synonyms: Thiophene-2-acetic acid, 98+%;2-THIOPHENE-2-ACETIC ACID;2-Thiophene;2-(Thien-2-yl)acetic acid 97%;2-(2-Thienyl)acetic acid;2-Thienylethanoic acid;Thiophen-2-ylacetic acid;2-Thiopheneacetic acid,98%
• CAS NO: 1918-77-0
• Molecular Formula: C₆H₆O₂S
• Molecular Weight: 142.18
• EINECS: 217-639-8
• Product Categories: Drug Intermediates;Heterocycles;Thiophene&Benzothiophene;Organic acids;Thiophens;Cephaloridine;thiophenes
• Mol File: 1918-77-0.mol

Chemical Properties

• Melting Point: 63-64 °C(lit.)
• Boiling Point: 160 °C22 mm Hg(lit.)
• Flash Point: 160°C/22mm
• Appearance: Slightly brown to brown/Crystalline Powder
• Density: 1.365 (estimate)
• Vapor Pressure: 0.00363mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 4.23±0.10(Predicted)
• Water Solubility: Soluble in water, ethanol, ether and carbon tetrachloride.
• BRN: 114551
• CAS DataBase Reference: 2-Thiopheneacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiopheneacetic acid(1918-77-0)
• EPA Substance Registry System: 2-Thiopheneacetic acid(1918-77-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-37-36/37/38
• Safety Statements: 26-36/37/39-45-24/25-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• TSCA: T
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 1918-77-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Thiopheneacetic acid is used as a pharmaceutical intermediate for the synthesis of cefaloridine and cefalotin sodium, which are antibiotics used to treat bacterial infections. Its role in the synthesis process is crucial for the development of these life-saving drugs.
Used in Material Science:
In the field of material science, 2-Thiopheneacetic acid is utilized in the preparation of rosette-like nanoscale gold materials. These materials have potential applications in various areas, such as catalysis, sensing, and drug delivery systems, due to their unique structural and electronic properties.
Used in Adsorption Studies:
The adsorption of 2-thiopheneacetic acid on XAD-4, NDA-100, and ND-90 resin has been investigated, which can be useful in understanding its interaction with different materials and potentially lead to new applications in separation or purification processes.
Used in Polymer Synthesis:
A new polymeric complex of Cu(II) and 2-thiopheneacetic acid has been synthesized and characterized by IR and Raman spectroscopy. This complex could have potential applications in various fields, such as electronics, sensors, or as a component in advanced materials.

Synthesis Reference(s)

Canadian Journal of Chemistry, 46, p. 1057, 1968 DOI: 10.1139/v68-179Journal of the American Chemical Society, 72, p. 4326, 1950

Purification Methods

Crystallise the acid from ligroin, hexane and/or distil it in a vacuum. The amide has m 148o (from H2O or pet ether). [Beilstein 18 H 293, 18 III/IV 4062, 18/6 V 207.]

InChI:InChI=1/C6H6O2S/c7-6(8)4-5-2-1-3-9-5/h1-3H,4H2,(H,7,8)/p-1

Synthetic route

ethyl thiophen-2-ylacetate (57382-97-5) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With water; sodium hydroxide In ethanol at 20℃; for 1h;	100%
With water; sodium hydroxide In ethanol at 20℃; for 1h;	100%

2-thiophenethanol (5402-55-1) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With oxygen; triethylamine at 80℃; for 15h; Reagent/catalyst; Temperature;	96.5%
With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium chloride; oxygen In 1,2-dichloro-ethane at 25℃; for 12h;	85%
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In aq. phosphate buffer; water; acetonitrile at 35℃; for 6h; Catalytic behavior; Reagent/catalyst; Temperature; Green chemistry;	85%
With iridium hexafluoride; sulphate-doped anatase; potassium oxide In dichloromethane at 85℃; Temperature;

methyl 2-thiopheneacetate (19432-68-9) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With sodium hydroxide for 2h; Heating;	94%

