orthoformic acid triethyl ester
malononitrile
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
With acetic anhydride at 110 - 140℃; Reflux; | 98% |
With acetic anhydride at 110 - 140℃; | 98% |
With acetic anhydride at 110 - 140℃; | 98% |
Conditions | Yield |
---|---|
With orthoformic acid triethyl ester at 140℃; | |
With orthoformic acid triethyl ester at 140℃; |
spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans
ethyl vinyl ether
A
2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
at 100℃; for 40h; sealed tube; | A 63% B 50% |
1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)urea
orthoformic acid triethyl ester
malononitrile
A
1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)ureidomethylenemalononitrile
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
at 70℃; for 12h; | A 52% B n/a |
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea
orthoformic acid triethyl ester
malononitrile
A
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)ureidomethylenemalononitrile
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
at 60℃; for 2h; | A 28% B n/a |
(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>
ethyl vinyl ether
A
2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
at 100℃; for 40h; sealed tube; | |
sealed tube; |
Conditions | Yield |
---|---|
With benzene |
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea
orthoformic acid triethyl ester
malononitrile
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
With triethylamine 1) 60 deg C, 2 h; 2) ethanol, reflux, 15 min.;; Yield given. Multistep reaction; |
orthoformic acid triethyl ester
malononitrile
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
With acetic anhydride at 110 - 140℃; Reflux; | 98% |
With acetic anhydride at 110 - 140℃; | 98% |
With acetic anhydride at 110 - 140℃; | 98% |
spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans
ethyl vinyl ether
A
2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
at 100℃; for 40h; sealed tube; | A 63% B 50% |
1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)urea
orthoformic acid triethyl ester
malononitrile
A
1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)ureidomethylenemalononitrile
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
at 70℃; for 12h; | A 52% B n/a |
1-(2',3',4',5'-Tetra-O-acetyl-β-D-glucopyranosyl)urea
orthoformic acid triethyl ester
malononitrile
A
1-(2',3',4',5'-Tetra-O-acetyl-β-D-glucopyranosyl)ureidomethylenemalononitrile
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
for 10h; | A 39% B n/a |
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea
orthoformic acid triethyl ester
malononitrile
A
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)ureidomethylenemalononitrile
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
at 60℃; for 2h; | A 28% B n/a |
acetic anhydride
orthoformic acid triethyl ester
malononitrile
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
With orthoformic acid triethyl ester at 140℃; | |
With orthoformic acid triethyl ester at 140℃; |
1-acetyl-3-(dicyanomethylene)-1,3-dihydro-2H-indol-2-one
ethyl vinyl ether
A
2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
B
2-ethoxy-4,4-dicyano-9-acetyl-2,3-dihydropyran<2,3-b>indole
(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>
spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans
E
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
In acetonitrile Product distribution; with solvent, room temp., or ethylvinylether as solvent, 100 deg C, Paar bomb; |
(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>
ethyl vinyl ether
A
2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
at 100℃; for 40h; sealed tube; | |
sealed tube; |
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea
orthoformic acid triethyl ester
malononitrile
B
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
With triethylamine 1) 60 deg C, 2 h; 2) ethanol, reflux, 15 min.;; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With benzene |
(2-fluorophenyl)hydrazine hydrochloride
