1075-06-5

Basic information

• Product Name: PHENYLGLYOXAL MONOHYDRATE
• Synonyms: BENZOYLFORMALDEHYDE MONOHYDRATE;2,2-DIHYDROXY-1-PHENYL-ETHANONE;PHENYLGLYOXAL;PHENYLGLYOXAL HYDRATE;PHENYLGLYOXAL MONOHYDRATE;P-PHENYLGLYOXAL MONOHYDRATE;2,2-dihydroxy-1-phenyl-ethanon;2,2-dihydroxy-acetophenon
• CAS NO: 1075-06-5
• Molecular Formula: C₈H₈O₃
• Molecular Weight: 152.15
• EINECS: 214-036-1
• Mol File: 1075-06-5.mol

Chemical Properties

• Melting Point: 76-79 °C(lit.)
• Boiling Point: 142 °C125 mm Hg(lit.)
• Flash Point: 142°C/125mm
• Appearance: White to light yellow or pinkish/Powder
• Density: 1.1603 (rough estimate)
• Vapor Pressure: 0.00469mmHg at 25°C
• Refractive Index: 1.5120 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 95% ethanol: soluble5%, clear to very slightly hazy, colorless t
• PKA: 10.97±0.41(Predicted)
• Water Solubility: Partly miscible with water.
• BRN: 1854721
• CAS DataBase Reference: PHENYLGLYOXAL MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: PHENYLGLYOXAL MONOHYDRATE(1075-06-5)
• EPA Substance Registry System: PHENYLGLYOXAL MONOHYDRATE(1075-06-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36
• WGK Germany: 3
• RTECS: MD3260000
• Hazardous Substances Data: 1075-06-5(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Applications:
PHENYLGLYOXAL MONOHYDRATE is used as a modifying agent for proteins, specifically for arginine groups. It is employed to modify pig muscle carbonic anhydrase III, which is crucial in the study of enzyme structure and function.
Used in Chemical Synthesis:
PHENYLGLYOXAL MONOHYDRATE serves as a key intermediate in the preparation of various chemical compounds, such as pyrrolinone and furan derivatives. These synthesized compounds find applications in different fields, including pharmaceuticals and materials science.
Used in Analytical Chemistry:
As a chemiluminescent reagent, PHENYLGLYOXAL MONOHYDRATE is utilized for the determination of purines, which are essential components of nucleic acids and play a significant role in various biological processes. This application aids in the development of sensitive and selective analytical methods for detecting and quantifying purines in biological samples.

Biochem/physiol Actions

Phenylglyoxal is a potent inhibitor of mitochondrial aldehyde dehydrogenase. It reacts with arginine residues in purified Hageman factor (HF, Factor XII) and causes inhibition of its coagulant properties.

InChI:InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,8,10-11H

Upstream product

• 3282-32-4 2-diazo-acetophenone 
• 1074-12-0 phenylglyoxal hydrate 
• 16273-01-1 (Phenylglyoxal)-butylthiohalbacetal 
• 82408-31-9 2-Hydroxy-2-(2-hydroxy-ethylsulfanyl)-1-phenyl-ethanone 
• 82408-33-1 C₁₀H₁₁⁽²⁾HO₃S 
• 82408-32-0 (1-Hydroxy-2-oxo-2-phenyl-ethylsulfanyl)-acetic acid ethyl ester 
• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 585-71-7 (1-bromoethyl)benzne 
• 40721-68-4 N-morpholino-1-phenylethan-1-imine 
• 98-85-1 1-Phenylethanol 
• 100-42-5 styrene 
• 4636-16-2 iodoacetophenone 

Downstream Products

• 611-71-2 MANDELIC ACID 
• 64163-13-9 1-hydroxy-5-phenyl-2(1H)-pyrazinone 
• 93733-54-1 phenyl-(N'-phenyl-ureido)-acetic acid 
• 32023-99-7 2-methyl-5-phenyl-3,5-dihydro-imidazol-4-one 
• 32282-53-4 2,4-diphenyl-4,5-dihydro-1⁽³⁾H-imidazole-4,5-diol 
• 942-72-3 3-amino-6-phenyl-1,2,4-triazine 
• 17199-29-0 (S)-Mandelic acid 
• 611-71-2 (R)-Mandelic Acid 
• 93-56-1 phenylethane 1,2-diol 
• 41270-61-5 3,5-diphenyl-1H-pyrazin-2-one 
• 34103-51-0 3-morpholin-4-yl-5-phenyl-[1,2,4]triazine 
• 57872-41-0 N-(α-Hydroxyphenacyl)-N-methyl-2-methoxyethylamin 
• 81374-84-7 Hydroxy-phenyl-thioacetic acid S-(2-morpholin-4-yl-ethyl) ester 
• 106492-21-1 2-Hydroxy-1-phenyl-2-(pyridin-2-ylamino)-ethanone 

