Welcome to LookChem.com Sign In|Join Free

CAS

  • or

104-55-2

Post Buying Request

104-55-2 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

104-55-2 Usage

Chemical Description

Cinnamaldehyde and crotonaldehyde are specific examples of a,b-unsaturated aldehydes.

Description

Cinnamaldehyde, also known as cinnamic aldehyde, benzylidene acetaldehyde, phenylacrolein, 3-phenylpropenal, or 3-phenyl-2-propenal, is a saturated aldehyde with an aromatic ring. It is a yellowish, oily liquid at room temperature, characterized by a strong, pungent, spicy, and cinnamon-like odor. It is naturally found in cinnamon leaves and bark, as well as in some essential oils and other plant products. Cinnamaldehyde is insoluble in water and many organic solvents but is miscible with alcohol and other flavoring oils. Exposure to air can result in thickening and oxidation.

Uses

Used in Flavor and Perfume Industry:
Cinnamaldehyde is used as a flavoring agent and an ingredient in fragrances for a variety of products, including soft drinks, ice creams, toothpaste, pastries, and chewing gum. It is also a common ingredient in perfumes for household products such as deodorizers, detergents, and soap. Its natural occurrence is in cinnamon, balsam of Tolu and Peru, hyacinth plant, and spices.
Used in Agriculture:
Cinnamaldehyde serves as an antifungal agent, corn rootworm attractant, and dog and cat repellent in the agricultural industry. It can be used on soil casing for mushrooms, row crops, turf, and all food commodities. However, it is not listed for use in EU countries.
Used in Insect Control:
Cinnamaldehyde has been used as an attractant for insect control, making it a valuable tool in managing pest populations in various settings.
Used in Corrosion Inhibition and Metal Coating:
Cinnamaldehyde has also found applications in the preparation of corrosion inhibitors and as a coating for metals, demonstrating its versatility in industrial uses.
Taste and Aroma Threshold Values:
Cinnamaldehyde has a taste threshold value of 0.5 ppm, with a spicy, cinnamon, and cinnamon bark taste. Its aroma threshold values are detectable at 50 to 750 ppb, indicating its potent and distinctive scent.

Air & Water Reactions

Thickens on exposure to air. May be unstable to prolonged exposure to air. Slightly water soluble .

Reactivity Profile

Cinnamaldehyde reacts with sodium hydroxide owing to aerobic oxidation.

Health Hazard

Cinnamaldehyde can cause moderate to severeskin irritation. Exposure to 40 mg in48 hours produced a severe irritation effecton human skin. The toxicity of this compoundwas low to moderate on test subjects,depending on the species and the toxicroutes. However, when given by oral routein large amounts, its poisoning effect wassevere. Amounts greater than 1500 mg/kghave produced a wide range of toxic effectsin rats, mice, and guinea pigs. The symptomswere respiratory stimulation, somnolence,convulsion, ataxia, coma, hypermotility, anddiarrhea.LD50 value, oral (guinea pigs): 1150 mg/kgCinnamaldehyde is a mutagen. Its carcinogeniceffect is not established.

Fire Hazard

Cinnamaldehyde is combustible.

Trade name

ADIOS?; ZIMTALDEHYDE?; ZIMTALDEHYDE? LIGHT

Contact allergens

This perfumed molecule is used as a fragrance in perfumes, a flavoring agent in soft drinks, ice creams, dentifrices, pastries, chewing-gum, etc. It can induce both contact urticaria and delayed-type reactions. It can be responsible for dermatitis in the perfume industry or in food handlers. Cinnamic aldehyde is contained in “fragrance mix.” As a fragrance allergen, it has to be mentioned by name in cosmetics within the EU.

Anticancer Research

This is promising in antitumor activity against NSCLC cells. The cells were inducedin apoptosis and also the epithelial-mesenchymal transition was reversed affectingthe Wnt/b-catenin pathway (Bouyahya et al. 2016).