Ethoxymethylenemalononitrile
5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere; | 100% |
With triethylamine for 4h; | 91% |
Stage #1: (2-fluorophenyl)hydrazine hydrochloride; Ethoxymethylenemalononitrile With triethylamine In ethanol for 0.666667h; Stage #2: In diethyl ether; hexane for 16h; | 67% |
With triethylamine | |
With sodium acetate In ethanol for 1h; Michael Addition; Reflux; |
5-hydrazino-2-chloro-benzamide
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
In ethanol for 18h; Heating / reflux; | 100% |
(2,4-difluorophenyl)hydrazinium chloride
Ethoxymethylenemalononitrile
5-amino-1-(2,4-difluorophenyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere; | 100% |
With sodium acetate; triethylamine In acetic acid at 15 - 60℃; for 3.5h; Large scale reaction; | 98% |
With triethylamine In ethanol for 1h; Heating / reflux; | |
With triethylamine In ethanol for 1h; Heating / reflux; |
o-chlorophenylhydrazine hydrochloride
Ethoxymethylenemalononitrile
5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere; | 100% |
With triethylamine | |
With sodium acetate In ethanol for 1h; Michael Addition; Reflux; |
o-tolylhydrazine hydrochloride
Ethoxymethylenemalononitrile
5-amino-1-o-tolyl-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere; | 100% |
With triethylamine In methanol |
C6H6F3N3*ClH
Ethoxymethylenemalononitrile
5-amino-1-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere; | 100% |
Ethoxymethylenemalononitrile
5-amino-1-(2,5-difluorophenyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In ethanol at 20℃; for 1h; | 100% |
Ethoxymethylenemalononitrile
5-amino-1-(2,6-difluorophenyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 20 - 75℃; for 1.66667h; Inert atmosphere; | 99% |
With sodium hydroxide In water; acetic acid at 0 - 60℃; for 4.2h; Large scale reaction; | 71% |
With triethylamine In ethanol at 20℃; for 1.66667h; Reflux; |
5-amino-2-methylbenzoxazole
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
In ethanol Ambient temperature; | 98% |
2-hydrazino-1,3-thiazole
Ethoxymethylenemalononitrile
5-amino-1-(1,3-thiazol-2-yl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol for 2h; Heating / reflux; | 98% |
In ethanol for 4h; Heating; |
Ethoxymethylenemalononitrile
3-(4-methylphenyl)-6-hydrazinopyridazine
5-amino-1-(6-p-tolyl-pyridazin-3-yl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | 98% |
Conditions | Yield |
---|---|
In ethanol at 120℃; for 1h; | 98% |
4-fluorophenylhydrazine
Ethoxymethylenemalononitrile
5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
In ethanol Reflux; | 97% |
In ethanol at 105℃; for 0.333333h; microwave irradiation; | 71% |
In ethanol for 2h; Reflux; | 61% |
4-fluorophenyhydrazine hydrochloride
Ethoxymethylenemalononitrile
5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
97% | |
With sodium ethanolate; sodium hydride In ethanol at 20℃; for 2h; Heating / reflux; | 86% |
With triethylamine In ethanol for 10h; Reflux; | 66% |
Ethoxymethylenemalononitrile
3-hydrazino-6-(p-methoxyphenyl)pyridazine
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 97% |
tert-butylhydrazine
Ethoxymethylenemalononitrile
5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 78℃; for 3h; | 96.3% |
With triethylamine In ethanol at 100℃; for 0.5h; Microwave irradiation; | 83% |
In ethanol at 70℃; for 18h; | 80% |
With sodium methylate In ethanol | 46 g (87%) |
With triethylamine In ethanol at 90℃; Inert atmosphere; |
phenylhydrazine
Ethoxymethylenemalononitrile
5-Amino-4-cyano-1-phenylpyrazole
Conditions | Yield |
---|---|
In ethanol for 1h; Reflux; | 96% |
In ethanol at 120℃; for 0.75h; Solvent; Temperature; Time; Reagent/catalyst; Sealed tube; Microwave irradiation; | 95% |
With silica gel In N,N-dimethyl acetamide for 0.15h; microwave irradiation; | 92% |
2-acetonylpyridine
Ethoxymethylenemalononitrile
1-Acetyl-4-imino-4H-quinolizine-3-carbonitrile
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide Ambient temperature; | 96% |
