73305-93-8

Usage

Uses

Used in Pharmaceutical Industry:
4-METHYL-THIOPHENE-2-CARBONITRILE is used as a key intermediate in the synthesis of N-(Heteroaryl)-sulfonamide derivatives. These derivatives are valuable as S100 inhibitors, which play a crucial role in various biological processes and have potential applications in the treatment of diseases related to the S100 protein family.
Used in Agrochemical Industry:
Although not explicitly mentioned in the provided materials, 4-METHYL-THIOPHENE-2-CARBONITRILE may also find applications in the agrochemical industry as a precursor for the development of novel pesticides or other agrochemical products. Its unique chemical structure allows for the creation of new compounds with potential pesticidal or herbicidal properties.

Synthetic route

4-methylthiophene-2-carbaldehyde (6030-36-0) → 4-methylthiophene-2-carbonitrile (73305-93-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; hydroxylamine hydrochloride / ethanol / 80 °C 2: potassium acetate / acetic anhydride / 4 h / 150 °C View Scheme

3-Methylthiophene (616-44-4) → 4-methylthiophene-2-carbonitrile (73305-93-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: pyridine; hydroxylamine hydrochloride / ethanol / 80 °C 3.1: potassium acetate / acetic anhydride / 4 h / 150 °C View Scheme

C6H7NOS (276692-16-1) → 4-methylthiophene-2-carbonitrile (73305-93-8)

Conditions	Yield
With potassium acetate In acetic anhydride at 150℃; for 4h;	3 g

4-methylthiophene-2-carbonitrile (73305-93-8) → 4-bromomethyl-thiophene-2-carbonitrile (186552-07-8)

Conditions	Yield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 8h; Reflux;	49%

4-methylthiophene-2-carbonitrile (73305-93-8) + succinic acid diethyl ester (123-25-1) → 3,6-bis(4-methylthiophene-2-yl)pyrrolo[3,4-c]pyrrolo-1,4(2H,5H)-dione (1429119-67-4)

Conditions	Yield
Stage #1: 4-methylthiophene-2-carbonitrile With iron(III) chloride; sodium In tert-Amyl alcohol at 75 - 120℃; Stage #2: succinic acid diethyl ester In tert-Amyl alcohol at 120℃; for 3.5h; Stage #3: With acetic acid In methanol; tert-Amyl alcohol at 50℃; for 0.5h; Reflux;	27.1%

4-methylthiophene-2-carbonitrile (73305-93-8) + 3-[(cyclopentylsulfanyl)methyl]-4-methoxyaniline (1343811-07-3) → N-{3-[(cyclopentylsulfanyl)methyl]-4-methoxyphenyl}-4-methylthiophene-2-carboximidamide (1569735-64-3)

Conditions	Yield
With aluminum (III) chloride In 1,2-dichloro-ethane at 115℃;	17%

4-methylthiophene-2-carbonitrile (73305-93-8) → 5-bromo-4-methyl-2-thiophenecarbonitrile (304854-52-2)

Conditions	Yield
With bromine In acetic acid at 20 - 40℃;

4-methylthiophene-2-carbonitrile (73305-93-8) → C12H12N4S2

Conditions	Yield
With sulfur; hydrazine hydrate In ethanol at 20℃; for 2h; Pinner amidine synthesis; Reflux;

4-methylthiophene-2-carbonitrile (73305-93-8) → 3,6-bis[4-methylthien-2-yl]-1,2,4,5-tetrazine (1286690-36-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfur; hydrazine hydrate / ethanol / 2 h / 20 °C / Reflux 2: isopentyl nitrite / chloroform / 20 °C View Scheme

4-methylthiophene-2-carbonitrile (73305-93-8) → 3,6-bis[4-methyl-5-bromothien-2-yl]-1,2,4,5-tetrazine (1286690-41-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfur; hydrazine hydrate / ethanol / 2 h / 20 °C / Reflux 2: isopentyl nitrite / chloroform / 20 °C 3: N-Bromosuccinimide; acetic acid / chloroform / 4 h / 80 °C View Scheme

4-methylthiophene-2-carbonitrile (73305-93-8) → 2,5-bis(2-hexyldecyl)-3,6-bis(4-methylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1429119-68-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium; iron(III) chloride / tert-Amyl alcohol / 75 - 120 °C 1.2: 3.5 h / 120 °C 1.3: 0.5 h / 50 °C / Reflux 2.1: potassium carbonate; 18-crown-6 ether / N,N-dimethyl-formamide / 16 h / 120 °C View Scheme

