Product Name

  • Name

    Etocrilene

  • EINECS 226-029-0
  • CAS No. 5232-99-5
  • Article Data17
  • CAS DataBase
  • Density 1.141 g/cm3
  • Solubility
  • Melting Point 97-99 ºC
  • Formula C18H15NO2
  • Boiling Point 407.6 ºC at 760 mmHg
  • Molecular Weight 277.323
  • Flash Point 199.4 ºC
  • Transport Information UN 3077 9/PG 3
  • Appearance
  • Safety 26-36-60-61
  • Risk Codes 36/37/38-50/53
  • Molecular Structure Molecular Structure of 5232-99-5 (Etocrilene)
  • Hazard Symbols IrritantXi；DangerousN
  • Synonyms Acrylicacid, 2-cyano-3,3-diphenyl-, ethyl ester (6CI,7CI,8CI);2-Cyano-3,3-diphenyl-2-propenoic acid ethyl ester;2-Cyano-3-phenylcinnamicacid ethyl ester;CE 2;CE 2 (ultraviolet absorber);Ethyl2-cyano-3,3-diphenyl-2-propenoate;Ethyl 2-cyano-3,3-diphenylacrylate;Ethyl2-cyano-3,3-diphenylpropenoate;Ethyl a-cyano-b,b-diphenylacrylate;Ethyl a-cyano-b-phenylcinnamate;Etocrylene;NSC 52678;Seesorb 501;UV Absorber 2;Uvinul 3035;Uvinul N 35;Viosorb 910;
  • PSA 50.09000
  • LogP 3.57518

Synthetic route

Benzophenone imine
1013-88-3

Benzophenone imine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

etocrylene
5232-99-5

etocrylene

Conditions
ConditionsYield
In methanol at 35 - 85℃; Inert atmosphere;96%
benzophenone
119-61-9

benzophenone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

etocrylene
5232-99-5

etocrylene

Conditions
ConditionsYield
With ammonium acetate; pyrographite In n-heptane for 15h; Ionic liquid; Reflux;94.1%
With acetic acid; 3-amino propanoic acid In benzene for 90h; Knoevenagel condensation; Heating;64%
benzophenone
119-61-9

benzophenone

ammonium acetate
631-61-8

ammonium acetate

acetic acid
64-19-7

acetic acid

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

benzene
71-43-2

benzene

etocrylene
5232-99-5

etocrylene

...Expand
ethanol
64-17-5

ethanol

octocrylene
6197-30-4

octocrylene

A

etocrylene
5232-99-5

etocrylene

B

2-ethylhexyl 2-ethoxy-4-phenylquinoline-3-carboxylate

2-ethylhexyl 2-ethoxy-4-phenylquinoline-3-carboxylate

Conditions
ConditionsYield
for 6h; Photolysis;
...Expand
2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

etocrylene
5232-99-5

etocrylene

octocrylene
6197-30-4

octocrylene

Conditions
ConditionsYield
In sodium carbonate99.8%
With sodium methylate In toluene for 8h; Reflux;144.3 g
3,6,9,12,15,18,21-heptaoxadocosan-1-ol
4437-01-8

3,6,9,12,15,18,21-heptaoxadocosan-1-ol

etocrylene
5232-99-5

etocrylene

2-cyano-3,3-diphenyl-acrylic acid [pluriol A350E] ester
1250862-76-0

2-cyano-3,3-diphenyl-acrylic acid [pluriol A350E] ester

Conditions
ConditionsYield
Stage #1: 3,6,9,12,15,18,21-heptaoxadocosan-1-ol; etocrylene; titanium(IV) isopropylate at 155℃; for 24h; Inert atmosphere;
Stage #2: With phosphoric acid In dichloromethane; water at 20℃; for 24h;		95%
Stage #1: 3,6,9,12,15,18,21-heptaoxadocosan-1-ol at 150℃; for 0.5h; Inert atmosphere;
Stage #2: etocrylene With titanium(IV) isopropylate at 155℃; for 24h;
Stage #3: With phosphoric acid In dichloromethane at 20℃; for 24h;		95%
3,6,9,12,15,18,21-heptaoxadocosan-1-ol
4437-01-8

