5232-99-5

Basic information

• Product Name: Etocrilene
• Synonyms: 2-cyano-3,3-diphenyl-2-propenoicaciethylester;2-cyano-3,3-diphenyl-acrylicaciethylester;2-Propenoicacid,2-cyano-3,3-diphenyl-,ethylester;3,3-dicyclopropyl-2-(ethoxycarbonyl)-acrylonitril;alpha-carbethoxy-beta,beta-biscyclopropylacrylonitrile;beta,beta-biscyclopropyl-alpha-carbethoxy-acrylonitril;ce2;ethyl2-cyano-3,3-diphenyl-2-propenoate
• CAS NO: 5232-99-5
• Molecular Formula: C₁₈H₁₅NO₂
• Molecular Weight: 277.32
• EINECS: 226-029-0
• Product Categories: C12 to C63Polymer Science;Carbonyl Compounds;Esters;Polymer Additives;Stabilizers
• Mol File: 5232-99-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 97-99 °C(lit.)
• Boiling Point: 174 °C0.2 mm Hg(lit.)
• Flash Point: 199.4 ºC
• Appearance: /
• Density: 1,05 g/cm3
• Vapor Pressure: 7.46E-07mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: Etocrilene(CAS DataBase Reference)
• NIST Chemistry Reference: Etocrilene(5232-99-5)
• EPA Substance Registry System: Etocrilene(5232-99-5)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-36-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• RTECS: AT6200000
• Hazardous Substances Data: 5232-99-5(Hazardous Substances Data)

Usage

Description

Etocrylene is an organic ester that appears as an off-white crystalline powder and functions as a UV absorber. When applied to the skin, this product absorbs UV rays. It can also be used to protect cosmetics and personal care products from deterioration. This product can be used in the formulation of sun protection products, as well as bath, skin, cleansing, hair, nail and fragrance products.

Uses

Ethyl 2-Cyano-3,3-diphenylacrylate is a sunscreen ingredient.

Synthesis Reference(s)

Journal of the American Chemical Society, 63, p. 3452, 1941 DOI: 10.1021/ja01857a057Tetrahedron Letters, 33, p. 7535, 1992 DOI: 10.1016/S0040-4039(00)60817-1

InChI:InChI=1/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

Synthetic route

Benzophenone imine (1013-88-3) + ethyl 2-cyanoacetate (105-56-6) → etocrylene (5232-99-5)

Conditions	Yield
In methanol at 35 - 85℃; Inert atmosphere;	96%

benzophenone (119-61-9) + ethyl 2-cyanoacetate (105-56-6) → etocrylene (5232-99-5)

Conditions	Yield
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) + ammonium acetate (631-61-8) + acetic acid (64-19-7) + ethyl 2-cyanoacetate (105-56-6) + benzene (71-43-2) → etocrylene (5232-99-5)

ethanol (64-17-5) + octocrylene (6197-30-4) → etocrylene (5232-99-5) + 2-ethylhexyl 2-ethoxy-4-phenylquinoline-3-carboxylate

Conditions	Yield
for 6h; Photolysis;

2-Ethylhexyl alcohol (104-76-7) + etocrylene (5232-99-5) → octocrylene (6197-30-4)

Conditions	Yield
In sodium carbonate	99.8%
With sodium methylate In toluene for 8h; Reflux;	144.3 g

3,6,9,12,15,18,21-heptaoxadocosan-1-ol (4437-01-8) + etocrylene (5232-99-5) → 2-cyano-3,3-diphenyl-acrylic acid [pluriol A350E] ester (1250862-76-0)

Conditions	Yield
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) + etocrylene (5232-99-5) → ethanol (64-17-5) + 2-cyano-3,3-diphenyl-acrylic acid [pluriol A350E] ester (1250862-76-0)

Conditions	Yield
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%

etocrylene (5232-99-5) → ethyl α-cyano-ββ-diphenylpropionate (25634-96-2)

Conditions	Yield
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) → 2-cyano-3,3-diphenylacrylic acid (10380-41-3)

Conditions	Yield
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 + etocrylene (5232-99-5) → 2-(4-chlorophenyl)-3,3-diphenyl-4-ethoxycarbonyl-5-amino-3H-pyrrole

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 65℃; for 2h;	81%
With samarium; iodine In tetrahydrofuran at 65℃; for 10h;	52%

Pentaerythritol (115-77-5) + etocrylene (5232-99-5) → pentaerythritol tetrakis(2-cyano-3,3-diphenylacrylate)