Relevant articles and documents

A Facile and Effective Procedure for Synthesis of Polyfunctionalized Bis (imidazolyl) Pyrrole/Imidazolyl Indole from Pyrrole/Indole with Arylglyoxals and N-aryl amidines

Heterocyclic systems containing bis (imidazolyl) pyrrole or imidazolyl indole moieties were synthesized by heterocyclization of pyrrole or indole with arylglyoxal monohydrates and N-aryl amidines in ethanol catalyzed by FeCl3 at room temperature. The paper reports a facile, efficient, and environmentally friendly protocol for the synthesis of new products. Products were isolated by simple filtration, and their structures were established from their spectroscopic data.

Series of Functionalized 5-(2-Arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1 H,3 H)-diones: A Water-Mediated Three-Component Catalyst-Free Protocol Revisited

A water-mediated and catalyst-free practical method for the synthesis of a new series of pharmaceutically interesting functionalized 5-(2-arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1H,3H)-diones has been accomplished based on a one-pot multicomponent reaction between arylglyoxal monohydrates, 2-aminopyridines/2-aminopyrimidine, and barbituric/N,N-dimethylbarbituric acids under reflux conditions. The salient features of this protocol are avoidance of any additive/catalyst and toxic organic solvents, use of water as reaction medium, clean reaction profiles, operational simplicity, ease of product isolation/purification without the aid of tedious column chromatography, good to excellent yields, and high atom-economy and low E-factor.

Synthesis of 4-Hydroxy-3-(2-arylimidazo[1,2-a]pyridin-3-yl)quinolin-2(1H)-ones in the Presence of DABCO as an Efficient Organocatalyst

The one-pot, three-component, synthesis of a new series of 4-hydroxy-3-(2-arylimidazo[1,2-a]pyridin-3-yl)quinolin-2(1H)-ones in the presence of DABCO as a catalyst has been achieved using aryl glyoxal monohydrates, quinoline-2,4(1H,3H)-dione, and 2-aminopyridine in H2O/EtOH under reflux conditions. The cheapness of organocatalyst, simple workup, operational simplicity, regioselectivity, and high yields are some advantages of this protocol.

One-pot, three-component synthesis of polyfunctionalized benzo[h]pyrazolo[3,4-b][1,6]naphthyridine and benzo[g]pyrazolo[3,4-b]quinoline derivatives in the presence of silver nanoparticles (AgNPs)

An efficient and straightforward protocol for one-pot, three-component reaction of aryl glyoxal monohydrates 1a-h, 5-amino-1-aryl-3-methylpyrazoles 2a,b and 4-hydroxyquinoline-2(1H)-one (3) or 2-hydroxy-1,4-naphthoquinone (4) using silver nanoparticles (AgNPs) as a high performance nanocatalyst in H2O/EtOH at 60°C afforded the corresponding polyfunctionalized benzo[h]pyrazolo[3,4-b][1,6]naphthyridines 5a-h and benzo[g]pyrazolo[3,4-b]quinolines 6a-i, respectively. Excellent catalytic activity, high yields, employing green media and green nanocatalyst, cost-effective and simple procedure are some notable advantages of using AgNPs as a noble metal nanocatalyst in this synthetic strategy. The structures of fused heterocycles were confirmed by their Fourier transform infrared, proton nuclear magnetic resonance (1H-NMR), and 13C-NMR spectral data and microanalysis.