3,6,9,12,15,18,21-heptaoxadocosan-1-ol

etocrylene
5232-99-5

etocrylene

A

ethanol
64-17-5

ethanol

B

2-cyano-3,3-diphenyl-acrylic acid [pluriol A350E] ester
1250862-76-0

2-cyano-3,3-diphenyl-acrylic acid [pluriol A350E] ester

Conditions
ConditionsYield
Stage #1: 3,6,9,12,15,18,21-heptaoxadocosan-1-ol; etocrylene With titanium(IV)isopropoxide at 150 - 155℃; for 25h; Inert atmosphere;
Stage #2: With phosphoric acid In water at 20℃; for 24h;		A n/a
B 95%
...Expand
etocrylene
5232-99-5

etocrylene

ethyl α-cyano-ββ-diphenylpropionate
25634-96-2

ethyl α-cyano-ββ-diphenylpropionate

Conditions
ConditionsYield
With copper(II) acetate monohydrate; tert-butyl alcohol In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Sealed tube; chemoselective reaction;94%
With methanol; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at 20℃; for 16h; Inert atmosphere; Irradiation; Sealed tube;93%
With lithium diisopropyl amide In tetrahydrofuran at 0℃;85%
etocrylene
5232-99-5

etocrylene

2-cyano-3,3-diphenylacrylic acid
10380-41-3

2-cyano-3,3-diphenylacrylic acid

Conditions
ConditionsYield
Stage #1: etocrylene With water; sodium hydroxide In methanol at 20℃;
Stage #2: With hydrogenchloride In methanol; water		92%
Hydrolysis;
Stage #1: etocrylene With sodium hydroxide In ethanol; water at 20℃; for 8h;
Stage #2: With hydrogenchloride In ethanol; water		3.2 g
4-Cyanochlorobenzene

4-Cyanochlorobenzene

etocrylene
5232-99-5

etocrylene

2-(4-chlorophenyl)-3,3-diphenyl-4-ethoxycarbonyl-5-amino-3H-pyrrole

2-(4-chlorophenyl)-3,3-diphenyl-4-ethoxycarbonyl-5-amino-3H-pyrrole

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 65℃; for 2h;81%
With samarium; iodine In tetrahydrofuran at 65℃; for 10h;52%
Pentaerythritol
115-77-5

Pentaerythritol

etocrylene
5232-99-5

etocrylene

pentaerythritol tetrakis(2-cyano-3,3-diphenylacrylate)

pentaerythritol tetrakis(2-cyano-3,3-diphenylacrylate)

Conditions
ConditionsYield
With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reagent/catalyst; Reflux;80.6%
etocrylene
5232-99-5

etocrylene

(1,3-dimethylimidazol-2-ylidene)borane
1211417-77-4

(1,3-dimethylimidazol-2-ylidene)borane

(2-cyano-3-ethoxy-3-oxo-1,1-diphenylpropyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate

(2-cyano-3-ethoxy-3-oxo-1,1-diphenylpropyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate

Conditions
ConditionsYield
With 1,3-dicyano-2,4,5,6-tetrakis(N,N-diphenylamino)-benzene In acetonitrile at 30℃; for 24h; Irradiation; Inert atmosphere; regioselective reaction;80%
3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

etocrylene
5232-99-5

etocrylene

2-(3-bromophenyl)-3,3-diphenyl-4-ethoxycarbonyl-5-amino-3H-pyrrole

2-(3-bromophenyl)-3,3-diphenyl-4-ethoxycarbonyl-5-amino-3H-pyrrole

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 65℃; for 2h;78%
etocrylene
5232-99-5

etocrylene

3-Methylbenzonitrile
620-22-4

3-Methylbenzonitrile

ethyl 2-amino-4,4-diphenyl-5-(3-methylphenyl)-4H-pyrrole-3-carboxylate

ethyl 2-amino-4,4-diphenyl-5-(3-methylphenyl)-4H-pyrrole-3-carboxylate

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 65℃; for 2.5h;78%
With samarium; iodine In tetrahydrofuran at 65℃; for 11h;57%
With iodine; magnesium In tetrahydrofuran for 1.25h; Heating;56%
etocrylene
5232-99-5

