93-99-2 Usage
Description
Phenyl benzoate is an organic compound with the chemical formula C13H10O2. It is a colorless to pale yellow crystalline solid that is slightly soluble in water but readily soluble in organic solvents. It is derived from the esterification of benzoic acid and phenol, and it possesses a pleasant, aromatic odor.
Uses
Used in Chemical Synthesis:
Phenyl benzoate is used as a key reagent in the synthesis of soluble polyimides using dianhydride/diamine derivatives. It plays a crucial role in the formation of these polymers, which have a wide range of applications in various industries due to their excellent thermal stability, mechanical properties, and chemical resistance.
Used in Pharmaceutical Industry:
Phenyl benzoate is used as an intermediate in the synthesis of various pharmaceutical compounds. Its aromatic nature and ester functionality make it a versatile building block for the development of new drugs and drug candidates.
Used in Fragrance Industry:
Due to its pleasant aroma, phenyl benzoate is used as a fragrance ingredient in the perfumery and cosmetics industry. It can be used to create a wide range of scents and is often used in combination with other fragrance compounds to achieve desired olfactory effects.
Used in Plasticizers Industry:
Phenyl benzoate is used as a plasticizer in the production of certain types of plastics and resins. Its ability to increase the flexibility and workability of these materials makes it a valuable component in the formulation of various plastic products.
Used in Dyes and Pigments Industry:
Phenyl benzoate is used as a precursor in the synthesis of dyes and pigments. Its aromatic structure and reactivity make it suitable for the production of a variety of colored compounds used in various applications, such as textiles, paints, and inks.
Preparation
A glass tube was charged with benzoic anhydride (1.13 g, 5.00 mmol), diphenyl carbonate (1.07 g, 5.00 mmol), and either Ti(OBu)4 (0.020 g, 0.059 mmol) or Sn(OMe)2Bu2 (0.017 g, 0.059 mmol) as catalyst. The reaction mixture was heated at 300 ℃ for 30 min. After cooling to room temperature, the crude product obtained was dissolved in dichloromethane (10 mL) and the solution was filtered. The solvent was evaporated and the product obtained after column chromatography (silica gel; CH2Cl2/cyclohexane, 4:1) was recrystallized from petroleum ether; yield 95%.
Synthesis Reference(s)
Canadian Journal of Chemistry, 61, p. 86, 1983 DOI: 10.1139/v83-015Synthesis, p. 908, 1983 DOI: 10.1055/s-1983-30561Tetrahedron Letters, 41, p. 1343, 2000 DOI: 10.1016/S0040-4039(99)02289-3
Safety Profile
Moderately toxic by ingestion. When heated it emits acrid smoke and irritating fumes.
Purification Methods
Crystallise the ester from EtOH using ca twice the volume needed for complete dissolution at 69o. [Beilstein 9 IV 303.]
Check Digit Verification of cas no
The CAS Registry Mumber 93-99-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 93-99:
(4*9)+(3*3)+(2*9)+(1*9)=72
72 % 10 = 2
So 93-99-2 is a valid CAS Registry Number.
InChI:InChI=1/C13H10O2/c14-13(11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H
93-99-2Relevant articles and documents
Synthesis, Characterization and Biological Evaluation of Schiff Base Transition Metal Complexes Derived from 4-Nitrobenzene-1,2-diamine and 5-Chloroisatin
Pal Singh, Netra,Kumar, Kaushal,Kumar, Gajendra,Kumar, Anuroop
, p. 2324 - 2328 (2020)
A series of transition metal complexes of the type [MLX2], where M = Mn(II), Fe(II), Co(II), Ni(II), X = Cl–/CH3COO– and L = Schiff base derived from 4-nitrobenzene-1,2-diamine and 5-chloroisatin have been synthesized and characterized by elemental analysis, molar conductance, IR, UV-visible, magnetic moments measurement, 1H & 13C NMR and mass spectral studies. On the basis of physico-chemical studies and spectral evaluation, an octahedral geometry have been proposed for all metal(II) complexes. The antimicrobial activity of ligand and its metal complexes have been additionally screened against bacteria and fungi. Metal(II) complexes show good activity as compared to ligand towards studied microorganisms and also metal complexes checked for their catalytic properties for benzoylation of phenol.
Hayashi,Nagakura
, p. 2862,2864 (1978)
Mechanically induced solvent-free esterification method at room temperature
Zheng, Lei,Sun, Chen,Xu, Wenhao,Dushkin, Alexandr V.,Polyakov, Nikolay,Su, Weike,Yu, Jingbo
, p. 5080 - 5085 (2021/02/05)
Herein, we describe two novel strategies for the synthesis of esters, as achieved under high-speed ball-milling (HSBM) conditions at room temperature. In the presence of I2 and KH2PO2, the reactions afford the desired esterification derivatives in 45% to 91% yields within 20 min of grinding. Meanwhile, using KI and P(OEt)3, esterification products can be obtained in 24% to 85% yields after 60 min of grinding. In addition, the I2/KH2PO2 protocol was successfully extended to the late-stage diversification of natural products showing the robustness of this useful approach. Further application of this method in the synthesis of inositol nicotinate was also discussed. This journal is
Hydrogen-bond-assisted transition-metal-free catalytic transformation of amides to esters
Huang, Changyu,Li, Jinpeng,Wang, Jiaquan,Zheng, Qingshu,Li, Zhenhua,Tu, Tao
, p. 66 - 71 (2020/11/18)
The amide C-N cleavage has drawn a broad interest in synthetic chemistry, biological process and pharmaceutical industry. Transition-metal, luxury ligand or excess base were always vital to the transformation. Here, we developed a transition-metal-free hydrogen-bond-assisted esterification of amides with only catalytic amount of base. The proposed crucial role of hydrogen bonding for assisting esterification was supported by control experiments, density functional theory (DFT) calculations and kinetic studies. Besides broad substrate scopes and excellent functional groups tolerance, this base-catalyzed protocol complements the conventional transition-metal-catalyzed esterification of amides and provides a new pathway to catalytic cleavage of amide C-N bonds for organic synthesis and pharmaceutical industry. [Figure not available: see fulltext.]