One-pot three-component synthesis of a series of 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles in the presence of aluminum oxide as a nanocatalyst

[Figure not available: see fulltext.] One-pot three-component reaction of arylglyoxals, 3-aryl-3-oxopropanenitriles, and 5-amino-1-aryl-3-methylpyrazoles using various solvent systems and different catalysts under reflux conditions afforded the corresponding 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]- pyridine-5-carbonitrile derivatives. The best yields (70–91%) were obtained using Al2O3 as a nanocatalyst in H2O–EtOH, 1:1, under reflux conditions. The simplicity of workup procedure, the novelty of pyrazolopyridines, green solvent system, easy preparation of a nanocatalyst, and good to excellent yields of the products are the advantages of this synthetic strategy. The structures of all products were confirmed by FT-IR, 1H and13C NMR, and mass spectral data.

Synthesis of biologically important, fluorescence active 5-hydroxy benzo[g]indoles through four-component domino condensations and their fluorescence "Turn-off" sensing of Fe(iii) ions

Several highly substituted 2-pyrrolyl-2-cyanoacetamides were prepared through four-component domino condensation of various easily available 1,3-dicarbonyl compounds, amines, arylglyoxals and malononitrile. Subsequently these cyanoacetamide derivatives were converted into biologically important 5-hydroxy benzo[g]indoles through thermal cyclization under metal-free conditions. The synthesized 5-hydroxy benzo[g]indoles are fluorescence active with good quantum yields (ΦF = ～0.50). They also show excellent fluorescence "Turn-off" sensing of Fe3+ ions (detection limit = ～1.2 × 10-6 M). The interaction of 5-hydroxy benzo[g]indoles with Fe3+ ions can also be monitored through UV-Vis spectral change and naked-eye colour change in the presence and absence of UV radiation. The 1H NMR titration unambiguously proves the formation of a complex between 5-hydroxy benzo[g]indoles and Fe3+ ion through the coordination of -OH groups with the metal. The binding constant of the complex (metal : ligand = 1 : 1) has been measured using Benesi-Hildebrand equation and found to be ～7.97 × 103 M-1.

Synthesis of Ethyl 2-Amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates by a One-pot, Three-Component Reaction in the Presence of TPAB

In this research, in order to synthesize a series of ethyl 2-amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates, a green and an efficient method is proposed through one-pot three-component reaction of substituted arylglyoxals, ethyl cyanoacetate, and 4-hydroxyquinolin-2(1H)-one in the presence of terapropylammonium bromide as a catalyst in good yields. All synthesized new substances were characterized by FTIR, 1H-NMR, and 13C-NMR spectral data and elemental analysis.

A Green Synthesis of 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile Derivatives by a One-pot Three-component Reaction

The synthesis of polyfunctionalized 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile derivatives by a green approach was achieved via one-pot three-component reaction of arylglyoxals, malononitrile, and 1,3-dimethyl-6-aminouracil in the presence of urea as organocatalyst in EtOH:H2O (1:1) at 60°C. This protocol provides a mild and fast procedure to structurally diverse bicyclic pyridopyrimidines in good to excellent yields.

The synthesis and ring opening of 3-aroyl(heteroaroyl)-1,2-dicyanocyclopropane-1,2-dicarboxylates

3-Aroyl-1,1,2,2-tetracyanocyclopropanes undergo ring opening under the action of acetates, carbonates and hydroxides of alkali metals, resulting in the formation of stable 2-aroyl-1,1,3,3-tetracyanopropenide salts, which are of interest as potential co-ligands in the coordination polymers and as ionic liquid components. A method for producing new electron-deficient cyclopropanes, dimethyl 3-aroyl(heteroaroyl)-1,2-dicyanocyclopropane-1,2-dicarboxylates and their reactions with potassium acetate leading to the formation of the corresponding propenides is described.

An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water

An improved synthesis of 2-ethyl-5-(2-hydroxy-4-oxoquinolin-3(4H)-ylidene)-6-aryl-5,6-dihydroimidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxide derivatives 4a-k via the reaction of aryl glyoxal monohydrates 1a-k, quinoline-2,4-diol 2 and 2-amino-[1,3,4]thiadiazole (3) in the presence of Et3N/sulfamic acid in H2O is described. This green protocol is characterized by the use of the readily available catalyst and reactants, short reaction times, operational simplicity and high yields of products. The structures of all compounds were characterized by 1H NMR, 13C NMR and Fourier-transform infrared (FT-IR) spectral data and microanalyses.