Entacapone supplier | CasNO.130929-57-6

Name
Entacapone
EINECS
CAS No. 130929-57-6
Article Data32
CAS DataBase
Density 1.392 g/cm³
Solubility
Melting Point 162-163 °C
Formula C₁₄H₁₅N₃O₅
Boiling Point 526.6 °C at 760 mmHg
Molecular Weight 305.29
Flash Point 272.3 °C
Transport Information
Appearance Yellow crystalline solid
Safety
Risk Codes R10; R20/21/22; R37/38; R41; R62; R38; R36/37/38
Molecular Structure
Hazard Symbols Xn,T,F
Synonyms Entacom;OR 611;2-Propenamide,2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (E)-;(E)-Entacapone;Comtan;
PSA 130.38000
LogP 2.30458

Synthetic route

: 345317-61-5
(E)-2-cyano-N,N-diethyl-3-(3-pivaloyloxy-4-hydroxy-5-nitrophenyl)propenamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With phosphate buffer at 37℃; pH=7.4; Kinetics;	100%

: 404860-98-6
(E)-2-cyano-N,N-diethyl-3-[3-t-butyloxycarbonyloxy-4-hydroxy-5-nitrophenyl]propenamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With phosphate buffer at 37℃; pH=7.4; Kinetics;	100%

: 857629-78-8
(2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Stage #1: (2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide With aluminum (III) chloride; triethylamine In dichloromethane at 0 - 5℃; for 3 - 4h; Heating / reflux; Stage #2: With hydrogenchloride In dichloromethane at 0 - 20℃; for 0.5h;	98%
With aluminum (III) chloride; triethylamine In dichloromethane	98%
Stage #1: (2E)-2-cyano-3-(3-methoxy-4-hydroxy-5-nitro-phenyl)-N,Ndiethylprop-2-enamide With aluminum (III) chloride; triethylamine In tetrahydrofuran at 0℃; Reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 6h; Solvent; Temperature; Time; Cooling;	92%

: 146698-91-1
2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With pyridine; aluminum (III) chloride In dichloromethane at 0 - 45℃; for 2.5h;	94.1%

: 1067233-93-5
3,4-dimethoxy entacapone

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Stage #1: 3,4-dimethoxy entacapone With aluminum (III) chloride In N,N-dimethyl-formamide at 5 - 80℃; for 15h; Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide at 5 - 30℃; for 2.5h; Product distribution / selectivity;	92%
Stage #1: 3,4-dimethoxy entacapone With pyridine; aluminum (III) chloride In N,N-dimethyl-formamide at 5 - 80℃; for 15h; Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide at 5 - 30℃; for 2h; Product distribution / selectivity;	80%
Stage #1: 3,4-dimethoxy entacapone With boron tribromide In dichloromethane at -15 - 20℃; Stage #2: With water In dichloromethane for 0.5h; Product distribution / selectivity;	74%
With aluminum (III) chloride In pyridine at 80℃;

: 1047659-01-7
entacapone; piperidine salt

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With hydrogenchloride In water; isopropyl alcohol at 20 - 30℃;	91.1%

: N,N-diethyl-2-cyano-3-(3-ethoxy-4-hydroxy-5-nitrophenyl)acrylamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With pyridine; aluminum (III) chloride In dichloromethane at 0 - 45℃; for 50h;	87.3%

: C15H16N3O5(1-)*C4H12N(1+)

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With pyridine; aluminum (III) chloride In chloroform at 0℃; for 0.5h; Reflux;	81.1%

: 26391-06-0
2-cyano-N,N-diethylacetamide

: 116313-85-0
3,4-dihydroxy-5-nitrobenzaldehyde

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With piperidine In 1,2-dimethoxyethane; n-heptane for 15 - 25h; Heating / reflux; Stage #2: In dichloromethane at 25 - 35℃; for 24h; Product distribution / selectivity;	75%
With piperidine In isopropyl alcohol for 12 - 15h; Heating / reflux;	75.5%
Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With acetic acid; diethylamine In toluene Knoevenagel Condensation; Stage #2: With hydrogen bromide In acetic acid; toluene at 20℃;	73.8%

