Product Name

  • Name

    Cinnamaldehyde

  • EINECS 203-213-9
  • CAS No. 104-55-2
  • Article Data711
  • CAS DataBase
  • Density 1.034 g/cm3
  • Solubility slightly soluble in water
  • Melting Point -9 - -4 °C(lit.)
  • Formula C9H8O
  • Boiling Point 246.8 °C at 760 mmHg
  • Molecular Weight 132.162
  • Flash Point 71.1 °C
  • Transport Information
  • Appearance yellow liquid with an odour of cinnamon
  • Safety 26-36/37
  • Risk Codes 36/37/38-43
  • Molecular Structure Molecular Structure of 104-55-2 (Cinnamaldehyde)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Propenal,3-phenyl-;3-Phenyl-2-propen-1-al;3-Phenyl-2-propenal;3-Phenyl-2-propenaldehyde;3-Phenyl-2-propene-1-al;3-Phenylacrolein;3-Phenylacrylaldehyde;3-Phenylpropenal;Abion CA;Benzylideneacetaldehyde;Cassia aldehyde;Cinnacure;Cinnamal;Cinnamic aldehyde;Cinnamite;Cinnamyl aldehyde;NSC16935;NSC 40346;Phenylacrolein;Zimtaldehyde;b-Phenylacrolein;Cinnamaldehyde/cinnamic aldehyde;
  • PSA 17.07000
  • LogP 1.89870

Synthetic route

3-Phenylpropenol
104-54-1

3-Phenylpropenol

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With dimethyl selenoxide In dichloromethane for 7h; Heating;100%
With 2,2'-bipyridylchromium peroxide In benzene for 1.25h; Heating;100%
With tert.-butylhydroperoxide; polystyrene-bound phenylselenic acid In tetrachloromethane for 63h; Heating;100%
cinnamyl-1,3-dithiane
26958-41-8

cinnamyl-1,3-dithiane

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With ammonium iodide; dihydrogen peroxide; sodium dodecyl-sulfate In water at 20℃; for 1h; micellar medium;100%
With dimethyl sulfoxide at 20℃; for 1h; Reagent/catalyst; Solvent;94%
With dihydrogen peroxide; iodine; sodium dodecyl-sulfate In water at 20℃; for 1h; Micellar solution;92%
3,3-diethoxyl-1-phenylprop-1-ene
7148-78-9

3,3-diethoxyl-1-phenylprop-1-ene

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With water at 20℃; for 2h;100%
With boron trifluoride diethyl etherate; tetraethylammonium iodide In chloroform for 2h; Heating;81%
With sulfuric acid In nitromethane for 48h; Ambient temperature; Yield given;
2-((E)-Styryl)-[1,3]dioxolane
83977-12-2, 5660-60-6

2-((E)-Styryl)-[1,3]dioxolane

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With water at 20℃; for 2h;100%
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 1h; Heating;97%
With tetrachlorosilane In dichloromethane at 20℃; for 0.25h;96%
(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With iodosylbenzene; 4 A molecular sieve; sodium ruthenate(VI) In dichloromethane at 20℃; for 3h; Oxidation;100%
With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 1-ethyl-3-methylimidazolium hexafluorophosphate In dichloromethane at 20℃; for 1h;95%
With N-Bromosuccinimide; β‐cyclodextrin In methanol; water; acetone at 20℃; for 8h;94%
3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 1h;100%
With bis(benzonitrile)palladium(II) dichloride; tert.-butylnitrite; oxygen; toluene-4-sulfonic acid; 1,3,5-trimethyl-benzene In tert-butyl alcohol at 25℃; under 760.051 Torr; for 7h;94%
With manganese(IV) oxide; benzyl-methyl-amine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 20℃; for 6h; Reagent/catalyst; Solvent;78%
cinnamaldehyde dimethylacetal
4364-06-1

cinnamaldehyde dimethylacetal

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With water at 20℃; for 2h;100%
With iron(III) p-toluenesulfonate hexahydrate In water at 20℃; for 4h;96%
2-hydroxy-4-phenyl-3-butenenitrile
61912-03-6