2,2,2-trichloro-1-(thien-2-yl)-ethanol (35320-27-5) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
Stage #1: 2,2,2-trichloro-1-(thien-2-yl)-ethanol With sodium tetrahydroborate; diphenyl diselenide In ethanol Inert atmosphere; Stage #2: With sodium hydroxide In ethanol at 40℃; Inert atmosphere;	94%

2-cyanomethylthiophene (20893-30-5) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With sodium hydroxide In water for 5h; Reflux;	93.4%
With water; potassium hydroxide In ethanol for 3h; Inert atmosphere; Reflux;	74%
With potassium hydroxide

N-((E)-1-Cyano-2-thiophen-2-yl-vinyl)-4,N-dimethyl-benzamide (89244-23-5, 89244-24-6) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 6h; Heating;	89%

2-methoxy-2-(thiophen-2-yl)acetic acid (5371-94-8) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With sodium chloride; iodine In water; acetic acid; ethyl acetate	86%

α-(N-Methylanilino)-β-(2-thienyl)acrylonitrile (91668-56-3) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 10h; Heating;	83%

2-oxo-3-(thiophen-2-yl)propanoic acid (15504-41-3) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With sodium perborate In water for 48h; Ambient temperature;	68%

thiophene-2-carbaldehyde (98-03-3) + Bromoform (75-25-2) + ethanethiol (75-08-1) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With potassium hydroxide In diethyl ether; water; dimethyl sulfoxide	58%

carbon dioxide (124-38-9) + N,N,N-trimethyl-1-(thiophen-2-yl)methanaminium trifluoromethanesulfonate → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; sodium carbonate; caesium carbonate In N,N-dimethyl-formamide at 25 - 30℃; for 36h; Schlenk technique; Glovebox; Sealed tube; Irradiation;	55%

((Z)-1-Dimethylamino-2-thiophen-2-yl-vinyl)-phosphonic acid diethyl ester (82670-75-5) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With hydrogenchloride Heating;	43%

carbon monoxide (201230-82-2) + 2-thiophenemethanol (636-72-6) → 2-Methylthiophene (554-14-3) + Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With hydrogen iodide; tetrakis(triphenylphosphine) palladium(0) In acetone at 90℃; under 68400 Torr; for 42h; Carbonylation; reduction;	A 12% B 18%

diazomethane (186581-53-3, 908094-01-9) + 2-Thiophenecarbonyl chloride (5271-67-0) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With diethyl ether Erwaermen einer Loesung des Reaktionsprodukts in Dioxan mit Silberoxid und Natriumthiosulfat in Wasser;

2-Chloromethylthiophene (765-50-4) → 2-methylthiophene-3-carboxylic acid (1918-78-1) + Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With diethyl ether; magnesium Behandeln des Reaktionsgemisches mit festem Kohlendioxid;

2-Acetylthiophene (88-15-3) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With 1,4-dioxane; ammonium polysulfide solution; sulfur Erhitzen des erhaltenen Saeureamids mit wss. Kalilauge;
With 1,4-dioxane; ammonium polysulfide solution; sulfur Erhitzen des erhaltenen Saeureamids mit wss. Salzsaeure;
Multi-step reaction with 2 steps 1: 83 percent / BF3*O(C2H5)3, Pb(OAc)4 / benzene / 11 h / Ambient temperature 2: 94 percent / aq. NaOH / 2 h / Heating View Scheme

2-thenyl magnesium chloride (19432-64-5) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) → 2-methylthiophene-3-carboxylic acid (1918-78-1) + Thiophene-2-acetic acid (1918-77-0)

isopropyl 2-(thiophen-2-yl)acetate (68100-13-0) → Thiophene-2-acetic acid (1918-77-0) + propene (187737-37-7)

Conditions	Yield
In gaseous matrix at 326.9℃; gas-phase Hammett replacement ς0 substituent constant was investigated;

tert-butyl 2-(thiophen-2-yl)acetate (58416-18-5) → Thiophene-2-acetic acid (1918-77-0) + isobutene (115-11-7)

Conditions	Yield
In gaseous matrix at 326.9℃; gas-phase Hammett replacement ς0 substituent constant was investigated;

α-thienylglycolic acid → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With phosphorus; hydrogen iodide

methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + <2>thienyl-methyl magnesium chloride → 2-methylthiophene-3-carboxylic acid (1918-78-1) + Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With diethyl ether

