1116-98-9

Basic information

• Product Name: tert-Butyl cyanoacetate
• Synonyms: TERT-BUTYL CYANOACETATE;T-BUTYL CYANOACETATE;CYANOACETIC ACID TERT-BUTYL ESTER;aceticacid,cyano-,1,1-dimethylethylester;Cyanoaceticacidbutylester;3-Oxo-3-tert-butoxypropanenitrile;Cyanoacetic acid 1,1-dimethylethyl ester;2-cyanoacetic acid tert-butyl ester
• CAS NO: 1116-98-9
• Molecular Formula: C₇H₁₁NO₂
• Molecular Weight: 141.17
• EINECS: 214-243-7
• Product Categories: C6 to C7;Carbonyl Compounds;Esters
• Mol File: 1116-98-9.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 40-42 °C0.1 mm Hg(lit.)
• Flash Point: 91°C
• Appearance: /
• Density: 0.988 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: n20/D 1.420
• Storage Temp.: 2-8°C
• Solubility: Difficult to mix.
• PKA: 3.21±0.10(Predicted)
• BRN: 1755933
• CAS DataBase Reference: tert-Butyl cyanoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl cyanoacetate(1116-98-9)
• EPA Substance Registry System: tert-Butyl cyanoacetate(1116-98-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• Hazardous Substances Data: 1116-98-9(Hazardous Substances Data)

Usage

Chemical Properties

Yellow liquid

Uses

tert-Butyl cyanoacetate is used in the synthesis of vinylogous urea and tert-butyl phenylcyanoacrylates. It is also used as a new additive for the sugar nucleoside base coupling step en route to DAPD with improved β-selectivity.

General Description

tert-Butyl cyanoacetate undergoes functionalization and decarboxylation to form 3-amino-4-alkyl isoquinolines.

Synthesis

tert-butyl cyanoacetate synthesis: 2-Cyanoacetic acid (1.701 g, 20 mmol) was suspended in a cetonitrile (20 ml) and tert-butanol (2.391 ml, 25.00 mmol). To this, a solution of N,N′-Dicyclohexylcarbodiimide (4.54 g, 22.00 mmol) in DCM (22 ml) was added under stirring at RT. The reaction mixture was stirred for 30 minutes, then filtered through Celite, and the solvents were evaporated. Proton NMR analysis of the residue showed complete conversion to the product. The product, tert-butyl cyanoacetate was not purified, but was taken straight through to the next reaction.1H NMR (400 MHz, CDCl 3 ) δ 3.37 (s, 2H), 1.50 (s, 9H).

Purification Methods

The IR spectrum of a film should have bands at 1742 (ester CO) and 2273 (CN), but no band at ca 3500 broad (OH) cm-1 . If it does not have the last-named band, then fractionally distil; otherwise dissolve in Et2O, wash with saturated aqueous NaHCO3, dry over K2CO3, evaporate Et2O, and distil the residue under a vacuum (see tert-butyl ethyl malonate for precautions to avoid decomposition during distillation). [Beech & Piggott J Chem Soc 423 1955, Dahn & Hauth Helv Chim Acta 42 1214 1959, Beilstein 2 I 255.]

InChI:InChI=1/C7H11NO2/c1-7(2,3)5(4-8)6(9)10/h5H,1-3H3,(H,9,10)/p-1

Synthetic route

cyanoacetic acid (372-09-8) + isobutene (115-11-7) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With boron trifluoride diethyl etherate In tetrahydrofuran at 10℃; under 12001.2 - 14251.4 Torr; for 0.133333h; Temperature; Solvent;	98%
With boron trifluoride diethyl etherate In dichloromethane at 10℃; for 7h; Reagent/catalyst; Temperature; Solvent; Large scale;	90%
With sulfuric acid; tert-butyl alcohol at -20℃;

cyanoacetic acid (372-09-8) + tert-butyl alcohol (75-65-0) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere;	86%
With dicyclohexyl-carbodiimide In acetonitrile at 25℃; for 5h;	84%
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 0.25h;	75%

tert-Butyl chloroacetate (107-59-5) + potassium cyanide (151-50-8) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With sodium iodide; tert-butyl alcohol

tert-Butyl chloroacetate (107-59-5) + potassium cyanide (151-50-8) → cyanoacetic acid tert-butyl ester (1116-98-9) + cyano-succinic acid di-tert-butyl ester (106271-05-0)

