103-95-7

Basic information

• Product Name: 3-(4-ISOPROPYLPHENYL)ISOBUTYRALDEHYDE
• Synonyms: (R,S)-p-Isopropyl-α-methylhydro-cinnamaldehyde;.alpha.-methyl-4-(1-methylethyl)-Benzenepropanal;3-(4-iso-Propylphenyl)-2-methylpropanal;3-(4-Isopropylphenyl)-2-methylpropanal;3-(p-Isopropylphenyl)isobutyraldehyde;3-p-;3-p-cumenyl-2;3-p-cumenyl-2-
• CAS NO: 103-95-7
• Molecular Formula: C₁₃H₁₈O
• Molecular Weight: 190.28
• EINECS: 203-161-7
• Product Categories: Pharmaceutical Raw Materials;Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 103-95-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 270 °C(lit.)
• Flash Point: 228 °F
• Appearance: /
• Density: 0.95 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00881mmHg at 25°C
• Refractive Index: n20/D 1.505(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly)
• Water Solubility: 66mg/L at 20℃
• Stability: Hygroscopic
• CAS DataBase Reference: 3-(4-ISOPROPYLPHENYL)ISOBUTYRALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-ISOPROPYLPHENYL)ISOBUTYRALDEHYDE(103-95-7)
• EPA Substance Registry System: 3-(4-ISOPROPYLPHENYL)ISOBUTYRALDEHYDE(103-95-7)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 26-36
• WGK Germany: 2
• RTECS: MW4900000
• Hazardous Substances Data: 103-95-7(Hazardous Substances Data)

Usage

Description

2-Methyl-3-(p-isopropylphenyl) propionaldehyde has a strong, flowery odor. May be prepared by condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst.

Chemical Properties

Different sources of media describe the Chemical Properties of 103-95-7 differently. You can refer to the following data:
1. 2-Methyl-3-(p-isopropylphenyl)-propionaldehyde has a strong, flowery odor
2. The commercially available racemate is a colorless to yellowish liquid with an intense floral odor reminiscent of Cyclamen europaeum (cyclamen, sowbread).Production. Two main processes are used for the industrial synthesis of cyclamen aldehyde:1) Alkaline condensation of 4-isopropylbenzaldehyde and propanal results, via the aldol, in the formation of 2-methyl-3-(4-isopropylphenyl)-2-propenal. The unsaturated aldehyde is hydrogenated selectively to the saturated aldehyde in the presence of potassium acetate and a suitable catalyst, such as palladium–alumina:2) Friedel–Crafts reaction of isopropylbenzene and 2-methylpropenal diacetate (methacrolein diacetate) in the presence of titanium tetrachloride/boron trifluoride etherate gives cyclamen aldehyde enolacetate, which is hydrolyzed to aldehyde:Uses. Cyclamen aldehyde is an important component for obtaining special blossomnotes in perfume compositions, particularly the cyclamen type. Because of its fresh, floral aspect, it is also used as the top note in many other blossomfragrances.

Occurrence

Reported found in nutmeg and starfruit.

Uses

Different sources of media describe the Uses of 103-95-7 differently. You can refer to the following data:
1. Cyclamen Aldehyde is a very powerful, floral, green note used in many perfumery applications to blend into fresh, floral, green or ozonic/marine accords. It is an ingredient with growing use and importance in helping to build replacement accords for materials disappearing from the Perfumers’ palette. Cyclamen has good overall stability except in extremes of pH. It has good tenacity and substantivity and represents very good value for money in new creations.
2. Cyclamal, is an ingredient in perfume. It can also be used in the synthesis of Cyclamen Alcohol (C987655).

Preparation

By condensation of cuminic aldehyde and propionaldehyde followed by hydrogenation in the presence of a catalyst

Safety Profile

Moderately toxic by ingestion. A human skin irritant. See also ALDEHYDES. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C13H18O/c1-10(2)13-6-4-12(5-7-13)8-11(3)9-14/h4-7,9-11H,8H2,1-3H3

Upstream product

• 831-97-0 α-methyl-p-isopropylcinnamaldehyde 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 71-43-2 benzene 
• 56208-30-1 3t-(4-isopropyl-phenyl)-2-methyl-allyl alcohol 
• 1252059-77-0 C₁₇H₂₄O₄ 
• 4756-19-8 2-methyl-3-[4-(methylethyl)phenyl]propanol 
• 122-03-2 (4-isopropylbenzaldehyde) 
• 98-82-8 Isopropylbenzene 
• 79-03-8 propionyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 4009-98-7 (methoxymethyl)triphenylphosphonium chloride 
• 10476-95-6 methallylidene diacetate 
• 2051-18-5 4-isopropylbenzyl chloride 

Downstream Products

• 191848-12-1 2,2-Difluoro-3-hydroxy-5-(4-isopropyl-phenyl)-4-methyl-pentanoic acid ethyl ester 
• 300393-39-9 2-[3-(p-isopropylphenyl)prol-2-yl]benzimidazole 
• 7149-24-8 2-methyl-3-(4-isopropylphenyl)propanal diethyl acetal 
• 1278571-34-8 (S)-diethyl 2-(3-(4-isopropylphenyl)-2-methylpropylidene)malonate 
• 1280206-03-2 [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-[3-(4-isopropyl-phenyl)-2-methyl-propyl]-amine 
• 1339940-56-5 C₅₀H₇₂N₁₀O₄ 

Relevant articles and documents

Selective Catalytic Hydrogenation in the presence of Lanthanide tris-β-Diketonates as "Protecting" Reagents

The selectivity of >C=C double bonds catalytic hydrogenation increases considerably in the presence of some lanthanide tris-β-diketonates for those unsaturated aldehydes and ketones possessing highly susceptible to reduction carbonyl group.It is a result of the selective co-ordination between the lanthanide complex added and the carbonyl group of a substrate.In most cases the complete protection of carbonyl groups is observed if the complex is added in equimolar amount to the substrate.A number of lanthanum tris-β-diketonates have been tested; the complexes with fluorinated ligands were demonstrated to ensure the highest selectivity of the hydrogenation.The correlation between the constants of equilibrium in reaction mixture and "protecting" activity of the complexes is discussed.A few examples demostrate the practical utilization of the lanthanum tris-β-diketonates to the selective hydrogenation of unsaturated aldehydes and ketones.

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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.

rabbit ear oxaldehyde a method of production

The invention relates to a cyclamen aldehyde production method. The method concretely comprises the following steps: mixing methylacrolein dipropionic acid with isopropyl benzene, slowly adding a titanium tetrachloride and trifluoromethanesulfonic acid mixed solution in a dropwise manner at a low temperature while stirring, reacting, slowly pouring a diluted hydrochloric acid solution into the above obtained reaction solution after completing the reaction, hydrolyzing, taking the obtained organic phase, adding sodium hydroxide and methanol, carrying out a de-esterification reaction, washing by using water after completing the de-esterification reaction, separating the obtained organic layer, and rectifying the above obtained crude product to obtain highly pure cyclamen aldehyde. An innovative titanium tetrachloride and catalytic amount trifluoromethanesulfonic acid double-acid catalysis mode is adopted, the concrete dropwise addition sequence, the reaction time and the temperature are limited, so side reactions are reduced, and the purity of the cyclamen aldehyde is improved; and isopropyl benzene is cheap and easily available, and can be simultaneously used as a solvent and a reactant without adding other solvents, so the method disclosed in the invention has great advantages in cost and three-waste control.