61495-04-3

Basic information

• Product Name: 2,2,2'-TRIMETHYLPROPIONANILIDE
• Synonyms: N-Pivaloyl-o-toluidine,99%;N-Pivaloyl-o-toluidine2,2,2'-Trimethylpropionanilide;2,2,2'-Trimethylpropionanilide ,99%;N-Pivaloyl-o-toluidine, 99% 5GR;N-Pivaloyl-O-toluidine, GC 98%;N-(2-Chlorophenyl)-2,2-dimethylpropanamide;2,2,2'-TRIMETHYLPROPIONANILIDE;N-PIVALOYL-O-TOLUIDINE
• CAS NO: 61495-04-3
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.27
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 61495-04-3.mol
• Article Data: 35

Chemical Properties

• Melting Point: 111-115 °C
• Boiling Point: 327.03°C (rough estimate)
• Flash Point: 189.8 °C
• Appearance: White/Crystalline Powder
• Density: 1.0096 (rough estimate)
• Vapor Pressure: 0.000338mmHg at 25°C
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.13±0.70(Predicted)
• CAS DataBase Reference: 2,2,2'-TRIMETHYLPROPIONANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2'-TRIMETHYLPROPIONANILIDE(61495-04-3)
• EPA Substance Registry System: 2,2,2'-TRIMETHYLPROPIONANILIDE(61495-04-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 61495-04-3(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

2,2,2′-Trimethylpropionanilide (2,2,2-N-pivaloyl-o-toluidine) may be used to determine the concentration of lithium diisopropylamide mono(tetrahydrofuran) via titration. It may be used to determine the concentrations of alkyllithiums by titration, to the colorimetric endpoint, indicated by the persistence of a yellow color in the solution.

InChI:InChI=1/C12H17NO/c1-9-7-5-6-8-10(9)13-11(14)12(2,3)4/h5-8H,1-4H3,(H,13,14)

Upstream product

• 3282-30-2 pivaloyl chloride 
• 95-53-4 o-toluidine 
• 754-10-9 2,2-dimethylpropionamide 
• 95-49-8 2-methylchlorobenzene 
• 75-84-3 2,2-dimethyl-propanol-1 
• 630-19-3 pivalaldehyde 
• 75-98-9 Trimethylacetic acid 

Downstream Products

• 124415-81-2 N-[2-[2-methylamino-2-(thien-2-yl)ethyl]phenyl]-2,2-dimethylpropanamide 
• 124415-83-4 (+/-)-2,2-dimethyl-N-<2-<2-(methylamino)-2-(3-methyl-2-thienyl)ethyl>phenyl>propanamide 
• 54856-58-5 2-tert-butyl-2,3-dihydro-1H-indole 
• 873055-09-5 2-tert-butyl-6-nitro-1H-indole 

Relevant articles and documents

Simple Direct Titration of Organolithium Reagents Using N-Pivaloyl-o-toluidine and/or N-pivaloyl-o-benzylaniline

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Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature

The unsymmetrical biaryls (Ar1-Ar2) produced by the catalytic cross-couplings of aryl halides (Ar1-halo) with aryl metallics (Ar2-M) in the loading ratio of 1:1 are popular in chemical synthesis. In contrast, there has been less precedence on the same biaryls produced effectively from two normal aryl C-H bonds with equivalent loading. Here, we report that, in a palladium/oxidant/acid catalytic system at room temperature, one arene (Ar1-H, 1 equiv) can highly selectively couple with the other one (Ar2-H, 1 equiv) to afford the target Ar1-Ar2 just by controlling the directing groups and the substituted groups on their phenyl rings. The utility of this one-one cross-coupling is also demonstrated by synthesis of a few bioactive molecules.

Ligand Promoted Olefination of Anilides for Indirectly Introducing Fluorinated Functional Groups via Palladium Catalyst

We report a palladium-catalyzed, ligand promoted, C-H fluorine-containing olefination of anilides with 4-bromo-3,3,4,4-tetrafluorobutene as the fluorinated reagent, which has a potential transformation into other compounds due to its -CF2CF2Br functional group. -CF2CF2H was obtained by using the mild reducing agent sodium borohydride. Bioactive compounds such as aminoglutethimide derivative and propham were well-tolerated in this reaction, both of which highlight the synthetic importance of this method.