1641-09-4

Basic information

• Product Name: 3-Thiophenecarbonitrile
• Synonyms: BUTTPARK 96\11-31;3-CYANOTHIOPHENE;3-THIOPHENECARBONITRILE;THIOPHENE-3-CARBONITRILE;Thiophene-3-carbonitrile 97%;3-Cyanothiophene, Thiophene-3-nitrile;3-Thiophenecarbonitrile,94%;3-Thiophenecarbonitr
• CAS NO: 1641-09-4
• Molecular Formula: C₅H₃NS
• Molecular Weight: 109.15
• EINECS: 216-687-7
• Product Categories: Sulphur Derivatives;Thiophene&Benzothiophene;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen
• Mol File: 1641-09-4.mol
• Article Data: 60

Chemical Properties

• Boiling Point: 82 °C10 mm Hg(lit.)
• Flash Point: 186 °F
• Appearance: Clear colorless/Liquid
• Density: 1.2 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.423mmHg at 25°C
• Refractive Index: n20/D 1.5630(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• BRN: 107104
• CAS DataBase Reference: 3-Thiophenecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Thiophenecarbonitrile(1641-09-4)
• EPA Substance Registry System: 3-Thiophenecarbonitrile(1641-09-4)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1641-09-4(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

3-Thiophenecarbonitrile can be used to synthesize the following:2,4-dinaphthyl-3-cyanothiophene via reaction with iodonaphthalene2,5-bis-tri(n-butyl)tin-3-cyanothiophene, a building block for the synthesis of new alternating (3-alkyl/3-cyano)thiophene copolymers

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 1670, 1979 DOI: 10.1021/jo01324a019Synthetic Communications, 20, p. 3153, 1990 DOI: 10.1080/00397919008051539

InChI:InChI=1/C5H3NS/c6-3-5-1-2-7-4-5/h1-2,4H

Synthetic route

3-hydroxymethyl-thiophene (71637-34-8) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 5h; Autoclave; High pressure;	99%
With ammonia; oxygen In 1,4-dioxane for 3h; Reflux;	91%
With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N-Phenylglycine; sodium hydroxide In methanol at 50℃; for 24h; Cooling with ice;	90%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonia; oxygen; copper(II) nitrate In water; dimethyl sulfoxide at 80℃; under 760.051 Torr; for 5h;	83%

3-thiophene carboxaldehyde (498-62-4) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With trifluorormethanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester In dichloromethane at 23℃; for 24h; Inert atmosphere;	98%
With hydroxylamine hydrochloride In methanol; water at 20℃; for 18h; Irradiation;	89%
With ammonium hydroxide; iodine	88%

2-thiophenecarboxaldehyde N,N-dimethylhydrazone (69819-67-6) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With HOF* CH3CN at 0℃;	96%

3-Bromothiophene (872-31-1) + sodium cyanide (773837-37-9) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With tri-tert-butyl phosphine; [Pd2(dba)5]; zinc In tetrahydrofuran; acetonitrile at 70℃; for 2h;	93%

N,N-Dimethyl-N'-[1-thiophen-3-yl-meth-(E)-ylidene]-hydrazine → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 2h;	91%

3-Bromothiophene (872-31-1) + K4[Fe(CN)6] → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With sodium carbonate; potassium iodide; N,N`-dimethylethylenediamine; copper(II) bis(tetrafluoroborate) In N,N-dimethyl acetamide at 140℃; for 16h;	90%
With sodium carbonate; palladium diacetate at 140℃; for 16h;	87%

2,2-diazido-1,2-di(thiophen-3-yl)ethanone + benzylamine (100-46-9) → 3-thiophenecarbonitrile (1641-09-4) + N-benzylthiophene-3-carboxamide (1048915-76-9)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	A 33 mg B 89%

Thien-3-ylboronic acid (6165-69-1) + benzyl thiocyanate (3012-37-1) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With copper(I) thiophene-2-carboxylate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 100℃; for 12h;	83%

3-Bromothiophene (872-31-1) + sodium cyanide (143-33-9) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With trans-chloro(1-naphthyl)bis-(triphenylphosphine)nickel(II); triphenylphosphine In ethanol for 1h; Heating;	82%
Stage #1: 3-Bromothiophene; sodium cyanide With potassium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In toluene at 110℃; for 24h; Stage #2: With ammonia In water; ethyl acetate; toluene at 25℃; for 0.166667h;

