72228-10-5

Basic information

• Product Name: 3,3-bis(4-methylphenyl)-2-propenal
• Synonyms: 3,3-bis(4-methylphenyl)-2-propenal
• CAS NO: 72228-10-5
• Molecular Weight: 236.313
• Mol File: 72228-10-5.mol

Chemical Properties

• CAS DataBase Reference: 3,3-bis(4-methylphenyl)-2-propenal(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-bis(4-methylphenyl)-2-propenal(72228-10-5)
• EPA Substance Registry System: 3,3-bis(4-methylphenyl)-2-propenal(72228-10-5)

Safety Data

• Hazardous Substances Data: 72228-10-5(Hazardous Substances Data)

Upstream product

• 624-31-7 4-tolyl iodide 
• 84118-65-0 1-(3-methoxy-prop-1-ynyl)-4-methyl-benzene 
• 2919-20-2 1,1-di(p-tolyl)ethylene 
• 93-61-8 N-methyl-N-phenylformamide 
• 107-18-6 allyl alcohol 
• 123-38-6 propionaldehyde 
• 93318-88-8 1,1-bis(4-methylphenyl)-2-propyn-1-ol 
• 7020-80-6 acetaldehyde N-tert-butylimine 
• 611-97-2 bis(p-methylphenyl)-methanone 
• 814-49-3 diethyl chlorophosphate 
• 121-44-8 triethylamine 

Downstream Products

• 95269-68-4 3,3-bis(4-methylphenyl)propionic acid 
• 93318-96-8 3,3-di-p-tolylacrylic acid 
• 142669-91-8 3,3-bis(4-methylphenyl)-2-propenenitrile 
• 1360807-17-5 (R)-2-benzoyl-3-(3-methoxyphenyl)-1-phenyl-6,6-di-p-tolylhex-5-ene-1,4-dione 
• 72228-11-6 1,1-Dicyano-4,4-di-p-tolyl-1,3-butadien 
• 120554-01-0 (E)-5,5-bis(4-methylphenyl)-2,4-pentadienoic acid 

Relevant articles and documents

Metalation of iminium ions formed in the reaction of tertiary amines with TiCl4

(equation presented) TiCl4 reacts with trialkylamines at 0-25°C to give iminium ions that on metalation followed by reaction with diaryl ketones, produce α,β-unsaturated aldehydes.

Deep eutectic solvent-catalyzed Meyer-Schuster rearrangement of propargylic alcohols under mild and bench reaction conditions

The Meyer-Schuster rearrangement of propargylic alcohols into α,β-unsaturated carbonyl compounds has been revisited by setting up an atom-economic process catalyzed by a deep eutectic solvent FeCl3·6H2O/glycerol. Isomerizations take place smoothly, at room temperature, under air and with short reaction times. The unique solubilizing properties of the eutectic mixture enabled the use of a substrate concentration up to 1.0 M with the medium being recycled up to ten runs without any loss of catalytic activity. This journal is

Metal- and Acid-Free Methyl Triflate Catalyzed Meyer-Schuster Rearrangement

A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer-Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.

Phase-vanishing method applied to condensation reactions using TiCl4

The phase-vanishing (PV) method using perfluorohexanes as the phase screen was applied to the aldol condensation using TiCl4 as the Lewis acid. A special test tube was used, in which an interface between the fluorous and organic layers was stirred, and cyclohexanone was treated with two equivalents of benzaldehyde derivatives under PV conditions to afford corresponding 2,6-dibenzylidencyclohexanone in good yields. The formyl-methylenation of ketones with triethylamine using TiCl4 was also demonstrated by the PV method.

A Weinreb Amide Based Building Block for Convenient Access to β,β-Diarylacroleins: Synthesis of 3-Arylindanones

Towards the synthesis of symmetrical and unsymmetrical β,β-diarylacroleins for assembling diarylmethine fragments present in biologically important molecules, we have developed a new Weinreb amide (WA) based building block, derived from propiolic acid. The WA functionality present in this compound allowed the sequential addition of various arylmagnesium bromide reagents in a controlled manner. The developed methodology for the access to β,β-diarylacroleins has been utilised for the synthesis of biologically important 3-arylindanone molecules. Synthesis of both symmetrical and unsymmetrical β,β-diarylacrolein and diarylmethine fragments, have been achieved via easily accessible and hitherto unknown Weinreb Amide (WA) based building block 11. The WA functionality allowed the sequential addition of nucleophiles such as arylmagnesium bromide in a controlled manner, which has enabled the synthesis of an important 3-arylindanone molecule.

Domino Reactions Containing Different Types of Heck Reactions for Selective 3,3- and 1,3-Diarylations of Propenol with Aryl Halides by Triple Catalysis

A new domino Heck-isomerization/Saegusa/Heck reaction of propenol with aryl iodides has been developed for the synthesis of 3,3-diaryl propenals by triple transition-metal catalysis. Moreover, we also developed the domino Heck-isomerization/Heck-type reaction of propenol with aryl iodides for the synthesis of 1,3-diaryl propanones by double transition-metal catalysis and the mediation of secondary amine or triple transition metal catalysis and aminocatalysis.

