17345-61-8

Basic information

• Product Name: 3,4-Dihydroxybenzonitrile
• Synonyms: AKOS B004053;BENZONITRILE, 3,4-DIHYDROXY-;PROTOCATECHUONITRILE;TIMTEC-BB SBB008582;Protocatachuonitrile;3,4-DIHYDROXYBENZONITRILE / PROTOCATECHUONITRILE;3,4-Dihydroxybenzonitrile, 98+%;3,4-Dihydroxybenzoni
• CAS NO: 17345-61-8
• Molecular Formula: C₇H₅NO₂
• Molecular Weight: 135.12
• EINECS: 241-367-9
• Product Categories: Aromatic Nitriles;Nitrile;Nitriles;API intermediates;Thiophenes ,Thiazolines/Thiazolidines
• Mol File: 17345-61-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: 155-159 °C(lit.)
• Boiling Point: 334.8 °C at 760 mmHg
• Flash Point: 156.3 °C
• Appearance: Off-white powder
• Density: 1.42 g/cm³
• Vapor Pressure: 6.43E-05mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 7.67±0.18(Predicted)
• Water Solubility: insoluble
• BRN: 2082204
• CAS DataBase Reference: 3,4-Dihydroxybenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Dihydroxybenzonitrile(17345-61-8)
• EPA Substance Registry System: 3,4-Dihydroxybenzonitrile(17345-61-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-36/37/39-26-22
• RIDADR: UN3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 17345-61-8(Hazardous Substances Data)

Usage

Description

3,4-Dihydroxybenzonitrile is an organic compound that can be synthesized from 4-hydroxy-3-methoxybenzonitrile or by reacting 3,4-dimethoxybenzonitrile, lithium diisopropylamide (LDA), and 1,3-dimethyl-2-imidazolidinone (DMEU). It is an off-white powder and is known for its versatile chemical properties, making it a valuable compound in various industries.

Uses

Used in Pharmaceutical Industry:
3,4-Dihydroxybenzonitrile is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a key component in the development of new drugs, particularly those targeting specific diseases or conditions.
Used in Chemical Synthesis:
3,4-Dihydroxybenzonitrile serves as a valuable building block in the synthesis of a wide range of organic compounds, including dyes, pigments, and other specialty chemicals. Its reactivity and functional groups make it a versatile starting material for various chemical reactions.
Used in Material Science:
In the field of material science, 3,4-dihydroxybenzonitrile can be used to develop novel materials with specific properties, such as improved conductivity, enhanced stability, or unique optical characteristics. Its incorporation into polymers or other materials can lead to the creation of advanced materials with potential applications in various industries.
Used in Research and Development:
3,4-Dihydroxybenzonitrile is also utilized in research and development settings, where it can be employed to study the properties of new compounds, test the effectiveness of various reaction conditions, or explore the potential applications of newly synthesized materials. Its unique chemical structure makes it an interesting subject for scientific investigation and experimentation.

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

Upstream product

• 861531-72-8 2-oxo-benzo[1,3]dioxole-5-carbonitrile 
• 203626-45-3 3,4-diacetoxy-benzonitrile 
• 3343-59-7 3,4-dihydroxybenzaldehyde oxime 
• 107-03-9 1-thiopropane 
• 4421-09-4 piperonylonitrile 
• 767-00-0 4-cyanophenol 
• 2024-83-1 veratronitrile 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 7732-18-5 water 
• 3897-89-0 4-(hydroxymethyl)benzene-1,2-diol 
• 37491-68-2 3,4-dihydroxybenzylamine 
• 120-57-0 piperonal 
• 4421-08-3 3-methoxy-4-hydroxybenzonitrile 

Downstream Products

• 519-34-6 maclurin 
• 103278-74-6 3,4-bis-[5-(4-cyano-phenoxy)-pentyloxy]-benzonitrile 
• 83306-82-5 3,4-Dihydroxybenzimidsaeureethylesterhydrochlorid 
• 185038-16-8 Trifluoro-methanesulfonic acid 5-cyano-2-trifluoromethanesulfonyloxy-phenyl ester 
• 244020-33-5 3,4-bis[3,7-(S)-dimethyl-6-octenyloxy]benzonitrile 

Relevant articles and documents

Mechanism of bromoxynil phototransformation: Effect of medium and surfactant

Bromoxynil (BXN, 3,5-dibromo-4-hydroxybenzonitrile) is a herbicide that is classified as a highly hazardous chemical, toxic for the reproduction. The processes and mechanisms regarding the fate of this compound in the environmental compartments subject to

Nitroxygenation of quercetin by HNO

The flavonol quercetin undergoes both enzymatic and non-enzymatic reactions with nitroxyl (HNO/NO-), similar to analogous reactions with dioxygen, but in which N is regioselectively found in the ring-cleaved product. Here we report on kinetic and thermodynamic analysis of the non-enzymatic nitroxygenation reaction in water, which is orders of magnitude faster than the comparable dioxygenation. The second order rate constants were determined from variable temperature reactions, which allowed determination of the reaction activation enthalpy (ΔH≠ = 9.4 kcal/mol), entropy (ΔS≠ = -8.3 cal/mol K), and free energy (ΔG≠ = 11.8 kcal/mol). The determined standard state energy (ΔGo) and activation free energy, as well as the low entropic energy of reaction, are consistent with a proposed single electron transfer (SET) rate determining step.

Method for preparing 3, 4-dihydroxybenzonitrile

The invention discloses a method for preparing 3, 4-dihydroxybenzonitrile, which comprises the following step of: contacting vanillin with hydroxylamine hydrochloride and halide so as to obtain the 3, 4-dihydroxybenzonitrile. The method has the advantages of simplicity in operation, few byproducts, high product yield and the like, thereby being beneficial to industrial production.

Anchimerically Assisted Selective Cleavage of Acid-Labile Aryl Alkyl Ethers by Aluminum Triiodide and N, N-Dimethylformamide Dimethyl Acetal

Aluminum triiodide is harnessed by N,N-dimethylformamide dimethyl acetal (DMF-DMA) for the selective cleavage of ethers via neighboring group participation. Various acid-labile functional groups, including carboxylate, allyl, tert-butyldimethylsilyl (TBS), and tert-butoxycarbonyl (Boc), suffer the conditions intact. The method offers an efficient approach to cleaving catechol monoalkyl ethers and to uncovering phenols from acetal-type protecting groups such as methoxymethyl (MOM), methoxyethoxymethyl (MEM), and tetrahydropyranyl (THP) chemoselectively.

Direct Synthesis of Nitriles from Carboxylic Acids Using Indium-Catalyzed Transnitrilation: Mechanistic and Kinetic Study

Aliphatic and aromatic carboxylic acids can be quantitatively converted to the corresponding nitriles in the presence of catalysts using acetonitrile both as a solvent and reactant at 200 °C. This transformation is based on the acid-nitrile exchange (i.e., transnitrilation) and uses a nontoxic and water resistant catalyst, indium trichloride (InCl3). The mechanism of the transnitrilation was investigated both experimentally and computationally and compared to the previously proposed mechanism. In contrast to the usually assumed formation of amide as an intermediate, transnitrilation is an equilibrium reaction and proceeds via an equilibrated Mumm reaction with the formation of an imide as an intermediate. A simple and reversible mechanism was proposed for this reaction, which was validated by kinetics measurement and by density functional theory calculations of the reaction intermediates and reaction mechanisms.