3-Bromothiophene (872-31-1) + potassiumhexacyanoferrate(II) trihydrate → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tris(2-morpholinophenyl)phosphine; potassium carbonate In water; tert-butyl alcohol at 85℃; for 5h; Schlenk technique; Inert atmosphere;	82%

zinc(II) cyanide (557-21-1) + 3-thiophenecarboxylic acid phenyl ester (14596-83-9) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); sodium formate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 170℃; for 48h; Glovebox; Sealed tube;	82%

thiophene-3-diazonium o-benzenedisulfonimide + tetra-n-butylammonium cyanide (10442-39-4) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
In acetonitrile at 22℃; for 1h; Sandmeyer Reaction;	81%

zinc(II) cyanide (557-21-1) + 2,4,6-tris(thiophen-3-yloxy)-1,3,5-triazine → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In 1,4-dioxane at 110℃; Inert atmosphere;	81%

3-Bromothiophene (872-31-1) + dicyanozinc (557-21-1) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide for 0.0416667h; Substitution; microwave irradiation;	80%
With 1,1'-bis-(diphenylphosphino)ferrocene; zinc; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl acetamide at 80℃; for 48h;

3-Bromothiophene (872-31-1) + zinc(II) cyanide (557-21-1) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With dichloro[9,9-dimethyl-4,5- bis(diphenylphosphino)xanthene]palladium (II); N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 85℃; Sealed tube;	79%

3-thiophenecarbaldoxime hydrochloride → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With 3 A molecular sieve at 135 - 350℃; under 0.01 Torr; for 0.25h; Pyrolysis;	77%
With acetic anhydride for 48h; Dehydration; Heating;

3-thienyl iodide (10486-61-0) + potassium hexacyanoferrate(II) trihydrate → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With tetrabutylammomium bromide; copper(II) acetate monohydrate In water at 20 - 140℃; Microwave irradiation;	77%

3-carbamoylthiophene (51460-47-0) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
at 285℃; for 1h; Temperature;	74%

3-Bromothiophene (872-31-1) + copper(l) cyanide → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
Stage #1: 3-Bromothiophene; copper(l) cyanide In N,N-dimethyl-formamide for 4h; Reflux; Stage #2: With hydrogenchloride; iron(III) chloride In water; N,N-dimethyl-formamide at 70℃; for 0.75h;	72%
In N,N-dimethyl-formamide for 16h; Reflux;	72%

3-(chloromethyl)thiophene (2746-23-8) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With sodium azide; palladium diacetate; XPhos In acetone at 80℃; for 12h; Inert atmosphere;	72%

3-chlorothiophene (17249-80-8) + zinc(II) cyanide (557-21-1) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
Stage #1: zinc(II) cyanide With aluminum oxide; Ni(xantphos)(o-tolyl)Cl for 1h; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: 3-chlorothiophene In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Schlenk technique; Inert atmosphere;	72%

3-chlorothiophene (17249-80-8) + potassiumhexacyanoferrate(II) trihydrate → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With C42H58NO3PPdS(2-); potassium acetate; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube;	71%

3-Bromothiophene (872-31-1) + potassium ferrocyanide → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With 10% Pd/C; sodium fluoride; potassium iodide In PEG4000; water at 160℃; for 2h; Microwave irradiation;	70%
With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 24h; Inert atmosphere;	56%

2-thiophenemethanol (636-72-6) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With potassium phosphate; ammonium formate In acetonitrile at 115℃; for 16h; Sealed tube; Green chemistry;	68%

3-ethynylthiophene (67237-53-0) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With trimethylsilylazide; silver carbonate In dimethyl sulfoxide at 100℃; for 12h;	63%

1-(thiophen-3-yl)-ethanone (1468-83-3) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With oxygen; copper(l) cyanide In dimethyl sulfoxide at 150℃;	63%

zinc(II) cyanide (557-21-1) + 1-(thiophene-3-carbonyl)piperidine-2,6-dione → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With palladium diacetate; cyclohexyldiphenylphosphine In 1,4-dioxane at 150℃; for 16h; Inert atmosphere; Schlenk technique; chemoselective reaction;	62%

(E)-benzyl 2-diazo-5-oxopent-3-enoate (1616777-26-4) + 3-(1-azidovinyl)thiophene → 3-thiophenecarbonitrile (1641-09-4) + benzyl (E)-2-(3-oxoprop-1-en-1-yl)-5-(thiophen-3-yl)-3,4-dihydro-2H-pyrrole-2-carboxylate

