4374-44-1

Basic information

• Product Name: 2,2-Dimethyl-4-phenylbutyricacid
• Synonyms: 2,2-Dimethyl-4-phenylbutyricacid;2,2-dimethyl-4-phenylbutanoic acid
• CAS NO: 4374-44-1
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25424
• Mol File: 4374-44-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 307°C at 760 mmHg
• Flash Point: 204.1°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 0.000325mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: 2,2-Dimethyl-4-phenylbutyricacid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-4-phenylbutyricacid(4374-44-1)
• EPA Substance Registry System: 2,2-Dimethyl-4-phenylbutyricacid(4374-44-1)

Safety Data

• Hazardous Substances Data: 4374-44-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 2500, 1967 DOI: 10.1021/ja00986a056Synthesis, p. 310, 1979 DOI: 10.1055/s-1979-28664

InChI:InChI=1/C12H16O2/c1-12(2,11(13)14)9-8-10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3,(H,13,14)

Upstream product

• 100-42-5 styrene 
• 79-31-2 isobutyric Acid 
• 71-43-2 benzene 
• 14308-33-9 2,2-dimethoxy-3,3-dimethyl-5-phenyl-2,3-dihydro-furan 
• 621-82-9 Cinnamic acid 
• 538-42-1 sodium cinnamate 
• 4610-69-9 (Z)-ethyl cinnamate 
• 15732-89-5 (E)-2,2-dimethyl-4-phenylbut-3-enoic acid 
• 140-10-3 cis-cinnamic acid 
• 94041-88-0 methyl (E)-2,2-dimethyl-4-phenyl-3-buten-1-oate 
• 38795-58-3 2-methyl-4-phenylbutyric acid methyl ester 
• 2046-17-5 methyl 3-(benzyl)propanoate 
• 100-52-7 benzaldehyde 
• 103-63-9 1-phenyl-2-bromoethane 

Downstream Products

• 36748-92-2 2,2-dimethyl-4-phenyl-butyryl chloride 
• 858815-43-7 4-(2,4-dinitro-phenyl)-2,2-dimethyl-butyric acid 
• 934832-52-7 N-benzyloxy-4-(2,2-dimethyl-4-phenyl-butyrylamino)-benzamide 
• 1361152-14-8 tert-butyl 2,2-dimethyl-4-phenylbutaneperoxoate 
• 1613145-75-7 2,2-dimethyl-4-phenyl-N-(quinolin-8-yl)butanamide 
• 103-07-1 1,1-dimethyl-3-phenylpropyl acetate 
• 79399-13-6 N-[1,1-dimethyl-3-phenylpropyl]acetamide 
• 20215-55-8 dihydro-3,3-dimethyl-5-phenylfuran-2(3H)-one 
• 1439367-46-0 (2,2-dimethyl-4-phenyl-butyl) 2-oxopyridine-1-carboxylate 
• 1439367-45-9 (2,2-dimethyl-4-phenyl-butyl) 2-pyridyl carbonate 
• 40654-84-0 2,2-dimethyl-4-phenylbutanal 

Relevant articles and documents

Rapid Construction of Tetralin, Chromane, and Indane Motifs via Cyclative C-H/C-H Coupling: Four-Step Total Synthesis of (±)-Russujaponol F

The development of practical C-H/C-H coupling reactions remains a challenging yet appealing synthetic venture because it circumvents the need to prefunctionalize both coupling partners for the generation of C-C bonds. Herein we report a cyclative C(sp3)-H/C(sp2)-H coupling reaction of free aliphatic acids enabled by a cyclopentane-based mono-N-protected β-amino acid ligand. This reaction uses inexpensive sodium percarbonate (Na2CO3·1.5H2O2) as the sole oxidant and generates water as the only byproduct. A range of biologically important scaffolds, including tetralins, chromanes, and indanes, can be easily prepared by this protocol. Finally, the synthetic application of this methodology is demonstrated by the concise total synthesis of (±)-russujaponol F in a four-step sequence starting from readily available phenylacetic acid and pivalic acid through sequential functionalizations of four C-H bonds.

Quaternary Centers by Nickel-Catalyzed Cross-Coupling of Tertiary Carboxylic Acids and (Hetero)Aryl Zinc Reagents

This work bridges a gap in the cross-coupling of aliphatic redox-active esters with aryl zinc reagents. Previously limited to primary, secondary, and specialized tertiary centers, a new protocol has been devised to enable the coupling of general tertiary systems using nickel catalysis. The scope of this operationally simple method is broad, and it can be used to simplify the synthesis of medicinally relevant motifs bearing quaternary centers.

Decarboxylative Alkylcarboxylation of α,β-Unsaturated Acids Enabled by Copper-Catalyzed Oxidative Coupling

A facile and general method for copper-catalyzed decarboxylative alkylcarboxylation of cinnamic acids with dimethyl 2,2′-azobis(2-methylpropionate) has been developed. The scope and versatility of the reaction was demonstrated, and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to provide desired β,γ-unsaturated esters in moderate to good yields. Moreover, α,β-unsaturated acids with a carbonyl group on the γ-position of acrylic acids also smoothly proceeded to furnish the desired products in good yields.