Safety Profile

Poison by intravenous and parenteral routes. Moderately toxic by ingestion and intraperitoneal routes. A severe human skin irritant. Mutation data reported. Combustible liquid. May ipte after a delay period in contact with NaOH. When heated to decomposition it emits acrid smoke and fumes. See also ALDEHYDES.

Synthesis

By isolation from natural sources; synthetically, by condensation of benzaldehyde with acetaldehyde in the presence of sodium or calcium hydroxide.

Potential Exposure

Botanical fungicide and insecticide. Used as an antifungal agent, corn rootworm attractant, and dog and cat repellent. Can be used on soil casing for mushrooms, row crops, turf, and all food commodities. Not listed for use in EU countries.

Shipping

UN1989 Aldehydes, n.o.s., Hazard Class: 3; Labels: 3-Flammable liquid

Incompatibilities

Aldehydes are frequently involved in selfcondensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, ketones, azo dyes, caustics, boranes, hydrazines

Waste Disposal

Incineration. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.

Check Digit Verification of cas no

The CAS Registry Mumber 104-55-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 104-55:
(5*1)+(4*0)+(3*4)+(2*5)+(1*5)=32
32 % 10 = 2
So 104-55-2 is a valid CAS Registry Number.
InChI:InChI=1/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4-

104-55-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Cinnamaldehyde

1.2 Other means of identification

Product number -
Other names Cinnamyl aldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-55-2 SDS

104-55-2Synthetic 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

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

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%
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%

104-55-2Related news

Platinum catalysed aerobic selective oxidation of Cinnamaldehyde (cas 104-55-2) to cinnamic acid08/11/2019

Aerobic selective oxidation of allylic aldehydes offers an atom and energy efficient route to unsaturated carboxylic acids, however suitable heterogeneous catalysts offering high selectivity and productivity have to date proved elusive. Herein, we demonstrate the direct aerobic oxidation of cinn...detailed

104-55-2Relevant articles and documents

Chemoselective deprotection of 1,3-oxathiolanes using Amberlyst 15 and glyoxylic acid under solvent free conditions

Chavan,Soni,Kamat

, p. 1251 - 1252 (2001)

Carbonyl compounds were regenerated from corresponding 1,3-oxathiolanes via equilibrium exchange with glyoxylic acid and Amberlyst 15 as the heterogeneous catalyst, under solvent free conditions.

Highly enantioselective control of dynamic cascade transformations by dual catalysis: Asymmetric synthesis of polysubstituted spirocyclic oxindoles

Afewerki, Samson,Ma, Guangning,Ibrahem, Ismail,Liu, Leifeng,Sun, Junliang,Crdova, Armando

, p. 1266 - 1272 (2015)

The highly enantioselective (up to >99.5:0.5 er) synthesis of polysubstituted spirocyclic oxindoles with four new contiguous stereocenters, including the spiro all-carbon quaternary center, is disclosed. It is accomplished by the highly stereoselective control of a dynamic conjugate/intramolecular allylic alkylation relay sequence based on the synergistic cooperation of metal and chiral amine catalysts in which the careful selection of organic ligand, metal complex, and chiral amine is essential. The intramolecular C-C bond-forming step occurred only when both the metal and chiral amine catalysts were present. (Chemical Equation Presented).

A convenient oxidative deprotection of tetrahydropyranyl ethers with iron (III) nitrate and clay under microwave irradiation in solvent free conditions

Heravi, Majid M.,Ajami, Dariush,Mojtahedi, Mohammad M.,Ghassemzadeh, Mitra

, p. 561 - 562 (1999)

The efficient and environmentally benign oxidative deprotection of tetrahydropyranyl ethers using montmorillonite supported iron(III) nitrate under microwave irradiation under solvent free conditions is described.

Silica gel supported chromium trioxide: An efficient reagent for oxidative cleavage of oximes to carbonyl compounds under mild condition

Bendale, Pravin M.,Khadilkar, Bhushan M.

