7324-58-5

Basic information

• Product Name: Propanoic acid, 2,2-dimethyl-, silver(1+) salt
• Synonyms: silver(I) 2,2-dimethylpropionate;Ag(OCOtBu);Ag(OPiv);silver(I) tert-butylcarboxylate;silver(I) trimethylacetate;AgOPiv
• CAS NO: 7324-58-5
• Molecular Formula: C5H10O2.Ag
• Molecular Weight: 208.993
• Mol File: 7324-58-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 240 °C (sublm)
• CAS DataBase Reference: Propanoic acid, 2,2-dimethyl-, silver(1+) salt(CAS DataBase Reference)
• NIST Chemistry Reference: Propanoic acid, 2,2-dimethyl-, silver(1+) salt(7324-58-5)
• EPA Substance Registry System: Propanoic acid, 2,2-dimethyl-, silver(1+) salt(7324-58-5)

Safety Data

• Hazardous Substances Data: 7324-58-5(Hazardous Substances Data)

Upstream product

• 7440-22-4 silver 
• 75-98-9 Trimethylacetic acid 

Downstream Products

• 95122-94-4 p-nitrobenzyl 6α-bromo-2β-<(pivaloyloxy)methyl>-2α-methylpenam-3α-carboxylate 1,1-dioxide 
• 101623-83-0 2,2-dimethylpropionyloxymethyl p-nitrophenyl carbonate 
• 19820-47-4 4-methoxyphenyl 2,2-dimethylpropionate 
• 30123-12-7 silver(I)pentafluorobenzene 
• 27644-18-4 pivaloyl bromide 

Relevant articles and documents

The standard enthalpy of formation of silver pivalate

The standard enthalpy of combustion of crystalline silver pivalate, (CH3)3CC(O)OAg (AgPiv), was determined in an isoperibolic calorimeter with a self-sealing steel bomb, Δc H 0 (AgPiv, cr)= -2786.9±5.6 kJ mol-1. The value of standard enthalpy of formation was derived for crystalline state: Δf H 0(AgPiv,cr)= -466.9±5.6 kJ mol-1. Using the enthalpy of sublimation, measured earlier, the enthalpy of formation of gaseous dimer was obtained: Δf H 0(Ag2Piv 2,g)= -787±14 kJ mol-1. The enthalpy of reaction (CH3)3CC(O)OAg(cr)=Ag(cr)+(CH3) 3CC(O)O.(g) was estimated, Δr H 0=202 kJ mol-1.

Palladium-Catalyzed, Site-Selective Direct Allylation of Aryl C-H Bonds by Silver-Mediated C-H Activation: A Synthetic and Mechanistic Investigation

We describe a method for the site-selective construction of a C(aryl)-C(sp3) bond by the palladium-catalyzed direct allylation of arenes with allylic pivalates in the presence of AgOPiv to afford the linear (E)-allylated arene with excellent regioselectivity; this reaction occurs with arenes that have not undergone site-selective and stereoselective direct allylation previously, such as monofluorobenzenes and non-fluorinated arenes. Mechanistic studies indicate that AgOPiv ligated by a phosphine reacts with the arene to form an arylsilver(I) species, presumably through a concerted metalation-deprotonation pathway. The activated aryl moiety is then transferred to an allylpalladium(II) intermediate formed by oxidative addition of the allylic pivalate to the Pd(0) complex. Subsequent reductive elimination furnishes the allyl-aryl coupled product. The aforementioned proposed intermediates, including an arylsilver complex, have been isolated, structurally characterized, and determined to be chemically and kinetically competent to undergo the proposed elementary steps of the catalytic cycle.

Redox-controlled selectivity of C-H activation in the oxidative cross-coupling of arenes

Gold brings us together: Taking advantage of the orthogonal reactivities of AuI and AuIII towards C-H activation of electron-poor and electron-rich arenes, respectively, a novel approach for the synthesis of biaryls through double C-H activation is proposed. Stoichiometric studies demonstrate that these oxidative couplings occur with high selectivity at low temperature. Copyright