Benzeneacetaldehyde, alpha-ethylidene- supplier

Name
2-PHENYL-2-BUTENAL
EINECS 224-567-0
CAS No. 4411-89-6
Article Data42
CAS DataBase
Density 0.99 g/cm³
Solubility Soluble in oil and ethanol. Insoluble in water.
Melting Point
Formula C₁₀H₁₀O
Boiling Point 271.6 °C at 760 mmHg
Molecular Weight 146.189
Flash Point 95.9 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Crotonaldehyde,2-phenyl- (7CI,8CI);Crotonaldehyde, a-phenyl- (4CI);2-Phenyl-2-butenal;2-Phenylcrotonaldehyde;a-Phenylcrotonaldehyde;
PSA 17.07000
LogP 2.28880

Synthetic route

: 90-15-3
α-naphthol

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)) In toluene at 90℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;	95%

: 673-32-5
1-Phenylprop-1-yne

: 201230-82-2
carbon monoxide

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B: 15174-47-7
α-methyl-trans-cinnamaldehyde

Conditions

Conditions	Yield
With hydrogen; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium(II) iodide In toluene at 70℃; under 75007.5 Torr; for 18h; Catalytic behavior; Reagent/catalyst; Autoclave;	A n/a B 83%

...Expand

: 113446-25-6
1-methoxy-1,3-diethoxy-2-phenylbutane

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With hydrogenchloride at 70 - 90℃; for 1h;	77.8%

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B: (Z)-6-hydroxy-2,5-diphenyl-2-vinylhex-4-enal

Conditions

Conditions	Yield
With [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; bis[2-(diphenylphosphino)phenyl] ether In N,N-dimethyl-formamide at 20℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;	A n/a B 75%

: 97699-36-0
2-phenyl-2-vinyloxirane

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B: 4-chloro-2-phenylbut-2-enal

Conditions

Conditions	Yield
With copper(II) choride dihydrate; lithium chloride In ethyl acetate for 1.5h;	A 8% B 59%

: 97699-36-0
2-phenyl-2-vinyloxirane

A: (E)-4-chloro-2-phenylbut-2-enal

B: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With copper(II) choride dihydrate; lithium chloride In ethyl acetate for 1.5h; Reflux; Inert atmosphere;	A 59% B 8%

: 64-18-6
formic acid

: 19261-14-4
1-phenyl-3-butene-1,2-diol

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
optically inactive 1-phenyl-butene-(3)-diol-(1.2) of mp: 43 degree;

: 1515-78-2
buta-1,3-dien-1-ylbenzene

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With diethyl ether; iodine; mercury(II) oxide anschliessend Behandeln mit AgNO3-Loesung;

: 174309-35-4
2-amino-1-phenyl-but-3-en-1-ol

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With acetic acid; sodium nitrite at 0℃;

: 122-78-1
phenylacetaldehyde

: 75-07-0
acetaldehyde

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With ethanol; sodium acetate at 110℃;

: 97699-36-0
2-phenyl-2-vinyloxirane

: 108-95-2
phenol

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B: 99321-81-0
1-Phenoxy-2-phenyl-but-3-en-2-ol

C: 99321-88-7
4-phenoxy-2-phenylbut-2-en-1-ol

D: 99321-88-7, 99321-89-8
4-phenoxy-2-phenylbut-2-en-1-ol

E: 99321-94-5
2-((E)-4-Hydroxy-3-phenyl-but-2-enyl)-phenol

F: 99321-94-5, 99321-95-6
2-((E)-4-Hydroxy-3-phenyl-but-2-enyl)-phenol

Conditions

Conditions	Yield
With sodium In 1,4-dioxane at 120℃; Product distribution;

...Expand

: 20248-57-1
2-phenyl-3-vinyloxirane

kieselguhr: kieselguhr

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
at 250℃; under 16 Torr;

: 20248-57-1
2-phenyl-3-vinyloxirane

magnesium bromide ether adduct: magnesium bromide ether adduct

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
at 110℃;

1.2-epoxy-1-phenyl-butene-(3): 1.2-epoxy-1-phenyl-butene-(3)

