1205-17-0

Basic information

• Product Name: 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal
• Synonyms: Tropional;α-Methyl-1,3-benzodioxole-5-propanal;2-Methyl-3-(3,4-methylenedioxyphenyl)propanal,97%;2-Methyl-3-(3,4-methylenedioxyphenyl)propanal,98+%;TROPINAL;2-methyl-3-(3,4-methylenedioxyphenyl)-propanol;2-Methyl-3-(3,4-Methylenedioxyphenyl)propanal, 97% 25ML;Heliofloral(Helional
• CAS NO: 1205-17-0
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21
• EINECS: 214-881-6
• Product Categories: Used in Cyclamen Lilacs flowers etc fragrance compound;Cosmetic Usage;Miscellaneous;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 1205-17-0.mol

Chemical Properties

• Boiling Point: 282 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear yellow liquid
• Density: 1.162 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0027mmHg at 25°C
• Refractive Index: n20/D 1.5335(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: 934mg/L at 20℃
• CAS DataBase Reference: 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal(1205-17-0)
• EPA Substance Registry System: 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal(1205-17-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: DF4922185
• Hazardous Substances Data: 1205-17-0(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 1205-17-0 differently. You can refer to the following data:
1. clear yellow liquid
2. 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal is a colorless to slightly yellow liquid, d204 1.159–1.167, n20D 1.531–1.536, with green, floral odor with top notes of ozone and newmown hay. It can be prepared either by condensation of heliotropin with propanal and subsequent partial hydrogenation of the intermediately formed unsaturated aldehyde or by Lewis catalyzed reaction of 1,2-methylenedioxybenzene with methacrolein diacetate followed by saponification of the corresponding enol acetate . The title compound can be used in perfumes for toiletries, for example, shaving creams and detergents.

Uses

2-Methyl-3-(3,4-methylenedioxyphenyl)-propanal is an aromatic aldehyde that was used in the investigation of human olfactory receptor 17-40 as an active part of a nanobiosensor.

Flammability and Explosibility

Notclassified

Trade name

Floramelon (Hangzhou), HelionalTM(IFF), Heliogan (Agan).

InChI:InChI=1/C11H12O3/c1-8(6-12)4-9-2-3-10-11(5-9)14-7-13-10/h2-3,5-6,8H,4,7H2,1H3/t8-/m1/s1

Upstream product

• 274-09-9 Methylenedioxybenzene 
• 78-85-3 2-methylpropenal 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 67-56-1 methanol 
• 1048372-09-3 1,2-bis(3-acetoxy-2-methyl-2-propenyl)-4,5-methylenedioxybenzene 
• 94-59-7 1-allyl-3,4-methylenedioxybenzene 
• 201230-82-2 carbon monoxide 
• 6974-47-6 (E)-3-(benzo[d][1,3]dioxol-6-yl)-2-methylacrylaldehyde 
• 1254780-81-8 C₂₂H₂₆O₆ 
• 6974-47-6 3-(1,3-benzodioxol-5-yl)-2-methylpropenal 
• 120-80-9 benzene-1,2-diol 
• 1310466-22-8 4-(2-methylallyl)-1,2-dihydroxybenzene 
• 120-58-1 isosafrole 

Relevant articles and documents

Hydroformylation of natural olefins with the [Rh(COD)(μ-OMe)]2/TPPTS complex in BMI-BF4/toluene biphasic medium: Observations on the interfacial role of CTAB in reactive systems

The complex [Rh(COD)(μ-OMe)]2 in presence of TPPTS (TPPTS = triphenylphosphinetrisulfonate) was evaluated as catalyst precursor for the in situ hydroformylation of natural olefins (eugenol, estragole and safrole) in biphasic media BMIm-BF4/toluene. Under moderate reaction conditions, the substrates showed the following reactivity order: eugenol > estragole > safrole. The rhodium system showed a high activity and selectivity towards the desired aldehydes. It was found that the use of cetyltrimethylammoniun bromide (CTAB) as phase transfer agent inhibits the hydroformylation reaction. The catalytic phase can be recycled up to four times without evident loss of activity or selectivity. In this work we report the use of an ionic liquid with hydrophilic character, without using water in the reaction medium.

Biphasic hydroformylation of substituted allylbenzenes with water-soluble rhodium or ruthenium complexes

The water-soluble complexes [Rh(CO)(Pz)(L)]2 and [HRu(CO)(CH3CN)(L)3][BF4] [L = TPPMS (m-sulfonatophenyl-diphenylphosphine) and TPPTS (tris-m-sulfonato- phenylphosphine)] were used for the first time as catalyst precursors for the hydroformylation of eugenol, estragole, safrole and trans-anethole under moderate conditions in biphasic media. Under mild reaction conditions the substrates showed the following reactivity order: eugenol > estragole ≈ safrole > trans-anethole. The use of cetyl-trimethylammonium chloride (CTAC) as phase transfer agent inhibits the isomerization reaction, reaching high selectivity for the hydroformylation products (80-94%). The catalytic phase can be recycled up to four times with a decrease in the activity over time but maintaining its high selectivity.

