67984-81-0

Basic information

• Product Name: 2,3-DIHYDROXYBENZONITRILE
• Synonyms: BENZONITRILE, 2,3-DIHYDROXY-;2,3-DIHYDROXYBENZONITRILE;3-Cyanocatechol
• CAS NO: 67984-81-0
• Molecular Formula: C₇H₅NO₂
• Molecular Weight: 135.12
• EINECS: 268-005-2
• Mol File: 67984-81-0.mol

Chemical Properties

• Melting Point: 192-193 °C
• Boiling Point: 305.2°C at 760 mmHg
• Flash Point: 138.4°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 0.000461mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.00±0.10(Predicted)
• CAS DataBase Reference: 2,3-DIHYDROXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDROXYBENZONITRILE(67984-81-0)
• EPA Substance Registry System: 2,3-DIHYDROXYBENZONITRILE(67984-81-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 67984-81-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dihydroxybenzonitrile is used as a building block for the synthesis of various drug molecules, leveraging its chemical properties to contribute to the development of new pharmaceuticals.
Used in Dye Production:
2,3-Dihydroxybenzonitrile is used as a key intermediate in the production of dyes, where its chemical structure plays a role in determining the color and properties of the final dye product.
Used as an Intermediate in Organic Synthesis:
2,3-DIHYDROXYBENZONITRILE serves as an intermediate in the synthesis of other organic compounds, facilitating the creation of a variety of chemical products through its reactive functional groups.
Used in Antioxidant Applications:
Due to its antioxidant properties, 2,3-dihydroxybenzonitrile can be utilized in applications requiring the prevention of oxidative damage, which is beneficial in various industrial processes and potentially in medical applications for the protection against oxidative stress-related conditions.
Used in Antibacterial Applications:
The antibacterial properties of 2,3-dihydroxybenzonitrile make it a candidate for use in applications where the inhibition of bacterial growth is necessary, such as in medical settings, water treatment, or as a preservative in various products.

InChI:InChI=1/C7H5NO2/c8-4-5-2-1-3-6(9)7(5)10/h1-3,9-10H

Upstream product

• 110827-84-4 2,3-dihydroxybenzaldehyde oxime 
• 108-24-7 acetic anhydride 
• 100-47-0 benzonitrile 
• 5653-62-3 2,3-dimethoxybenzonitrile 
• 7797-83-3 2H-benzo[d]1,3-dioxolane-4-carbaldehyde 
• 138769-96-7 (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 1521-39-7 2,3-dimethoxybenzamide 
• 7169-06-4 2,3-dimethoxybenzoyl chloride 
• 1521-38-6 2,3-dimethoxybenzoic acid 
• 19337-60-1 3-iodo-1,2-benzenediol 
• 2179-92-2 tri-n-butyltin cyanide 
• 611-20-1 salicylonitrile 

Downstream Products

• 847355-88-8 (S)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid 
• 28911-18-4 5-formyl-2,3-dihydroxybenzonitrile 
• 1037282-58-8 2-hydroxy-3-(3,6,9-trioxadecyloxy)benzonitrile 
• 1268613-20-2 C₈H₉NO₃ 
• 739326-10-4 2,3-dihydroxybenzamidoxime 
• 1346427-97-1 2-hydroxy-3-(3,6-dioxaheptyloxy)benzonitrile 
• 1346427-20-0 2-(2-hydroxy-3-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-4,5-dihydro-1H-imidazole-4-carboxylic acid 
• 1346427-99-3 ethyl 2-hydroxy-3-(2-(2-methoxyethoxy)ethoxy)benzimidate hydrochloride 
• 1346428-01-0 methyl 2-(2-hydroxy-3-(2-(2-methoxyethoxy)ethoxy)phenyl)-4-methyl-4,5-dihydro-1H-imidazole-4-carboxylate 
• 1204751-09-6 (S)-4,5-dihydro-2-[2-hydroxy-3-(3,6-dioxaheptyloxy)phenyl]-4-methyl-4-thiazolecarboxylic acid 
• 1360431-26-0 2-hydroxy-3-(3,6,9,12-tetraoxatridecyloxy)benzonitrile 
• 1443045-62-2 2-cyano-6-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)phenolate 
• 303-38-8 2,3-Dihydroxybenzoic acid 
• 945635-15-4 (4,5)-2-(2-hydroxy-3-{2-[2-(2-methoxyethoxy)ethoxy]-ethoxy}phenyl)-4-methyl-4,5-dihydrothiazole-1,3-thiazole-4-carboxylic acid 

Relevant articles and documents

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

Arene cis-Diol Dehydrogenase-Catalysed Regio- and Stereoselective Oxidation of Arene-, Cycloalkane- and Cycloalkene-cis-diols to Yield Catechols and Chiral α-Ketols

Benzene cis-diol dehydrogenase and naphthalene cis-diol dehydrogenase enzymes, expressed in Pseudomonas putida wild-type and Escherichia coli recombinant strains, were used to investigate regioselectivity and stereoselectivity during dehydrogenations of arene, cyclic alkane and cyclic alkene vicinal cis-diols. The dehydrogenase-catalysed production of enantiopure cis-diols, α-ketols and catechols, using benzene cis-diol dehydrogenase and naphthalene cis-diol dehydrogenase, involved both kinetic resolution and asymmetric synthesis methods. The chemoenzymatic production and applications of catechol bioproducts in synthesis were investigated.