etocrylene

potassium ferrocyanide

potassium ferrocyanide

ethyl 2,3-dicyano-3,3-diphenylpropanoate
94258-41-0

ethyl 2,3-dicyano-3,3-diphenylpropanoate

Conditions
ConditionsYield
Stage #1: potassium ferrocyanide With benzoyl chloride at 160℃; for 3h; Green chemistry;
Stage #2: etocrylene With potassium carbonate In ethanol at 20℃; for 6h; Green chemistry; chemoselective reaction;		77%
etocrylene
5232-99-5

etocrylene

piperonylonitrile
4421-09-4

piperonylonitrile

ethyl 2-amino-5-(3,4-methylenedioxyphenyl)-4,4-diphenyl-4H-pyrrole-3-carboxylate

ethyl 2-amino-5-(3,4-methylenedioxyphenyl)-4,4-diphenyl-4H-pyrrole-3-carboxylate

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 65℃; for 3h;76%
With iodine; magnesium In tetrahydrofuran for 2h; Heating;43%
etocrylene
5232-99-5

etocrylene

4-methoxybenzonitrile
874-90-8

4-methoxybenzonitrile

ethyl 2-amino-4,4-diphenyl-5-(4-methoxyphenyl)-4H-pyrrole-3-carboxylate

ethyl 2-amino-4,4-diphenyl-5-(4-methoxyphenyl)-4H-pyrrole-3-carboxylate

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 65℃; for 2.5h;75%
With samarium; iodine In tetrahydrofuran at 65℃; for 10h;60%
With iodine; magnesium In tetrahydrofuran for 1.5h; Heating;47%
etocrylene
5232-99-5

etocrylene

4-cyano-N,N-dimethylaniline
1197-19-9

4-cyano-N,N-dimethylaniline

ethyl 2-amino-5-(4-dimethylaminophenyl)-4,4-diphenyl-4H-pyrrole-3-carboxylate

ethyl 2-amino-5-(4-dimethylaminophenyl)-4,4-diphenyl-4H-pyrrole-3-carboxylate

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 65℃; for 3h;73%
With iodine; magnesium In tetrahydrofuran for 0.125h; Heating;50%
etocrylene
5232-99-5

etocrylene

benzonitrile
100-47-0

benzonitrile

ethyl 2-amino-4,4,5-triphenyl-4H-pyrrole-3-carboxylate

ethyl 2-amino-4,4,5-triphenyl-4H-pyrrole-3-carboxylate

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 65℃; for 2h;72%
With samarium; iodine In tetrahydrofuran at 65℃; for 10h;55%
With iodine; magnesium In tetrahydrofuran for 1.33333h; Heating;52%
etocrylene
5232-99-5

etocrylene

3,3-diphenylacrylonitrile
3531-24-6

3,3-diphenylacrylonitrile

Conditions
ConditionsYield
With water; sodium chloride In dimethyl sulfoxide at 160 - 170℃; for 4h; Krapcho decarboxylation;72%
etocrylene
5232-99-5

etocrylene

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

ethyl 2-cyano-2-((methyl(phenyl)amino)methyl)-3,3-diphenylpropanoate

ethyl 2-cyano-2-((methyl(phenyl)amino)methyl)-3,3-diphenylpropanoate

Conditions
ConditionsYield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; caesium carbonate In acetonitrile at 25℃; for 16h; Inert atmosphere; Irradiation; Sealed tube; regioselective reaction;67%
etocrylene
5232-99-5

etocrylene

cyclohexanone
108-94-1

cyclohexanone

2,2-pentamethylene-3,3-diphenyl-4-ethoxycarbonyl-5-amino-2,3-dihydrofuran

2,2-pentamethylene-3,3-diphenyl-4-ethoxycarbonyl-5-amino-2,3-dihydrofuran

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃;59%
etocrylene
5232-99-5

etocrylene

4,4'-dimethylbenzaldazine
4702-76-5, 139030-29-8

4,4'-dimethylbenzaldazine

2-amino-1-[(4-methyl-benzylidene)-amino]-4,4-diphenyl-5-p-tolyl-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