Conditions	Yield
With water; tert-butyl alcohol

bromoacetic acid tert-butyl ester (5292-43-3) + potassium cyanide (151-50-8) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With methanol

cyanoacetic acid chloride (16130-58-8) + tert-butyl alcohol (75-65-0) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With diethyl ether; N,N-dimethyl-aniline

bromoacetic acid tert-butyl ester (5292-43-3) + tetraethylammoniumcyanide (13435-20-6) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
In dichloromethane

C23H25I2NO2 + cyanoacetic acid tert-butyl ester (1116-98-9) → C29H35I2NO4

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 50℃;	100%

bromobenzene (108-86-1) + cyanoacetic acid tert-butyl ester (1116-98-9) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) → Benzoylacetonitrile (614-16-4)

Conditions

Yield

Stage #1: bromobenzene; cyanoacetic acid tert-butyl ester; 9-methyl-9H-fluorene-9-carbonyl chloride With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; magnesium chloride; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 18h; Glovebox; Inert atmosphere; Stage #2: With formic acid In 1,4-dioxane Reagent/catalyst; Inert atmosphere;

100%

cyanoacetic acid tert-butyl ester (1116-98-9) + 2,4-dibromo-1,3-thiazole (4175-77-3) → tert-butyl 2-(4-bromothiazol-2-yl)-2-cyanoacetate

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one for 16h;	100%

cyanoacetic acid tert-butyl ester (1116-98-9) + cyclohexanone (108-94-1) → 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid tert-butyl ester (92932-02-0)

Conditions	Yield
With morpholine; sulfur In ethanol at 50℃;	99%
With sulfur; diethylamine In ethanol Gewald cyclization; Reflux;	95%
With morpholine; sulfur In ethanol at 45℃; for 5h;	89%

morpholine (110-91-8) + 2-methyltetrahydro-4H-pyran-4-one (1193-20-0) + cyanoacetic acid tert-butyl ester (1116-98-9) → tert-butyl 2-amino-5-methyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (1373497-01-8)

Conditions	Yield
With hydrogen sulfide In ethanol; ethyl acetate	99%

cyanoacetic acid tert-butyl ester (1116-98-9) + (6-chloropyridazin-3-yl)-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]methanone → tert-butyl 2-cyano-2-[6-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carbonyl]pyridazin-3-yl]acetate

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester With sodium hydride In 1,4-dioxane at 20℃; for 1h; Stage #2: (6-chloropyridazin-3-yl)-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]methanone In 1,4-dioxane at 100℃; for 16h;	99%

cyanoacetic acid (372-09-8) + isobutene (115-11-7) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With boron trifluoride diethyl etherate In tetrahydrofuran at 10℃; under 12001.2 - 14251.4 Torr; for 0.133333h; Temperature; Solvent;	98%
With boron trifluoride diethyl etherate In dichloromethane at 10℃; for 7h; Reagent/catalyst; Temperature; Solvent; Large scale;	90%
With sulfuric acid; tert-butyl alcohol at -20℃;

cyanoacetic acid (372-09-8) + tert-butyl alcohol (75-65-0) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 5h; Reagent/catalyst; Temperature; Inert atmosphere;	86%
With dicyclohexyl-carbodiimide In acetonitrile at 25℃; for 5h;	84%
With dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 0.25h;	75%

tert-Butyl chloroacetate (107-59-5) + potassium cyanide (151-50-8) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With sodium iodide; tert-butyl alcohol

tert-Butyl chloroacetate (107-59-5) + potassium cyanide (151-50-8) → cyanoacetic acid tert-butyl ester (1116-98-9) + cyano-succinic acid di-tert-butyl ester (106271-05-0)

Conditions	Yield
With water; tert-butyl alcohol

bromoacetic acid tert-butyl ester (5292-43-3) + potassium cyanide (151-50-8) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With methanol

cyanoacetic acid chloride (16130-58-8) + tert-butyl alcohol (75-65-0) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
With diethyl ether; N,N-dimethyl-aniline

bromoacetic acid tert-butyl ester (5292-43-3) + tetraethylammoniumcyanide (13435-20-6) → cyanoacetic acid tert-butyl ester (1116-98-9)