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With magnesium bromide ethyl etherate at 110 - 115℃;
With kieselguhr at 250℃; under 16 Torr;

1-phenyl-butene-(3)-diol-(1.2): 1-phenyl-butene-(3)-diol-(1.2)

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With formic acid
With sulfuric acid

: 7664-93-9
sulfuric acid

: 19261-14-4
1-phenyl-3-butene-1,2-diol

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B compound C20H20O2: compound C20H20O2

Conditions

Conditions	Yield
optically inactive 1-phenyl-butene-(3)-diol-(1.2) of mp: 43 degree;

...Expand

: 174309-35-4
2-amino-1-phenyl-but-3-en-1-ol

: 64-19-7
acetic acid

sodium nitrite: sodium nitrite

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
at 0℃;

...Expand

: 4747-15-3
1-(2-methoxyvinyl)benzene

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / zinc chloride / ethyl acetate 2: 77.8 percent / 18percent aq. HCl / 1 h / 70 - 90 °C View Scheme

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
With titanium(IV) isopropylate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; o-phenylenebis(diphenylphosphine) In toluene at 24℃; for 18h; Glovebox; Inert atmosphere;	> 95 %Spectr.
With dichloro(1,5-cyclooctadiene)palladium(II); silver trifluoromethanesulfonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In dichloromethane at 80℃; for 2h;

: 591-87-7
Allyl acetate

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B: C13H14O

Conditions

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 100℃; for 4h; Reagent/catalyst; Temperature; Sealed tube; chemoselective reaction;	A n/a B 76 %Spectr.

...Expand

: 591-87-7
Allyl acetate

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B: C13H14O

C: C20H20O2

Conditions

Conditions	Yield
With [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 50℃; for 12h; Sealed tube; chemoselective reaction;	A n/a B 43 %Spectr. C n/a

...Expand

: 591-87-7
Allyl acetate

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B: 3-phenyl-4-hydroxy-2-butenyl acetate

C: C13H14O

D: C20H20O2

Conditions

Conditions	Yield
With [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 20℃; for 12h; Reagent/catalyst; Sealed tube; chemoselective reaction;	A n/a B n/a C 34 %Spectr. D n/a

...Expand

: 591-87-7
Allyl acetate

: 1459246-62-8
4-phenyl-4-vinyl-1,3-dioxolan -2-one

A: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

B: 3-phenyl-4-hydroxy-2-butenyl acetate

C: C13H14O

Conditions

Conditions	Yield
With [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; bis[2-(diphenylphosphino)phenyl] ether In tetrahydrofuran at 0℃; for 12h; Sealed tube; chemoselective reaction;	A n/a B n/a C 20 %Spectr.

...Expand

: 98-86-2
acetophenone

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 72 h / 20 °C 2: tetrahydrofuran / 2.5 h / -78 °C 3: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C 4: copper(II) choride dihydrate; lithium chloride / ethyl acetate / 1.5 h View Scheme
Multi-step reaction with 5 steps 1: bromine / diethyl ether / 0 - 20 °C 2: sodium formate; methanol / Reflux 3: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 5: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; dichloro(1,5-cyclooctadiene)palladium(II); silver trifluoromethanesulfonate / dichloromethane / 2 h / 80 °C View Scheme

: 70-11-1
α-bromoacetophenone

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 2.5 h / -78 °C 2: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C 3: copper(II) choride dihydrate; lithium chloride / ethyl acetate / 1.5 h View Scheme
Multi-step reaction with 4 steps 1: sodium formate; methanol / Reflux 2: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 4: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; dichloro(1,5-cyclooctadiene)palladium(II); silver trifluoromethanesulfonate / dichloromethane / 2 h / 80 °C View Scheme

: 582-24-1
1-phenyl-2-hydroxyethanone

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 3: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; dichloro(1,5-cyclooctadiene)palladium(II); silver trifluoromethanesulfonate / dichloromethane / 2 h / 80 °C View Scheme