, p. 665 - 669 (2000)

A facile, efficient oxidative deblocking of aldoximes and ketoximes to their corresponding aldehydes and ketones have been achieved by using silica gel supported chromium trioxide.

Preparation and characterization of laccases immobilized on magnetic nanoparticles and their application as a recyclable nanobiocatalyst for the aerobic oxidation of alcohols in the presence of TEMPO

Rouhani, Shamila,Rostami, Amin,Salimi, Abdollah

, p. 26709 - 26718 (2016)

Laccase from Trametes versicolor was immobilized on a modified magnetic nanoparticle (MNP-Laccase) through a covalent attachment method. The morphology, structure, magnetic property and chemical composition of the immobilized laccase (MNP-Laccase) were characterized using scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), alternating gradient force magnetometry (AGFM), energy-dispersive X-ray spectroscopy (EDX) and thermogravimetric analysis (TGA) techniques. The MNPs-Laccase retained the activity and exhibited higher resistance to pH and temperature changes. We have used MNPs-Laccase as a magnetically recoverable nanobiocatalyst for the mild, environmentally friendly and selective aerobic oxidation of benzylic and allylic alcohols to corresponding aldehydes in the presence of TEMPO as a redox mediator at room temperature. The magnetic nanobiocatalyst was easily and rapidly recovered by applying an external magnet device and reused up to 6 reaction runs without considerable loss of reactivity.

Catalytic oxidation of aromatic oxygenates by the heterogeneous catalyst Co-ZIF-9

Zakzeski, Joseph,Dbczak, Agnieszka,Bruijnincx, Pieter C.A.,Weckhuysen, Bert M.

, p. 79 - 85 (2011)

The catalytic activity of Co-ZIF-9, a zeolitic imidazolate framework of sodalite topology, in the oxidation of small aromatic molecules including phthalan, vanillyl alcohol, guaiacol, syringol, veratryl alcohol, and cinnamyl alcohol by molecular oxygen has been investigated. Co-ZIF-9 selectively oxidized the substrates and thus represents a promising heterogeneous catalyst for the oxidation of small aromatic substrates. Phthalan was converted to three different products, i.e. phthalide, phthalaldehyde, and small amounts of phthalic acid. In addition to phthalan, the alcohol functionality of vanillyl alcohol, veratryl alcohol, and cinnamyl alcohol was also similarly oxidized to yield the corresponding aldehydes in high yields and excellent selectivity. The effect of solvent, temperature and NaOH addition on the Co-ZIF-9 catalytic system has been studied. The presence of NaOH in the solution greatly enhanced the oxidation activity. The structure and stability of the heterogeneous catalyst was probed by UV-vis diffuse reflection spectroscopy, confirming the coordination geometry of cobalt in the catalyst framework, thermal gravimetric analysis, establishing the thermal stability of the structure, and XRD to monitor crystallinity of the catalyst. The heterogeneous nature of the catalyst was established by a hot filtration experiment, ICP analysis of the liquid phase, and by UV-vis absorption spectroscopy on the hot filtered reaction mixture.

-

Lalancette et al.

, p. 3058 (1972)

-

Controllable Encapsulation of "clean" Metal Clusters within MOFs through Kinetic Modulation: Towards Advanced Heterogeneous Nanocatalysts

Liu, Hongli,Chang, Lina,Bai, Cuihua,Chen, Liyu,Luque, Rafael,Li, Yingwei

, p. 5019 - 5023 (2016)

Surfactant-free tiny Pt clusters were successfully encapsulated within MOFs with controllable size and spatial distribution by a novel kinetically modulated one-step strategy. Our synthesis relies on the rational manipulation of the reduction rate of Pt i

Synthesis, characterization, and catalytic activity of a water soluble copper(II) and nickel(II) heterobimetallic complex [CuNi(μ-OH)(μ-OH2)(μ-OAc)(bpy)2](ClO4)2 in aqueous medium in the absence of a base and co-catalyst

Lal, Ram A.,Kumar, Arvind,Syiemlieh, Ibanphylla,Kurbah, Sunshine D.