2-hydroxy-4-phenyl-3-butenenitrile

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With (η(6)-benzene)chloro[1,2-bis(diphenylphosphino)ethane]ruthenium(II) chloride In benzene at 120℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;100%
cinnamonitrile
4360-47-8

cinnamonitrile

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide at 60℃; for 6h; High pressure; Green chemistry;99.9%
With formic acid; platinum(IV) oxide In water at 55 - 60℃; for 20h;56%
1,1-diacetoxy-3-phenylprop-2-ene
37973-54-9, 64847-78-5

1,1-diacetoxy-3-phenylprop-2-ene

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With tin(ll) chloride In acetonitrile at 25℃; for 0.0333333h; Hydrolysis;99%
With pyrographite In dichloromethane for 0.25h; Heating;98%
With iron(II) sulfate In dichloromethane for 0.25h; Heating;98%
iodobenzene
591-50-4

iodobenzene

(E)-3-(tri-n-butylstannyl)-2-propenal
81925-30-6, 149538-53-4, 219726-39-3

(E)-3-(tri-n-butylstannyl)-2-propenal

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With Pd-NHC star polymer P3 In d7-N,N-dimethylformamide at 20℃; for 19h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling);99%
2-styryl-benzo[1,3]dithiole
68498-19-1

2-styryl-benzo[1,3]dithiole

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With tetrafluoroboric acid; mercury(II) oxide In tetrahydrofuran for 5h; Ambient temperature;98%
cinnamaldoxime
13372-81-1

cinnamaldoxime

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With 1H-imidazole; [bis(acetoxy)iodo]benzene; Cu(AAOPD) In acetonitrile at 20℃; for 0.166667h;98%
With benzyltriphenylphosphonium dichromate In acetonitrile for 0.333333h; Oxidation; Heating;97%
With 1,4-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane chlorochromate In acetonitrile for 0.25h; Heating;95%
trimethylsilyl cinnamyl ether
109283-53-6, 141427-94-3, 18042-41-6

trimethylsilyl cinnamyl ether

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With n-butyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.166667h; Heating;98%
With manganese(IV) oxide; aluminium trichloride In acetonitrile for 0.25h; Oxidation; Heating;93%
With N-benzyl-N,N-dimethyl anilinium peroxodisulfate In acetonitrile for 0.116667h; Reflux;93%
5,5-Dimethyl-2-((E)-styryl)-[1,3]dioxane

5,5-Dimethyl-2-((E)-styryl)-[1,3]dioxane

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With sodium perborate In acetic acid at 25℃; for 8h;98%
With iron(III) p-toluenesulfonate hexahydrate In water for 1h; Reflux;74%
With water at 80℃; for 24h;17%
2-styryl-1,3-oxathiolane
80563-94-6

2-styryl-1,3-oxathiolane

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With N-Bromosuccinimide; water In acetone at 20℃; for 1.66667h; Hydrolysis;98%
With Glyoxilic acid; Amberlyst 15 for 0.025h; microwave irradiation;93%
Stage #1: 2-styryl-1,3-oxathiolane In ethanol at 20℃;
Stage #2: With water In ethanol at 20℃;		86%
2-((E)-Styryl)-[1,3]dioxane
5663-34-3

2-((E)-Styryl)-[1,3]dioxane

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With iron(III) chloride hexahydrate; acetaldehyde In dichloromethane at 20℃; for 0.25h;98%
3-phenyl-2-propenyl tetrahydro-2H-pyran-2-yl ether
99441-44-8, 80356-15-6

3-phenyl-2-propenyl tetrahydro-2H-pyran-2-yl ether

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With chromium(VI) oxide; HZSM-5 zeolite for 0.0166667h; microwave irradiation;95%
With aluminium trichloride; tetramethylammonium chlorochromate In acetonitrile for 0.916667h; Heating;92%
With zinc dichromate(VI) at 20℃;90%
1,1-dipropionyloxy-3-phenylprop-2-ene

1,1-dipropionyloxy-3-phenylprop-2-ene

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol at 20℃; for 0.4h;95%
1,1-diisobutyryloxy-3-phenylprop-2-ene