Conditions	Yield
With dirhodium tetraacetate In dichloromethane at 25℃; for 12h; Inert atmosphere;	A n/a B 62%

thiophen-3-yl-acetic acid (6964-21-2) → 3-thiophenecarbonitrile (1641-09-4)

Conditions	Yield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 120℃; for 21h; Green chemistry;	53%

3-thiophenecarbonitrile (1641-09-4) → 3-carbamoylthiophene (51460-47-0)

Conditions	Yield
With copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In nitromethane; water at 20 - 100℃; for 1h;	100%
With [RuH(tBu-PNP(-))(CO)]; water In tert-butyl alcohol at 20℃; for 24h;	99%
With manganese(IV) oxide; water In isopropyl alcohol at 70℃; under 5171.62 Torr; for 0.333333h;	98%

3-thiophenecarbonitrile (1641-09-4) + 3-(4-chlorophenyl)-[1,2,3]triazolo[1,5-a]pyridine (78539-93-2) → 1-(4-chlorophenyl)-3-(thiophen-3-yl)imidazo[1,5-a]pyridine

Conditions	Yield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane; 1,2-dichloro-benzene at 160℃; for 16h; Sealed tube;	99%

3-thiophenecarbonitrile (1641-09-4) → N-hydroxythiophene-3-formamidine (58905-71-8)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol for 5h; Reflux;	99%

3-thiophenecarbonitrile (1641-09-4) → 5-(thiophen-3-yl)-1H-tetrazole (59918-86-4)

Conditions	Yield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide for 0.25h; Cycloaddition; microwave irradiation;	98%
Stage #1: 3-thiophenecarbonitrile With sodium azide; zinc dibromide In N,N-dimethyl-formamide Heating / reflux; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide at 20℃;	98%
With sodium azide; cerium(III) chloride heptahydrate In water; isopropyl alcohol at 160℃; for 1h; Microwave irradiation;	98%

3-thiophenecarbonitrile (1641-09-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C17H25B2NO4S (916454-58-5)

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In pentane at 20℃; for 1.5h; Schlenk technique; Inert atmosphere;	98%
(1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 20℃; for 0.5h;	85%

3-thiophenecarbonitrile (1641-09-4) + nitromethane (75-52-5) → (Z)-2-nitro-1-(thiophen-3-yl)ethen-1-amine

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene at 85℃; for 1h; Aza-Henry Reaction; Molecular sieve;	95%

3-thiophenecarbonitrile (1641-09-4) + Quinoline N-oxide (1613-37-2) → N-(quinolin-2-yl)thiophene-3-carboxamide

Conditions	Yield
With lignin sulfonic acid for 0.333333h; Microwave irradiation;	94%
With toluene-4-sulfonic acid at 150℃; for 12h;	88%

3-thiophenecarbonitrile (1641-09-4) + 1-iodocyclohexane (626-62-0) → 3-cyano-2-cyclohexylthiophene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane; caesium carbonate at 110℃; for 36h; Inert atmosphere; Schlenk technique; regioselective reaction;	92%

3-thiophenecarbonitrile (1641-09-4) + 1-(4-fluorophenyl)ethanone (403-42-9) → 4-(4-fluorophenyl)-2,6-di(thiophen-3-yl)pyrimidine

Conditions	Yield
With sodium hydroxide; copper dichloride at 120℃; for 24h; Schlenk technique; Inert atmosphere;	92%

3-thiophenecarbonitrile (1641-09-4) → 5-nitrothiophene-3-carboxamide (36050-09-6)

Conditions	Yield
With sulfuric acid; potassium nitrate for 16h; Ambient temperature;	91%

3-thiophenecarbonitrile (1641-09-4) + 1-Adamantanecarboxylic acid (828-51-3) → 2-(1-adamantyl)-3-cyanothiophene

Conditions	Yield
With [Co(dyimethylglyoximate(1-))2(pyridine)2]PF6; tetrabutylammonium acetate In ethyl acetate at 40 - 44℃; for 30h; Irradiation; Schlenk technique; Inert atmosphere;	91%

3-thiophenecarbonitrile (1641-09-4) + N-allyl-N-phenylamine (589-09-3) → N-allyl-N-phenylthiophene-3-carboximidamide (1402238-79-2)

Conditions	Yield
Stage #1: N-allyl-N-phenylamine With trimethylaluminum In toluene at 0 - 20℃; Stage #2: 3-thiophenecarbonitrile In toluene at 100℃;	90%