Conditions	Yield
In dichloromethane

C23H25I2NO2 + cyanoacetic acid tert-butyl ester (1116-98-9) → C29H35I2NO4

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 50℃;	100%

bromobenzene (108-86-1) + cyanoacetic acid tert-butyl ester (1116-98-9) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) → Benzoylacetonitrile (614-16-4)

Conditions

Yield

Stage #1: bromobenzene; cyanoacetic acid tert-butyl ester; 9-methyl-9H-fluorene-9-carbonyl chloride With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; magnesium chloride; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 18h; Glovebox; Inert atmosphere; Stage #2: With formic acid In 1,4-dioxane Reagent/catalyst; Inert atmosphere;

100%

cyanoacetic acid tert-butyl ester (1116-98-9) + 2,4-dibromo-1,3-thiazole (4175-77-3) → tert-butyl 2-(4-bromothiazol-2-yl)-2-cyanoacetate

Conditions	Yield
With potassium carbonate In 1-methyl-pyrrolidin-2-one for 16h;	100%

cyanoacetic acid tert-butyl ester (1116-98-9) + cyclohexanone (108-94-1) → 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid tert-butyl ester (92932-02-0)

Conditions	Yield
With morpholine; sulfur In ethanol at 50℃;	99%
With sulfur; diethylamine In ethanol Gewald cyclization; Reflux;	95%
With morpholine; sulfur In ethanol at 45℃; for 5h;	89%

morpholine (110-91-8) + 2-methyltetrahydro-4H-pyran-4-one (1193-20-0) + cyanoacetic acid tert-butyl ester (1116-98-9) → tert-butyl 2-amino-5-methyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (1373497-01-8)

Conditions	Yield
With hydrogen sulfide In ethanol; ethyl acetate	99%

cyanoacetic acid tert-butyl ester (1116-98-9) + (6-chloropyridazin-3-yl)-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]methanone → tert-butyl 2-cyano-2-[6-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine-6-carbonyl]pyridazin-3-yl]acetate

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester With sodium hydride In 1,4-dioxane at 20℃; for 1h; Stage #2: (6-chloropyridazin-3-yl)-[2-(indan-2-ylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]methanone In 1,4-dioxane at 100℃; for 16h;	99%

cyanoacetic acid tert-butyl ester (1116-98-9) + 3 -bromo-6-chloro-2-methoxypyridine + methyl iodide (74-88-4) → 2-(6-chloro-2-methoxypyridin-3-yl)propanenitrile

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester; 3 -bromo-6-chloro-2-methoxypyridine With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium t-butanolate In 1,4-dioxane at 75℃; for 3.91667h; Inert atmosphere; Stage #2: methyl iodide In 1,4-dioxane at 20℃;	99%
Stage #1: cyanoacetic acid tert-butyl ester; 3 -bromo-6-chloro-2-methoxypyridine With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium t-butanolate In 1,4-dioxane at 75℃; for 3.91667h; Inert atmosphere; Stage #2: methyl iodide In 1,4-dioxane at 18 - 25℃;

cyanoacetic acid tert-butyl ester (1116-98-9) + C15H18N2O2 → C22H28N2O2

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester; C15H18N2O2 With C39H38N3O2P; potassium carbonate; silver(l) oxide at 20℃; for 24h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene for 6h; enantioselective reaction;	99%

cyanoacetic acid tert-butyl ester (1116-98-9) + C13H12N2O4 → C20H22N2O4

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester; C13H12N2O4 With C39H38N3O2P; potassium carbonate; silver(l) oxide In toluene at 0℃; for 24h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene for 6h; enantioselective reaction;	99%

cyanoacetic acid tert-butyl ester (1116-98-9) + C21H16N2O5S → C28H26N2O5S

Conditions	Yield
With C39H38N3O2P; potassium carbonate; silver(l) oxide at 20℃; enantioselective reaction;	99%

cyanoacetic acid tert-butyl ester (1116-98-9) + 4-chlorobenzoic anhydride (790-41-0) → tert-butyl 2-(4-chlorophenyl)-2-cyanoacetate (724767-52-6)