1,1-diisobutyryloxy-3-phenylprop-2-ene

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In methanol at 20℃; for 1h;95%
3-Phenylpropenol
104-54-1

3-Phenylpropenol

A

3-Phenyl-1-propanol
122-97-4

3-Phenyl-1-propanol

B

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With oxygen; potassium hydroxide In chloroform; water at 10℃; under 760.051 Torr; for 8h;A 5%
B 95%
With C28H37ClOOsP2; oxygen In toluene at 120℃; under 760.051 Torr; for 24h;
With phosphinito complex of palladium(II) In N,N-dimethyl-formamide at 80℃; for 24h;A 6 %Spectr.
B 24 %Spectr.
cinnamyl chloride
2687-12-9

cinnamyl chloride

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With 1-dodecyl-3-methylimidazolium iron chloride; periodic acid at 30℃; for 2h;94%
With water; sodium hydroxide at 20℃; for 0.0833333h; Microwave irradiation;87%
With sodium periodate In dichloromethane at 40 - 50℃; Ionic liquid;85%
With trimethylamine-N-oxide In dichloromethane; dimethyl sulfoxide for 6h; -20 deg C to r.t.;60%
Multi-step reaction with 2 steps
1: 88 percent / dimethylformamide
2: 1.) PdCl2, NaCl, NaOAc; 2.) O2 / 1.) AcOH, reflux; 2.) CH3CN, irradiation λ=366 nm
View Scheme
2-styryl-1,3-dithiolane
5616-58-0

2-styryl-1,3-dithiolane

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With thionyl chloride; dihydrogen peroxide In acetonitrile at 25℃; for 0.0166667h;93%
With silica gel In neat (no solvent) at 20℃; for 0.05h;92%
With oxygen; 2,4,6-tris(p-chlorophenyl)pyrylium perchlorate In dichloromethane for 1h; Irradiation;41%
cinnamaldehyde oxime
59336-59-3

cinnamaldehyde oxime

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With quinolinium dichromate(VI) In acetonitrile for 1.5h; Heating;93%
With water In acetone for 0.025h; microwave irradiation;93%
With silica gel; iron(III) chloride for 0.00833333h; microwave irradiation;90%
1-Phenyl-2-propyn-1-ol
4187-87-5

1-Phenyl-2-propyn-1-ol

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
toluene-4-sulfonic acid; tetrabutylammonium perrhenate In dichloromethane for 2h; Ambient temperature;92%
With [Ag{μ2-N,S-(1,3,5-triaza-7-phosphaadamantane)=NP(=S)(OEt)2}]x[SbF6]x In water at 160℃; for 5h; Microwave irradiation;91%
With methanesulfonic acid; iron(II) chloride tetrahydrate In 1,2-dichloro-ethane at 60℃; for 3h; Meyer-Schuster Rearrangement;90%
1-phenylpropene
637-50-3

1-phenylpropene

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With tert.-butylhydroperoxide; Ru(2,4,13,15-tetraphenyl-1,5,12,16-tetraaza-tricyclo[14.2.2.06,11]eicosa-4,6(11),7,9,12-pentaene)Cl2 In acetonitrile at 20℃; for 3h; Reagent/catalyst; Irradiation;92%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water Ambient temperature; Yield given;
cinnamaldehyde semicarbazone
3839-82-5

cinnamaldehyde semicarbazone

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With NTPPPODS In water; acetonitrile for 0.416667h; Reflux;92%
With bismuth(III) chloride; benzyltriphenylphosphonium peroxymonosulfate In acetonitrile for 2h; Heating;75%
With aluminium trichloride; benzyltriphenylphosphonium chlorochromate In acetonitrile for 1.5h; Heating;75%
(α-styryl)(ethoxy)carbene chromium pentacarbonyl

(α-styryl)(ethoxy)carbene chromium pentacarbonyl

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With hexamethylenetetramine; water In tetrahydrofuran at 20℃; for 24h;92%
(E)-styrylaldehyde oxime
21737-13-3