3-thiophenecarbonitrile (1641-09-4) + aniline (62-53-3) → N-phenyl thiophene carboxamidine-3 (59918-76-2)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide; mineral oil at 0 - 20℃; Inert atmosphere;	90%

3-thiophenecarbonitrile (1641-09-4) + 3-chloro-aniline (108-42-9) → C11H9ClN2S

Conditions	Yield
With sodium hydride In dimethyl sulfoxide; mineral oil at 0 - 20℃; Inert atmosphere;	90%

3-thiophenecarbonitrile (1641-09-4) + 3-phenyl-[1,2,3]triazolo[1,5-a]pyridine (832-81-5) → 1-phenyl-3-(thiophen-3-yl)imidazo[1,5-a]pyridine

Conditions	Yield
With boron trifluoride diethyl etherate In 1,2-dichloro-ethane; 1,2-dichloro-benzene at 160℃; for 16h; Sealed tube;	89%

3-thiophenecarbonitrile (1641-09-4) + diphenyl acetylene (501-65-5) → 6,7-diphenylthieno[3,2-c]pyridin-4(5H)-one (1444611-61-3)

Conditions	Yield
With potassium hexafluorophosphate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; oxygen; copper diacetate In acetic acid at 120℃; for 10h;	88%

3-thiophenecarbonitrile (1641-09-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-N-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(thiophen-3-ylmethyl)-1,3,2-dioxaborolan-2-amine

Conditions	Yield
With C52H58N4P2Zn2 In neat (no solvent) at 20℃; for 0.0333333h; Green chemistry;	88%
With silver hexafluoroantimonate at 60℃; for 24h; Inert atmosphere; Glovebox;	82%
With [(Me3Si)2N]2Th[κ2-(N,C)-CH2Si(CH3)2N(SiMe3)] In benzene-d6 at 80℃; for 6h; Catalytic behavior; Sealed tube;	75 %Spectr.

3-thiophenecarbonitrile (1641-09-4) → 2-iodothiophene-3-carbonitrile (18800-01-6)

Conditions	Yield
Stage #1: 3-thiophenecarbonitrile With 2,2,6,6-tetramethylpiperidinyl-lithium at -78℃; Stage #2: With iodine Further stages.;	87%
Stage #1: 3-thiophenecarbonitrile With zinc(II) chloride In tetrahydrofuran at 25℃; for 0.166667h; Stage #2: With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at 60℃; for 0.333333h; Microwave irradiation; Stage #3: With tetrakis(triphenylphosphine) palladium(0); iodine In tetrahydrofuran at 25℃; for 12h;	68%
Stage #1: 3-thiophenecarbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h; Stage #2: With N-iodo-succinimide In tetrahydrofuran

3-thiophenecarbonitrile (1641-09-4) + 1-iodoadamantane (768-93-4) → 2-(1-adamantyl)-3-cyanothiophene

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); 1,3-bis-(diphenylphosphino)propane; caesium carbonate at 110℃; for 72h; Inert atmosphere; Schlenk technique; regioselective reaction;	86%

3-thiophenecarbonitrile (1641-09-4) + carbon dioxide (124-38-9) → 3-cyanothiophene-2-carboxylic acid (58231-00-8)

Conditions	Yield
With 2,3,6,7-tetramethoxy-9(10H)-anthracenone; caesium carbonate In dimethyl sulfoxide at 25℃; under 2280.15 Torr; for 18h; Irradiation; Sealed tube; regioselective reaction;	86%

3-thiophenecarbonitrile (1641-09-4) → thiophene-3-thiocarboxamide (24044-76-6)

Conditions	Yield
Stage #1: 3-thiophenecarbonitrile With calcium hydride; tiolacetic acid at 80℃; for 1h; Stage #2: With water In ethyl acetate at 20℃;	85%
With hydrogenchloride; O,S-diethyl-dithiophosphoric acid In ethyl acetate Ambient temperature;	84%
With sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 130℃; for 2.5h;	82%
With pyridine; diammonium sulfide; triethylamine In water at 50℃;

3-thiophenecarbonitrile (1641-09-4) → (3-thienylmethyl)amine (27757-86-4)