Bioreduction of α-methylcinnamaldehyde derivatives: Chemo-enzymatic asymmetric synthesis of Lilial and Helional

Nonracemic aryl-substituted α-methyldihydrocinnamaldehyde derivatives employed as olfactory principles in perfumes (Lilial, Helional) were obtained via enzymatic reduction of the corresponding cinnamaldehyde precursors using cloned and overexpressed ene-reductases. (R)-Enantiomers were obtained using the old-yellow-enzyme (OYE) homolog YqjM from Bacillus subtilis and 12-oxophytodienoic acid reductase isoenzyme OPR1 from tomato (e.e. max 53%), and (S)-aldehydes were furnished in up to 97% e.e. using isoenzyme OPR3, nicotinamide 2-cyclohexene-1-one reductase NCR from Zymomonas mobilis and yeast OYE isoenzymes 1-3 under optimised reaction conditions in the presence of t-butyl methyl ether as the co-solvent. The stereochemical outcome of the reduction of α-methylcinnamaldehyde using NCR and OYEs 1-3 [previously reported to be (R)] was unambiguously corrected to be (S).

Arylation of β-methallyl alcohol catalyzed by Pd(OAc)2 in combination with P(t-Bu)3: application to fragrance synthesis

Pd(OAc)2 in combination with P(t-Bu)3 catalyzes the coupling of β-methallyl alcohol with 1-bromo-3,4-(methylenedioxy)benzene (1a), 1-bromo-4-methoxybenzene (1b), or 1-bromo-4-tert-butylbenzene (1c). The reaction affords the corresponding 2-methyl-3-aryl-propanals, which are valuable floral fragrances. With 1a or 1b high reaction rates are obtained at 130 °C using NMP/water mixtures and an inorganic base such as Na2CO3. The chemoselectivity of the reaction is almost complete, so that the process appears practically feasible. In contrast, the coupling of β-methallyl alcohol with 1c proceeds with low reaction rates.

Synthesis method of helional

The invention relates to a synthesis method of helional, and belongs to the technical field of organic synthesis. According to the synthesis method of helional, the method comprises the following step: at the reaction temperature of 60-80 DEG C, in a reaction kettle provided with rising microbubbles, carrying out catalytic reaction by taking methylacrolein and benzodioxole as raw materials and taking Bronsted acid as a catalyst to synthesize the helional in one step. The chemical reaction formula is shown in the specification. The synthesis method of the helional can be carried out under low pressure or normal pressure. In the method, inert gas and gaseous methylacrolein are mixed according to a specific proportion, and the mixed gas is pumped into a reactor filled with benzodioxole through the reinforced microbubble reactor, so that methylacrolein and benzodioxole react quickly, and side reaction caused by unstable methylacrolein is avoided. In the conventional method, methylacrolein needs to react with acetic anhydride for protection, and then react with benzodioxole for deprotection, and thus chemical wastes are generated.

Catalytic Selective Oxidative Coupling of Secondary N-Alkylanilines: An Approach to Azoxyarene

Azoxyarenes are among important scaffolds in organic molecules. Direct oxidative coupling of primary anilines provides a concise fashion to construct them. However, whether these scaffolds can be prepared from secondary N-alkylanilines is not well explored. Here, we present a catalytic selective oxidative coupling of secondary N-alkylaniline to afford azoxyarene with tungsten catalyst under mild conditions. In addition, azoxy can be viewed as a bioisostere of alkene and amide. Several "azoxyarene analogues" of the corresponding bioactive alkenes and amides showed comparable promising anticancer activities.

Asymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis

A palladium-catalyzed asymmetric α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.

The present invention relates to a new process for the preparation of heliotropine

The invention relates to a method for preparing helional and discloses a method which comprises steps of carrying out Claisen-Schmidt condensation reaction between heliotropin serving as a raw material and propionaldehyde under the catalysis of strong-basicity ion exchange resin, and further performing catalytic hydrogenation so as to obtain the target product. The method is characterized in that the strong-basicity ion exchange resin is used to replace other strong bases for catalyzing Claisen-Schmidt condensation reaction, the reaction yield is greatly improved, disproportionation reaction which can cause relevant impurities is avoided, and the purification is easy. The method is a route which is high in yield, low in cost, safe and applicable for industrial synthesis.

An easily recoverable and recyclable homogeneous polyester-based Pd catalytic system for the hydrogenation of α,β-unsaturated carbonyl compounds

Abstract Homogeneous catalysis is an efficient tool to carry out hydrogenation processes but the major drawback is represented by the separation of the expensive catalyst from the product mixture. In this view we prepared a polyester-based Pd catalytic system that offers the advantages of both homogenous and heterogeneous catalyses: efficacy, selectivity and recyclability. Here its application in the hydrogenation of selected α,β-unsaturated carbonyl compounds is described.

Rhodium catalyzed aqueous biphasic hydroformylation of naturally occurring allylbenzenes in the presence of water-soluble phosphorus ligands

The rhodium-catalyzed hydroformylation of eugenol was performed in aqueous biphasic systems using various water soluble phosphines: TPPTS (triphenylphosphinetrisulphonated); BDPPETS (bisdiphenylphosphinoethanetetrasulphonated), BDPPPTS (bisdiphenylphosphi