(E)-styrylaldehyde oxime

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Conditions
ConditionsYield
With aluminium trichloride; 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate at 20℃; for 0.00722222h;92%
With 1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate In dichloromethane for 0.00722222h; Irradiation;92%
2-thioxo-4-thiazolidinone
141-84-4

2-thioxo-4-thiazolidinone

3-phenyl-propenal
104-55-2

3-phenyl-propenal

5-(3-phenyl-allylidene)-2-thioxo-thiazolidin-4-on e
15328-87-7

5-(3-phenyl-allylidene)-2-thioxo-thiazolidin-4-on e

Conditions
ConditionsYield
With ammonium acetate; acetic acid In toluene Reflux;100%
With thiourea; urea at 110℃; for 0.1h; Knoevenagel condensation; Neat (no solvent);91%
With sodium hydroxide
4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-phenyl-propenal
104-55-2

3-phenyl-propenal

N-(4-Methoxyphenyl)-3-phenylpropenaldimine
15286-52-9, 22835-33-2, 80542-40-1, 88315-63-3, 101535-86-8, 123525-44-0

N-(4-Methoxyphenyl)-3-phenylpropenaldimine

Conditions
ConditionsYield
piperidine In ethanol for 5h; Heating;100%
With magnesium sulfate In dichloromethane at 20℃;100%
In ethyl 2-hydroxypropionate; water at 20℃; for 0.025h;96%
N-Phenylhydroxylamine
100-65-2

N-Phenylhydroxylamine

3-phenyl-propenal
104-55-2

3-phenyl-propenal

cinnamaldehyde-(N-phenyl oxime )
37056-75-0, 1070670-27-7

cinnamaldehyde-(N-phenyl oxime )

Conditions
ConditionsYield
In chloroform at 0℃;100%
In water Ambient temperature;93%
ethylenediamine
107-15-3

ethylenediamine

3-phenyl-propenal
104-55-2

3-phenyl-propenal

N,N'-bis(styrylmethylene)ethane-1,2-diamine
3080-97-5

N,N'-bis(styrylmethylene)ethane-1,2-diamine

Conditions
ConditionsYield
In ethanol for 1h; Condensation; Heating;100%
With sodium hydrogen sulfate; silica gel for 0.0333333h; microwave irradiation;89%
In ethanol Reflux; Inert atmosphere; Schlenk technique;78%
aniline
62-53-3

aniline

3-phenyl-propenal
104-55-2

3-phenyl-propenal

N-(3-phenylallylidene)benzenamine
953-21-9

N-(3-phenylallylidene)benzenamine

Conditions
ConditionsYield
With zirconocene dichloride In dichloromethane at 40℃; Schlenk technique; Inert atmosphere;100%
With magnesium sulfate In dichloromethane at 20℃;100%
In ethyl 2-hydroxypropionate; water at 20℃; for 0.0666667h;98%
semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

3-phenyl-propenal
104-55-2

3-phenyl-propenal

cinnamaldehyde semicarbazone
3839-82-5

cinnamaldehyde semicarbazone

Conditions
ConditionsYield
With acetic acid In water for 0.5h; Reflux;100%
With aluminum oxide In water; tert-butyl alcohol for 0.0833333h;90%
With ethanol
In ethanol
3-phenyl-propenal
104-55-2

3-phenyl-propenal

acetophenone
98-86-2

acetophenone

1,5-diphenylpenta-2,4-dien-1-one
614-57-3, 29179-25-7, 132794-05-9, 134589-76-7, 135623-99-3

1,5-diphenylpenta-2,4-dien-1-one

Conditions
ConditionsYield
Stage #1: acetophenone With sodium hydroxide In ethanol; water at 0 - 5℃;
Stage #2: 3-phenyl-propenal In ethanol; water		100%
With poly(N-vinylimidazole) In neat (no solvent) at 20℃; for 0.666667h; Aldol Condensation; Sonication; Green chemistry;92%
With sodium hydroxide In ethanol; water90%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

Conditions
ConditionsYield
With formic acid; 3,7-dimethyl10-p-tolyl-5-deazaflavins at 120℃; for 25h;100%
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran Ambient temperature;99%
With 0.42C23H20N4O4*2Cl(1-)*Zn(2+)*10.16H2O*0.58Pd(2+)*0.58C23H20N4O4(1-); hydrogen In tetrahydrofuran at 20℃; under 760.051 Torr; for 1h;99%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

