80407-68-7

Usage

Uses

Used in Chemical and Pharmaceutical Production:
3,4-Bis(2-methoxyethoxy)benzonitrile is used as a raw material or intermediate for the production of other chemicals and pharmaceuticals, leveraging its unique structural properties to facilitate the synthesis of various compounds.
Used in Solvent Applications:
3,4-Bis(2-methoxyethoxy)benzonitrile is used as a solvent in various industries due to its ability to dissolve a wide range of materials, making it a versatile component in processes that require the dissolution of diverse substances.
Used in Organic Synthesis:
3,4-Bis(2-methoxyethoxy)benzonitrile is utilized in organic synthesis for its capacity to participate in a variety of chemical reactions, contributing to the creation of new organic compounds with specific properties and applications.
Used in Electrochemical Devices:
3,4-Bis(2-methoxyethoxy)benzonitrile is studied for its potential use in electrochemical devices, capitalizing on its high stability and low volatility to enhance the performance and reliability of such devices.
Used as an Electrolyte Additive:
In the field of electrochemistry, 3,4-Bis(2-methoxyethoxy)benzonitrile is considered for use as an electrolyte additive to improve the efficiency and stability of electrolytes in batteries and other energy storage systems.

Upstream product

• 1006377-63-4 C₁₃H₁₉NO₅ 
• 1418289-91-4 3,4-bis(2-methoxyethoxy)-benzamide 
• 819813-71-3 3,4-bis(2-methoxyethoxy)-benzoic acid 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 627-42-9 2-chloroethyl methyl ether 
• 17345-61-8 3,4-dihydroxybenzonitrile 
• 4421-08-3 3-methoxy-4-hydroxybenzonitrile 
• 121-33-5 vanillin 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 80407-64-3 3,4-bis(2-methoxyethoxy)benzaldehyde 

Downstream Products

• 236750-65-5 4,5-bis(2-methoxyethoxy)-2-nitrobenzonitrile 
• 950596-58-4 2-amino-4,5-bis-(2-methoxyethoxy)-benzonitrile 
• 950596-59-5 N′-[2-cyano-4,5-{bis(2-methoxyethoxy)phenyl}]-N,N-dimethylformamidine 
• 183321-74-6 erlotinib 
• 1172625-04-5 4,5-bis(2-methoxyethoxy)-2-nitrobenzamide 
• 236750-62-2 2-amino-4,5-bis[(2-methoxy)ethoxy]benzamide 
• 183319-69-9 erlotinib hydrochloride 
• 183322-18-1 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline 
• 179688-29-0 6,7-bis(2-methoxyethoxy)-3,4-dihydroquinazolin-4-one 

Relevant academic research and scientific papers

HCl·DMPU-assisted one-pot and metal-free conversion of aldehydes to nitriles

We report an efficient HCl·DMPU assisted one-pot conversion of aldehydes into nitriles. The use of HCl·DMPU as both an acidic source as well as a non-nucleophilic base constitutes an environmentally mild alternative for the preparation of nitriles. Our protocol proceeds smoothly without the use of toxic reagents and metal catalysts. Diverse functionalized aromatic, aliphatic and allylic aldehydes incorporating various functional groups were successfully converted to nitriles in excellent to quantitative yields. This protocol is characterized by a broad substrate scope, mild reaction conditions, and high scalability. This journal is

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

Preparation method of erlotinib hydrochloride intermediate

The invention provides a preparation method of an erlotinib hydrochloride intermediate. The preparation method comprises following steps: removing the methyl of vanillin, performing esterification, converting an aldehyde group into a nitrile group, and carrying out nitration, reduction, hydrolysis, and ring forming reactions. The reaction route is represented in the description. The technology isreasonable, the operation is simple, the cost is low, and the reaction yield is high.

Synthesis method of erlotinib hydrochloride

The invention discloses a synthesis method of erlotinib hydrochloride. The synthesis method comprises the following steps: (1) at a first working section: preparing 3-methoxyl-4-hydroxybenzonitrile from vanillin and hydroxylammonium chloride; (2) at a second working section: synthesizing 3,4-dihydroxybenzonitrile; (3) at a third working section: synthesizing 3,4-di(2-methoxyethoxy)phenylacetonitrile; (4) at a fourth section: synthesizing 4,5-di(2-methoxyethoxy)-2-nitrophenylacetonitrile; (5) at a fifth working section: synthesizing 4,5-di(2-methoxyethoxy)-2-aminophenylacetonitrile hydrochloride; and (6) at a sixth working section: synthesizing the erlotinib hydrochloride. The synthesis method of the erlotinib hydrochloride, disclosed by the invention, has the advantages of reasonable design, easiness of obtaining raw materials, relatively low production cost, simplicity and easiness of operation and is suitable for industrial production.

