57194-69-1

Basic information

• Product Name: TRANS-CINNAMALDEHYDE
• Synonyms: cis-3-phenyl-propenal;(Z)-forM;cis-Cinnamaldehyde;(Z)-3-Phenyl-2-propenal;(2Z)-3-phenylprop-2-enal
• CAS NO: 57194-69-1
• Molecular Formula: C₉H₈O
• Molecular Weight: 132.15922
• Mol File: 57194-69-1.mol

Chemical Properties

• Boiling Point: 246.8°Cat760mmHg
• Flash Point: 71.1°C
• Appearance: /
• Density: 1.034g/cm³
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Air Sensitive, Light Sensitive, Temperature Sensitive
• CAS DataBase Reference: TRANS-CINNAMALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-CINNAMALDEHYDE(57194-69-1)
• EPA Substance Registry System: TRANS-CINNAMALDEHYDE(57194-69-1)

Safety Data

• Hazardous Substances Data: 57194-69-1(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
TRANS-CINNAMALDEHYDE is used as a key ingredient in the flavor and fragrance industry for its strong, sweet, and pungent odor. It is widely used in the production of perfumes, colognes, and other scented products due to its characteristic aroma.
Used in Antimicrobial Applications:
TRANS-CINNAMALDEHYDE is used as an antibacterial agent against Escherichia Coli and Salmonella in vitro. It causes cell structural damage, resulting in leakage of cellular content, making it an effective agent in combating bacterial infections.
Used in Synthesis of Nanomaterials:
TRANS-CINNAMALDEHYDE is derived from (Z)-Cinnamyl Alcohol (C442105), a useful synthetic intermediate. It is also used as a reagent in the synthesis of one-dimensional ZnO nanorods with well-defined morphology, which serve as highly selective photocatalysts in various applications.

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 6142-95-6 phenylpropargyl aldehyde diethyl acetal 
• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 64-18-6 formic acid 
• 588-73-8 (Z)-β-bromostyrene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 33603-89-3 (Z)-2-chloro-3-phenyl-2-propenal 
• 7148-78-9 3,3-diethoxyl-1-phenylprop-1-ene 
• 81149-95-3 cis-cinnamaldehyde diethyl acetal 
• 127896-07-5 α,α-bis(trimethylsilyl)-tert-butylacetaldehyde imine 
• 100-52-7 benzaldehyde 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 145091-91-4 3-hydroxy-5-phenyl-1H-pyrazole 

Downstream Products

• 30204-42-3 7-hydroxy-5-phenyl-5H-2,3,6,7-tetrahydrothiazolo[2,3-a]pyrimidine 
• 112403-22-2 2,2'-(3-phenylprop-2-ene-1,1-diyl)bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) 
• 139483-97-9 (2R,4R)-4-(2-Hydroxy-4,4-dimethyl-6-oxo-cyclohex-1-enyl)-7,7-dimethyl-2-phenyl-2,3,4,6,7,8-hexahydro-chromen-5-one 
• 78830-74-7 2-styryl-4-methacryloyloxymethyl-1,3-dioxolane 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 79866-71-0 1-Phenyl-5-((1Z,3Z)-4-phenyl-buta-1,3-dienyl)-1H-tetrazole 
• 71154-14-8 (E)-3-hydroxy-5-phenylpent-4-enenitrile 
• 14371-10-9 (E)-3-phenylpropenal 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 41109-94-8 (2E,4E)-2-cyano-5-phenyl-2,4-pentadienoic acid methyl ester 
• 372076-36-3 6-phenyl-3(Z),5(Z)-hexadien-1-ol 

Relevant articles and documents

Gold(I)-catalyzed intermolecular cycloaddition of allenamides with α,β-unsaturated hydrazones: Efficient access to highly substituted cyclobutanes

α,β-Unsaturated N,N-dialkyl hydrazones undergo a mild [2 + 2] cycloaddition to allenamides when treated with a suitable gold catalyst. The method, which represents the first application of N,N-dialkyl hydrazones in gold catalysis, is compatible with a wide variety of substituents at the alkenyl moiety of the hydrazone component, proceeds with excellent levels of regio- and diastereoselectivity, and provides densely substituted cyclobutanes with good to excellent yields.