Palladium-catalyzed dehydrogenative β-arylation of simple saturated carbonyls by aryl halides

(Chemical Equation Presented) A versatile palladium-catalyzed synthesis of highly substituted α,β-unsaturated carbonyl compounds has been developed. In contrast to the known Heck-type coupling reaction of unsaturated carbonyl compounds with aryl halides, the present methodology allows the use of stable and readily available saturated carbonyl compounds as the alkene source. In addition, the reaction proceeds well with low catalyst loadings and does not require any expensive metal oxidants or ligands. A variety of saturated aldehydes, ketones, and esters are compatible for the reaction with aryl halides under the developed reaction conditions to afford α,β-unsaturated carbonyl compounds in good to excellent yields. A possible reaction mechanism involves a palladium-catalyzed dehydrogenation followed by Heck-type cross couplings.

[PF6]2 As catalyst for the meyer-schuster rearrangement of arylpropargylic alcohols under mild conditions

The novel iridium complex [IrCpNCMe2PPh2Me][PF6]2 I efficiently catalyzed the Meyer-Schuster rearrangement of selected arylpropargylic alcohols into α,β-unsaturated aldehydes under mild conditions and without the need of a co-catalyst. A mechanism involving a hydroxy alkenylcarbene intermediate is proposed. [IrCpNCMe2PPh2Me][PF6]2 efficiently catalyzes the rearrangement of propargylic alcohols into α,β-unsaturated aldehydes under mild conditions and without the need of a co-catalyst.

Synthesis and reactivity of new rhenium(I) complexes containing iminophosphorane-phosphine ligands: Application to the catalytic isomerization of propargylic alcohols in ionic liquids

[ReBr(CO)5] reacts with the iminophosphorane-phosphine ligands Ph2PCH2P(=NR)Ph2 (R = P(=O)(OEt)2 (1a), P(=O)(OPh)2 (1b), P(=S)(OEt)2 (1c), P(=S)(OPh) 2 (1d), 4-C6F4CHO (1e), 4-C6F 4CN (1f), 4-C5F4N (1g)) affording the neutral complexes [ReBr(κ2-P,X-Ph2PCH2P{=NP(=X) (OR)2}Ph2)(CO)3] (X = O, R = Et (2a), Ph (2b); X = S, R = Et (2c), Ph (2d)) and [ReBr{κ2-P,N-Ph 2PCH2P(=NR)Ph2}(CO)3] (R = P(=O)(OEt)2 (3a), P(=O)(OPh)2 (3b), 4-C6F 4CHO (3e), 4-C6F4CN (3f), 4-C5F 4N (3g)). The reactivity of the cationic complex [Re(κ 3-P,N,S-Ph2PCH2P{=NP(=S)(OPh) 2}Ph2)(CO)3][SbF6] (4d) has been explored allowing the synthesis of the cationic [Re(L)(κ2-P,S- Ph2PCH2P{=NP(=S)(OPh)2}Ph2)(CO) 3][SbF6] (L = acetone (5a), CH3C≡N (5b), pyridine (5c), PPh3 (5d)) and the neutral [ReY(κ2-P, S-Ph2PCH2P{=NP(=S)(OPh)2}Ph2)(CO) 3] (Y = Cl (6a), I (6b), N3 (6c)) complexes. The catalytic activity of complex 4d in the regioselective isomerization of terminal propargylic alcohols HC≡CCR1R2(OH) into α,β-unsaturated aldehydes R1R2C=CHCHO or ketones R3R4C=CR1COMe (if R2 = CHR3R4) under neutral conditions in ionic liquids has being studied. Isolation and X-ray characterization of the key intermediate rhenium(I) oxocyclocarbene complex [Re{=C(CH2)3O} (κ2-P,S-Ph2PCH2P{=NP(=S)(OPh) 2}Ph2)(CO)3][SbF6] (5e) seems to indicate that the catalytic reaction proceeds through tautomerization of the terminal alkynols to yield vinilydene-type species.

New Ag(I)-iminophosphorane coordination polymers as efficient catalysts precursors for the MW-assisted meyer-schuster rearrangement of propargylic alcohols in water

Treatment of the N-thiophosphorylated iminophosphorane ligands (PTA)=NP(=S)(OR)2 [PTA = 1,3,5-triaza-7-phosphaadamantane, 3a and 3b] and (DAPTA)=NP(=S)(OR)2 [DAPTA = 3,7-diacetyl-1,3,7-triaza-5- bicyclo[3.3.1]nonane, 4a and 4b] with an equimolecular amount of AgSbF 6 leads to high-yield formation of the new one-dimensional coordination polymers [Ag{μ2-N,S-(PTA)=NP(=S)(OR) 2}]x[SbF6]x (5a and 5b) and [Ag{μ2-O,S-(DAPTA)=NP(=S)(OR)2}]x[SbF 6]x (6a and 6b), respectively. These new (iminophosphorane)silver(I) coordination polymers are efficient catalyst precursors for the Meyer-Schuster isomerization of both terminal and internal alkynols. Reactions proceeded in water, under aerobic conditions and using microwave irradiation as heating source, to afford the corresponding α,β-unsaturated carbonyl compounds in excellent yields, without the addition of any cocatalyst. Remarkably, it should be noted that this catalytic system can be recycled up to 10 consecutive runs (1st cycle 45 min, 99%; 10th cycle 6 h, 97%). ESI-MS analysis of 5a in water has been carried out providing valuable insight into the monomeric active species responsible for catalytic activity in water.