: 26391-06-0
2-cyano-N,N-diethylacetamide

: 116313-85-0
3,4-dihydroxy-5-nitrobenzaldehyde

A: 130929-57-6
entacapone

B: 145195-63-7
(2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide

Conditions

Conditions	Yield
Stage #1: 2-cyano-N,N-diethylacetamide; 3,4-dihydroxy-5-nitrobenzaldehyde With piperidine In isopropyl alcohol for 12 - 15h; Heating / reflux; Stage #2: With acetic acid In isopropyl alcohol at 20℃;	A 75.5% B n/a
piperidine; methylamine hydrochloride In butan-1-ol at 82℃; for 4 - 5h; Product distribution / selectivity;
piperidine; methylamine hydrochloride In i-Amyl alcohol at 89 - 90℃; for 3h; Product distribution / selectivity;

...Expand

: 2-cyano-3-(3-hydroxy-4-methoxy-5-nitrophenyl)prop-2-eneamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Stage #1: 2-cyano-3-(3-hydroxy-4-methoxy-5-nitrophenyl)prop-2-eneamide With triethylamine In ethanol at 70 - 75℃; for 14h; Stage #2: With hydrogenchloride In water Time;	55%

: 404860-97-5
(E)-2-cyano-N,N-diethyl-3-[3,4-bis(pivaloyloxymethoxy)-5-nitrophenyl]propenamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With phosphate buffer at 37℃; for 4h; pH=7.4; Kinetics;	20%

: 145195-63-7
(2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With hydrogenchloride In water; toluene at 7 - 20℃; for 4h; Heating / reflux;	14%

: 686349-59-7
entacapone

: 130929-57-6
entacapone

Conditions

Conditions	Yield
iodine In ethyl acetate for 10 - 12h; Product distribution / selectivity; Heating / reflux; Isomerisation;
With hydrogen bromide; acetic acid In water at 15 - 90℃; for 23 - 26h;
With hydrogen bromide; acetic acid at 90℃;

N,N-Hydrochloric diethylcyanoacetamide: N,N-Hydrochloric diethylcyanoacetamide

: 116313-85-0
3,4-dihydroxy-5-nitrobenzaldehyde

: 130929-57-6
entacapone

Conditions

Conditions	Yield
	2.23 g (73%)

: 146698-91-1
2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxy-5-nitrophenyl)prop-2-enamide

A: 130929-57-6
entacapone

B: 145195-63-7
(2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide

Conditions

Conditions	Yield
With pyridine; aluminum (III) chloride In dichloromethane at 0 - 55℃; for 3.08333 - 4.25h;

: 6635-20-7
isonitrovanillin

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen bromide / water / 4 h / Reflux 2: 1-methyl-piperazine / methanol / 20 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: piperidine; acetic acid / ethanol / 3 h / Reflux 2.1: N,N-dimethyl-formamide; bis(trichloromethyl) carbonate / chloroform / 2 h / Reflux 2.2: 2 h 3.1: aluminum (III) chloride; pyridine / chloroform / 0.5 h / 0 °C / Reflux View Scheme
Multi-step reaction with 4 steps 1: piperidine; acetic acid / ethanol / 3 h / Reflux 2: thionyl chloride / Reflux 3: ethyl acetate / Cooling with ice 4: aluminum (III) chloride; pyridine / chloroform / 0.5 h / 0 °C / Reflux View Scheme

: 121-33-5
vanillin

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: nitric acid; acetic acid / 0 - 20 °C 2: hydrogen bromide / water / 4 h / Reflux 3: 1-methyl-piperazine / methanol / 20 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: acetic acid; diethylamine / toluene / Reflux 2: nitric acid 3: aluminum (III) chloride / N,N-dimethyl-formamide / 100 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid; diethylamine / cyclohexane / Reflux 2.1: sodium nitrite; nitric acid / dichloromethane / 2 h / 20 °C 3.1: aluminum (III) chloride; triethylamine / tetrahydrofuran / 0 °C / Reflux 3.2: 6 h / Cooling View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid; nitric acid / water / 4 h / 15 - 30 °C 2.1: tetrabutylammomium bromide; aluminum (III) chloride / dichloromethane / 0.5 h / 0 - 10 °C / Reflux 2.2: 25 h / 0 - 10 °C / Reflux 3.1: piperidine / isopropyl alcohol / 23 h / Reflux View Scheme

: 134610-30-3
3,4-dimethoxy-5-nitrobenzoyl chloride

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / -5 °C 2: sodium tris(acetoxy)borohydride / 45 °C 3: aluminum (III) chloride / pyridine / 80 °C View Scheme

: 160391-70-8
(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)prop-2-enoic acid

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / 25 - 80 °C 2: diethylamine / dichloromethane / 2.33 h / -5 - 0 °C View Scheme

: 893419-47-1
(2E)-2-cyano-3-(3-methoxy-4-hydroxy-phenyl)-N,N-diethylprop-2-enamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid 2: aluminum (III) chloride / N,N-dimethyl-formamide / 100 °C View Scheme