: 1159837-56-5
1,2-dihydroxy-2-phenyl-3-butene

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; dichloro(1,5-cyclooctadiene)palladium(II); silver trifluoromethanesulfonate / dichloromethane / 2 h / 80 °C View Scheme

: 70-11-1
α-bromoacetophenone

A: (E)-4-chloro-2-phenylbut-2-enal

B: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere 2: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere 3: lithium chloride; copper(II) choride dihydrate / ethyl acetate / 1.5 h / Reflux; Inert atmosphere View Scheme

: 120609-13-4
1-Bromo-2-phenyl-3-buten-2-ol

A: (E)-4-chloro-2-phenylbut-2-enal

B: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere 2: lithium chloride; copper(II) choride dihydrate / ethyl acetate / 1.5 h / Reflux; Inert atmosphere View Scheme

: 930-88-1
N-methylmaleimide

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 621-84-1
O-benzyl carbamate

: N-(2-methyl-5-phenyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl)-benzyloxycarbonylamine

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 110℃;	98%

...Expand

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 762-21-0
acetylenedicarboxylic acid diethyl ester

: biphenyl-3,4-dicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With acetamide; toluene-4-sulfonic acid In 1-methyl-pyrrolidin-2-one at 120℃; for 24h;	91%

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 1352211-40-5
(1-bromovinyl)triisopropylsilane

: C21H34OSi

Conditions

Conditions	Yield
Stage #1: (1-bromovinyl)triisopropylsilane With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: (E/Z)-2-phenylcrotonaldehyde In tetrahydrofuran at -78℃; for 1h;	90%

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

lithium dimethylcuprate: lithium dimethylcuprate

: 2439-44-3
3-methyl-2-phenylbutanal

Conditions

Conditions	Yield
In diethyl ether at -23℃; for 0.25h;	78%

: 75-77-4
chloro-trimethyl-silane

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 107905-17-9
1-trimethylsilyloxy-2-phenyl-1,3-butadiene

Conditions

Conditions	Yield
With triethylamine; zinc(II) chloride at 50℃;	61%

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 28353-74-4
(E)-3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime

A: 1426022-60-7
4-methyl-3-phenyl-5,6-dihydrobenzo[h]quinoline

B: 1426022-62-9
2-methyl-3-phenyl-5,6-dihydrobenzo[h]quinoline

Conditions

Conditions	Yield
With copper(l) iodide; diisopropylamine In dimethyl sulfoxide at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;	A 41% B 13%

...Expand

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 28353-74-4
(E)-3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime

: 1426022-60-7
4-methyl-3-phenyl-5,6-dihydrobenzo[h]quinoline

Conditions

Conditions	Yield
With copper(l) iodide; pyrrolidinium perchlorate In dimethyl sulfoxide at 60℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; regioselective reaction;	36%

: 5526-38-5
4-hydroxy-6-phenyl-2H-pyran-2-one

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 1206159-77-4
(2RS)-2-methyl-3,7-diphenyl-2H,5H-pyrano[4,3-b]pyran-5-one

Conditions

Conditions	Yield
With calcium sulfate; 3-amino propanoic acid In isopropyl alcohol at 82℃; for 1h; domino Knoevenagel condensation/electrocyclization; Inert atmosphere;	34%

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 62-53-3
aniline

: 53646-85-8
1,3-diphenyl-1H-pyrrole

Conditions

Conditions	Yield
With iodine In toluene at 20℃; for 8h;	32%

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 75-16-1
methylmagnesium bromide

: 4743-68-4
3-phenyl-4-methyl-3-buten-2-ol

Conditions

Conditions	Yield
With diethyl ether

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 2-phenyl-crotonaldehyde-semicarbazone

: 557-93-7
2-bromoprop-1-ene

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

A: 38552-66-8
2-methyl-4-phenyl-hexa-1,4-dien-3-ol

B: 58654-03-8
3,4-dimethyl-pent-4-enal

Conditions

Conditions	Yield
(i) Mg, THF, (ii) /BRN= 1856381/, Et2O; Multistep reaction;

...Expand

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 5551-18-8
<1-Hydroxy-propen-(1)-yl>-benzol-formiat