2-diazo-1-(thiophen-2-yl)ethanone (72676-21-2) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
With silver(l) oxide In 1,4-dioxane Rearrangement;

2-Thiophenecarbonyl chloride (5271-67-0) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: aq. Ag2O / dioxane View Scheme
Multi-step reaction with 2 steps 1: diethyl ether / Erwaermen des Reaktionsprodukts mit Silberoxid und Methanol View Scheme

2-thiophenylcarboxylic acid (527-72-0) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: (COCl)2; DMF / CH2Cl2 2: diethyl ether / 0 °C 3: aq. Ag2O / dioxane View Scheme

thiophene-2-carbaldehyde (98-03-3) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 68 percent / KH / tetrahydrofuran / 4 h / Ambient temperature 2: 83 percent / 10percent aq. HCl / tetrahydrofuran / 10 h / Heating View Scheme

2-ethynyl-thiophene (4298-52-6) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: benzene, NaHCO3 / methanol / 110 h / Heating 2: 2N NaOH View Scheme
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 °C / Inert atmosphere 2.1: oxone||potassium monopersulfate triple salt; water / acetone / 12 h / 50 °C / Inert atmosphere View Scheme

3-thiophen-2-yl-2-thioxo-propionic acid (89677-36-1) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol; hydroxylamine 2: acetic acid anhydride 3: aq.-ethanolic KOH-solution View Scheme

5-(2'-thiophenemethylene)rhodamine (6319-47-7, 98800-08-9, 98800-09-0) → Thiophene-2-acetic acid (1918-77-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. NaOH solution 2: ethanol; hydroxylamine 3: acetic acid anhydride 4: aq.-ethanolic KOH-solution View Scheme

methanol (67-56-1) + Thiophene-2-acetic acid (1918-77-0) → methyl 2-thiopheneacetate (19432-68-9)

Conditions	Yield
With hydrogenchloride for 3h; Heating;	100%
With thionyl chloride at 0 - 20℃; for 18h;	100%
With thionyl chloride at 0 - 20℃; for 18h;	100%

Thiophene-2-acetic acid (1918-77-0) + 5,6-dimethoxy-2-(N-propylamino)indan (162751-96-4) → N-(5,6-dimethoxy-indan-2-yl)-N-propyl-2-thiophen-2-yl-acetamide (745060-18-8)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In dichloromethane at 20℃; for 24h;	100%

Thiophene-2-acetic acid (1918-77-0) + benzylamine (100-46-9) → N-benzyl-2-(thiophen-2-yl)acetamide

Conditions	Yield
With (2-(thiophen-2-ylmethyl)phenyl)boronic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; Molecular sieve;	99%
With bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Sealed tube; Inert atmosphere;	90%

Thiophene-2-acetic acid (1918-77-0) + oxalyl dichloride (79-37-8) → 2-(2'-Thienyl)methyl-penem-3-carboxylic Acid

Conditions	Yield
	98.8%

Thiophene-2-acetic acid (1918-77-0) + 4'-methoxy-N-(azulen-1-ylmethylene)aniline (854154-95-3) → 1-(azulen-1'-yl)-2-(thien-2''-yl)ethene (652142-07-9)

Conditions	Yield
for 0.25h; Heating;	98%
for 0.5h; Heating;	98%

hydrogenchloride (7647-01-0) + Thiophene-2-acetic acid (1918-77-0) + lead(II) nitrate + potassium hydroxide → [Pb(thiophene-2-acetate)2(H2O)]n

Conditions	Yield
Stage #1: hydrogenchloride; lead(II) nitrate; potassium hydroxide at 70℃; for 0.5h; Green chemistry; Stage #2: Thiophene-2-acetic acid for 6h; Heating; Green chemistry;	98%

Thiophene-2-acetic acid (1918-77-0) + aniline (62-53-3) → N-phenyl-2-(thiophen-2-yl)acetamide (69047-40-1)

