32597-29-8

Basic information

• Product Name: 2,2-Dimethyl-N-(3-methylphenyl)propanamide
• Synonyms: 2,2-Dimethyl-N-(3-methylphenyl)propanamide;N-tert-butoxylcarbonyl-3-methylaniline
• CAS NO: 32597-29-8
• Molecular Formula: C₁₂H₁₇NO
• Molecular Weight: 191.27
• Mol File: 32597-29-8.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-Dimethyl-N-(3-methylphenyl)propanamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-N-(3-methylphenyl)propanamide(32597-29-8)
• EPA Substance Registry System: 2,2-Dimethyl-N-(3-methylphenyl)propanamide(32597-29-8)

Safety Data

• Hazardous Substances Data: 32597-29-8(Hazardous Substances Data)

Usage

General Description

2,2-Dimethyl-N-(3-methylphenyl)propanamide, also known as DMAA, is a synthetic compound that is categorized as a central nervous system stimulant. It is structurally similar to amphetamine and ephedrine and is commonly used as a performance-enhancing drug and a dietary supplement. DMAA has been associated with various adverse health effects, including elevated blood pressure, cardiovascular events, and even death. Due to these safety concerns, many countries have banned or restricted the use of DMAA in dietary supplements, and it is considered a prohibited substance in many sports organizations.

Upstream product

• 3282-30-2 pivaloyl chloride 
• 108-44-1 1-amino-3-methylbenzene 
• 126246-65-9 2,2-Dimethyl-N-(3-trimethylsilanylmethyl-phenyl)-propionamide 

Downstream Products

• 1309448-77-8 N-(2-(4-chlorobenzoyl)phenyl)pivalamide 
• 1351697-64-7 C₁₉H₂₀ClNO₂ 
• 1551376-69-2 N-(2-bromo-5-methylphenyl)pivalamide 
• 59517-21-4 4,4′-dimethyl-[1,1′-biphenyl]-2,2′-diamine 
• 70298-82-7 2’,5’-dimethylpivalanilide 
• 1580516-22-8 ethyl 2-benzamido-2-(4-methyl-2-pivalamidophenyl)acetate 

Relevant articles and documents

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.

Para -Selective copper-catalyzed C(sp2)-H amidation/dimerization of anilides via a radical pathway

Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp2)-H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C-N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The regioselectivity is confirmed by single-crystal X-ray studies.

Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature

The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.