PROCESS FOR PREPARATION OF 2,3-DIHYDROXY BENZONITRILE

The present invention relates to one pot process for the preparation of 2,3-dihydroxy benzonitrile from 2,3-dialkoxy benzoic acid without prior isolation of the intermediates. Further the invention relates to the preparation of 2,3-dihydroxy benzonitrile by dealkylation of 2,3-dialkoxy benzonitrile using suitable aluminum salt-amine complex.

IMPROVED PROCESS FOR PREPARATION OF 2,3-DIHYDROXY BENZONITRILE

Disclosed is one pot process of the preparation of 2,3-dihydroxy benzonitrile from 2,3-dialkoxy benzoic acid without prior isolation of the intermediates. Further disclosed is the preparation of 2,3-dihydroxy benzonitrile by dealkylation of 2,3-dialkoxy benzonitrile using suitable aluminum salt-amine complex.

Synthesis of acinetobactin

A structure involving the absolute configuration of acinetobactin (1b) was clarified. It was reconfirmed that preacinetobactin (1a) produced 1b by a rearrangement reaction.

A comparative study of the synthesis of 3-substituted catechols using an enzymatic and a chemoenzymatic method

A series of cis-dihydrodiol metabolites, available from the bacterial dioxygenase-catalysed oxidation of monosubstituted benzene substrates using Pseudomonas putida UV4 , have been converted to the corresponding catechols using both a heterogeneous catalyst (Pd/c) and a naphthalene cis-diol dehydrogenase enzyme present in whole cells of the recombinant strain Escherichia coli DH5α(pUC129: nar B). A comparative study of the merits of both routes to 3-substituted catechols has been carried out and the two methods have been found to be complementary. A similarity in mechanism for catechol formation under both enzymatic and chemoenzymatic conditions, involving regioselective oxidation of the hydroxyl group at C-1, has been found using deuterium labelled toluene cis-dihydrodiols. The potential, of combining a biocatalytic step (dioxygenase-catalysed cis-dihydroxylation) with a chemocatalytic step (Pd/C-catalysed dehydrogenation), into a one-pot route to catechols, from the parent substituted benzene substrates, has been realised.

Sodium bis(trimethylsilyl)amide in the oxidative conversion of aldehydes to nitriles

The feasibility of the Me3Si species acting as a nucleofuge was investigated in compounds containing the NSiMe3 moiety. Treatment of various aromatic aldehydes with 2.2 equiv. of NaN(SiMe3)2 at 185°C in a sealed tube produced the corresponding nitriles in high yields (81-98%). In these reactions, NaN(SiMe3)2 acted as an oxidizing agent. Results from control experiments indicate that the Me 3Si unit can depart efficiently from the NSiMe3 moiety of N-silylimine intermediates. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Partition-variant desferrithiocin analogues: Organ targeting and increased iron clearance

Altering the lipophilicity (log Papp) of desferrithiocin analogues can change the organ distribution of the chelators and lead to enhanced iron clearance. For example, alkylation of (S)-2-(2,4-dihydroxyphenyl)- 4,5-dihydro-4-methyl-4-thiazolecarboxylic acid [(S)-4′-(HO)-DADFT] and its analogues to more lipophilic compounds, such as (S)-4,5-dihydro-2-(2-hydroxy-4- methoxyphenyl)-4-methyl-4-thiazolecarboxylic acid [(S)-4′-(CH 3O)-DADFT], provides ligands that achieved between a 3- and 8-fold increase in chelator concentrations in the heart, liver, and pancreas (the organs most at risk in iron-overload disease) of treated rodents. The 4′-O-methylated compounds are demethylated to their hydroxylated counterparts in rodents; furthermore, this O-demethylation takes place in both rodent and human liver microsomes. The relationship between chelator lipophilicity and iron-clearing efficacy in the iron-overloaded Cebus apella primate is further underscored by a comparison of the iron-clearing efficiency of (S)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-4-methyl-4-thiazolecarboxylic acid [(S)-3′-(HO)-DADFT] and its 3′-(CH3O) counterpart. Finally, these DFT analogues are shown to be both inhibitors of the iron-mediated oxidation of ascorbate as well as effective radical scavengers.

Isolation of bright blue fluorescent substances from sonochemical hydroxylation of methyl p-cyanobenzoate

Sonochemical hydroxylation of methyl p-cyanobenzoate (1a) in water gave a bright blue fluorescence, which are mainly ascribed to three new fluorescent compounds, 3-hydroxy, 2,3- and 2,5-dihydroxy derivatives of 1a. Other benzenes substituted with electron-withdrawing groups also gave similar fluorescence from their hydroxylated derivatives. Among the fluorescence substances, methyl 2,5-dihydroxybenzoate was supposed to be applicable for a fluorescent chemosensor.