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -45℃; for 0.75h; Inert atmosphere; Stage #2: 4-chlorobenzoic anhydride In tetrahydrofuran; hexane at -45℃; for 1h; Inert atmosphere;	98%
Stage #1: cyanoacetic acid tert-butyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -45℃; for 0.75h; Stage #2: 4-chlorobenzoic anhydride In tetrahydrofuran; hexane at -45 - 20℃; Further stages.;

cyanoacetic acid tert-butyl ester (1116-98-9) + 5-Bromo-2-chloropyrimidine (32779-36-5) → tert-butyl 2-(5-bromopyrimidin-2-yl)-2-cyanoacetic acid (1305329-97-8)

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 5-Bromo-2-chloropyrimidine In tetrahydrofuran at 20℃; for 18h;	98%
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 3h;	35.72%

2-chloro-5-nitro-3-(trifluoromethyl)pyridine (99368-67-9) + cyanoacetic acid tert-butyl ester (1116-98-9) → tert-butyl 2-cyano-2-(5-nitro-3-(trifluoromethyl)pyridin-2-yl)acetate

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 50℃; for 10h;	98%
With potassium carbonate In tetrahydrofuran at 50℃; for 10h; Temperature;	98%

cyanoacetic acid tert-butyl ester (1116-98-9) + 2,4,5,6-tetrafluoropyrimidine (767-79-3) → potassium-2-(tert-butoxy)-1-cyano-2-oxo-1-(2,5,6-trifluoropyrimidin-4-yl)ethan-1-ide

Conditions	Yield
Stage #1: 2,4,5,6-tetrafluoropyrimidine With potassium carbonate In acetonitrile Stage #2: cyanoacetic acid tert-butyl ester In acetonitrile at 20℃; for 72h;	98%

cyanoacetic acid tert-butyl ester (1116-98-9) + C20H17NO5S → C27H27NO5S

Conditions	Yield
With C39H38N3O2P; potassium carbonate; silver(l) oxide at 20℃; Reagent/catalyst; enantioselective reaction;	98%

1-phenylmethyl-4-piperidone (3612-20-2) + cyanoacetic acid tert-butyl ester (1116-98-9) → tert-butyl 2-amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylate (872530-68-2)

Conditions	Yield
With morpholine; sulfur at 20℃; for 48h; Gewald Aminoheterocycles Synthesis;	97%
With morpholine; sulfur In ethanol at 45℃; for 5h;	86%
With morpholine; sulfur In ethanol at 50℃; for 2h;

cyanoacetic acid tert-butyl ester (1116-98-9) + 1-ethoxycarbonylmethyl-3-(1-pyrrolidinylmethylene)-3H-indolium bromide (75629-56-0) → 2-cyano-3-(1-ethoxycarbonylmethyl-1H-indol-3-yl)-acrylic acid (866601-48-1)

Conditions	Yield
With sodium ethanolate In ethanol; chloroform at 20℃;	97%

cyanoacetic acid tert-butyl ester (1116-98-9) + cycloheptanone (502-42-1) → tert-butyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate (885115-88-8)

Conditions	Yield
With morpholine; sulfur In ethanol at 45℃;	97%
With morpholine; sulfur In ethanol for 16h; Gewald Aminoheterocycles Synthesis; Reflux;	64%
With morpholine; sulfur In ethanol at 45℃; for 24h; Gewald Aminoheterocycles Synthesis;

cyanoacetic acid tert-butyl ester (1116-98-9) + benzoic acid anhydride (93-97-0) → 2-t-butoxycarbonyl-2-phenylacetonitrile (115549-32-1)

Conditions	Yield
Stage #1: cyanoacetic acid tert-butyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -45℃; for 0.75h; Inert atmosphere; Stage #2: benzoic acid anhydride In tetrahydrofuran; hexane at -45℃; for 1h; Inert atmosphere;	97%
Stage #1: cyanoacetic acid tert-butyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -45℃; for 0.75h; Stage #2: benzoic acid anhydride In tetrahydrofuran; hexane at -45 - 20℃; Further stages.;

cyanoacetic acid tert-butyl ester (1116-98-9) → tert-butyl α-cyano-α-diazoacetate (1236004-44-6)

