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 
• 78-85-3 2-methylpropenal 
• 98-82-8 Isopropylbenzene 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 71-43-2 benzene 
• 122-03-2 (4-isopropylbenzaldehyde) 
• 1252059-77-0 C₁₇H₂₄O₄ 
• 4756-19-8 2-methyl-3-[4-(methylethyl)phenyl]propanol 
• 10476-95-6 methallylidene diacetate 
• 6839-77-6 Acetat v. 2-Methyl-3-<4-isopropyl-phenyl>-propen-(1)-ol-(1) 
• 61668-36-8 bromo-2 trimethylsilyloxy-1 propene-1 
• 405506-94-7 (4-isopropylbenzyl)magnesium chloride 
• 855151-22-3 2,3-epoxy-4-(4-isopropyl-phenyl)-3-methyl-butyric acid ethyl ester 

Downstream Products

• 4756-19-8 2-methyl-3-[4-(methylethyl)phenyl]propanol 
• 191848-12-1 2,2-Difluoro-3-hydroxy-5-(4-isopropyl-phenyl)-4-methyl-pentanoic acid ethyl ester 
• 30127-31-2 1-isobutyl-4-isopropyl-cyclohexane 
• 7149-24-8 2-methyl-3-(4-isopropylphenyl)propanal diethyl acetal 
• 72845-85-3 2-methyl-3-(4-isopropylphenyl)propanal ethylene acetal 
• 1073495-47-2 9-fluoro-1-{[4-({2-methyl-3-[4-(1-methylethyl)phenyl]propyl}amino)-1-piperidinyl]methyl}-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one monotrifluoroacetate 
• 1169830-71-0 C₂₀H₂₅NO 
• 1235835-39-8 6-(benzylamino)-5-(4-isopropylbenzyl)-5-methylbicyclo[2.2.2]octan-2-one 
• 1236831-94-9 6-(benzylamino)-5-(4-isopropylbenzyl)-5-methylbicyclo[2.2.2]octan-2-one 
• 1280206-03-2 [5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-[3-(4-isopropyl-phenyl)-2-methyl-propyl]-amine 

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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Ru-Catalyzed Cross-Dehydrogenative Coupling between Primary Alcohols to Guerbet Alcohol Derivatives: With Relevance for Fragrance Synthesis

A simple method has been developed for the cross dehydrogenative coupling between two different primary alcohols using readily available RuCl2(PPh3)3 as a precatalyst through the borrowing-hydrogen approach. The present methodology is applicable to a large variety of alcohol derivatives including long chain aliphatic alcohols and heteroaryl alcohols. In addition, the methodology was applied in a straightforward protocol to synthesize commercially available fragrances such as Rosaphen and Cyclamenaldehyde in good yields.

Industrial production method of high-content cyclamen aldehyde

The invention discloses a production method of high-content cyclamen aldehyde, relating to the technical field of fine chemical engineering production. After isopropyl benzene and propionyl chloride used as initial raw materials are subjected to acylation reaction, selective hydrogenation is carried out to synthesize cyclamen aldehyde, so the method has the advantages of accessible raw materials and high yield. Ethanol is used as an organic solvent for hydrogenation reaction, thereby overcoming the defects of incomplete reaction or excess hydrogenation and inactivation of the recycled catalyst in the hydrogenation process, and controlling the content of ortho-cyclamen aldehyde of the side reaction at 0.5% or below. Besides, a high-vacuum falling film fractionating tower is used for separating and purifying the cyclamen aldehyde, so that the cyclamen alcohol content in the cyclamen aldehyde finished product is controlled at 0.5% or below; and thus, the singlet content in the final product reaches 98.5% or above, and the final product has pure and soft fragrance and satisfies the requirement for essence blending.