1504-74-1

Usage

Uses

Used in Flavor and Fragrance Industry:
2'-Methoxycinnamaldehyde is used as a flavoring agent for its sweet, spicy, and warm taste, making it suitable for the creation of various food and beverage products. Its warm, spicy, and floral odor with fruity undertones also makes it an ideal component for the fragrance industry, where it can be used to create a wide range of scent profiles.
Used in the Cosmetic Industry:
Due to its pleasant odor and flavor, 2'-Methoxycinnamaldehyde can be used in the cosmetic industry as an additive to enhance the sensory experience of products such as perfumes, lotions, and other personal care items.
Used in the Pharmaceutical Industry:
2'-Methoxycinnamaldehyde may have potential applications in the pharmaceutical industry, particularly in the development of drugs that require a sweet, spicy, or warm taste or odor. Its chemical properties could also be exploited for the synthesis of other bioactive compounds with potential therapeutic uses.

Preparation

It is formed after a long contact period between salicylaldehyde and acetaldehyde in diluted alkaline solution; it may also be formed by condensation of salicylaldehyde methylether with acetaldehyde under alkaline conditions; from the corresponding oxime. It may be isolated and purified from powdered cinnamon.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Aldehydes, such as 2'-Methoxycinnamaldehyde, are frequently involved in self-condensation 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.

Fire Hazard

2'-Methoxycinnamaldehyde is flammable.

InChI:InChI=1/C10H10O2/c1-12-10-7-3-2-5-9(10)6-4-8-11/h2-8H,1H3/b6-4+

Upstream product

• 109-92-2 ethyl vinyl ether 
• 135-02-4 ortho-anisaldehyde 
• 75-07-0 acetaldehyde 
• 1504-61-6 2-methoxycinnamyl alcohol 
• 33877-05-3 ethyl 3-(2-methoxyphenyl)acrylate 
• 90-02-8 salicylaldehyde 
• 15854-58-7 3-(2-methoxyphenyl)acrylic acid methyl ester 
• 385-00-2 2,6-difluorobenzoic acid 
• 75-27-4 bromodichloromethane 
• 612-15-7 o-methoxystyrene 
• 624-67-9 Propargylic aldehyde 
• 100-66-3 methoxybenzene 
• 2136-75-6 (triphenylphosphoranylidene)acetaldehyde 
• 3698-28-0 2-allylanisole 

Downstream Products

• 1504-61-6 2-methoxycinnamyl alcohol 
• 148119-36-2 DD⁽¹⁷⁵⁾D₀₀₈₃₂ 
• 130786-83-3 [(E)-3-(2-Methoxy-phenyl)-prop-2-en-(E)-ylidene]-[3-methyl-5-((E)-styryl)-isoxazol-4-yl]-amine 
• 117069-09-7 2-[(E)-3-(2-Methoxy-phenyl)-prop-2-en-(E)-ylidene]-6-[(E)-3-(2-methoxy-phenyl)-prop-2-en-(Z)-ylidene]-4-methyl-cyclohexanone 
• 120991-80-2 N-<3-(2-methoxyphenyl)propyl>-1,4-diaminobutane 
• 117069-05-3 2-[(E)-3-(2-Methoxy-phenyl)-prop-2-en-(Z)-ylidene]-5-[(E)-3-(2-methoxy-phenyl)-prop-2-en-(E)-ylidene]-cyclopentanone 
• 117069-10-0 2-[(E)-3-(2-Methoxy-phenyl)-prop-2-en-(Z)-ylidene]-7-[(E)-3-(2-methoxy-phenyl)-prop-2-en-(E)-ylidene]-cycloheptanone 
• 264598-04-1 <3-(2-Methoxy-phenyl)-allyliden>-malonsaeure 
• 10493-37-5 3-(2-methoxyphenyl)propan-1-ol 
• 579-75-9 2-Methoxybenzoic acid 
• 69-72-7 salicylic acid 
• 898822-63-4 1-(2-methoxy-phenyl)-4-methyl-penta-1,4-dien-3-one 

Relevant academic research and scientific papers

Stabilization and activation of unstable propynal in the zeolite nanospace and its application to addition reactions

Propynal (HC≡C-CHO), having both a C≡C triple bond and a formyl group in a molecule, is a promising building block but its labile property to easily polymerize often narrows its application for organic synthesis. In a similar way to unstable molecules, such as formaldehyde and acrolein, propynal is also stabilized and remains unchanged in supercages of Na-Y zeolite for over 30 days at ambient temperature. There, the carbonyl oxygen atoms of propynal coordinate to sodium ions in Na-Y which was proved by a 13C-DD/MAS-NMR analysis. In addition, propynal adsorbed in zeolite is sufficiently activated to allow unprecedented reactions; i.e., (1) a 1,3-dipolar cycloaddition with electron-deficient α-diazocarbonyl compounds, (2) a 1,4-addition with mono-, di-, and trimethoxy-substituted benzenes, and (3) a [2 + 2] cycloaddition of unactivated cycloalkenes. The nanospace of the zeolites keeps the products from dimerization during reaction (1) and from successive side-reactions in reaction (2). Quantum chemical calculations demonstrated that reaction (3) proceeds via a one-step-like non-concerted mechanism to afford the corresponding [2 + 2] cycloadducts. These three reactions can produce valuable synthetic intermediates retaining both a formyl group and a C=C double bond.

