1009-62-7

Basic information

• Product Name: 2,2-Dimethyl-3-phenylpropionaldehyde
• Synonyms: 2,2-dimethyl-3-phenylpropionaldehyde;Benzenepropanal, .alpha.,.alpha.-dimethyl-;3-Phenyl-2,2-dimethyl-1-propanone;Benzenepropanal, a,a-diMethyl-
• CAS NO: 1009-62-7
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• EINECS: 213-771-5
• Mol File: 1009-62-7.mol

Chemical Properties

• Boiling Point: 228.5°Cat760mmHg
• Flash Point: 95.8°C
• Appearance: COA
• Density: 0.959g/cm³
• Vapor Pressure: 0.0732mmHg at 25°C
• Refractive Index: 1.501
• CAS DataBase Reference: 2,2-Dimethyl-3-phenylpropionaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-3-phenylpropionaldehyde(1009-62-7)
• EPA Substance Registry System: 2,2-Dimethyl-3-phenylpropionaldehyde(1009-62-7)

Safety Data

• Hazardous Substances Data: 1009-62-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 85, p. 2178, 1963 DOI: 10.1021/ja00897a040The Journal of Organic Chemistry, 39, p. 3102, 1974 DOI: 10.1021/jo00935a009

InChI:InChI=1/C11H14O/c1-11(2,9-12)8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3

Upstream product

• 55089-28-6 2-(1,1-dimethyl-2-phenyl-ethyl)-4,5-dihydro-thiazole 
• 30857-43-3 Dimethyl-2,2-phenyl-3-propanal-cyclohexylimin 
• 2403-57-8 1-(2-methylprop-1-en-1-yl)pyrrolidine 
• 100-39-0 benzyl bromide 
• 52278-95-2 2-Benzyl-2-methylpropanal-N-tert.-butylimin 
• 91496-52-5 2-Oxo-3,3-dimethyl-4-phenyl-buttersaeure 
• 14478-14-9 1-acetyloxy-2-methylpropene 
• 24401-30-7 Dimethyl-<2.2-dimethyl-3-phenyl-propyliden>-ammoniumbromid 
• 88304-20-5 N-(2-methylpropylidene)cyclohexanamine 
• 100-44-7 benzyl chloride 
• 6852-60-4 N-tert-butyl-2-methylpropanimine 
• 78-84-2 isobutyraldehyde 
• 13351-61-6 2,2-dimethyl-3-phenyl-1-propanol 
• 78-82-0 Isobutyronitrile 

Downstream Products

• 67682-19-3 α,β,β-trimethyl-benzenepropanol 
• 52279-01-3 5-Hydroxy-2,2,6,6-tetramethyl-7-phenyl-heptan-3-one 
• 13031-10-2 2,2-Dimethyl-1,3-diphenyl-1-propanol 
• 141422-22-2 3,3-Dimethyl-4-phenyl-1,2-butanediol 
• 113460-11-0 (E)-4,4-dimethyl-5-phenylpent-2-ene 
• 109387-95-3 2-(1,1-Dimethyl-2-phenylethyl)-4-methylenetetrahydrofuran 
• 84896-37-7 threo-7-phenyl-4,6,6-trimethyl-5-(trimethylsiloxy)-3-heptanone 
• 84896-40-2 6-ethyl-5-methyl-2,4-bis(1,1-dimethyl-2-phenylethyl)-6-(trimethylsiloxy)-1,3-dioxacyclohexane 
• 109720-70-9 [2,2-Dimethyl-3-phenyl-prop-(E)-ylidene]-((Z)-4-trimethylsilanyl-but-3-enyl)-amine 
• 113686-99-0 ((1S,2S)-2-Hydroxy-1,3,3-trimethyl-4-phenyl-butyl)-triphenyl-phosphonium; iodide 
• 4963-91-1 1-phenylphospholane-1-oxide 
• 113705-05-8 (cis-7-phenyl-6,6-dimethyl-hept-4-en-1-yl)-diphenylphosphine oxide 
• 113460-16-5 C₂₇H₃₁OP 
• 113460-12-1 (Z)-4,4-dimethyl-5-phenylpent-2-ene 

Relevant articles and documents

Toward a mild dehydroformylation using base-metal catalysis

Dehydroformylation, or the reaction of aldehydes to produce alkenes, hydrogen gas, and carbon monoxide, is a powerful transformation that is underdeveloped despite the high industrial importance of the reverse reaction, hydroformylation. Interestingly, nature routinely performs a related transformation, oxidative dehydroformylation, in the biosynthesis of cholesterol and related sterols under mild conditions using base-metal catalysts. In contrast, chemists have recently developed a non-oxidative dehydroformylation method; however, it requires high temperatures and a precious-metal catalyst. Careful study of both approaches has informed our efforts to design a base-metal catalyzed, mild dehydroformylation method that incorporates benefits from each while avoiding several of their respective disadvantages. Importantly, we show that cooperative base metal catalysis presents a powerful, mechanistically unique approach to reactions which are difficult to achieve using conventional catalyst design.