, p. 2722 - 2735 (2017)

A copper(II)–nickel(II)-based catalyst system has been synthesized and characterized by elemental analysis, molar conductance, mass spectra, magnetic moment, EPR, UV-Vis, IR spectroscopy, and cyclic voltammetry. The structure of the complex was established by X-ray crystallography. The complex is an efficient catalyst, which oxidizes primary and secondary alcohols to the corresponding aldehydes and ketones at 70?°C employing 15% H2O2 as the oxidant in the absence of a base and co-catalyst.

Synthetic scope of Ru(OH)x/Al2O3-catalyzed hydrogen-transfer reactions: An application to reduction of allylic alcohols by a sequential process of isomerization/meerwein-ponndorf-verley-iype reduction

Kim, Jung Won,Koike, Takeshi,Kotani, Miyuki,Yamaguchi, Kazuya,Mizuno, Noritaka

, p. 4104 - 4109 (2008)

Reduction of allylic alcohols can be promoted efficiently by the supported ruthenium catalyst Ru(OH)x/Al2O3. Various allylic alcohols were converted to saturated alcohols in excellent yields by using 2-propanol without any additives. This Ru(OHx/Al 2O3-catalyzed reduction of a dienol proceeds only at the allylic double bond to afford the corresponding enol, and chemoselective isomerization and reduction can be realized under similar conditions. The catalysis is truly heterogeneous and the high catalytic performance can be maintained during at least three recycles of the Ru(OH)x/Al 2O3 catalyst. The transformation of allylic alcohols to saturated alcohols consists of three sequential reactions: oxidation of allylic alcohols to α,β-un-saturated carbonyl compounds; reduction of α,β-unsaturated carbonyl compounds to saturated carbonyl compounds; and reduction of saturated carbonyl compounds to saturated alcohols.

Oxidation of alcohols to carbonyl compounds with a new potassium permanganate adsorbed on Kieselguhr reagent

Lou, Ji-Dong,Lou, Wen-Xing

, p. 3697 - 3699 (1997)

A new reagent, potassium permanganate adsorbed on kieselguhr, suitable for the oxidation of alcohols to the corresponding carbonyl compounds is described.

Highly efficient, organocatalytic aerobic alcohol oxidation

Shibuya, Masatoshi,Osada, Yuji,Sasano, Yusuke,Tomizawa, Masaki,Iwabuchi, Yoshiharu

, p. 6497 - 6500 (2011)

5-Fluoro-2-azaadamantane N-oxyl (5-F-AZADO) realizes a simple, organocatalytic aerobic alcohol oxidation system that has a wide scope under mild conditions at ambient pressure and temperature and is weakly acidic and halogen- and transition-metal-free. The oxoammonium nitrate (5-F-AZADO +NO3-) works as a bifunctional catalyst of 5-F-AZADO and NOx that enables the catalytic aerobic oxidation of alcohols by itself (a metal-salt-free system).

Unveiling of a Trinuclear Cyclic Peroxidovanadate: A Potential Oxidant in Vanadium-Catalyzed Reactions

Krivosudsky, Luká?,Schwendt, Peter,Gyepes, Róbert

, p. 6306 - 6311 (2015)

The first peroxidovanadium trimer was prepared in the form of its tetrabutylammonium salt, (NBu4)3[V3O3(O2)6]·2H2O. Its X-ray structure analysis revealed a unique cyclic structur

Development of manganese(VI) oxidising agents soluble in organic solvents

Ellis, Rhys,Lee, Kee-Han,Ainsworth, Matthew,Kerr, Alexander,Viseux, Eddy M. E.

, p. 1371 - 1373 (2012)

Two manganate(VI) reagents have been prepared from permanganate salts that show excellent oxidising properties in common organic solvents. Georg Thieme Verlag Stuttgart · New York.