Conditions	Yield
Stage #1: 3-thiophenecarbonitrile With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 50℃; for 4.33333h; Inert atmosphere; Stage #2: With water; sodium hydroxide In tetrahydrofuran at 30℃; Inert atmosphere;	85%
With [Ru(H)(BH4)(CO)(PPh3)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2 yl)methyl)propylamine)]; hydrogen In isopropyl alcohol at 130℃; for 3h; Inert atmosphere; Autoclave;	82%
With borane-ammonia complex; C15H30Cl2CoN3P In hexane at 120℃; for 16h; Sealed tube; Inert atmosphere; chemoselective reaction;	80%

3-thiophenecarbonitrile (1641-09-4) + benzoyl chloride (98-88-4) → 2-benzoylthiophene-3-carbonitrile (30011-74-6)

Conditions	Yield
Stage #1: 3-thiophenecarbonitrile With zinc(II) chloride In tetrahydrofuran at 25℃; for 0.166667h; Stage #2: With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at 60℃; for 0.333333h; Microwave irradiation; Stage #3: benzoyl chloride With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 25℃; for 12h;	85%

Upstream product

• 148134-23-0 3-thiophenecarboxaldehyde oxime 
• 616-44-4 3-Methylthiophene 
• 872-31-1 3-Bromothiophene 
• 143-33-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 557-21-1 dicyanozinc 
• 6165-69-1 Thien-3-ylboronic acid 
• 3012-37-1 benzyl thiocyanate 
• 10486-61-0 3-thienyl iodide 
• 17249-80-8 3-chlorothiophene 
• 6964-21-2 thiophen-3-yl-acetic acid 
• 557-21-1 zinc(II) cyanide 
• 135205-66-2 N?cyanosuccinimide 
• 20731-74-2 3-(methylthio)thiophene 

Downstream Products

• 6453-99-2 3-benzoylthiophene 
• 88-13-1 3-Thiophene carboxylic acid 
• 437606-44-5 2,5-diphenyl-3-thiophenecarbonitrile 
• 18800-01-6 2-iodothiophene-3-carbonitrile 
• 177662-65-6 N-[4-(methylsulfonyl)-phenyl]-2-thiophenecarboximidamide 
• 1112971-73-9 (CO)5W((CH₃)3Si)2CHPC(C₆H₅)NC(C₄H₃S)N 
• 58905-71-8 N'-hydroxythiophene-3-carboximidamide 
• 1353717-27-7 4-(3-cyanothiophen-2-yl)benzonitrile 
• 1353717-63-1 C₁₂H₆N₂S 
• 1353717-28-8 4-(3-cyanothiophen-2-yl)benzaldehyde 
• 1353717-64-2 C₁₂H₇NOS 
• 1353717-65-3 C₁₁H₆N₂O₂S 
• 1353717-29-9 4-(3-cyanothiophen-2-yl)nitrobenzene 
• 1616735-76-2 C₁₄H₁₀N₄S 

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A series of benzodithiophene-thiophene-based alternating copolymers were synthesized with different side-chains, and their photovoltaic characteristics were examined. The choice of solubilizing side-chains influences significantly the chain conformation, frontier orbital energy levels, intermolecular organization, and the resulting optical, morphological, and photovoltaic properties. The incorporation of an e-withdrawing carbonyl group in the side-chain decreased the highest occupied molecular orbital (HOMO, ca. -5.4 eV) level and improved the chain planarity through intrachain hydrogen bonding. The shortest π-π stacking distance (3.72 ?) was also measured for the alkylcarbonyl-substituted BDTCOT:PC71BM blended film by two dimensional grazing incidence X-ray scattering. With compared to other polymers, the BDTCOT:PC71BM device showed a substantially improved open-circuit voltage and short-circuit current density, leading to a 4.66% power conversion efficiency. The side-chains need to be designed to be multifunctional to induce a deep HOMO level and chain planarity (for interchain ordering) as well as good solution processability.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation

The performances of heterogeneous catalysts can be effectively tuned by changing the catalyst structures. Here we report a controllable nitrile synthesis from alcohol ammoxidation, where the nitrile hydration side reaction could be efficiently prevented by changing the manganese oxide catalysts. α-Mn2O3 based catalysts are highly selective for nitrile synthesis, but MnO2-based catalysts including α, β, γ, and δ phases favour the amide production from tandem ammoxidation and hydration steps. Multiple structural, kinetic, and spectroscopic investigations reveal that water decomposition is hindered on α-Mn2O3, thus to switch off the nitrile hydration. In addition, the selectivity-control feature of manganese oxide catalysts is mainly related to their crystalline nature rather than oxide morphology, although the morphological issue is usually regarded as a crucial factor in many reactions.