3-Phenylpropenol
104-54-1

3-Phenylpropenol

Conditions
ConditionsYield
With diphenylsilane; cesium fluoride at 25℃; for 0.05h;100%
With C28H28Cl2N4Pd; hydrogen In methanol at 30 - 35℃; under 760.051 Torr; for 8h; chemoselective reaction;100%
With C8H15BN2OS2; scandium tris(trifluoromethanesulfonate) In dichloromethane at 20℃; Reagent/catalyst; Schlenk technique; Inert atmosphere;100%
acetic anhydride
108-24-7

acetic anhydride

3-phenyl-propenal
104-55-2

3-phenyl-propenal

Acetic acid 1-phenylsulfanylmethyl-but-2-ynyl ester

Acetic acid 1-phenylsulfanylmethyl-but-2-ynyl ester

Conditions
ConditionsYield
With pyridine; dmap100%
5-chloro-1H-indole-2-carbohydrazide
20948-67-8

5-chloro-1H-indole-2-carbohydrazide

3-phenyl-propenal
104-55-2

3-phenyl-propenal

5-Chlor-N'-(styrylmethylen)-2-indolcarbohydrazid
97132-94-0

5-Chlor-N'-(styrylmethylen)-2-indolcarbohydrazid

Conditions
ConditionsYield
In ethanol for 3h; Heating;100%
ethylene glycol
107-21-1

ethylene glycol

3-phenyl-propenal
104-55-2

3-phenyl-propenal

2-((E)-Styryl)-[1,3]dioxolane
83977-12-2, 5660-60-6

2-((E)-Styryl)-[1,3]dioxolane

Conditions
ConditionsYield
aluminum oxide In tetrachloromethane for 24h; Heating;100%
With natural kaolinitic clay In benzene for 2h; Heating;93%
With cationite KU-2 (H+) In water; benzene at 80℃; Dean-Stark;90%
thiosemicarbazide
79-19-6

thiosemicarbazide

3-phenyl-propenal
104-55-2

3-phenyl-propenal

cinnamaldehyde thiosemicarbazone
5351-70-2

cinnamaldehyde thiosemicarbazone

Conditions
ConditionsYield
With acetic acid In water for 0.5h; Reflux;100%
In methanol90%
With hydrogenchloride In ethanol at 20℃; for 3h;90%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

3-phenyl-propenal
104-55-2

3-phenyl-propenal

cinnamyl-1,3-dithiane
26958-41-8

cinnamyl-1,3-dithiane

Conditions
ConditionsYield
With thionyl chloride; silica gel In benzene at 20℃; for 5h;100%
tellurium tetrachloride In 1,2-dichloro-ethane for 3h; Ambient temperature;99%
With lithium trifluoromethanesulfonate at 90℃; for 0.0833333h; Alkylation;98%
3-bromo-3,3-difluropropene
420-90-6

3-bromo-3,3-difluropropene

3-phenyl-propenal
104-55-2

3-phenyl-propenal

4,4-difluoro-1-phenylhexa-1,5-dien-3-ol
88257-89-0

4,4-difluoro-1-phenylhexa-1,5-dien-3-ol

Conditions
ConditionsYield
With indium In water at 20℃; for 3h; Addition;100%
With zinc In tetrahydrofuran 1.) 0 deg C to RT, 4.5 h; 2.) RT, overnight;74%
3-(benzimidazol-2-ylmethyl)thiazolidine-2,4-dione
105192-15-2

3-(benzimidazol-2-ylmethyl)thiazolidine-2,4-dione

3-phenyl-propenal
104-55-2

3-phenyl-propenal

3-(1H-Benzoimidazol-2-ylmethyl)-5-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-thiazolidine-2,4-dione
105192-22-1

3-(1H-Benzoimidazol-2-ylmethyl)-5-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-thiazolidine-2,4-dione