2-amino-1-[(4-methyl-benzylidene)-amino]-4,4-diphenyl-5-p-tolyl-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃;55%
1,1,1,2,2,2-hexamethyldisilane
1450-14-2

1,1,1,2,2,2-hexamethyldisilane

etocrylene
5232-99-5

etocrylene

3,3-diphenyl-2-(trimethylsilyl)-2-propenoic acid ethyl ester
110046-19-0

3,3-diphenyl-2-(trimethylsilyl)-2-propenoic acid ethyl ester

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer In ethyl-cyclohexane at 130℃; for 3h; Inert atmosphere;54%
etocrylene
5232-99-5

etocrylene

1,2-di(benzylidene)hydrazine
588-68-1

1,2-di(benzylidene)hydrazine

2-Amino-4,4,5-triphenyl-1-{[1-phenyl-meth-(E)-ylidene]-amino}-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

2-Amino-4,4,5-triphenyl-1-{[1-phenyl-meth-(E)-ylidene]-amino}-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at 20℃;53%
4-methyl-chalcone
4224-87-7

4-methyl-chalcone

etocrylene
5232-99-5

etocrylene

1-amino-2-ethoxycarbonyl-3,3-diphenyl-4-(p-methylphenyl)-5-benzoylcyclopentene

1-amino-2-ethoxycarbonyl-3,3-diphenyl-4-(p-methylphenyl)-5-benzoylcyclopentene

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at -20℃; for 2h;51%
1,1-Diphenylethylene
530-48-3

1,1-Diphenylethylene

n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

etocrylene
5232-99-5

etocrylene

A

1,1-diphenylhex-1-ene
1530-19-4

1,1-diphenylhex-1-ene

B

1,1-diphenyl hexane
1530-04-7

1,1-diphenyl hexane

C

ethyl α-cyano-ββ-diphenylpropionate
25634-96-2

ethyl α-cyano-ββ-diphenylpropionate

D

2-Cyano-3,3-diphenyl-heptanoic acid ethyl ester

2-Cyano-3,3-diphenyl-heptanoic acid ethyl ester

Conditions
ConditionsYield
In diethyl ether at 23℃; for 2.5h; Product distribution; various solvents, time, temperature;A 32%
B 16%
C 43%
D 4%
...Expand
etocrylene
5232-99-5

etocrylene

O-ethyl 2-cyano-3,3-diphenyl-2-propenethioic acid

O-ethyl 2-cyano-3,3-diphenyl-2-propenethioic acid

Conditions
ConditionsYield
With tetraphosphorus decasulfide; Hexamethyldisiloxane In xylene Heating;42%
With tetraphosphorus decasulfide; Hexamethyldisiloxane In xylene for 20h; Heating;42%
With Lawessons reagent In xylene at 140℃; for 12h;39%
etocrylene
5232-99-5

etocrylene

3-(3-bromophenyl)-1-phenylprop-2-en-1-one
29816-74-8

3-(3-bromophenyl)-1-phenylprop-2-en-1-one

1-amino-2-ethoxycarbonyl-3,3-diphenyl-4-(m-bromophenyl)-5-benzoylcyclopentene

1-amino-2-ethoxycarbonyl-3,3-diphenyl-4-(m-bromophenyl)-5-benzoylcyclopentene

Conditions
ConditionsYield
With samarium diiodide In tetrahydrofuran at -20℃; for 2h;39%
etocrylene
5232-99-5

etocrylene

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

fullerene-C60
99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0

fullerene-C60

A

1’-amino-1’-ethyl(diphenylmethylidene)acetyl-(60-Ih)[5,6]fullero[2’,3’:1,9]cyclopropane

1’-amino-1’-ethyl(diphenylmethylidene)acetyl-(60-Ih)[5,6]fullero[2’,3’:1,9]cyclopropane

