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Chemical Structure| 104-55-2 Chemical Structure| 104-55-2
Chemical Structure| 104-55-2

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Cinnamaldehyde is a major and a bioactive compound isolated from the leaves of Cinnamomum osmophloeum kaneh. Cinnamaldehyde is a cytokine production inhibitor. Cinnamaldehyde has anti-bacteria, anti-oxidation, and anti-inflammatory properties .

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Product Details of Cinnamaldehyde

CAS No. :104-55-2
Formula : C9H8O
M.W : 132.16
SMILES Code : O=CC=CC1=CC=CC=C1
MDL No. :MFCD00007000
InChI Key :KJPRLNWUNMBNBZ-QPJJXVBHSA-N
Pubchem ID :637511

Safety of Cinnamaldehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H317-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of Cinnamaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 104-55-2 ]

[ 104-55-2 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 14447-15-5 ]
  • [ 104-55-2 ]
  • 2-cyano-5-phenyl-penta-2,4-dienoic acid propyl ester [ No CAS ]
  • 2
  • [ 2002-24-6 ]
  • [ 104-55-2 ]
  • [ 138558-09-5 ]
  • 2-[bis-(3-phenyl-propyl)-amino]-ethanol [ No CAS ]
  • 3
  • [ 30709-67-2 ]
  • [ 104-55-2 ]
  • [ 72192-67-7 ]
  • 4
  • [ 35661-51-9 ]
  • [ 104-55-2 ]
  • [ 74105-58-1 ]
  • 5
  • [ 84-67-3 ]
  • [ 151-50-8 ]
  • [ 104-55-2 ]
  • [ 139555-30-9 ]
  • 6
  • [ 83465-22-9 ]
  • [ 104-55-2 ]
  • N-(3-phenylallyl)valiolamine [ No CAS ]
  • 8
  • [ 7647-01-0 ]
  • 3-bromo-<i>N</i>-(2,3-dibromo-3-phenyl-propyliden)-aniline [ No CAS ]
  • [ 615-55-4 ]
  • [ 104-55-2 ]
  • 9
  • [ 57611-47-9 ]
  • [ 104-55-2 ]
  • methyl 3-benzyl-6-hydroxy-9-oxo-8-phenyl-azabicyclo[3.3.1]nonane-1-carboxylate [ No CAS ]
  • methyl 3-benzyl-6-hydroxy-9-oxo-8-phenyl-azabicyclo[3.3.1]nonane-1-carboxylate [ No CAS ]
  • methyl 3-benzyl-6-hydroxy-9-oxo-8-phenyl-azabicyclo[3.3.1]nonane-1-carboxylate [ No CAS ]
  • 10
  • [ 34800-90-3 ]
  • [ 104-55-2 ]
  • 1-(1-naphthylacetyl)-2-cinnamylidenehydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.0% In ethanol;Reflux; General procedure: solutionof acid hydrazide (0.01 mol) and appropriate benzaldehyde/acetophenone (0.01 mol) in ethanol was refluxed for 5-6 h. The precipitated title compounds were then filtered off, washed with water and recrystallized from ethanol.
  • 11
  • [ 92138-20-0 ]
  • [ 104-55-2 ]
  • [ 955117-18-7 ]
YieldReaction ConditionsOperation in experiment
In isopropyl alcohol; for 3h;Heating / reflux; Example 2 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 20 mg Huperzine A, and 77 mg cinnamaldehyde were refluxed in 2 mL isopropanol for 3 hours. Solvent was removed under vacuum. The crude reaction mixture was dissolved in 3 mL anhydrous THF and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H).
In isopropyl alcohol; for 3h;Heating / reflux; Example 2 (5R,9R,11E)-5-(3-phenylprop-2-en-1-ylideneamino)-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-5,9-methanocycloocta[b]pyridin-2(1H)-one 20 mg of Huperzine A, 77 mg of cinnamaldehyde were refluxed in 2 mL of isopropanol for 3 hours, and then solvent was removed under vacuum, 3 mL of anhydrous THF added and purified with prep. TLC (CHCl3: methanol=9:1) to give 28 mg of title product. MS: 357 (M+H).
  • 12
  • [ 71510-95-7 ]
  • [ 104-55-2 ]
  • C15H19NO4 [ No CAS ]
  • [ 323203-12-9 ]
  • 13