Method for synthesizing 2 -methoxycinnamaldehyde

The invention provides a synthetic method of 2 -methoxycinnamaldehyde, and belongs to the technical field of organic synthesis. The synthesis method provided by the invention comprises the following steps: (1) methylation reaction of 2 - hydroxybenzaldehyde and a methylation reagent under the action of a quaternary ammonium salt catalyst to obtain 2 - methoxybenzaldehyde. (2) Under alkaline conditions, 2 - methoxybenzaldehyde is subjected to a condensation reaction with acetaldehyde to obtain 2 -methoxycinnamaldehyde. 2 - Hydroxybenzaldehyde is used as a starting material, and the method has the advantages of wide sources and low cost. The method has the advantages of short synthetic route and less side reaction, and the obtained 2 -methoxycinnamaldehyde has high yield and purity and is suitable for industrial popularization and application. The results show that the yield 2 - and the purity ≥ 90% of ≥ 95% -methoxycinnamaldehyde obtained by the synthesis method provided by the invention are high.

Method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and diphosphine ligand used in method

The invention discloses a method for preparing olefine aldehyde by catalyzing terminal alkyne or terminal conjugated eneyne and a diphosphine ligand used in the method. According to the invention, indole-substituted phosphoramidite diphosphine ligand which is stable in air and insensitive to light is synthesized by utilizing a continuous one-pot method, and the indole-substituted phosphoramidite diphosphine ligand and a rhodium catalyst are used for jointly catalyzing to successfully achieve a hydroformylation reaction of aromatic terminal alkyne and terminal conjugated eneyne under the condition of synthesis gas for the first time, so that an olefine aldehyde structure compound can be rapidly and massively prepared, and particularly, a polyolefine aldehyde structure compound which is more difficult to synthesize in the prior art can be easily prepared and synthesized, and a novel method is provided for synthesis and modification of drug molecules, intermediates and chemical products.

Highly Regio- A nd Enantioselective Hydrogenation of Conjugated α-Substituted Dienoic Acids

Highly regio- A nd enantioselective hydrogenation of conjugated α-substituted dienoic acids was realized for the first time using Trifer-Rh complex, providing a straightforward method for the synthesis of chiral α-substituted ?,?′-unsaturated acids. DFT calculations revealed N+H-O hydrogen bonding interaction is formed to stabilize the transition state and the coordination of 4,5-double bond to Rh(III) center would facilitate the reductive elimination process. This hydrogenation provided a gram-scale synthesis of the precursor of sacubitril.

Highly Enantioselective Synthesis of Functionalized Glutarimide Using Oxidative N-Heterocyclic Carbene Catalysis: A Formal Synthesis of (?)-Paroxetine

A simple yet highly effective approach toward enantioselective synthesis of trans-3,4-disubstituted glutarimides from readily available starting materials is developed using oxidative N-heterocyclic carbene catalysis. The catalytic reaction involves a formal [3 + 3] annulation between enals and substituted malonamides enabling the production of glutarimide derivatives in a single chemical operation via concomitant formation of C-C and C-N bonds. The reaction offers easy access to a broad range of functionalized glutarimides with excellent enantioselectivity and good yield. Synthetic application of the method is demonstrated via formal synthesis of (?)-paroxetine and other bioactive molecules.

Palladium-catalyzed salt-free double decarboxylative aryl allylation

This report describes a palladium-catalyzed decarboxylative aryl allylation between unactivated benzoic acids and allylic carbonates. This transformation successfully couples a variety of carbonates and benzoic acids in good yield (up to 94%) using 1 mol% palladium. This salt free allyl-arylation proceeds without added base, copper, or silver. The only stoichiometric byproducts are carbon dioxide and tert-butanol.

Copper-catalyzed formylation of alkenyl C-H bonds using BrCHCl2 as a stoichiometric formylating reagent

The first example of copper-catalyzed direct formylation of alkenyl C-H bonds for the facile synthesis of α,β-unsaturated aldehydes has been developed. This transformation has demonstrated high reactivity, mild reaction conditions and a broad substrate scope. BrCHCl2 is expected to be developed as an efficient stoichiometric C1 building block in organic synthesis.

Dehydrogenative Synthesis of Linear α,β-Unsaturated Aldehydes with Oxygen at Room Temperature Enabled by tBuONO

Synthesis of linear α,β-unsaturated aldehydes via a room-temperature oxidative dehydrogenation has been realized by the cocatalysis of an organic nitrite and palladium with molecular oxygen as the sole clean oxidant. Linear α,β-unsaturated aldehydes could be efficiently prepared under aerobic catalytic conditions directly from the corresponding saturated linear aldehydes. Besides linear products, the aromatic analogy could also be smoothly achieved by the same standard method. The organic nitrite redox cocatalyst and alcohol solvent play a key role for realizing this method.

Selectivity Modulation of the Ley–Griffith TPAP Oxidation with N-Oxide Salts

A wide variety of novel non-hygroscopic N-oxide tetraphenylborate salts were synthesized and evaluated as co-oxidants in the Ley–Griffith (TPAP) oxidation of benzylic and allylic alcohols under non-anhydrous conditions. The novel DABCOO·TPB (2:1) salt was herein unearthed as a viable competitor to the first-generation NMO·TPB (2:1) salt, but more importantly gave increased performance under oxidative competition. X-ray crystal structure analysis and NMR spectroscopy revealed that depending on the crystallization conditions 1:1, 2:1 or 3:2 N-oxide–tetraphenylborate salts could be formed.

One-Pot Synthesis of (S)-Baclofen via Aldol Condensation of Acetaldehyde with Diphenylprolinol Silyl Ether Mediated Asymmetric Michael Reaction as a Key Step

An efficient asymmetric total synthesis of (S)-baclofen was accomplished via a one-pot operation from commercially available materials using sequential reactions, such as aldol condensation of acetaldehyde, diphenylprolinol silyl ether mediated asymmetric Michael reaction of nitromethane, Kraus-Pinnick oxidation, and Raney Ni reduction. Highly enantioenriched baclofen was obtained in one pot with a good yield over four reactions.