93-99-2

Basic information

• Product Name: Phenyl benzoate
• Synonyms: diphenylcarboxylate;phenol,benzoate;PHENYL BENZOATE;BENZOIC ACID PHENYL ESTER;Phenylbenzoate,99%;Benzoic acid phenyl;Phenyl benzoate,Benzoic acid phenyl ester;Phenyl benzoate, 99% 100GR
• CAS NO: 93-99-2
• Molecular Formula: C₁₃H₁₀O₂
• Molecular Weight: 198.22
• EINECS: 202-293-2
• Product Categories: Functional Materials;Liquid Crystals & Related Compounds;Phenyl Esters (Liquid Crystals);Building Blocks;C12 to C63;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 93-99-2.mol
• Article Data: 402

Chemical Properties

• Melting Point: 68-70 °C(lit.)
• Boiling Point: 298-299 °C(lit.)
• Flash Point: 298-299°C
• Appearance: White/Fine Crystalline Powder
• Density: 1.235
• Vapor Pressure: 0.000479mmHg at 25°C
• Refractive Index: 1.5954 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: alcohol: freely soluble (hot)
• Water Solubility: Soluble in ethanol, ethyl ether and chloroform. Insoluble in water.
• Stability: Stable. Incompatible with strong oxidizing agents, strong acids, strong bases.
• Merck: 14,7275
• BRN: 1566346
• CAS DataBase Reference: Phenyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenyl benzoate(93-99-2)
• EPA Substance Registry System: Phenyl benzoate(93-99-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-38
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DH6299500
• TSCA: Yes
• Hazardous Substances Data: 93-99-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Phenyl Benzoate is a key reagent in the synthesis of soluble polyimides using dianhydride/diamine derivatives.

Definition

ChEBI: A benzoate ester obtained by the formal condensation of phenol with benzoic acid.

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

General Description

Phenyl benzoate is a phenyl ester of benzoic acid. Crystal structure of phenyl benzoate has been determined from 844 microdensitometer-measured intensities. All bond lengths and angles were reported to be normal. Phenyl benzoate undergoes Fries rearrangement catalyzed by heteropoly acids to yield the acylated phenols and esters.

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.]

InChI:InChI=1/C13H10O2/c14-13(11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H

Upstream product

• 7074-00-2 peroxybenzoic acid phenylisopropyl ester 
• 1885-14-9 phenyl chloroformate 
• 71-43-2 benzene 
• 781-33-9 2-methyl-1,1-diphenylpropene 
• 558-37-2 tert-butylethylene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 10496-82-9 2,2,3,3-tetraphenylbutane 
• 498-66-8 norbornene 
• 2186-29-0 1,1-diphenylethyl hydroperoxide 
• 6652-29-5 2-phenoxy-1,2-diphenylethanone 
• 4237-46-1 α-phenylbenzoin 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 118017-04-2 diphenylcarbonyl oxide 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 20736-37-2 triphenyldiketone 
• 37529-67-2 N-(4-methylthiazol-2-yl)benzamide 
• 25491-42-3 ethyl 2,2-dimethyl-3-oxo-3-phenylpropionate 
• 3559-04-4 N-benzoyl-benzenesulfonamide 
• 33357-46-9 N-(quinolin-2-yl)benzamide 
• 54918-25-1 3-acetyl-6-β-D-glucopyranosyloxy-2-hydroxy-benzophenone 
• 16513-74-9 <4-(Benzoyloxy)phenyl>phenylketon 
• 1137-42-4 4-Hydroxybenzophenone 
• 127-71-9 sulfabenzamide 
• 3743-28-0 N-(3-hydroxyphenyl)benzamide 
• 76967-60-7 C₁₅H₁₄O 
• 31991-79-4 N,N'-pentane-1,5-diyldibenzamide 
• 5692-29-5 N-benzoyl-1,5-diaminopentane 
• 29833-52-1 N-benzoyl-1,5-diaminopentane hydrochloride 

Relevant articles and documents

Synthesis, Characterization and Biological Evaluation of Schiff Base Transition Metal Complexes Derived from 4-Nitrobenzene-1,2-diamine and 5-Chloroisatin

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.

Mechanically induced solvent-free esterification method at room temperature

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

N,O-Benzyl Protection of Structurally Varied Amines and Phenols Using Wells-Dawson Heteropolyacid Catalyst

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