ethyl (1,4-dihydro-5,8-dimethoxy-4-oxoquinolin-2-yl)acetate
Ethoxymethylenemalononitrile
1-Amino-2-cyano-7,10-dimethoxy-6-oxo-6H-pyrido[1,2-a]quinoline-4-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
at 100℃; for 1h; | 96% |
2-amino-1-benzylideneamino-4-phenyl-1H-imidazole
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
In acetonitrile for 1h; Heating; | 96% |
tertbutylhydrazine hydrochloride
Ethoxymethylenemalononitrile
5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol; water at 78℃; for 3h; | 96% |
With triethylamine In ethanol at 78℃; for 3h; | 96% |
With triethylamine In ethanol for 3h; Reflux; | 95% |
3,7-dimethyl-4-(4-nitrophenyl)-2,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-5-ylhydrazine
Ethoxymethylenemalononitrile
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | 96% |
N-cyclopropyl-3-hydrazino-4-methyl-benzamide trifluoroacetic acid salt
Ethoxymethylenemalononitrile
3-(5-amino-4-cyano-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In ethanol at 65℃; for 3h; | 96% |
Ethoxymethylenemalononitrile
5-amino-1-(4,4-difluorocyclohexyl)-1H-pyrazol-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 50℃; for 2h; | 96% |
C2HF3O2*C6H12F2N2
Ethoxymethylenemalononitrile
5-amino-1-(4,4-difluorocyclohexyl)-1H-pyrazol-4-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol at 50℃; for 2h; | 96% |
With triethylamine In ethanol at 50℃; for 2h; | 96% |
3-hydrazino-6-phenylpyridazine
Ethoxymethylenemalononitrile
5-amino-1-(6-phenyl-pyridazin-3-yl)-1H-pyrazole-4-carbonitrile
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 96% |
In ethanol for 2h; Reflux; | 84% |
Ethoxymethylenemalononitrile
(1-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-hydrazine
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | 96% |
Structure of Ethoxymethylenemalononitrile (CAS NO.123-06-8):
IUPAC Name: 2-(ethoxymethylidene)propanedinitrile
Empirical Formula: C6H6N2O
Molecular Weight: 122.1246
EINECS: 204-597-0
Index of Refraction: 1.461
Molar Refractivity: 31.31 cm3
Molar Volume: 114.1 cm3
Polarizability: 12.41×10-24cm3
Surface Tension: 41.9 dyne/cm
Density: 1.07 g/cm3
Flash Point: 135.1 °C
Enthalpy of Vaporization: 53.59 kJ/mol
Melting Point: 64-66 °C(lit.)
Boiling Point: 296.1 °C at 760 mmHg
Vapour Pressure: 0.00146 mmHg at 25°C
Water Solubility: insoluble
Physical Appearance: Off White to Pale Yellow
Product Categories: Pharmaceutical Intermediates;Aliphatic Compound;Miscellaneous;API intermediates;Various Intermediates;Intermediates;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
1. | ipr-mus LD50:50 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 . |
Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.
Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NOx and CN−. See also NITRILES.
Hazard Codes: Xn,Xi,T
Risk Statements: 22-42/43-23/24/25-43-20/21/22
22: Harmful if swallowed
42/43: May cause sensitization by inhalation and skin contact
23/24/25: Toxic by inhalation, in contact with skin and if swallowed
43: May cause sensitization by skin contact
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
Safety Statements: 22-36/37-45-36/37/39-26-36-24/25
22: Do not breathe dust
36/37: Wear suitable protective clothing and gloves
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37/39: Wear suitable protective clothing, gloves and eye/face protection
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
24/25: Avoid contact with skin and eyes
RIDADR: 3439
WGK Germany: 3
RTECS: OO3850000
F: 21: Sensitive to humidity.
HazardClass: 6.1
PackingGroup: III
1. First Aid Measures
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Eyes:
Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
2. Handling and Storage
Storage:
Store in a tightly closed container. Store in a cool, dry area away from incompatible substances.
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Use with adequate ventilation. Use only in a chemical fume hood. Wash clothing before reuse. Do not breathe dust.
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