84224-29-3

Usage

Uses

Used in Pharmaceutical Industry:
4-hydroxy-2-methoxybenzonitrile is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical sector, 4-hydroxy-2-methoxybenzonitrile serves as a crucial building block for the creation of new agrochemicals, contributing to the development of more effective and environmentally friendly products.
Used in Organic Compounds Synthesis:
4-hydroxy-2-methoxybenzonitrile is utilized as a versatile starting material for the synthesis of a wide range of organic compounds, thanks to its reactive functional groups.
Used in Dye and Pigment Manufacturing:
4-hydroxy-2-methoxybenzonitrile is used as an intermediate in the production of dyes and pigments, contributing to the creation of vibrant colors and specialized coatings for various applications.
Used in Specialty Chemicals Production:
4-hydroxy-2-methoxybenzonitrile plays a significant role in the manufacturing of specialty chemicals, where its unique properties are harnessed to create high-value products for niche markets.
Used in Medicinal and Biochemical Research:
Due to its potential biological activities, 4-hydroxy-2-methoxybenzonitrile is of interest in medicinal and biochemical research, where it may contribute to the discovery of new therapeutic agents and diagnostic tools.

Upstream product

• 2942-58-7 diethyl cyanophosphonate 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 330793-38-9 4-bromo-2-methoxybenzonitrile 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 90111-34-5 4-hydroxy-2-methoxybenzoic acid 
• 84224-28-2 4-hydroxy-2-methoxybenzamide 
• 18278-34-7 4-hydroxy-2-methoxybenzaldehyde 
• 4107-65-7 2,4-dimethoxybenzonitrile 
• 155912-31-5 4-hydroxy-2-methoxy-benzaldehyde-oxime 
• 108-24-7 acetic anhydride 
• 101714-11-8 5-cyano-2-hydroxy-4-methoxy-benzoic acid 

Downstream Products

• 84223-69-8 2,2'-Dimethoxy-4,4'-pentamethylendioxydibenzonitril 
• 1187026-36-3 C₁₁H₁₂N₂O₂S 

Relevant academic research and scientific papers

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Development of Decarboxylative Cyanation Reactions for C-13/C-14 Carboxylic Acid Labeling Using an Electrophilic Cyanating Reagent

Degradation-reconstruction approaches for isotope labeling synthesis have been known for their remarkable efficiency, but applications are scarce due to some fundamental limitations of the chemistries developed to date. The decarboxylative cyanation reaction, as a degradation-reconstruction approach, is especially useful in rapid carboxylic acid carbon isotope labeling, however development toward its application as a widespread technique has stalled at the early stages due to numerous limitations which include somewhat narrow applicability. Employing the electrophilic cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as the cyano source, efficient decarboxylative cyanation chemistry has been developed for aryl and alkyl carboxylic acids respectively with two rationally designed reaction pathways. The reactions provided good yields of nitrile products from carboxylic acids, with complete retention of isotopic purity from the [13CN]-NCTS used. The reaction conditions are relatively mild requiring no oxidant and no excess toxic heavy metal and the reagent [13/14CN]-NCTS is a stable, easy-to-handle crystalline solid that can be prepared quickly and effectively from the readily available [13/14C]-KCN. The following work describes this novel and efficient method for alkyl and aryl carboxylic acid isotopic labeling using a single reagent.

THIOPHENE DERIVATIVES AS AGONISTS OF S1P1/EDG1

The invention relates to novel thiophene derivatives (1), their preparation and their use as pharmaceutically active compounds.Said compounds particularly act as immunomodulating agents. Formula (I).