Barium dichromate [BaCr2O7], a mild reagent for oxidation of alcohols to their corresponding carbonyls in non-aqueous polar aprotic media

Mottaghinejad, Enayatollah,Shaafi,Ghasemzadeh

, p. 8823 - 8824 (2004)

Barium dichromate is used as a mild oxidizing agent for the selective conversion of primary and secondary alcohols to their corresponding aldehydes and ketones, respectively. Over-oxidation does not occur and primary alcohols undergo oxidation to the aldehyde. Primary and secondary benzylic alcohols are oxidized faster and more efficiently. Barium dichromate is used as a mild oxidizing agent for the selective conversion of primary and secondary alcohols to their corresponding aldehydes and ketones, respectively. Over-oxidation does not occur and primary alcohols undergo oxidation to the aldehyde. Primary and secondary benzylic alcohols are oxidized faster and more efficiently.

Selective aerobic oxidation of alcohols by using manganese oxide nanoparticles as an efficient heterogeneous catalyst

Sun, Hua-Yin,Hua, Qing,Guo, Feng-Feng,Wang, Zhi-Yong,Huang, Wei-Xin

, p. 569 - 573 (2012)

Manganese oxide (Mn3O4) nanoparticles have been successfully innovated to be efficient catalysts not only for the aerobic oxidation of various alcohols to aldehydes or ketones, but also for the selective aerobic oxidation of mixed alcohols. Copyright

Immobilized magnetic nano catalyst for oxidation of alcohol

Bhat, Pooja B.,Rajarao, Ravindra,Sahajwalla, Veena,Bhat, Badekai Ramachandra

, p. 42 - 49 (2015)

Covalent attachment of Schiff base on magnetic nanoparticles yielded good selectivity for oxidation of alcohols. The ferromagnetic interaction in the complex added comprehensive advantage in enhancing the catalytic activity of the nanocatalyst. A greener approach for alcohol oxidation was achieved in solventless method with good yield (>78%). Leaching experiments confirmed a strong interaction between magnetic support and complex. The catalyst showed significant conversion even after 5 catalytic runs.

Effective oxidation of alcohols under heterogeneous conditions with a new reagent: Manganese dioxide supported on graphite

Lou, Ji-Dong,Lu, Xiu Lian,Huang, Li-Hong,Wang, Qiang,Zou, Xiao-Nan

, p. 1342 - 1345 (2011)

A new reagent, manganese dioxide supported on graphite, under heterogeneous conditions at reflux is described for the oxidation of benzylic and allylic alcohols into the corresponding aldehydes and ketones, respectively. The main advantage of the present oxidation is that the insoluble solid support, graphite, provides a particular reaction environment capable of enhancing the reaction selectivity and reactivity. Moreover, it turns out to be very profitable in the workup, which becomes reduced to a mere filtration. The mechanism for this oxidation is also discussed. Copyright Taylor & Francis Group, LLC.

Highly Enantioselective Synthesis of Alkylpyridine Derivatives through a Michael/Michael/Aldol Cascade Reaction

Meazza, Marta,Potter, Michael,Pitak, Mateusz B.,Coles, Simon J.,Mazzanti, Andrea,Rios, Ramon

, p. 719 - 725 (2017)

A method for the synthesis of pyridine derivatives based on a triple cascade reaction catalyzed by chiral secondary amines was developed. The resulting cyclohexenes (three C–C bonds were formed) were obtained in good yields with good diastereoselectivities and excellent enantioselectivities.