Conditions
ConditionsYield
With sodium acetate In acetic acid for 12h; Heating;100%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

phenylhydrazine
100-63-0

phenylhydrazine

cinnamaldehyde phenylhydrazone
1216-15-5

cinnamaldehyde phenylhydrazone

Conditions
ConditionsYield
piperidine In ethanol for 5h; Heating;100%
With oxidized single-walled carbon nanotubes(SWCNs-COOH) In ethanol at 80℃; for 0.75h;98%
With Dowex resin acid form In ethanol for 0.75h;88%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

1-methyl-1-aminoguanidinium iodide

1-methyl-1-aminoguanidinium iodide

N-Diaminomethylene-N-methyl-N'-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-diazenium; iodide

N-Diaminomethylene-N-methyl-N'-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-diazenium; iodide

Conditions
ConditionsYield
In methanol at 20℃; for 336h;100%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

benzylamine
100-46-9

benzylamine

1-benzyl-4-phenyl-1-aza-1,3-butadiene
77499-86-6, 99333-56-9, 119353-37-6, 60293-41-6

1-benzyl-4-phenyl-1-aza-1,3-butadiene

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 6h; Schlenk technique; Inert atmosphere;100%
With 1-butyl-3-methylimidazolium Tetrafluoroborate In neat (no solvent) at 60℃; for 2h; Reagent/catalyst; Inert atmosphere; Electrolysis;95%
In methanol at 20℃; Molecular sieve;79%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

2-cyano-5-phenyl-2,4-pentadien carboxylic acid methyl ester
85620-43-5

2-cyano-5-phenyl-2,4-pentadien carboxylic acid methyl ester

Conditions
ConditionsYield
aluminum oxide for 0.05h; Ambient temperature;100%
With diammonium phosphate In water at 20℃; Knoevenagel condensation;90%
With Porcine Pancreas Lipase In water; tert-butyl alcohol at 40℃; for 120h; Knoevenagel Condensation; Enzymatic reaction; stereoselective reaction;89%
With aluminum oxide; ammonium acetate for 0.0333333h; Knoevenagel condensation; microwave irradiation (850 watt);70%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

α-chloro-cinnamaldehyde
18365-42-9

α-chloro-cinnamaldehyde

Conditions
ConditionsYield
With pyridine; Phenylselenyl chloride In dichloromethane at 37℃; for 96h;100%
Multi-step reaction with 2 steps
1: chloroform; chlorine
2: glacial acetic acid; potassium acetate
View Scheme
Multi-step reaction with 2 steps
1: carbon tetrachloride; chlorine / -5 °C
2: aqueous sodium acetate
View Scheme
benzaldehyde
100-52-7

benzaldehyde

3-phenyl-propenal
104-55-2

3-phenyl-propenal

2-((E)-Styryl)-[1,3]dioxolane
83977-12-2, 5660-60-6

2-((E)-Styryl)-[1,3]dioxolane

Conditions
ConditionsYield
With monoaluminum phosphate In acetonitrile for 1.5h; Heating;100%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

(2E)-3-phenyl-2-propen-1-ol

A

o-terphenyl
84-15-1

o-terphenyl

B

3,3-bis(3-phenyl-2-propen-1-yl)pentane-2,4-dione
106536-22-5

3,3-bis(3-phenyl-2-propen-1-yl)pentane-2,4-dione

C

C18H16

C18H16

Conditions
ConditionsYield
With triphenylphosphine; palladium(II) acetylacetonate In 1,4-dioxane for 91h; Heating;A 43%
B 100%
C n/a
With triphenylphosphine; palladium(II) acetylacetonate In 1,4-dioxane for 24h; Heating;A 16%
B 89%
C 37%
...Expand
3-phenyl-propenal
104-55-2

3-phenyl-propenal

lithium tetrabutylindate

lithium tetrabutylindate

1-phenyl-1-hepten-3-ol
20157-19-1

1-phenyl-1-hepten-3-ol

Conditions
ConditionsYield
for 2h; Ambient temperature;100%
3-phenyl-propenal
104-55-2