Direct Conversion of Nitriles to α-Alkylated Aldehydes

An efficient one-pot process for direct conversion of primary and secondary nitriles to α-alkylated aldehydes has been developed.

Radical Carbonyl Propargylation by Dual Catalysis

Carbonyl propargylation has been established as a valuable tool in the realm of carbon–carbon bond forming reactions. The 1,3-enyne moiety has been recognized as an alternative pronucleophile in the above transformation through an ionic mechanism. Herein, we report for the first time, the radical carbonyl propargylation through dual chromium/photoredox catalysis. A library of valuable homopropargylic alcohols bearing all-carbon quaternary centers could be obtained by a catalytic radical three-component coupling of 1,3-enynes, aldehydes and suitable radical precursors (41 examples). This redox-neutral multi-component reaction occurs under very mild conditions and shows high functional group tolerance. Remarkably, bench-stable, non-toxic, and inexpensive CrCl3 could be employed as a chromium source. Preliminary mechanistic investigations suggest a radical-polar crossover mechanism, which offers a complementary and novel approach towards the preparation of valuable synthetic architectures from simple chemicals.

Visible light photoredox catalyzed deprotection of 1,3-oxathiolanes

An efficient visible light photoredox catalyzed aerobic deprotection of 1,3-oxathiolanes using organic dye Eosin Y as a photocatalyst is disclosed. The deprotection procedure features the use of a metal-free catalyst, mild conditions, a broad range of substrate scope, and good functional group tolerance. 35 examples were tested under the standard conditions and most of them afforded the deprotected products in modest to high yields.

Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation

We report a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N,N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our catalyst protocol enables a two-step semisynthesis of (+)-yohimbenone and dehomologation of feedstock olefins.

Palladium-Catalyzed C(sp3)?H Arylation of Primary Amines Using a Catalytic Alkyl Acetal to Form a Transient Directing Group

C?H Functionalization of amines is a prominent challenge due to the strong complexation of amines to transition metal catalysts, and therefore typically requires derivatization at nitrogen with a directing group. Transient directing groups (TDGs) permit C?H functionalization in a single operation, without needing these additional steps for directing group installation and removal. Here we report a palladium catalyzed γ-C?H arylation of amines using catalytic amounts of alkyl acetals as transient activators (e.g. commercially available (2,2-dimethoxyethoxy)benzene). This simple additive enables arylation of amines with a wide range of aryl iodides. Key structural features of the novel TDG are examined, demonstrating an important role for the masked carbonyl and ether functionalities. Detailed kinetic (RPKA) and mechanistic investigations determine the order in all reagents, and identify cyclopalladation as the turnover limiting step. Finally, the discovery of an unprecedented off-cycle free-amine directed ?-cyclopalladation of the arylation product is reported.

Ketenimines from Isocyanides and Allyl Carbonates: Palladium-Catalyzed Synthesis of β,γ-Unsaturated Amides and Tetrazoles

The reaction of allyl ethyl carbonates with isocyanides in the presence of a catalytic amount of Pd(OAc)2provided ketenimines through β-hydride elimination of the allyl imidoylpalladium intermediates. The insertion of the isocyanide into the π-allyl Pd complex proceeded via an unusual η1-allyl Pd species. The resulting ketenimines were hydrolyzed to β,γ-unsaturated carboxamides during purification by flash column chromatography on silica gel or converted in situ into 1,5-disubstituted tetrazoles by [3+2] cycloaddition with hydrazoic acid or trimethylsilyl azide.

Z-Selective ring opening of vinyl oxetanes with dialkyl dithiophosphate nucleophiles

Dialkyl dithiophosphates selectively ring open vinyl oxetanes in excellent yields under mild reaction conditions to form useful allylic thiophosphate products with high Z-selectivity. The Royal Society of Chemistry 2013.

Indium-catalyzed coupling reaction between silyl enolates and alkyl chlorides or alkyl ethers

The coupling reactions of alkyl chlorides with silyl enolates catalyzed by InBr3, and the coupling reactions of alkyl ethers with silyl enolates catalyzed by the combined Lewis acid of InBr3/Me3SiBr are described. In both reaction systems, various types of silyl enolates were used to give corresponding α-alkylated esters, ketones, carboxylic acids, amides, thioesters, and aldehydes.

Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide

Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of α-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl chloride, and allylsilane or alkynylsilane.