Application of the SPE Method to Organic Electrochemistry-X. Behaviors of the Manganese Redox Couple Incorporated in Pt-Nafion and Their Mediatory Oxidation of Cinnamyl Alcohol to Cinnamaldehyd

The electrochemical behavior of a manganese redox couple incorporated into an SPE (Solid Polymer Electrolyte) composite electrode using Nafion (Pt-Nafion) was examined as a mediator for electroorganic synthesis.The mediatory reaction of the redox couple w

Sulfur-controlled and rhodium-catalyzed formal (3 + 3) transannulation of thioacyl carbenes with alk-2-enals and mechanistic insights

A rhodium-catalyzed denitrogenative formal (3 + 3) transannulation of 1,2,3-thiadiazoles with alk-2-enals is achieved, producing 2,3-dihydrothiopyran-4-ones in moderate to excellent yields. An inverse KIE of 0.49 is obtained, suggesting the reversibility of the oxidative addition of thioacyl Rh(i) carbenes to alk-2-enals. The late-stage structural modifications of steroid compounds are realized. Moreover, our studies show that thioacyl carbenes have different reactivities to those of α-oxo and α-imino carbenes, and highlight the importance of heteroatoms in deciding the reactivities of heterovinyl carbenes.

Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation

In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.

8π Electrocyclic Reaction of Phosphonate Derivatives: Access to Seven-Membered Cross-Conjugated Cyclic Trienes

An anionic 8π electrocyclic reaction of 4-(diethoxyphosphoryl)-1,3,6-heptatriene derivatives was developed. Under the influence of a base, the substrate underwent deprotonation at the C5 position followed by the 8π electrocyclization of the resulting hept

Tandem oxidation-dehydrogenation of (hetero)arylated primary alcohols via perruthenate catalysis

Tandem oxidative-dehydrogenation of primary alcohols to give a,b-unsaturated aldehydes in one pot are rare transformations in organic synthesis, with only two methods currently available. Reported herein is a novel method using the bench-stable salt methyltriphenylphosphonium perruthenate (MTP3), and a new co-oxidant NEMO&middoPF6 (NEMO = N-ethyl-N-hydroxymorpholinium) which provides unsaturated aldehydes in low to moderate yields. The Ley-Griffith oxidation of (hetero)arylated primary alcohols with N-oxide co-oxidants NMO (NMO = N-methylmorpholine N-oxide)/NEMO, is expanded by addition of the N-oxide salt NEMO&middoPF6 to convert the intermediate saturated aldehyde into its unsaturated counterpart. The discovery, method development, reaction scope, and associated challenges of this method are highlighted. The conceptual value of late-stage dehydrogenation in natural product synthesis is demonstrated via the synthesis of a polyene scaffold related to auxarconjugatin B.

Essential structural features of (2Z,4E)-5-phenylpenta-2,4-dienoic acid for inhibition of root gravitropism

Previously, we found (2Z,4E)-5-phenylpenta-2,4-dienoic acid (ku-76) to be a selective inhibitor of root gravitropic bending of lettuce radicles at 5 μM, with no concomitant growth inhibition. Here, we describe a structure-activity relationship study of ku

Customizing Photoredox Properties of PXX-based Dyes through Energy Level Rigid Shifts of Frontier Molecular Orbitals

Here we describe the synthesis of electron-rich PXX derivatives in which the energy levels of the excited states have been rigidly shifted through the insertion of imide groups. This has allowed the development of a new series of oxygen-doped photoredox-active chromophores with improved oxidizing and reducing properties. Capitalizing on the dehalogenation of organic halides as a model reaction, we could investigate the photooxidative and photoreductive potential of these molecules in model chemical transformations. Depending on the substrate, solvent and dye the reaction mechanism can follow different paths. This prompted us to consider the first chemoselective transformation protocol, in which two different C?Br bonds could be chemoselectively reacted through the sequential photoactivation of two different colorants.

Visible-Light-Promoted Nickel- and Organic-Dye-Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent

A simple formylation reaction of aryl halides, aryl triflates, and vinyl bromides under synergistic nickel- and organic-dye-mediated photoredox catalysis is reported. Distinct from widely used palladium-catalyzed formylation processes, this reaction proceeds by a two-step mechanistic sequence involving initial in situ generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN-mediated photoredox reaction. The formyl-radical equivalent then undergoes nickel-catalyzed substitution reactions with aryl halides and triflates and vinyl bromides to form the corresponding aldehyde products. Significantly, besides aryl bromides, less reactive aryl chlorides and triflates and vinyl halides serve as effective substrates for this process. Since the mild conditions involved in this reaction tolerate a plethora of functional groups, the process can be applied to the efficient preparation of diverse aromatic aldehydes.

Stereoselective organocatalytic oxidation of alcohols to enals: A homologation method to prepare polyenes

A novel method for organocatalytic oxidation through oxidative enamine catalysis was developed with excellent compatibility for the direct syntheses of enals from simple saturated alcohols. By using this amine-catalyzed IBX-oxidation, a wide range of aromatic and aliphatic substituted enals were successfully generated in high yields and exclusively stereoselective E-geometry. Moreover, varying the solvents and/or the loading amounts of IBX allowed for the selective oxidation of alcohols and aldehydes. Importantly, the homologous application of this method provided a selective and efficient way of preparing various highly sensitive conjugated polyene frameworks, which are enriched in natural products.