Conditions	Yield
With triethylamine; Phenyl N-phenylphosphoramidochloridate In dichloromethane for 1h; Ambient temperature;	97%
With zeolite-HY In neat (no solvent) for 1h; Irradiation;	97%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20 - 25℃; for 1h;	90%
Stage #1: Thiophene-2-acetic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1h; Stage #2: aniline In tetrahydrofuran at 20℃; for 2h;	81%

Thiophene-2-acetic acid (1918-77-0) → 2-thiophenethanol (5402-55-1)

Conditions	Yield
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 6h;	97%
With tricarbonyl(η(4)-cycloocta-1,5-diene)iron; phenylsilane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; UV-irradiation; chemoselective reaction;	95%
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In chloroform at 60℃; for 2h; Inert atmosphere;	73%

Thiophene-2-acetic acid (1918-77-0) + phenyl isocyanate (1197040-29-1) → N-formyl-N-phenyl-2-(thiophen-2-yl)acetamide (1414349-67-9)

Conditions	Yield
In toluene at 110℃; Sealed tube; Inert atmosphere;	97%

Thiophene-2-acetic acid (1918-77-0) + 4-Methoxyphenethylamine (55-81-2) → N-(2-(4-methoxyphenyl)ethyl)-2-thiophen-2-ylacetamide (349433-11-0)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	97%

Thiophene-2-acetic acid (1918-77-0) + silver nitrate → silver(I) 2-thiopheneacetate

Conditions	Yield
With triethylamine In ethanol; acetonitrile at 0℃; for 2h; Inert atmosphere; Schlenk technique;	97%
With triethylamine In ethanol; acetonitrile at 0℃; for 2h;	97%

Thiophene-2-acetic acid (1918-77-0) + diethyl 4-(6-hydroxyhexan-2-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate → diethyl 2,6-dimethyl-4-(6-(2-(thiophen-2-yl)acetoxy)hexan-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;	97%

Thiophene-2-acetic acid (1918-77-0) + o-toluidine (95-53-4) → 2-(thiophen-2-yl)-N-(o-tolyl)acetamide (69047-43-4)

Conditions	Yield
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane at 20 - 25℃; for 1h;	96%

Thiophene-2-acetic acid (1918-77-0) + chloro-trimethyl-silane (75-77-4) → trimethylsilyl 2-(thien-2-yl)acetate (934415-23-3)

Conditions	Yield
Stage #1: Thiophene-2-acetic acid With pyridine In tetrahydrofuran at 0℃; for 0.5h; Stage #2: chloro-trimethyl-silane With 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran at 0 - 20℃; for 12h;	96%

piperidine (110-89-4) + Thiophene-2-acetic acid (1918-77-0) → 1-(piperidin-1-yl)-2-(thiophen-2-yl)ethan-1-one (114373-80-7)

Conditions	Yield
With tris(2,2,2-trifluoroethyl) borate for 24h; Dean-Stark; Reflux;	96%
With zirconium(IV) chloride In tetrahydrofuran at 70℃; for 24h; Molecular sieve; Inert atmosphere;	78%

morpholine (110-91-8) + Thiophene-2-acetic acid (1918-77-0) → 1-morpholino-2-(thiophen-2-yl)ethan-1-one

Conditions	Yield
With phenylsilane In acetonitrile at 20℃; for 2.5h;	96%

Thiophene-2-acetic acid (1918-77-0) + ethanol (64-17-5) → ethyl thiophen-2-ylacetate (57382-97-5)

Conditions	Yield
With hydrogenchloride In water at 70℃; for 19h;	95%
With hydrogenchloride In water at 20 - 70℃; for 19h;	95%
With sulfuric acid Reflux;	71%

Thiophene-2-acetic acid (1918-77-0) + tantalum pentaethoxide (150747-55-0) → [Ta(OC2H5)3(C4H3SCH2COO)2] (98605-57-3)

Conditions	Yield
In benzene byproducts: C2H5OH; react. under anhydrous conditions, addn. of 2-thiopheneacetic acid to asoln. of Ta(OEt)5 in benzene (2:1 molar ratio), refluxing for 8 h; collecting of liberated ethanol azeotropically, distg. off excess solvent, drying in vac., elem. anal.;	95%