B

1-ethyl-1,2-dihydrofullerene

1-ethyl-1,2-dihydrofullerene

Conditions
ConditionsYield
Stage #1: ethylmagnesium bromide; fullerene-C60 With titanium(IV) isopropylate In diethyl ether; chlorobenzene at 0 - 100℃; Inert atmosphere;
Stage #2: etocrylene; ethylmagnesium bromide In diethyl ether; chlorobenzene at 100℃; for 0.25h;
Stage #3: With hydrogenchloride; water In diethyl ether; chlorobenzene		A 33%
B n/a
...Expand
diazomethane
186581-53-3, 908094-01-9

diazomethane

etocrylene
5232-99-5

etocrylene

ethyl α-cyano-β-benzyl-β-phenylacrylate
151130-13-1

ethyl α-cyano-β-benzyl-β-phenylacrylate

Conditions
ConditionsYield
In diethyl ether; dichloromethane at 10℃; for 24h;28%
piperidine
110-89-4

piperidine

etocrylene
5232-99-5

etocrylene

A

3,3-diphenylacrylonitrile
3531-24-6

3,3-diphenylacrylonitrile

B

2-(piperidinocarbonyl)-3,3-diphenylacrylonitrile

2-(piperidinocarbonyl)-3,3-diphenylacrylonitrile

Conditions
ConditionsYield
In toluene at 100℃; for 72h;A 7.5%
B 10.5%
...Expand

Etocrilene Consensus Reports

Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Etocrilene Specification

The 3,3-Dicyclopropyl-2-(ethoxycarbonyl)-acrylonitrile, with its CAS registry number 5232-99-5, has the IUPAC name of ethyl 2-cyano-3,3-diphenylprop-2-enoate. As used as a pharmaceutical intermediate, its product categories are including C12 to C63 Polymer Science; Carbonyl Compounds; Esters; Polymer Additives; Stabilizers.

The physical properties of this chemical are as below: (1)ACD/LogP: 4.52; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 3; (4)#H bond donors: 0; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 50.09; (7)Index of Refraction: 1.577; (8)Molar Refractivity: 80.61 cm3; (9)Molar Volume: 243 cm3; (10)Polarizability: 31.95×10-24 cm3; (11)Surface Tension: 46.1 dyne/cm; (12)Density: 1.141 g/cm3; (13)Flash Point: 199.4 °C; (14)Enthalpy of Vaporization: 65.95 kJ/mol; (15)Boiling Point: 407.6 °C at 760 mmHg; (16)Vapour Pressure: 7.46E-07 mmHg at 25°C; (17)Exact Mass: 277.110279; (18)MonoIsotopic Mass: 277.110279; (19)Topological Polar Surface Area: 50.1; (20)Heavy Atom Count: 21; (21)Complexity: 411.

Use of this chemical: 3,3-Dicyclopropyl-2-(ethoxycarbonyl)-acrylonitrile could react to produce 2-cyano-3,3-diphenyl-propionic acid ethyl ester. This reaction could happen in the presence of the reagent of palladium/charcoal and acetone in the condition of Hydrogenation.

When you are dealing with this chemical, you should be very careful. For one thing, it is irritating to eyes, respiratory system and skin and then may cause inflammation to the skin or other mucous membranes. For another thing, it is dangerous for the environment which may present an immediate or delayed danger to one or more components of the environment. For being very toxic to aquatic organisms, it may cause long-term adverse effects in the aquatic environment.

Therefore, you should wear suitable protective clothing. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. When store it, this material and its container must be disposed of as hazardous waste and remember to avoid releasing to the environment. You could also refer to special instructions/safety data sheet.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CCOC(=O)C(=C(C1=CC=CC=C1)C2=CC=CC=C2)C#N
(2)InChI: InChI=1S/C18H15NO2/c1-2-21-18(20)16(13-19)17(14-9-5-3-6-10-14)15-11-7-4-8-12-15/h3-12H,2H2,1H3
(3)InChIKey: IAJNXBNRYMEYAZ-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,

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