From surface-inspired oxovanadium silsesquioxane models to active catalysts for the oxidation of alcohols with O2-The cinnamic acid/ metavanadate system

Ohde, Christian,Limberg, Christian

, p. 6892 - 6899 (2010)

Silsesquioxane dioxovanadate(V) complexes were investigated with respect to their potential as a catalyst for the oxidative dehydrogenation of alcohols with O2 as an oxidant. The turnover frequencies determined were comparatively low, but during the oxidation of cinnamic alcohol an increase in activity was observed in the course of the process, which was inspected more closely. It turned out that during the oxidation of cinnamic alcohol, not only was the aldehyde formed but also cinnamic acid, which in turn reacts with the silsesquioxane complex employed to give NBu4- [O2V(O 2CC2H2Ph)2], which can also be obtained from NBu4VO3 and cinnamic acid and represents a far more active catalyst, not only for cinnamic alcohol but also for other activated alcohols and hydrocarbons. The rate-determining step of the conversion corresponds to an hydrogen-atom abstraction from the C-H units, as shown by the determination of the kinetic isotope effect in case of 9-hydroxyfluorene, and the reoxidation of the reduced catalyst proceeds via a peroxo intermediate, which is also capable of oxidizing one alcohol equivalent. Furthermore the influence of the organic residues at the carboxylate ligands on the catalyst performance was investigated, which showed that the activity increases with decreasing pKs value. Moreover, it was found that during the oxidation the catalyst slowly decomposes, but can be regenerated by addition of excessive carboxylic acid.

Palladium-Catalyzed Allylic C-H Oxidative Annulation for Assembly of Functionalized 2-Substituted Quinoline Derivatives

Li, Chunsheng,Li, Jianxiao,An, Yanni,Peng, Jianwen,Wu, Wanqing,Jiang, Huanfeng

, p. 12189 - 12196 (2016)

An efficient and practical palladium-catalyzed aerobic oxidative approach to afford functionalized 2-substituted quinolines in moderate to good yields from readily available allylbenzenes with aniline is developed. The present annulation process has high functional-group tolerance and high atom economy, making it a valuable and practical method in synthetic and medicinal chemistry. Moreover, this transformation is supposed to proceed through oxidation of allylic C-H functionalization to form C-C and C-N bonds in one pot.

Direct synthesis of Fe(III) immobilized Zr-based metal–organic framework for aerobic oxidation reaction

Shu, Xin,Yu, Ying,Jiang, Yi,Luan, Yi,Ramella, Daniele

, (2017)

A Zr-based metal–organic framework with bipyridine units (UiO-67) has been utilized for the immobilization of catalytically active iron species via a post-synthetic metalation method. UiO-67 bipyridine MOF was synthesized through a simple solvothermal method and was shown to have a UiO-type structure. Post-synthetic metalation of UiO-67 MOF was performed for the immobilization of the catalytically active FeCl3. FT-IR and EDX element map suggested that FeCl3 is coordinately bonded to the UiO-67 bipyridine framework. The synthesized UiO-67-FeCl3 catalyst was used for the aerobic oxidation of alcohols and benzylic compounds in the presence of molecular oxygen. In addition, the UiO-67-FeCl3 catalyst can be reused as a solid heterogeneous catalyst without compromising its activity and selectivity.

The Aldol Reaction under High-Intensity Ultrasound: A Novel Approach to an Old Reaction

Cravotto, Giancarlo,Demetri, Alberto,Nano, Gian Mario,Palmisano, Giovanni,Penoni, Andrea,Tagliapietra, Silvia

, p. 4438 - 4444 (2003)

We have employed high-intensity ultrasound (HIU) to reinvestigate the aldol reaction (AR) in water. A number of aldols that under usual conditions would undergo elimination were isolated in acceptable to good yields. Within 15-30 min, acetophenone reacted with non-enolizable aldehydes to afford the aldol exclusively, while under conventional conditions (stirring or heating under reflux) the same compounds either failed to react or gave, after several hours, the enone, often in complex product mixtures. A library of polyols was obtained starting from a series of acetophenones and excess formaldehyde. Benzaldehyde reacted with a series of 1,3-dicarbonyl compounds to afford the corresponding bis(benzylidene) adducts. The results proved to be highly reproducible because the relevant sonochemical parameters were rigorously controlled. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Organische Synthesen mit Uebergangsmetall-Komplexen. LXV. Aldehyde durch Hydrolyse der M=C-Bindung von Alkoxycarben-Chromkomplexen mit Wasser / Urotropin. Ein zweikerniger verbrueckter (β-Amino)vinylcarben-Chromkomplex durch Fragmentierung von Urotropin