Thiophene-2-acetic acid (1918-77-0) + 4-Bromo-benzene-1,2-diamine (1575-37-7) → 6-bromo-2-(thiophen-2-ylmethyl)-1H-benzo[d]imidazole (1340048-81-8)

Conditions	Yield
Stage #1: Thiophene-2-acetic acid With borane-THF In tetrahydrofuran; toluene at 20℃; for 0.5h; Cooling with ice; Stage #2: 4-Bromo-benzene-1,2-diamine In tetrahydrofuran; toluene for 12h; Reflux;	95%

Thiophene-2-acetic acid (1918-77-0) + Cyclohexyl isocyanide (931-53-3) → (Z)-3-(cyclohexylamino)-3-oxo-1-(thiophen-2-yl)prop-1-en-2-yl 2-(thiophen-2-yl)acetate (1414349-77-1)

Conditions	Yield
In nitromethane at 40℃; for 24h; Solvent; Concentration; Temperature; Sealed tube;	95%

Thiophene-2-acetic acid (1918-77-0) + 3,4-methylenedioxyphenylethylamine (1484-85-1) → N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-(thiophen-2-yl)acetamide (92851-34-8)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 6h;	95%
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	74%

Thiophene-2-acetic acid (1918-77-0) → thiophene-2-carbaldehyde (98-03-3)

Conditions	Yield
With potassium carbonate In chloroform at 20℃; for 24h; Irradiation; Inert atmosphere;	95%
With dipotassium peroxodisulfate In water at 90℃; for 12h; Green chemistry;	75%
With oxygen; copper diacetate In dimethyl sulfoxide at 120℃; for 18h; Sealed tube;	72%

Thiophene-2-acetic acid (1918-77-0) + hexachloro[60]fullerene (151013-83-1) → C90H25ClO10S5

Conditions	Yield
With tin(IV) chloride In 1,2-dichloro-benzene at 70 - 80℃; for 1h; Inert atmosphere;	95%

Thiophene-2-acetic acid (1918-77-0) → 2-thienylacetic acid chloride (39098-97-0)

Conditions	Yield
With bis(trichloromethyl) carbonate; N,N-dimethyl-formamide In dichloromethane at -10 - 0℃; for 5h; Temperature; Reagent/catalyst;	94.7%
With phosgene; 4-cyclopentylaminopyridine hydrobromide In toluene	92%
With 1-butyl-3-methylimidazolium hydroxide; thionyl chloride In chloroform at 10℃; for 8h; Reagent/catalyst; Temperature;	89.8%

Thiophene-2-acetic acid (1918-77-0) + (6R,7R)-7-Amino-3-(4,4-dimethyl-5-methylsulfanyl-4H-imidazol-2-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (124876-28-4) → (6R,7R)-3-(4,4-Dimethyl-5-methylsulfanyl-4H-imidazol-2-ylsulfanylmethyl)-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (124876-32-0)

Conditions	Yield
With N,N-bis(trimethylsilyl)acetamide; trichlorophosphate In ethyl acetate; N,N-dimethyl-formamide Ambient temperature;	94%

Upstream product

• 29683-77-0 2-chloro-1-(thiophen-2-yl)ethanone 
• 68100-13-0 isopropyl 2-(thiophen-2-yl)acetate 
• 19432-64-5 2-thienylmagnesium chloride 
• 15719-64-9 methylammonium carbonate 
• 57382-97-5 ethyl thiophen-2-ylacetate 
• 19432-68-9 methyl 2-thiopheneacetate 
• 88-15-3 2-Acetylthiophene 
• 20893-30-5 2-cyanomethylthiophene 
• 765-50-4 2-Chloromethylthiophene 
• 186581-53-3 diazomethane 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 15022-15-8 2-thienylacetaldehyde 
• 66643-82-1 methyl β-(2-thienyl)glycidate 
• 600708-53-0 3-thiophen-2-yl-oxirane-2-carboxylic acid ethyl ester 

