CAS No.130929-57-6,Entacapone Suppliers

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Basic Information

Molecular Structure:
CAS No.:	130929-57-6
Name:	Entacapone
Article Data:	32

Formula:	C₁₄H₁₅N₃O₅
Molecular Weight:	305.29
Synonyms:	Entacom;OR 611;2-Propenamide,2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-, (E)-;(E)-Entacapone;Comtan;
Density:	1.392 g/cm³
Melting Point:	162-163 °C
Boiling Point:	526.6 °C at 760 mmHg
Flash Point:	272.3 °C
Appearance:	Yellow crystalline solid
Hazard Symbols:	Xn,T,F
Risk Codes:	R10; R20/21/22; R37/38; R41; R62; R38; R36/37/38
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

Raw Materials

121-33-5

Total:181 Page 1 of 5 1 2 3 4 5 Next>>

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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