Conditions	Yield
With perfluorobutanesulfonyl azide; triethylamine In dichloromethane at 20℃; Inert atmosphere;	97%
With sodium azide; 3-Carboxybenzenesulfonyl chloride; potassium carbonate In water at 20℃; for 1h;	71%
With pyridine; triflic azide In hexane; acetonitrile for 24h; Inert atmosphere;	69%
With pyridine; triflic azide In hexane; acetonitrile at 20℃; for 24h; Inert atmosphere;
Stage #1: cyanoacetic acid tert-butyl ester With potassium carbonate; Methanesulfonyl azide In water at 20℃; Stage #2: With water; potassium carbonate at 20℃; for 3h;

cyanoacetic acid tert-butyl ester (1116-98-9) + 4,6-dimethoxypyrimidin-2-yl methyl sulfone (113583-35-0) → tert-butyl 2-cyano-2-(4,6-dimethoxypyrimidin-2-yl)acetate (1225226-84-5)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 6h; Inert atmosphere;	97%
With potassium carbonate In acetonitrile for 24h; Reflux;	87.3%

cyanoacetic acid tert-butyl ester (1116-98-9) + 5-(2-bromophenyl)-4-phenyl-1H-1,2,3-triazole → tert-butyl 5-amino-1-phenyl[1,2,3]triazolo[5,1-a]isoquinoline-6-carboxylate

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In dimethyl sulfoxide at 80℃; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;	97%

cyanoacetic acid tert-butyl ester (1116-98-9) + 5-(2-bromophenyl)-4-(4-nitrophenyl)-1H-1,2,3-triazole → tert-butyl 5-amino-1-(4-nitrophenyl)[1,2,3]triazolo[5,1-a]isoquinoline-6-carboxylate

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In dimethyl sulfoxide at 80℃; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;	97%

cyanoacetic acid tert-butyl ester (1116-98-9) + C56H57NOS3 → C63H66N2O2S3

Conditions	Yield
With piperidine In tetrahydrofuran	96%

bromobenzene (108-86-1) + cyanoacetic acid tert-butyl ester (1116-98-9) + 9-methylfluorene-9-([(13)C]-carbonyl) chloride (1072315-89-9) → [3-13C]-3-oxo-3-phenylpropanenitrile

Conditions

Yield

Stage #1: bromobenzene; cyanoacetic acid tert-butyl ester; 9-methylfluorene-9-([(13)C]-carbonyl) chloride With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; magnesium chloride; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane at 100℃; for 18h; Glovebox; Inert atmosphere; Stage #2: With formic acid In 1,4-dioxane Inert atmosphere;

96%

cyanoacetic acid tert-butyl ester (1116-98-9) + 5-ethoxy-1-methyl-3,4-dihydro-2H-pyrrolium; tetrafluoroborate (41948-92-9) → Cyano-[1-methyl-pyrrolidin-(2E)-ylidene]-acetic acid tert-butyl ester (125138-99-0)

Conditions	Yield
With sodium methylate In tetrahydrofuran for 1h; Ambient temperature;	95%

cyanoacetic acid tert-butyl ester (1116-98-9) + C20H14NO(1+)*I3(1-) (86194-06-1) → Cyano-[1-oxo-2,3-diphenyl-1H-indolizin-(7E)-ylidene]-acetic acid tert-butyl ester (121030-45-3)

Conditions	Yield
With pyridine for 1h; Ambient temperature;	95%

cyanoacetic acid tert-butyl ester (1116-98-9) + 4-hydroxy-benzaldehyde (123-08-0) → (E)-tert-butyl 2-cyano-3-(4-hydroxyphenyl)acrylate

Conditions	Yield
With C8H18NO3(1+)*C2H4NO2(1-) In water at 20℃; Knoevenagel Condensation;	95%
With piperidine In dichloromethane at 20℃; for 20h; Knoevenagel Condensation; Inert atmosphere;	71%
With piperidine In ethanol Heating;
With piperidine In dichloromethane at 20℃; Inert atmosphere;

cyanoacetic acid tert-butyl ester (1116-98-9) + benzaldehyde (100-52-7) → α-Cyanzimtsaeure-tert-butylester (1145-55-7)