  • [ 35613-44-6 ]
  • [ 104-55-2 ]
  • [ 1198328-55-0 ]
  • 14
  • [ 399-25-7 ]
  • [ 104-55-2 ]
  • C17H16FNO3 [ No CAS ]
  • 15
  • [ 399-25-7 ]
  • [ 104-55-2 ]
  • [ 1296869-83-4 ]
  • 16
  • [ 104-55-2 ]
  • [ 13214-64-7 ]
  • [ 68766-78-9 ]
  • 17
  • [ 865370-16-7 ]
  • [ 104-55-2 ]
  • [ 1374003-26-5 ]
  • C19H24N2O5 [ No CAS ]
  • [ 1374003-77-6 ]
  • 18
  • [ 606-25-7 ]
  • [ 104-55-2 ]
  • C19H15NO2S [ No CAS ]
  • 19
  • [ 104-55-2 ]
  • [ 5234-26-4 ]
  • C19H17NO2 [ No CAS ]
  • 20
  • [ 14208-35-6 ]
  • [ 104-55-2 ]
  • C21H17NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In ethanol; at 20℃; To a clear solution of 3a (1mmol) in EtOH containing 2, 4, 6-trimethoxy benzaldehyde (1mmol), 40% KOH was added and the resulting reaction mixture was stirred for complition of the reaction at r.t. (TLC control). The separated solid was filtered, washed with excess of water, neutralized with dil HCl, dried over anhydrous Na2SO4, recrystallised from ethanol to obtain product 13. The product was pure enough for further reactions.
  • 21
  • [ 456-14-4 ]
  • [ 104-55-2 ]
  • [ 76128-69-3 ]
YieldReaction ConditionsOperation in experiment
77% With oxygen; potassium hydroxide; In dimethyl sulfoxide; at 120℃; under 760.051 Torr; for 12h;Green chemistry; General procedure: A mixture of benzamidine hydrochloride 1a (0.25mmol), cinnamaldehyde 2a (0.30mol) and KOH (0.50mmol, 2equiv.) was stirred in DMSO (1.0mL) under 1atm O2 atmosphere at 120°C for 12h. After completion of the reaction (monitored by TLC), water (10mL) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The combined organic layers were then dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the desired product 3aa as a white solid (using the mixture of petroleum ether and ethyl acetate as eluents).
  • 22
  • [ 57297-29-7 ]
  • [ 104-55-2 ]
  • 2-cyclopropyl-4-phenyl-pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With oxygen; potassium hydroxide; In dimethyl sulfoxide; at 120℃; under 760.051 Torr; for 12h;Green chemistry; General procedure: A mixture of benzamidine hydrochloride 1a (0.25mmol), cinnamaldehyde 2a (0.30mol) and KOH (0.50mmol, 2equiv.) was stirred in DMSO (1.0mL) under 1atm O2 atmosphere at 120°C for 12h. After completion of the reaction (monitored by TLC), water (10mL) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The combined organic layers were then dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the desired product 3aa as a white solid (using the mixture of petroleum ether and ethyl acetate as eluents).
  • 23
  • [ 57497-39-9 ]
  • [ 104-55-2 ]
  • [ 109460-99-3 ]
  • 24
  • [ 78364-55-3 ]
  • [ 104-55-2 ]
  • C16H12FN3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 70 - 80℃; for 3h; General procedure: The mixture of <strong>[78364-55-3]6-fluoro-2-hydrazinylbenzo[d]thiazole</strong> (2) (0.01 mol) and benzalde-hyde/substituted benzaldehyde (0.01 mol) was reuxed in ethanol (15 ml) at 70?80 °C for 3 h. The separated product obtained was ltered off, washed withdistilled water and recrystallized from methanol to give the correspondinghydrazone. The product obtained was further dissolved in acetic acid (20 ml) atroom temperature followed by the addition of sodium acetate (0.5 g). Bromine(2 mmol) in acetic acid (10 ml) was added dropwise to the reuxing reactionmixture. After 1 h, the mixture was poured onto crushed ice (100 g). The precipitateobtained was ltered off and crystallized from ethanol-dimethylformamide (1:1) togive crystals of (3a?3t).
