938-16-9

Basic information

• Product Name: 2,2-DIMETHYLPROPIOPHENONE
• Synonyms: 2,2-DIMETHYLPROPIOPHENONE;2,2-DIMETHYLPHENYL-1-PROPANONE;ALPHA,ALPHA,ALPHA-TRIMETHYLACETOPHENONE;1-Propanone,2,2-dimethyl-1-phenyl-;2,2-Dimethyl-1-phenyl-1-propanone;2,2-dimethyl-1-phenyl-propan-1-one;alpha,alpha-Dimethylpropiophenone;Phenyl tert-butyl ketone
• CAS NO: 938-16-9
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• EINECS: 213-338-0
• Mol File: 938-16-9.mol

Chemical Properties

• Boiling Point: 219-222 °C(lit.)
• Flash Point: 189 °F
• Appearance: /
• Density: 0.97 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.116mmHg at 25°C
• Refractive Index: n20/D 1.508(lit.)
• Water Solubility: Not miscible with water.
• BRN: 1906460
• CAS DataBase Reference: 2,2-DIMETHYLPROPIOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIMETHYLPROPIOPHENONE(938-16-9)
• EPA Substance Registry System: 2,2-DIMETHYLPROPIOPHENONE(938-16-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 938-16-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis Industry:
2,2-DIMETHYLPROPIOPHENONE is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the development of new molecules with desired properties.
Used in Pharmaceutical Industry:
2,2-DIMETHYLPROPIOPHENONE is used as a starting material for the synthesis of various pharmaceutical compounds, particularly those with potential therapeutic applications. Its unique structure and reactivity enable the development of new drugs with improved efficacy and safety profiles.
Used in Material Science:
2,2-DIMETHYLPROPIOPHENONE is used in the development of novel materials with specific properties, such as polymers, coatings, and adhesives. Its unique structure and reactivity contribute to the creation of materials with enhanced performance characteristics, such as improved durability, stability, and functionality.
Used in Research and Development:
2,2-DIMETHYLPROPIOPHENONE is used as a research compound in academic and industrial laboratories to explore its chemical properties, reactivity, and potential applications. Its unique structure and synthesis method provide valuable insights into the development of new synthetic routes and the discovery of new compounds with diverse applications.

Synthesis Reference(s)

Tetrahedron, 39, p. 3207, 1983 DOI: 10.1016/S0040-4020(01)91568-6Tetrahedron Letters, 37, p. 5381, 1996 DOI: 10.1016/0040-4039(96)01083-0Synthesis, p. 662, 1974 DOI: 10.1055/s-1974-23397

InChI:InChI=1/C11H14O/c1-11(2,3)10(12)9-7-5-4-6-8-9/h4-8H,1-3H3

Upstream product

• 85-44-9 phthalic anhydride 
• 94327-55-6 ethyl 3-hydroxy-4,4-dimethyl-3-phenylpentanoate 
• 630-18-2 tert-butyl isocyanide 
• 754-10-9 2,2-dimethylpropionamide 
• 3835-64-1 2,2-dimethyl-1-phenylpropan-1-ol 
• 3282-30-2 pivaloyl chloride 
• 677-22-5 tert-butylmagnesium chloride 
• 98-88-4 benzoyl chloride 
• 100-47-0 benzonitrile 
• 159681-58-0 di-tert-butylcadmium 
• 93-97-0 benzoic acid anhydride 
• 74-83-9 methyl bromide 
• 98-86-2 acetophenone 
• 74-88-4 methyl iodide 

Downstream Products

• 75-98-9 Trimethylacetic acid 
• 1518-32-7 1-tert-butyl-1,3-diphenyl-2-propyn-1-ol 
• 34235-13-7 3-phenyl-2,2-dimethylpentan-3-ol 
• 21811-48-3 3,3-dimethyl-2-phenyl-butan-2-ol 
• 3835-64-1 2,2-dimethyl-1-phenylpropan-1-ol 
• 1657-60-9 2,2-dimethyl-1,1-diphenyl-propan-1-ol 
• 770-85-4 2-methyl-2-phenylbutan-3-one 
• 6668-41-3 pivalophenone oxime 
• 1007-26-7 (2,2-dimethyl-1-propyl)benzene 
• 23439-91-0 (1S)-2,2-dimethyl-1-phenyl-1-propanol 
• 23439-91-0 2,2-dimethyl-1-phenyl-1-propanol 
• 121223-91-4 1-phenyl-1,1-dichloro-2,2-dimethylpropane 
• 860701-38-8 1-deuterio-2,2-dimethyl-1-phenyl-propan-1-ol 
• 94327-55-6 ethyl 3-hydroxy-4,4-dimethyl-3-phenylpentanoate 

Relevant articles and documents

Palladium-NHC (NHC = N-heterocyclic Carbene)-Catalyzed Suzuki-Miyaura Cross-Coupling of Alkyl Amides

