33646-40-1

Basic information

• Product Name: (4-methoxyphenyl)glycolonitrile
• Synonyms: (4-methoxyphenyl)glycolonitrile;4-Methoxymandelonitrile;(p-Methoxyphenyl)glycolonitrile;4-Methoxy-α-hydroxybenzeneacetonitrile;Hydroxy(4-methoxyphenyl)acetonitrile;p-Methoxymandelonitrile;p-Methoxy-α-hydroxybenzeneacetonitrile;USAF A-13796
• CAS NO: 33646-40-1
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17326
• EINECS: 251-614-2
• Mol File: 33646-40-1.mol
• Article Data: 119

Chemical Properties

• Melting Point: 57-58 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• Boiling Point: 334.4°Cat760mmHg
• Flash Point: 156.1°C
• Appearance: /
• Density: 1.183g/cm³
• Vapor Pressure: 5.05E-05mmHg at 25°C
• Refractive Index: 1.55
• PKA: 10.57±0.20(Predicted)
• CAS DataBase Reference: (4-methoxyphenyl)glycolonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (4-methoxyphenyl)glycolonitrile(33646-40-1)
• EPA Substance Registry System: (4-methoxyphenyl)glycolonitrile(33646-40-1)

Safety Data

• Hazardous Substances Data: 33646-40-1(Hazardous Substances Data)

Usage

General Description

(4-methoxyphenyl)glycolonitrile, also known as p-methoxyphenylglycolonitrile, is a chemical compound with the molecular formula C9H9NO2. It is a white powder with a molecular weight of 163.17 g/mol. This chemical is used in various applications, including as a building block in organic synthesis and as a raw material in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. It is also used as an intermediate in the synthesis of dyes and pigments. Additionally, (4-methoxyphenyl)glycolonitrile has been studied for its potential use in developing new materials and in medicinal and biological research. However, it is important to handle this chemical with care as it may pose health risks if not used properly.

InChI:InChI=1/C9H9NO2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5,9,11H,1H3

Upstream product

• 151-50-8 potassium cyanide 
• 123-11-5 4-methoxy-benzaldehyde 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 71680-52-9 ammonium cyanide 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 143-33-9 sodium cyanide 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 104-87-0 4-methyl-benzaldehyde 
• 66985-48-6 2-(4-methoxyphenyl)-2-(trimethylsilyloxy)acetonitrile 
• 99843-19-3 acetoxy-(4-methoxy-phenyl)-acetonitrile 
• 177186-34-4 (S)-2-(4-methoxyphenyl)-2-(trimethylsiloxy)acetonitrile 
• 105-13-5 4-Methoxybenzyl alcohol 
• 104-93-8 p-methylanizole 

Downstream Products

• 112671-80-4 2-[2]furyl-5-(4-methoxy-phenyl)-oxazole 
• 15913-13-0 4-methoxy-DL-mandelic acid-propyl ester 
• 62921-42-0 5-(4-methoxyphenyl)-2-phenyl-1,3-oxazole 
• 54867-73-1 2-(4-methoxyphenyl)-5-(4-methoxyphenyl)oxazole 
• 6275-26-9 2,2-bis(4-methoxyphenyl)acetonitrile 
• 74185-58-3 5-(4-methoxy-phenyl)-2-styryl-oxazole 
• 75133-95-8 ethyl 2,3-dicyano-3-(4-methoxyphenyl)propanoate 
• 858806-79-8 2-cyano-2-[cyano-(4-methoxy-phenyl)-methyl]-succinic acid diethyl ester 
• 861377-36-8 ethoxycarbonylamino-(4-methoxy-phenyl)-acetonitrile 
• 23860-99-3 1-(4-methoxy-phenyl)-1H-naphtho[2,1-b]furan-2-one 
• 101097-05-6 2-(4-hydroxyphenyl)-2-(4-methoxyphenyl)acetonitrile 
• 83530-84-1 α-(5-o-nitrophenyl-1,3,4-thiadiazol-2-yl-amino)-p-anisylacetonitrile 
• 58327-37-0 α-Chloro-α-(4-methoxyphenyl)acetonitrile 
• 21165-16-2 2-hydroxy-2-(4-methoxyphenyl)acetamide 

Relevant articles and documents

Constructing a triangular metallacycle with salen-Al and its application to a catalytic cyanosilylation reaction

A triangular metallosalen-based metallacycle was constructed in quantitative yield by the self-assembly of a 180° bis(pyridyl)salen-Al complex and a 60° diplatinum(ii) acceptor in a 1?:?1 stoichiometric ratio. This metallacycle was then successfully used to cyanosilylate a wide range of benzaldehydes with trimethylsilyl cyanide.

Synthesis and antitumor activity of sacroflavonoside

Sacroflavonoside, a new derivative of diphenylethene, was isolated from Artemisia sacrorum, which have been found to possess the inhibitory effect on the proliferation of gastric carcinoma cells (MKN-45) in vitro in our previous studies. With anisaldehyde (SM-A) as starting material, the sacroflavonoside was synthesized by nucleophilic addition, electrophilic substitution and dehydration cyclization. The structure of sacroflavonoside was established by 1 D (1H NMR and 13C NMR) and 2 D-NMR (HSQC and HMBC) spectral analysis. The antitumor activity and potential mechanism against MKN-45 cells of sacroflavonoside were evaluated in vitro. The results showed that sacroflavonoside could significantly induce MKN-45 cells apoptosis and autophagy by increasing the expression of Bax, Caspase-3, Beclin1 and LC3-II proteins and decreasing the expression of Bcl-2 protein at low micromole level. This investigation provided a valuable lead structure for the development of antitumor drugs.

Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond Functionalization

In this study, we combined photo-organo redox catalysis and biocatalysis to achieve asymmetric C–H bond functionalization of simple alkane starting materials. The photo-organo catalyst anthraquinone sulfate (SAS) was employed to oxyfunctionalise alkanes to aldehydes and ketones. We coupled this light-driven reaction with asymmetric enzymatic functionalisations to yield chiral hydroxynitriles, amines, acyloins and α-chiral ketones with up to 99 % ee. In addition, we demonstrate functional group interconversion to alcohols, esters and carboxylic acids. The transformations can be performed as concurrent tandem reactions. We identified the degradation of substrates and inhibition of the biocatalysts as limiting factors affecting compatibility, due to reactive oxygen species generated in the photocatalytic step. These incompatibilities were addressed by reaction engineering, such as applying a two-phase system or temporal and spatial separation of the catalysts. Using a selection of eleven starting alkanes, one photo-organo catalyst and 8 diverse biocatalysts, we synthesized 26 products and report for the model compounds benzoin and mandelonitrile > 97 % ee at gram scale.