Downstream Products

• 209349-06-4 C₂₇H₃₂N₂O₂S₃ 
• 1026540-19-1 5-(carboxymethyl)-2-thiophenebutyric acid 
• 142371-33-3 (Z)-3-[5-((E)-2-Carboxy-2-phenyl-vinyl)-thiophen-2-yl]-2-thiophen-2-yl-acrylic acid 
• 142371-34-4 (Z)-3-[5-((E)-2-Methoxycarbonyl-2-phenyl-vinyl)-thiophen-2-yl]-2-thiophen-2-yl-acrylic acid methyl ester 
• 69930-82-1 3-acetoxymethyl-7c-methoxy-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-4-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 39098-97-0 2-thienylacetic acid chloride 
• 19432-68-9 methyl 2-thiopheneacetate 
• 115996-22-0 N-<2-(3,4-dimethoxyphenyl)ethyl>-2-(2-thienyl)ethanamide 
• 131269-20-0 2-(2'-thienyl)3-phenyl-<1H>-inden-1-one 

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The invention belongs to the field of synthesis of thiophene medical intermediates, discloses a method for efficiently preparing the thiophene medical intermediates, and particularly discloses a process for synthesizing 2-thiopheneacetic acid from 2-thiopheneethanol through a catalytic reaction, catalyzing the 2-thiopheneacetic acid to generate a 2-thiopheneacetyl chloride crude product and then purifying the 2-thiopheneacetyl chloride crude product. The reaction conditions are mild, the product purity is high, the synthesis efficiency is high, and the yield reaches 90% or above.

Oxidation of Alkynyl Boronates to Carboxylic Acids, Esters, and Amides

A general efficient protocol was developed for the synthesis of carboxylic acids, esters, and amides through oxidation of alkynyl boronates, generated directly from terminal alkynes. This protocol represents the first example of C(sp)?B bond oxidation. This approach displays a broad substrate scope, including aryl and alkyl alkynes, and exhibits excellent functional group tolerance. Water, primary and secondary alcohols, and amines are suitable nucleophiles for this transformation. Notably, amino acids and peptides can be used as nucleophiles, providing an efficient method for the synthesis and modification of peptides. The practicability of this methodology was further highlighted by the preparation of pharmaceutical molecules.

Synthesis method of 2-thiopheneacetic acid

The invention provides a synthesis method of 2-thiopheneacetic acid, which is characterized by comprising the following steps: (1) acylation reaction: carrying out Friedel-Crafts reaction on thiopheneand 2-chloroacetyl chloride as raw materials to obtain 2-chloroacetyl thiophene; and (2) rearrangement reaction: carrying out a Favanskii rearrangement reaction on the 2-chloroacetyl thiophene underan alkaline condition to obtain the 2-thiopheneacetic acid. The method is wide in raw material source, low in cost, few in steps, simple to operate, high in safety, small in pollution and easy to industrialize. Friedel-Crafts reaction and Favanskii rearrangement reaction are adopted, the conversion rate of the two reactions is high, the selectivity is good, the operation of the reaction process issimple, no special reagent is needed, the raw materials are cheap and easy to obtain, the requirement for equipment is not high, the product yield is high, few impurities are contained, and the method has remarkable advantages and practical value.

Preparation method of 2-thiopheneacetyl chloride

The invention discloses a preparation method of 2-thiopheneacetyl chloride, and belongs to the technical field of chemical synthesis. The preparation method comprises the following steps: (1) dissolving 2-thiopheneethanol in an organic solvent, and reacting at 50-120 DEG C under the action of a solid acid catalyst, an alkali and an oxidant to prepare 2-thiopheneacetic acid, wherein the oxidant isoxygen or hydrogen peroxide; and (2) dissolving 2-thiopheneacetic acid in an organic solvent, and dropwise adding thionyl chloride to carry out an acylating chlorination reaction by taking an alkalineionic liquid as a catalyst so as to prepare 2-thiopheneacetyl chloride. The preparation method is simple in route, easy in obtaining of raw materials, mild in reaction conditions, and capable of realizing few byproducts and easy purification and separation due to adoption of oxygen or hydrogen peroxide as the oxidant in synthesis of 2-thiopheneacetic acid; and when the acylating chlorination reaction of 2-thiopheneacetic acid is carried out, the basic ionic liquid is adopted as the catalyst, the reaction process is stable and easy to control, the product yield is high, few byproducts are produced, so the method is an efficient and green synthesis process.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.