  • 25
  • [ 4187-87-5 ]
  • [ 90-63-1 ]
  • [ 104-55-2 ]
  • 26
  • [ 104-53-0 ]
  • [ 399-25-7 ]
  • [ 104-55-2 ]
  • (S)-3-benzyl-5-(2-fluorophenyl)-6-phenethyl-3,4-dihydro-2H-pyran-2-one [ No CAS ]
  • 27
  • [ 39549-79-6 ]
  • [ 104-55-2 ]
  • 7-methyl-2-phenethylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In toluene; at 120℃; for 12h;Inert atmosphere; Under nitrogen atmosphere, <strong>[39549-79-6]2-amino-4-methylbenzamide</strong> (150 mg, 1 mmol), [Cp*IrCl2]2 (8 mg, 0.01 mmol, 1 molpercent), toluene (1.0 mL), cinnamaldehyde (132 mg, 1 mmol)Add to a 25 mL Schlenk reaction flask.The mixture was reacted at 120°C for 12 hours and then cooled to room temperature.The solvent was removed in vacuo under reduced pressure and then purified by column chromatography (developer: ethyl acetate/petroleum ether) to give the pure target compound, yield: 80percent.
  • 28
  • [ 5900-59-4 ]
  • [ 104-55-2 ]
  • 7-chloro-2-phenylethylquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; In toluene; at 120℃; for 12h;Inert atmosphere; Under nitrogen protection, <strong>[5900-59-4]2-amino-4-chlorobenzamide</strong> (171 mg, 1 mmol), [Cp*IrCl2]2 (8 mg, 0.01 mmol, 1 molpercent), toluene (1.0 mL), cinnamaldehyde (132 mg, 1 mmol)Add 25mL Schlenk reaction flasks one by one.The mixture was reacted at 120°C for 12 hours and then cooled to room temperature.The solvent was removed in vacuo under reduced pressure and then purified by column chromatography (developer: ethyl acetate/petroleum ether) to give the pure target compound in a yield of 86
  • 29
  • [ 525-03-1 ]
  • [ 104-55-2 ]
  • (E)-N-((E)-3-phenylallylidene)-9H-fluoren-9-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; for 0.5h;Molecular sieve; 9H-fluoren-9-amine (English name: 9H-fluoren-9-amine, 1 mmol), cinnamaldehyde (1 mmol), stirred with molecular sieve (0.3 g) in dichloromethane (5 ml) at room temperature for half time Hours and then filtered to remove the solvent to give Substrate-1.1-5.
  • 30
  • [ 104-55-2 ]
  • [ 122-72-5 ]
  • (R*,R*)-6-oxo-3,4-diphenylhexyl acetate [ No CAS ]
  • (R*,S*)-6-oxo-3,4-diphenylhexyl acetate [ No CAS ]
  • 31
  • [ 15181-11-0 ]
  • [ 104-55-2 ]
  • (S)-4-(3,5-di-tert-butylphenyl)-3-phenylbutanal [ No CAS ]
  • (R)-4-(3,5-di-tert-butylphenyl)-3-phenylbutanal [ No CAS ]
  • 32
  • [ 1190-39-2 ]
  • [ 104-55-2 ]
  • dibutyl (E)-2-(3-(dimethyl(phenyl)silyl)-3-phenylprop-1-en-1-yl)malonate [ No CAS ]
  • dibutyl (E)-2-(1-(dimethyl(phenyl)silyl)-3-phenylallyl)malonate [ No CAS ]
  • 33
  • [ 1190-39-2 ]
  • [ 104-55-2 ]
  • C20H26O4 [ No CAS ]
  • 34
  • [ 41220-29-5 ]
  • [ 104-55-2 ]
  • [ 19006-81-6 ]
  • 35
  • [ 6761-52-0 ]
  • [ 104-55-2 ]
  • 3-amino-N'-(3-phenylprop-2-en-1-ylidene)pyrazine-2-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% for 0.166667h;Microwave irradiation; General procedure: Second step consists of condensation of <strong>[6761-52-0]3-aminopyrazine-2-carbohydrazide</strong> (0.5 gm, 0.003 mol) with aromatic aldehydes (0.5 gm, 0.008 mol) using microwaveirradiation (8 - 10 min, 350 W). After cooling and filtration,the product was recrystallized using ethanol [6, 9] (Fig. 1).
 

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