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

etocrylene (5232-99-5) + (1,3-dimethylimidazol-2-ylidene)borane (1211417-77-4) → (2-cyano-3-ethoxy-3-oxo-1,1-diphenylpropyl)(1,3-dimethyl-1H-imidazol-3-ium-2-yl)dihydroborate

Conditions	Yield
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) + etocrylene (5232-99-5) → 2-(3-bromophenyl)-3,3-diphenyl-4-ethoxycarbonyl-5-amino-3H-pyrrole

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 65℃; for 2h;	78%

etocrylene (5232-99-5) + 3-Methylbenzonitrile (620-22-4) → ethyl 2-amino-4,4-diphenyl-5-(3-methylphenyl)-4H-pyrrole-3-carboxylate

Conditions	Yield
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) + potassium ferrocyanide → ethyl 2,3-dicyano-3,3-diphenylpropanoate (94258-41-0)

Conditions	Yield
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) + piperonylonitrile (4421-09-4) → ethyl 2-amino-5-(3,4-methylenedioxyphenyl)-4,4-diphenyl-4H-pyrrole-3-carboxylate

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 65℃; for 3h;	76%
With iodine; magnesium In tetrahydrofuran for 2h; Heating;	43%

etocrylene (5232-99-5) + 4-methoxybenzonitrile (874-90-8) → ethyl 2-amino-4,4-diphenyl-5-(4-methoxyphenyl)-4H-pyrrole-3-carboxylate

Conditions	Yield
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) + 4-cyano-N,N-dimethylaniline (1197-19-9) → ethyl 2-amino-5-(4-dimethylaminophenyl)-4,4-diphenyl-4H-pyrrole-3-carboxylate

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 65℃; for 3h;	73%
With iodine; magnesium In tetrahydrofuran for 0.125h; Heating;	50%

etocrylene (5232-99-5) + benzonitrile (100-47-0) → ethyl 2-amino-4,4,5-triphenyl-4H-pyrrole-3-carboxylate

Conditions	Yield
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) → 3,3-diphenylacrylonitrile (3531-24-6)

Conditions	Yield
With water; sodium chloride In dimethyl sulfoxide at 160 - 170℃; for 4h; Krapcho decarboxylation;	72%

etocrylene (5232-99-5) + N,N-dimethyl-aniline (121-69-7) → ethyl 2-cyano-2-((methyl(phenyl)amino)methyl)-3,3-diphenylpropanoate

Conditions	Yield
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) + cyclohexanone (108-94-1) → 2,2-pentamethylene-3,3-diphenyl-4-ethoxycarbonyl-5-amino-2,3-dihydrofuran

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃;	59%

etocrylene (5232-99-5) + 4,4'-dimethylbenzaldazine (4702-76-5, 139030-29-8) → 2-amino-1-[(4-methyl-benzylidene)-amino]-4,4-diphenyl-5-p-tolyl-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃;	55%

1,1,1,2,2,2-hexamethyldisilane (1450-14-2) + etocrylene (5232-99-5) → 3,3-diphenyl-2-(trimethylsilyl)-2-propenoic acid ethyl ester (110046-19-0)

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

etocrylene (5232-99-5) + 1,2-di(benzylidene)hydrazine (588-68-1) → 2-Amino-4,4,5-triphenyl-1-{[1-phenyl-meth-(E)-ylidene]-amino}-4,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester

Conditions	Yield
With samarium diiodide In tetrahydrofuran at 20℃;	53%

4-methyl-chalcone (4224-87-7) + etocrylene (5232-99-5) → 1-amino-2-ethoxycarbonyl-3,3-diphenyl-4-(p-methylphenyl)-5-benzoylcyclopentene

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -20℃; for 2h;	51%

1,1-Diphenylethylene (530-48-3) + n-butyllithium (109-72-8, 29786-93-4) + etocrylene (5232-99-5) → 1,1-diphenylhex-1-ene (1530-19-4) + 1,1-diphenyl hexane (1530-04-7) + ethyl α-cyano-ββ-diphenylpropionate (25634-96-2) + 2-Cyano-3,3-diphenyl-heptanoic acid ethyl ester

Conditions	Yield
In diethyl ether at 23℃; for 2.5h; Product distribution; various solvents, time, temperature;	A 32% B 16% C 43% D 4%

etocrylene (5232-99-5) → O-ethyl 2-cyano-3,3-diphenyl-2-propenethioic acid

Conditions	Yield
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) + 3-(3-bromophenyl)-1-phenylprop-2-en-1-one (29816-74-8) → 1-amino-2-ethoxycarbonyl-3,3-diphenyl-4-(m-bromophenyl)-5-benzoylcyclopentene