3-phenyl-propenal

2-hydroxyethanethiol
60-24-2

2-hydroxyethanethiol

2-styryl-1,3-oxathiolane
80563-94-6

2-styryl-1,3-oxathiolane

Conditions
ConditionsYield
With PPA; silica gel In 1,2-dichloro-ethane at 20℃; for 0.5h;100%
TiCl4 on montmorillonite In dichloromethane for 1h; Heating;95%
bis(acetylacetonato)dioxidomolybdenum(VI) In acetonitrile at 20℃; for 3.5h;92%

Cinnamaldehyde History

 Cinnamaldehyde (CAS NO.104-55-2) was isolated from cinnamon essential oil in 1834 by Dumas and Péligot and synthesized in the laboratory by Chiozza in 1856.

Cinnamaldehyde Specification

1. Introduction of Cinnamaldehyde
Cinnamaldehyde is the organic compound that gives cinnamon its flavor and odor. This pale yellow, viscous liquid occurs naturally in the bark of cinnamon trees and other species of the genus Cinnamomum. The IUPAC Name of it is (E)-3-phenylprop-2-enal. 

2. Properties of Cinnamaldehyde
Index of Refraction: 1.577
Molar Refractivity: 42.32 cm3
Molar Volume: 127.7 cm3
Polarizability: 16.78×10-24cm3
Surface Tension: 38.9 dyne/cm
Density: 1.034 g/cm3
Flash Point: 71.1 °C
Enthalpy of Vaporization: 48.4 kJ/mol 
Melting Point: −9-−4 °C(lit.)
Boiling Point: 246.8 °C at 760 mmHg
Vapour Pressure: 0.0265 mmHg at 25°C 
Water Solubility: Slightly soluble 
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. 
Physical Appearance: yellow liquid with an odour of cinnamon
Product Categories: Pharmaceutical Intermediates;Aromatic Aldehydes & Derivatives (substituted);Alphabetical Listings;C-DFlavors and Fragrances;Certified Natural Products;Flavors and Fragrances

3. Structure Descriptors of Cinnamaldehyde
The molecule of cinnamaldehyde consists of a phenyl group attached to an unsaturated aldehyde. As such, the molecule can be viewed as a derivative of acrolein. Its color is due to the π → π* transition: increased conjugation in comparison with acrolein shifts this band towards the visible.

4. Toxicity of Cinnamaldehyde

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 1160mg/kg (1160mg/kg) BEHAVIORAL: COMA Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   FAO Nutrition Meetings Report Series. Vol. 44A, Pg. 16, 1967.
mouse LD50 intravenous 75mg/kg (75mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#07571,
mouse LD50 oral 2225mg/kg (2225mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION		 Yakugaku Zasshi. Journal of Pharmacy. Vol. 92, Pg. 135, 1972.
mouse LDLo parenteral 200mg/kg (200mg/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 7, Pg. 687, 1955.
rat LD50 oral 2220mg/kg (2220mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"		 Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

5. Safety Information of Cinnamaldehyde

Hazard Codes: IrritantXi
Risk Statements: 36/37/38-43 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R43:May cause sensitization by skin contact.
Safety Statements: 26-36/37 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 3
RTECS: GD6476000
F: 10-23
HS Code: 29122900

6. Preparation of Cinnamaldehyde
Although Cinnamaldehyde is obtained from Chinese cassia oils, it is synthesized by action of alkali upon a mixture of benzaldehyde and acetaldehyde.
      C6H5CH=O + CH3CH=O → C6H5CH=CHCH=O
This and most other products for fragrances must be purified by, for example, vacuum fractionation.

7. Use of Cinnamaldehyde
1) The extensive use for Cinnamaldehyde is as a flavoring.Concentrations required for flavoring food items like chewing gum,  candy, ice cream,and beverages range from 9 to 4900 ppm (that is, less than 0.5%).
2) Cinnamaldehyde is used in some perfumes of natural, sweet, or fruity scents. Almond, apricot, butterscotch, and other aromas may partially employ the compound for their pleasant smells.
3) Cinnamaldehyde can be used as a food adulterant; powdered beechnut husk aromatized with cinnamaldehyde can be marketed as powdered cinnamon.
4) Cinnamaldehyde is also used as a fungicide. .

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