Conditions

Conditions	Yield
With peracetic acid; diacetyl peroxide; acetic anhydride In acetic acid for 10.5h;

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 100-44-7
benzyl chloride

: 13881-18-0
3,5-Diphenyl-4-hydroxy-penten-(2)

Conditions

Conditions	Yield
(i) Mg, Et2O, (ii) /BRN= 1856381/; Multistep reaction;

: 96610-59-2
ethyl 2-butyl-3-oxooctanoate

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: (E)-2,4-Dibutyl-5-hydroxy-3-oxo-6-phenyl-oct-6-enoic acid ethyl ester

Conditions

Conditions	Yield
With n-butyllithium; sodium hydride Yield given. Multistep reaction;

: 16666-78-7
propylidenetriphenylphosphorane

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 3-Phenyl-2,4-heptadien

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 5927-18-4
trimethyl phosphonoacetate

: Methyl-4-phenyl-2,4-hexadienoat

Conditions

Conditions	Yield
(i) NaH, (ii) /BRN= 1856381/; Multistep reaction;

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 104-55-2
3-phenyl-propenal

: 2928-27-0
(1,1':4',1''-terphenyl)-2'-carbaldehyde

Conditions

Conditions	Yield
With magnesium oxide at 280℃; under 20 Torr;

: 4411-89-6
(E/Z)-2-phenylcrotonaldehyde

: 1504-75-2
3-(4-methylphenyl)acrylaldehyde

: 21235-95-0
2'-Formyl-4-methyl-p-terphenyl

Conditions

Conditions	Yield
With magnesium oxide at 280℃; under 20 Torr;

Benzeneacetaldehyde, alpha-ethylidene- Specification

The Benzeneacetaldehyde, alpha-ethylidene-, with the CAS registry number 4411-89-6, is also known as alpha-Phenylcrotonaldehyde. It belongs to the product categories of Alphabetical Listings; Flavors and Fragrances; O-P. Its EINECS registry number is 224-567-0. This chemical's molecular formula is C₁₀H₁₀O and molecular weight is 146.19. Its IUPAC name is called (E)-2-phenylbut-2-enal.

Physical properties of Benzeneacetaldehyde, alpha-ethylidene-: (1)ACD/LogP: 2.68; (2)ACD/LogD (pH 5.5): 2.68; (3)ACD/LogD (pH 7.4): 2.68; (4)ACD/BCF (pH 5.5): 63.59; (5)ACD/BCF (pH 7.4): 63.59; (6)ACD/KOC (pH 5.5): 679.94; (7)ACD/KOC (pH 7.4): 679.94; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.53; (11)Molar Refractivity: 45.6 cm³; (12)Molar Volume: 147.5 cm³; (13)Surface Tension: 35 dyne/cm; (14)Density: 0.99 g/cm³; (15)Flash Point: 95.9 °C; (16)Enthalpy of Vaporization: 50.98 kJ/mol; (17)Boiling Point: 271.6 °C at 760 mmHg; (18)Vapour Pressure: 0.00639 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-methoxy-1,3-diethoxy-2-phenylbutane. This reaction will need reagent 18percent aq. HCl. The reaction time is 1 hour with reaction temperature of 70 - 90 °C. The yield is about 77.8%.

Uses of Benzeneacetaldehyde, alpha-ethylidene-: it can be used to produce 1-trimethylsilyloxy-2-phenyl-1,3-butadiene at temperature of 50 °C. This reaction will need reagent triethylamine, zinc chloride. The yield is about 61%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC=C(C=O)C1=CC=CC=C1
(2)Isomeric SMILES: C/C=C(/C=O)\C1=CC=CC=C1
(3)InChI: InChI=1S/C10H10O/c1-2-9(8-11)10-6-4-3-5-7-10/h2-8H,1H3/b9-2-
(4)InChIKey: DYAOGZLLMZQVHY-MBXJOHMKSA-N

Product Name

2-PHENYL-2-BUTENAL

Synthetic route

Benzeneacetaldehyde, alpha-ethylidene- Specification

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