Aumann, Rudolf,Hinterding, Peter,Krueger, Carl,Goddard, Richard

, p. 145 - 150 (1993)

The Cr=C bonds of aryl- and alkenyl(ethoxy)carbene chromium complexes 1a-d are hydrolysed under mild reaction conditions with high chemoselectivity in presence of hexamethylenetetramine (urotropine), 2, to give aldehydes 4a-d and (urotropine)Cr(CO)5, 3.The alkynyl(ethoxy)carbene chromium complex 1e reacts with urotropine in a completely different fashion and forms a binuclear (β-amino)vinylcarbene complex, 5, by fragmentation of the urotropine skeleton.

Shaken not stirred; Oxidation of alcohols with sodium dichromate

Lou, Ji-Dong,Gao, Chun-Ling,Ma, Yi-Chun,Huang, Li-Hong,Li, Li

, p. 311 - 313 (2006)

Efficient and selective oxidation of primary alcohols to the corresponding aldehydes with sodium dichromate at room temperature under solvent-free conditions by shaking is described. This new procedure can also successfully oxidise secondary alcohols.

An efficient Pd@Pro-GO heterogeneous catalyst for the α, β-dehydrogenation of saturated aldehyde and ketones

Pan, Gao-Fei,Wang, Zhe,Chang, Yi-Yuan,Hao, Yue,Wang, Yi-Chen,Xing, Rui-Guang

supporting information, (2021/12/30)

An Efficient Pd@Pro-GO heterogeneous catalyst was developed that can promote the α, β-dehydrogenation of saturated aldehyde and ketones in the yield of 73% ? 92% at mild conditions without extra oxidants and additives. Pd@Pro-GO heterogeneous catalyst was synthesized via two steps: firstly, the Pro-GO was obtained by the esterification reaction between graphene oxide (GO) and N-(tert-Butoxycarbonyl)-L-proline (Boc-Pro-OH), followed by removing the protection group tert-Butoxycarbonyl (Boc), which endowed the proline-functionalized GO with both the lewis acid site (COOH) and the bronsted base site (NH), besides, the pyrrolidine of proline also can form imine with aldehydes to activate these substrates; Second, palladium was dispersed on the proline-functionalized GO (Pro-GO) to obtained heterogeneous catalyst Pd@Pro-GO. Mechanistic studies have shown that the Pd@Pro-GO-catalyzed α,β-dehydrogenation of saturated aldehyde and ketones was realized by an improved heterogeneously catalyzed Saegusa oxidation reaction. Based on the obove characteristics, the Pd@Pro-GO will be widely used in the transition metal catalytic field.

Preparation method for catalytic synthesis of dihydropyrone compound containing 1, 3-enyne functional group by N-heterocyclic carbene

-

Paragraph 0014-0015, (2021/01/12)

The invention discloses a preparation method for catalytic synthesis of dihydropyrone compound containing 1, 3-enyne functional group by N-heterocyclic carbene, which is characterized in that the derivative is shown as a general formula (1), in the formula, R1 is phenyl, substituted benzene, naphthalene, furan, thiophene or alkyl; R2 is phenyl, substituted benzene, furan or thiophene; and R3 is phenyl, substituted benzene, thiophene or alkyl. The dihydropyrone compound containing 1,3-enyne functional group can be effectively and efficiently prepared from reactant molecules alpha, beta-unsaturated aldehyde and 1,3-enyne aldehyde with simple structural units under the catalysis of N-heterocyclic carbene, and the dihydropyrone derivative has the advantages of good substrate universality, excellent yield, high enantioselectivity and the like.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 104-55-2