Br?nsted Acid Catalyzed Nitrile Synthesis from Aldehydes Using Oximes via Transoximation at Ambient Temperature

The Br?nsted acid-catalyzed synthesis of nitriles is described via transoximation under mild conditions using an O-protected oxime as a more stable equivalent of explosive O-protected hydroxylamines. The nitrile was generated via an O-protected aldoxime produced from the aldehyde and an O-protected oxime through transoximation. The reaction could be performed on a 1 g scale.

Method for preparing compound

The invention provides a method for preparing a compound as shown in a formula I which is described in the specification. The method comprises a step of contacting a compound as shown in a formula III which is described in the specification or a derivative thereof with a compound as shown in a formula II which is described in the specification so as to obtain the compound as shown in the formula I. In the formulas, R1 and R2 are hydrogen, alkoxy groups or heteroaromatic rings, preferably alkoxy groups; and R is hydrogen, an alkyl group, a phenyl group, a substituted phenyl group or a naphthyl group. The compound as shown in the formula I is a tinib drug intermediate 6,7-disubstituted quinazolinone. According to the method provided in embodiments in the invention, aldoketones are used as cyclization raw materials in replacement of carboxylic acids for preparation of tinib drug intermediate, and since the aldoketones are not corrosive, the method has low requirements on reaction equipment and is more favorable for industrial production.

Compounds for use in inhibiting HIV capsid assembly

The present invention relates to a compound or a pharmaceutically acceptable salt or solvate thereof for use in inhibiting HIV capsid assembly, the compound comprising the core structure wherein E is CR7or S, and wherein f is 0 or 1, and wherein in case E is S, f is 0, and wherein the core structure is at least substituted in 2 and 4 position, and wherein the residue R6 and R7, are, independently of each other, selected from the group consisting of -H, -D, -alkyl, alkoxy, alkenyl, alkynyl, halides, -NO2, - OH, - NH2, -NHR4#, -CN, -S(O)R4#, -SO2R4#, -P(O)R4#R5#, -P(O)(OR4#)R5#, - P(O)(OR4#)(OR5#), -C(O)NR4#R5#, -C(O)SR4#, -C(O)R4#, -C(O)O-R4#, alkoxy and glycol chains; and wherein R6 may optionally form a cyclic residue, with a further substituent present 5 or 6 position, and wherein R4# and R5# are, independently of each other, selected from the group consisting of -H, -alkyl, -alkenyl, - heterocycloalkyl, aryl and heteroaryl.

COMPOUNDS FOR USE IN INHIBITING HIV CAPSID ASSEMBLY

The present invention relates to a compound or a pharmaceutically acceptable salt or solvate thereof for use in inhibiting HIV capsid assembly, the compound comprising the core structure wherein E is CR7or S, and wherein f is 0 or 1, and wherein in case E is S, f is 0, and wherein the core structure is at least substituted in 2 and 4 position, and wherein the residue R6 and R7, are, independently of each other, selected from the group consisting of -H, -D, -alkyl, alkoxy, alkenyl, alkynyl, halides, -NO2, - OH, -NH2, -NHR4#, -CN, - S(O)R4#, -SO2R4#, -P(O)R4#R5#, -P(O)(OR4#)R5#, -P(O)(OR4#)(OR5#), -C(O)NR4#R5#, - C(O)SR4#, -C(O)R4#, -C(O)O-R4#, alkoxy and glycol chains; and wherein R6 may optionally form a cyclic residue, with a further substituent present 5 or 6 position, and wherein R4# and R5# are, independently of each other, selected from the group consisting of -H, -alkyl, -alkenyl, -heterocyclo alkyl, aryl and heteroaryl.

An improved convergent approach for synthesis of erlotinib, a tyrosine kinase inhibitor, via a ring closure reaction of phenyl benzamidine intermediate

An improved convergent and economical method has been developed for the synthesis of erlotinib, a 4-anilinoquinazoline and an EGFR-tyrosine kinase inhibitor for treatment of non-small-cell lung cancer. The final two steps for the formation of this 4-anilinoquinazoline from suitable 2-aminobenzonitrile intermediate and 3-ethynylaniline were modified and were performed in a simple one-pot reaction. The ring-closing mechanism for the formation of erlotinib from the suitable formamidine intermediate and 3-ethynylaniline was investigated and determined to proceed via the formation of phenyl benzamidine intermediate rather than involving Dimroth rearrangement reported earlier. The new benzamidine intermediate was isolated for the first time and characterized. Copyright

One-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones and synthesis of gefitinib and erlotinib hydrochloride

A simple and efficient one-pot conversion of 2-nitrobenzonitriles to quinazolin-4(3H)-ones involving reduction, formylation, hydrolysis and cyclization is reported. These quinazolinones have been used for making in economical way the anticancer drug molecules gefitinib (Iressa) and erlotinib HCl (Tarceva).