Conditions	Yield
quaternary ammonium-ordered porous silicate composite In benzene at 80℃; for 6h; Knoevenagel condensation;	95%
With piperidine In ethanol at 70℃; for 19h;	76%
With C21H13N3O6(2-)*Zn(2+)*2H2O In tetrahydrofuran at 50℃; for 1.5h; Knoevenagel Condensation;	45%

Upstream product

• 107-59-5 tert-Butyl chloroacetate 
• 151-50-8 potassium cyanide 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 372-09-8 cyanoacetic acid 
• 75-65-0 tert-butyl alcohol 
• 115-11-7 isobutene 
• 13435-20-6 tetraethylammoniumcyanide 
• 16130-58-8 cyanoacetic acid chloride 

Downstream Products

• 26823-02-9 5-(4-methoxyphenyl)-5-oxopentanenitrile 
• 2469-99-0 Cyanoaceton 
• 83476-48-6 C₃₅H₃₃NO₁₀ 
• 91827-14-4 (Z)-2-Cyano-3-hydroxy-5-(4-hydroxy-3-methoxy-phenyl)-pent-2-enoic acid tert-butyl ester 
• 93559-06-9 (Z)-2-Cyano-3-hydroxy-5-(4-hydroxy-phenyl)-pent-2-enoic acid tert-butyl ester 
• 100066-86-2 2-Amino-1-cyclohexyl-4,5-dimethyl-1H-pyrrole-3-carboxylic acid tert-butyl ester 
• 100066-79-3 1-Benzyl-2-amino-3-t-butoxycarbonyl-4,5-dimethylpyrrole 
• 93559-07-0 (Z)-5-(3,4-Bis-benzyloxy-phenyl)-2-cyano-3-hydroxy-pent-2-enoic acid tert-butyl ester 
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Relevant articles and documents

Studies in isoxazole chemistry. 5. N-alkylation and N-acylation of 5-amino-3-(5-nitro-2-furyl)isoxazoles.

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Synthesis, photo-electrochemical properties and dye-sensitized solar cell performance of d-π-A structured porphyrins

Two new dye sensitizers 5-(N,N-4-(diphenylamino)phenyl)-10-(4-(tert-butyl- 2-cyanoacrylate)phenyl)porphyrin (TP) and 5-(N, N-4-(bis(4-butylphenyl) amino) phenyl)-10-(4-(tert-butyl-2-cyanoacrylate)phenyl)porphyrin (BUTP) with cyanoacrylic acid as electron acceptor were synthesized and researched. BUTP has strong absorption in a wide range of 300-726 nm. DSSCs sensitized by BUTP displayed a power conversion efficiency (η) 5.33%, JSC 12.21 mA cm-2, Voc 0.68 V, FF 0.65, under the illumination of AM 1.5 G. Spectral properties, electrochemical properties, photovoltaic and electrochemical impedance properties of TP and BUTP were also investigated. Considering its simple synthesis, both TP and BUTP were qualified sensitizers for DSSCs.

Synthesis method of tert-butyl cyanoacetate

The invention belongs to the technical field of organic chemistry, and particularly relates to a synthesis method of tert-butyl cyanoacetate. Cyanoacetic acid and isobutene are subjected to a catalytic esterification reaction in an organic solvent in the presence of Lewis acid to obtain tert-butyl cyanoacetate. The method provided by the invention has the advantages of cheap and easily available raw materials, mild reaction conditions, simple operation, simple post-treatment, low cost, high product yield and high product purity, and is easy for industrial production.

Development of the First Two-Pore Domain Potassium Channel TWIK-Related K+ Channel 1-Selective Agonist Possessing in Vivo Antinociceptive Activity

The TWIK-related K+ channel, TREK-1, has recently emerged as an attractive therapeutic target for the development of a novel class of analgesic drugs, suggesting that activation of TREK-1 could result in pain inhibition. Here, we report the synthesis of a series of substituted acrylic acids (1-54) based on our previous work with caffeate esters. The analogues were evaluated for their ability to modulate TREK-1 channel by electrophysiology and for their in vivo antinociceptive activity (acetic acid-induced writhing and hot plate assays), leading to the identification of a series of novel molecules able to activate TREK-1 and displaying potent antinociceptive activity in vivo. Furyl analogue 36 is the most promising of the series.