Synthetic method of 2-thiopheneacetic acid

The invention discloses a synthetic method of 2-thiopheneacetic acid and belongs to the technical field of synthesis of intermediates. The synthetic method comprises the following steps: synthesis of3-(2-thiophene)-2,3-epoxy sodium propionate: taking 2-thiophenecarboxaldehyde and chloracetate as raw materials, carrying out Darzen reaction to synthesize epoxy acid ester and then hydrolyzing to obtain the 3-(2-thiophene)-2,3-epoxy sodium propionate; synthesis of 2-thiopheneacetic acid: acidizing the 3-(2-thiophene)-2,3-epoxy sodium propionate, carrying out decarboxylation rearrangement to obtain 2-thiophene acetaldehyde and then carrying out Pinnick oxidation reaction to obtain the 2-thiopheneacetic acid. In the synthesis method of the 2-thiopheneacetic acid provided by the invention, Darzen reaction and Pinnick oxidation reaction are adopted; due to high conversion rate of the Darzen reaction and good selectivity of Pinnick oxidation, the product has the advantages of high yield, fewercontained impurities, significant advantages and practical value.

Design and evolution of an enzyme with a non-canonical organocatalytic mechanism

The combination of computational design and laboratory evolution is a powerful and potentially versatile strategy for the development of enzymes with new functions1–4. However, the limited functionality presented by the genetic code restricts the range of catalytic mechanisms that are accessible in designed active sites. Inspired by mechanistic strategies from small-molecule organocatalysis5, here we report the generation of a hydrolytic enzyme that uses Nδ-methylhistidine as a non-canonical catalytic nucleophile. Histidine methylation is essential for catalytic function because it prevents the formation of unreactive acyl-enzyme intermediates, which has been a long-standing challenge when using canonical nucleophiles in enzyme design6–10. Enzyme performance was optimized using directed evolution protocols adapted to an expanded genetic code, affording a biocatalyst capable of accelerating ester hydrolysis with greater than 9,000-fold increased efficiency over free Nδ-methylhistidine in solution. Crystallographic snapshots along the evolutionary trajectory highlight the catalytic devices that are responsible for this increase in efficiency. Nδ-methylhistidine can be considered to be a genetically encodable surrogate of the widely employed nucleophilic catalyst dimethylaminopyridine11, and its use will create opportunities to design and engineer enzymes for a wealth of valuable chemical transformations.

Compounding method for 2-thiopheneacetyl chloride

The invention discloses a compounding method for 2-thiopheneacetyl chloride and belongs to the technical field of organic synthesis. The 2-thiopheneacetyl chloride is compounded by taking thiophene asa raw material through following three-step reaction: 1) acquiring 2-thiophene acetate through the F-C reaction of thiophene and glycolate under the existence of catalyst; 2) hydrolyzing the 2-thiophene acetate under the existence of acid, thereby acquiring 2-thiopheneacetic acid; 3) treating the 2-thiopheneacetic acid in the manner of acylating chlorination with thionyl chloride under the catalysis of pyridine, thereby acquiring 2-thiopheneacetyl chloride. The compounding method for 2-thiopheneacetyl chloride has the characteristics of easily acquired raw materials and simple and convenientoperation and is suitable for industrial production.

Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts

Cross-electrophile couplings between two electrophiles are powerful and economic methods to generate C-C bonds in the presence of stoichiometric external reductants. Herein, we report a novel strategy to realize the first external-reductant-free cross-electrophile coupling via visible-light photoredox catalysis. A variety of tetraalkyl ammonium salts, bearing primary, secondary, and tertiary C-N bonds, undergo selective couplings with aldehydes/ketone and CO2. Notably, the in situ generated byproduct, trimethylamine, is efficiently utilized as the electron donor. Moreover, this protocol exhibits mild reaction conditions, low catalyst loading, broad substrate scope, good functional group tolerance, and facile scalability. Mechanistic studies indicate that benzyl radicals and anions might be generated as the key intermediates via photocatalysis, providing a new direction for cross-electrophile couplings.