Conditions	Yield
With samarium diiodide In tetrahydrofuran at -20℃; for 2h;	39%

etocrylene (5232-99-5) + ethylmagnesium bromide (925-90-6) + 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) → 1’-amino-1’-ethyl(diphenylmethylidene)acetyl-(60-Ih)[5,6]fullero[2’,3’:1,9]cyclopropane + 1-ethyl-1,2-dihydrofullerene

Conditions	Yield
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

diazomethane (186581-53-3, 908094-01-9) + etocrylene (5232-99-5) → ethyl α-cyano-β-benzyl-β-phenylacrylate (151130-13-1)

Conditions	Yield
In diethyl ether; dichloromethane at 10℃; for 24h;	28%

piperidine (110-89-4) + etocrylene (5232-99-5) → 3,3-diphenylacrylonitrile (3531-24-6) + 2-(piperidinocarbonyl)-3,3-diphenylacrylonitrile

Conditions	Yield
In toluene at 100℃; for 72h;	A 7.5% B 10.5%

Upstream product

• 64-17-5 ethanol 
• 6197-30-4 octocrylene 
• 119-61-9 benzophenone 
• 105-56-6 ethyl 2-cyanoacetate 
• 1013-88-3 Benzophenone imine 
• 631-61-8 ammonium acetate 
• 64-19-7 acetic acid 
• 71-43-2 benzene 

Downstream Products

• 10380-41-3 2-cyano-3,3-diphenylacrylic acid 
• 25634-96-2 ethyl α-cyano-ββ-diphenylpropionate 
• 92856-05-8 2-benzhydrylidene-malonamic acid 
• 2103-38-0 (+/-)-2-Aethyl-2,3-dicyan-3,3-diphenyl-propionsaeure-aethylester 
• 4056-37-5 2,2-diphenyl-succinonitrile 
• 2103-09-5 (+/-)-2-Benzyl-2,3-dicyan-3,3-diphenyl-propionsaeure-aethylester 
• 3884-42-2 (+/-)-2-Allyl-2,3-dicyan-3,3-diphenyl-propionsaeure-aethylester 
• 2103-39-1 (+/-)-2,3-Dicyan-2-methyl-3,3-diphenyl-propionsaeure-aethylester 
• 137768-28-6 ethyl <α-(9,10-dihydro-9-anthryl)benzhydryl>cyanoacetate 
• 31002-34-3 1-Cyano-2,2-diphenylcyclopropane-1-carboxylic acid 
• 1530-19-4 1,1-diphenylhex-1-ene 
• 1530-04-7 1,1-diphenyl hexane 
• 6197-30-4 octocrylene 
• 3531-24-6 3,3-diphenylacrylonitrile 

Relevant articles and documents

Investigation of the sunscreen octocrylene's interaction with amino acid analogs in the presence of UV radiation

Octocrylene is an organic UV filter, commonly used in sunscreens and cosmetics, which can give rise to both contact and photocontact allergy. Our aim was to investigate octocrylene's interaction with amino acid analogs in the presence of UV radiation to b

Preparation method of cyanoacrylate ultraviolet light absorber

The invention provides a preparation method of a cyanoacrylate ultraviolet light absorber. Benzophenone compounds represented by general formula I with cyanoacetate under a weakly alkaline condition by using activated carbon grafted acidic ionic liquid as a catalyst to generate a compound represented by general formula II. The preparation method of the cyanoacrylate ultraviolet light absorber adopts the activated carbon grafted acidic ionic liquid catalyst to replace acetic acid, so that the preparation method has the advantages of easiness in recycling of the catalyst, high product yield, fewthree wastes, and convenience in post-treatment, and is an economical, practical and environment-friendly technology.

Synthesis of coumarins via PIDA/I2-mediated oxidative cyclization of substituted phenylacrylic acids

A variety of functionalized coumarins were synthesized from substituted phenylacrylic acids via PIDA/I2-mediated and irradiation-promoted oxidative carbon-oxygen bond formation. Our studies show that the oxygen in the pendant carboxylic acid group cyclizes favorably to the aryl ring that is cis to it. The main advantages of this method include good functional group tolerance and the transition-metal-free characteristic. The Royal Society of Chemistry 2013.