NOVEL AMINOMETHYL BENZENE DERIVATIVES

The invention relates to novel aminomethyl benzene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunomodulating agents. (I) wherein A represents one of the groups (I), (I), (I) and

Compounds useful in therapy

Compounds of formula (I), [image] or pharmaceutically acceptable derivatives thereof, wherein: R1 represents H, C1-6-alkyl, C1-6alkyloxy, C3-8cycloalkyl, or halo; R2 represents H, C1-6alkyl (optionally substituted by R3), phenyl (optionally substituted by CN), or Het; R3 represents OH, CN, Het, —R4—C1-6alkyl, or CONR5R6; R4 represents —CO2—, or —O—; R5 and R6 independently represent H, C1-6alkyl (optionally substituted by OR7) or C3-8cycloalkyl; R7 represents H or C1-6alkyl; Het represents a five or six membered aromatic heterocyclic group containing (i) from one to four nitrogen heteroatom(s) or (ii) one or two nitrogen heteroatom(s) and one oxygen or one sulphur heteroatom or (iii) one or two oxygen or sulphur heteroatom(s), said heterocyclic group being optionally substituted by one or more groups selected from CN and C1-6 alkyl; R8 represents C1-6alkyl, C1-6alkyloxy, C3-8cycloalkyl, or halo; R9 and R10 independently represent H, C1-6alkyl, C1-6alkyloxy, CN, CF3 or halo; may be useful for treating endometriosis, uterine fibroids (leiomyomata), menorrhagia, adenomyosis, primary and secondary dysmenorrhoea (including symptoms of dyspareunia, dyschexia and chronic pelvic pain), or chronic pelvic pain syndrome.

2-(Diethylamino)ethanethiol, a new reagent for the odorless deprotection of aromatic methyl ethers

A new reagent for the deprotection of aromatic methyl ethers, 2-(diethylamino)ethanethiol, is reported. This compound, commercially available as its HCl salt, affords the corresponding phenols in good to excellent yields on a wide variety of substrates. A clear advantage of this method over the use of more common thiols, such as ethanethiol, is the easy extraction of both the deprotecting reagent and the byproduct 2-(diethylamino)ethyl methyl sulfide into the aqueous phase by quenching with dilute acid, which allows an essentially odorless workup.

Sodium Bis(trimethylsily)amide and Lithium Diisopropylamide in Deprotection of Alkyl Aryl Ethers: α-Effect of Silicon

Removal of methyl, benzyl, and methylene groups from alkyl aryl ethers is among the most popular deprotecting methods in organic synthesis. Alkali organoamides NaN(SiMe3)2 and LiN(i-Pr)2, often used as organic bases, have been developed as efficient deprotecting agents. Treatment of aryl methyl ethers with 1.5 equiv of NaN(SiMe3)2 or LiN(i-Pr)2 in THF and 1,3-dimethyl-2-imidazolidinone in a sealed tube at 185 °C produced the corresponding phenol derivatives in good to excellent yields (80-97percent). Removal of the methylene unit from benzodioxole derivatives was also accomplished by use of 2.5 equiv of these alkali organoamides. The corresponding catechols were obtained in 93-99percent yields. The activity of NaN(SiMe3)2 was proven lower than that of LiN(i-Pr)2; it is due to the steric congestion and the α-stabilizing effect of the silyl groups. Thus selective mono-O-demethylation of o-dimethoxybenzenes can be achieved by the use of NaN(SiMe3)2 but not LiN(i-Pr)2. O-Debenzylation of aryl benzyl ethers, however, can be accomplished by the use of LiN(i-Pr)2.

Regiospesific Arylation of 1,4-Benzoquinone Cyanohydrin Phosphate: Synthesis of 3-Aryl-4-hydroxybenzonitriles

Reaction of 1,4-benzoquinones (1a,b) with diethyl phosphorocyanidate and lithium cyanide was found to give the monocyanophosphates (2a,b).When catalysed by BF3*OEt2, the cyanophosphates (2a,b) reacted with aromatic and heteroaromatic compounds (indole, thiophene, and furan derivatives) to give 3-aryl-4-hydroxybenzonitriles.Under the same conditions ethyl 1-methylindole-2-carboxylate and 2,5-dimethylfuran were converted into 6-oxobenzopyranoindole-2-carbonitriles (15a,b) and benzofuran-5-carbonitriles (22a,b) by reaction with the cyanophosphates (2a,b), respectively.