: 2-cyano-3-(3,4-dimethoxy-5-nitrophenyl)-3-hydroxy-N,N-diethyl-prop-2-enamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tris(acetoxy)borohydride / 45 °C 2: aluminum (III) chloride / pyridine / 80 °C View Scheme

: 1291066-63-1
(2E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-2-propenoyl chloride

: 130929-57-6
entacapone

Conditions

Conditions	Yield
With diethylamine In dichloromethane at -5 - 0℃; for 2.33333h;

: 26391-06-0
2-cyano-N,N-diethylacetamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; diethylamine / toluene / Reflux 2: nitric acid 3: aluminum (III) chloride / N,N-dimethyl-formamide / 100 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid; diethylamine / cyclohexane / Reflux 2.1: sodium nitrite; nitric acid / dichloromethane / 2 h / 20 °C 3.1: aluminum (III) chloride; triethylamine / tetrahydrofuran / 0 °C / Reflux 3.2: 6 h / Cooling View Scheme

: 116313-85-0
3,4-dihydroxy-5-nitrobenzaldehyde

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: piperidine; acetic acid / ethanol / 4 h / 80 °C 2: thionyl chloride / 25 - 80 °C 3: diethylamine / dichloromethane / 2.33 h / -5 - 0 °C View Scheme

: 91004-48-7
4,5-Dimethoxy-3-nitrobenzoic acid

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / toluene / 60 °C 2: sodium hydride / tetrahydrofuran / -5 °C 3: sodium tris(acetoxy)borohydride / 45 °C 4: aluminum (III) chloride / pyridine / 80 °C View Scheme

: 203861-62-5
2-methoxy-4-iodophenol

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine / N,N-dimethyl-formamide / 5 h / 95 - 100 °C / Inert atmosphere 2: nitric acid; acetic acid / 15 °C 3: pyridine; aluminum (III) chloride / dichloromethane / 0 - 45 °C View Scheme

: 53793-77-4
2-cyano-N,N-diethylacrylamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine / N,N-dimethyl-formamide / 5 h / 95 - 100 °C / Inert atmosphere 2: nitric acid; acetic acid / 15 °C 3: pyridine; aluminum (III) chloride / dichloromethane / 0 - 45 °C View Scheme

: 6635-20-7
isonitrovanillin

: 26391-06-0
2-cyano-N,N-diethylacetamide

: 130929-57-6
entacapone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: IRA 96 resin / toluene / Reflux 2: triethylamine; ethanol / 12 h / 70 - 75 °C View Scheme

: 141-75-3
butyryl chloride

: 130929-57-6
entacapone

: (E)-2-cyano-N,N-diethyl-3-[3,4-dibutyryloxy-5-nitrophenyl]propenamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 15h;	93%

: 109-89-7
diethylamine

: 130929-57-6
entacapone

: C14H15N3O5*C4H11N

Conditions

Conditions	Yield
In ethanol at 25 - 30℃;	92%

: 130929-57-6
entacapone

: 145195-63-7
(2Z)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2-propenamide

: 1047659-02-8
entacapone; sodium salt

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 20℃;	87.1%

: 89941-82-2
(pivaloyloxy)acetic acid

: 130929-57-6
entacapone

: (E)-2-cyano-N,N-diethyl-3-[3,4-bis(pivaloyloxyacetyloxy)-5-nitrophenyl]propenamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 20℃;	85%

: 7087-68-5
N-ethyl-N,N-diisopropylamine

: 130929-57-6
entacapone

: C14H15N3O5*C8H19N

Conditions

Conditions	Yield
In ethanol at 25 - 30℃;	80%

: 121-44-8
triethylamine

: 130929-57-6
entacapone

: C14H15N3O5*C6H15N

Conditions

Conditions	Yield
In ethanol at 25 - 30℃;	78%

: 110-89-4
piperidine

: 130929-57-6
entacapone

: 1047659-01-7
entacapone; piperidine salt

Conditions

Conditions	Yield
In ethanol at 25 - 30℃;	77%
In ethanol

: 110-91-8
morpholine

: 130929-57-6
entacapone

: C14H15N3O5*C4H9NO

Conditions

Conditions	Yield
In ethanol at 25 - 30℃;	76%

: 108-24-7
acetic anhydride

: 130929-57-6
entacapone

: (E)-2-cyano-N,N-diethyl-3-(3,4-diacetyloxy-5-nitrophenyl)propenamide

Conditions

Conditions	Yield
With sulfuric acid In ethyl acetate at 50℃; for 2h;	74%

: 24424-99-5
di-tert-butyl dicarbonate

: 130929-57-6
entacapone

: 404860-98-6
(E)-2-cyano-N,N-diethyl-3-[3-t-butyloxycarbonyloxy-4-hydroxy-5-nitrophenyl]propenamide