We report the Pd-catalyzed Suzuki-Miyaura cross-coupling of aliphatic amides. Although tremendous advances have been made in the cross-coupling of aromatic amides, C-C bond formation from aliphatic amides by selective N-C(O) cleavage has remained a major challenge. This longstanding problem in Pd catalysis has been addressed herein by a combination of (1) the discovery of N,N-pym/Boc amides as a class of readily accessible amide-based reagents for cross-coupling and (2) steric tuning of well-defined Pd(II)-NHC catalysts for cross-coupling. The methodology is effective for the cross-coupling of an array of 3°, 2°, and 1° aliphatic amide derivatives. The catalyst system is user-friendly, since the catalysts are readily available and are air- and bench-stable. Mechanistic studies strongly support an amide bond twist and external nN → π*C═O/Ar delocalization as a unified enabling feature of N,N-pym/Boc amides in selective N-C(O) bond activation. The method provides a rare example of Pd-NHC-catalyzed cross-coupling of aliphatic acyl amide electrophiles.

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Method for oxidative cracking of compound containing unsaturated double bonds

The invention relates to a method for oxidative cracking of a compound containing unsaturated double bonds. The method comprises the following steps: (A) providing a compound (I) containing unsaturated double bonds, a trifluoromethyl-containing reagent and a catalyst, wherein the catalyst is shown as a formula (II): M(O)mL1yL2z (II), M, L1, L2, m, y, z, R1, R2 and R3 being defined in the specification; and (B) mixing the compound containing the unsaturated double bonds and the trifluoromethyl-containing reagent, and performing an oxidative cracking reaction on the compound containing the unsaturated double bonds in the presence of air or oxygen by using the catalyst to obtain a compound represented by formula (III),.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):

Rhodium-Catalyzed and Chiral Zinc Carboxylate-Assisted Allenylation of Benzamides via Kinetic Resolution

Enantioenriched allenes are important building blocks. While they have been accessed by other coupling methodologies, enantioenriched allenes have been rarely obtained via C-H activation. In this work, kinetic resolution of tertiary propargyl alcohols as an allenylating reagent has been realized via rhodium(III)-catalyzed C-H allenylation of benzamides. The reaction proceeded efficiently under mild conditions, and both the allenylated products and the propargyl alcohols were obtained in high enantioselectivities with an s-factor of up to 139. The resolution results from bias of the two propargylic substituents and is assisted by a chiral zinc carboxylate additive.

Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions

A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.

Mild oxidation of benzyl alcohols to benzyl aldehydes or ketones catalyzed by visible light

Induced by visible light, mild oxidation condition to prepare benzyl aldehydes or ketones have been developed by using bromotrichloromethane as photochemical oxidant. This method avoids high temperature, pressure and peroxidation with only visible light as the green driving force.

METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND

A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method comprises the following step: (A) providing a compound (I) with an unsaturated double bond, a reagent with trifluoromethyl, and a catalyst; wherein the catalyst is represented by the following formula (II): M(O)mL1yL2z (II); wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and (B) mixing the compound with an unsaturated double bond and the reagent with a trifluoromethyl to perform an oxidation of the compound with the unsaturated double bond by using the catalyst at air or an oxygen condition to get a compound presented as formula (III):

A metal-free heterogeneous photocatalyst for the selective oxidative cleavage of CC bonds in aryl olefins: via harvesting direct solar energy

Selective cleavage of CC bonds is highly important for the synthesis of carbonyl containing fine chemicals and pharmaceuticals. Novel methodologies such as ozonolysis reactions, Lemieux-Johnson oxidation reaction etc. already exist. Parallel to these, catalytic methods using homogeneous catalysts also have been discovered. Considering the various advantages of heterogeneous catalysts such as recyclability and stability, couple of transition metal-based heterogeneous catalysts have been applied for this reaction. However, the pharmaceutical industries prefer to use metal-free catalysts (especially transition metal-free) to avoid further leaching in the final products. This is for sure a big challenge to an organic chemist and to the pharmaceutical industries. To make this feasible, a mild and efficient protocol has been developed using polymeric carbon nitrides (PCN) as metal-free heterogeneous photocatalysts to convert various olefins into the corresponding carbonyls. Later, this catalyst has been applied in the gram scale synthesis of pharmaceutical drugs using direct solar energy. Detailed mechanistic studies revealed the actual role of oxygen, the catalyst, and the light source.

Donor-Flexible Bis(pyridylidene amide) Ligands for Highly Efficient Ruthenium-Catalyzed Olefin Oxidation

An exceptionally efficient ruthenium-based catalyst for olefin oxidation has been designed by exploiting N,N′-bis(pyridylidene)oxalamide (bisPYA) as a donor-flexible ligand. The dynamic donor ability of the bisPYA ligand, imparted by variable zwitterionic and neutral resonance structure contributions, paired with the redox activity of ruthenium provided catalytic activity for Lemieux–Johnson-type oxidative cleavage of olefins to efficiently prepare ketones and aldehydes. The ruthenium bisPYA complex significantly outperforms state-of-the-art systems and displays extraordinary catalytic activity in this oxidation, reaching turnover frequencies of 650 000 h?1 and turnover numbers of several millions.