1268380-10-4

Basic information

• Product Name: C₁₄H₁₀O₄
• Synonyms: C₁₄H₁₀O₄
• CAS NO: 1268380-10-4
• Molecular Weight: 242.231
• Mol File: 1268380-10-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: C₁₄H₁₀O₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₄H₁₀O₄(1268380-10-4)
• EPA Substance Registry System: C₁₄H₁₀O₄(1268380-10-4)

Safety Data

• Hazardous Substances Data: 1268380-10-4(Hazardous Substances Data)

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 1885-14-9 phenyl chloroformate 

Downstream Products

• 81256-74-8 sodium salicylat 
• 38697-17-5 sodium salt of meta-hydroxybenzaldehyde 
• 16641-71-7 1-(phenoxycarbonyl)piperidine 
• 100-83-4 meta-hydroxybenzaldehyde 
• 13932-55-3 phenyl carbonic acid 

Relevant articles and documents

Kinetic study on nucleophilic displacement reactions of phenyl Y-substituted phenyl carbonates with 1,8-diazabicyclo[5.4.0]undec-7-ene: Effects of amine nature on reaction mechanism

Second-order rate constants (kN) for nucleophilic displacement reactions of phenyl Y-substituted phenyl carbonates (7a-7l) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C have been measured spectrophotometrically. The Br?nsted-type plot for the reactions of 7a-7l with DBU is linear with βlg = -0.48, indicating that the reactions proceed through a concerted mechanism, which is in contrast to the stepwise mechanism reported previously for the corresponding reactions with ethylamine (a primary amine) and piperidine (a secondary amine). The Hammett plots correlated with σ- and σo constants exhibit many scattered points. In contrast, the Yukawa-Tsuno plot results in an excellent linear correlation with ρY = 1.27 and r = 0.57, implying that a negative charge develops partially on the O atom of the leaving group in the transition state. The bulky DBU is less reactive than the primary and secondary amines toward substrates possessing a weakly basic leaving group. It has been concluded that steric hindrance exerted by DBU in the plausible intermediate (T±) forces the reactions to proceed through a concerted mechanism because expulsion of the leaving group from T± could reduce the steric hindrance.

Leaving-group substituent controls reactivity and reaction mechanism in aminolysis of phenyl y-substituted-phenyl carbonates

A kinetic study is reported for the nucleophilic substitution reactions of phenyl Y-substituted-phenyl carbonates (5a-5k) with piperidine in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The plots of k obsd vs. [piperidine] for the reactions of substrates possessing a strong electron-withdrawing group (EWG) in the leaving group (i.e., 5a-5i) are linear and pass through the origin. In contrast, the plots for the reactions of substrates bearing a weak EWG or no substituent (i.e., 5j or 5k) curve upward, indicating that the electronic nature of the substituent Y in the leaving group governs the reaction mechanism. Thus, it has been suggested that the reactions of 5a-5i proceed through a stepwise mechanism with a zwitterionic tetrahedral intermediate (i.e., T±) while those of 5j and 5k proceed through a stepwise mechanism with two intermediates (i.e., T± and its deprotonated form T-). The slope of the Bronsted-type plot for the second-order rate constants (i.e., kN or Kk2) changes from -0.41 to -1.89 as the leaving-group basicity increases, indicating that a change in the rate-determining step (RDS) occurs. The reactions of 5a-5k with piperidine result in larger k1 values than the corresponding reactions with ethylamine. Copyright