4-methylthiophene-2-carbonitrile (73305-93-8) → 3,6-bis(5-bromo-4-methylthiophen-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1429119-69-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium; iron(III) chloride / tert-Amyl alcohol / 75 - 120 °C 1.2: 3.5 h / 120 °C 1.3: 0.5 h / 50 °C / Reflux 2.1: potassium carbonate; 18-crown-6 ether / N,N-dimethyl-formamide / 16 h / 120 °C 3.1: N-Bromosuccinimide / chloroform / 48 h / 20 - 50 °C View Scheme

4-methylthiophene-2-carbonitrile (73305-93-8) → C6H4ClNO2S2

Conditions	Yield
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 8 h / Reflux 2: acetone / 2 h / 20 °C 3: chlorine; acetic acid; water View Scheme

4-methylthiophene-2-carbonitrile (73305-93-8) → 4-[(acetylsulfanyl)methyl]thiophene-2-carbonitrile

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 8 h / Reflux 2: acetone / 2 h / 20 °C View Scheme

4-methylthiophene-2-carbonitrile (73305-93-8) → N-(5-chloro-3-methoxypyridin-2-yl)-1-(5-cyanothiophen-3-yl)methanesulfonamide

Conditions	Yield
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 8 h / Reflux 2: acetone / 2 h / 20 °C 3: chlorine; acetic acid; water 4: pyridine / dichloromethane / 12 h / 20 °C View Scheme

4-methylthiophene-2-carbonitrile (73305-93-8) + ethyl 4-[2-(2-hydroxy-4-nitrophenyl)hydrazinylidene]-5-oxo-2-(thiophen-2-yl)-4,5-dihydro-1H-pyrrole-3-carboxylate (1470324-65-2) → 3-(4-methylthiophen-2-yl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions	Yield
Stage #1: ethyl 4-[2-(2-hydroxy-4-nitrophenyl)hydrazinylidene]-5-oxo-2-(thiophen-2-yl)-4,5-dihydro-1H-pyrrole-3-carboxylate With iron(III) chloride; sodium In tert-Amyl alcohol at 95℃; for 2h; Stage #2: 4-methylthiophene-2-carbonitrile In tert-Amyl alcohol at 120℃; for 3h;

4-methylthiophene-2-carbonitrile (73305-93-8) → C47H74N2O2S2

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium; iron(III) chloride / tert-Amyl alcohol / 2 h / 95 °C 1.2: 3 h / 120 °C 2.1: potassium carbonate; 18-crown-6 ether / N,N-dimethyl-formamide / 16 h / 120 °C View Scheme

4-methylthiophene-2-carbonitrile (73305-93-8) → C47H72Br2N2O2S2

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium; iron(III) chloride / tert-Amyl alcohol / 2 h / 95 °C 1.2: 3 h / 120 °C 2.1: potassium carbonate; 18-crown-6 ether / N,N-dimethyl-formamide / 16 h / 120 °C 3.1: bromine / chloroform View Scheme

Upstream product

• 276692-16-1 C₆H₇NOS 
• 616-44-4 3-Methylthiophene 
• 6030-36-0 4-methylthiophene-2-carbaldehyde 

Downstream Products

• 186552-07-8 4-bromomethyl-thiophene-2-carbonitrile 
• 1569735-64-3 N-{3-[(cyclopentylsulfanyl)methyl]-4-methoxyphenyl}-4-methylthiophene-2-carboximidamide 
• 1429119-69-6 3,6-bis(5-bromo-4-methylthiophen-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 1429119-68-5 2,5-bis(2-hexyldecyl)-3,6-bis(4-methylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 304854-52-2 5-bromo-4-methyl-2-thiophenecarbonitrile 

Relevant academic research and scientific papers

Alternating copolymers of dithienyl-s-tetrazine and cyclopentadithiophene for organic photovoltaic applications

As a new emerging electron deficient building block, s-tetrazine (Tz) shows high electron affinity, which is even higher than the commonly used benzothiadiazole units. This property makes Tz a very promising electron withdrawing unit for low band gap conjugated polymers, especially for organic solar cell materials. We report the synthesis and property of five alternating copolymers of s-tetrazine and cyclopenta[2,1-b:3,4-b′]dithiophene (CPDT), which are bridged with a thiophene unit. Methyl, hexyl, and/or 2-ethylhexyl groups are introduced onto thiophene and CPDT units to tune the solubility, UV absorption, frontier molecular orbital energy levels, and interchain stacking property of the resulting polymers. These polymers are stable up to 220 °C and decompose to dinitrile compounds with the breaking of Tz linkage at a higher temperature. Efficient bulk heterojunction solar cells were fabricated by blending these polymers with (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM), and they reached a power conversion efficiency up to 5.53% under simulated AM 1.5 G irradiation of 100 mW/cm2. The morphological structures of the active layers from different polymers or under different processing conditions were then analyzed by atomic force microscopy (AFM) and correlated with their device performance.