Conditions

Conditions	Yield
With 15-crown-5; sodium carbonate In tetrahydrofuran at 50℃; for 12h;	64%

: 53064-79-2
iodomethyl pivaloate

: 130929-57-6
entacapone

: 404860-97-5
(E)-2-cyano-N,N-diethyl-3-[3,4-bis(pivaloyloxymethoxy)-5-nitrophenyl]propenamide

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃;	56%

: 130929-57-6
entacapone

: (valeroyloxy)acetic acid

: (E)-2-cyano-N,N-diethyl-3-[3,4-bis(valeryloxyacetyloxy)-5-nitrophenyl]propenamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	52%

: 1538-75-6
2,2-dimethylpropanoic anhydride

: 130929-57-6
entacapone

: 345317-61-5
(E)-2-cyano-N,N-diethyl-3-(3-pivaloyloxy-4-hydroxy-5-nitrophenyl)propenamide

Conditions

Conditions	Yield
With sulfuric acid at 50℃; for 2h;	48%

: 130929-57-6
entacapone

A: 2-cyano-N,N-diethyl-3-(2-hydroxy-7-nitro-2-oxo-2λ5-benzo[1,3,2]dioxaphosphol-5-yl)-acrylamide

B: C14H13N3O8P(3-)*3Na(1+)

Conditions

Conditions	Yield
Stage #1: entacapone With pyridine; trichlorophosphate at 0 - 20℃; for 2h; phosphorylation; Stage #2: With sodium hydroxide In methanol Hydrolysis;	A n/a B 45%

: 3282-30-2
pivaloyl chloride

: 130929-57-6
entacapone

: (E)-2-cyano-N,N-diethyl-3-[3,4-dipivaloyloxy-5-nitrophenyl]propenamide

Conditions

Conditions	Yield
With pyridine; dmap at 20℃; for 15h;	45%

: 130929-57-6
entacapone

: 13831-31-7
Acetoxyacetyl chloride

: (E)-2-cyano-N,N-diethyl-3-[3,4-bis(acetoxyacetyloxy)-5-nitrophenyl]propenamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 15h;	28%

Entacapone Specification

The Entacapone is an organic compound with the formula C₁₄H₁₅N₃O₅. The IUPAC name of this chemical is (E)-2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethylprop-2-enamide. With the CAS registry number 130929-57-6, it is also named as 2-propenamide, 2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (2E)-. The product's categories are Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a yellow crystalline solid, which is a drug that functions as a catechol-O-methyl transferase (COMT) inhibitor. It is used in the treatment of Parkinson's disease.

Physical properties about Entacapone are: (1)ACD/LogP: 2.38; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 0.36; (4)ACD/BCF (pH 5.5): 15.66; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 194.12; (7)ACD/KOC (pH 7.4): 4.46; (8)#H bond acceptors: 8; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 7; (11)Polar Surface Area: 108.38 Å²; (12)Index of Refraction: 1.641; (13)Molar Refractivity: 79.12 cm³; (14)Molar Volume: 219.2 cm³; (15)Polarizability: 31.36×10^-24cm³; (16)Surface Tension: 68.1 dyne/cm; (17)Density: 1.392 g/cm³; (18)Flash Point: 272.3 °C; (19)Enthalpy of Vaporization: 83.11 kJ/mol; (20)Boiling Point: 526.6 °C at 760 mmHg; (21)Vapour Pressure: 1.05E-11 mmHg at 25°C.

Preparation: this chemical can be prepared by 3,4-dihydroxy-5-nitrobenzaldehyde and N, N-diethyl cyano acetamide. This reaction will need catalyst piperidine acetate. The yield is about 80%.

You can still convert the following datas into molecular structure:
(1)SMILES: [O-][N+](=O)c1cc(\C=C(/C#N)C(=O)N(CC)CC)cc(O)c1O
(2)InChI: InChI=1/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
(3)InChIKey: JRURYQJSLYLRLN-BJMVGYQFBD
(4)Std. InChI: InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
(5)Std. InChIKey: JRURYQJSLYLRLN-BJMVGYQFSA-N

Product Name

Entacapone

Synthetic route

Entacapone Specification

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