1591-37-3

Basic information

• Product Name: 2-amino-6-methoxybenzonitrile
• Synonyms: 2-amino-6-methoxybenzonitrile;2-AMino-6-Methoxy-benzonitril
• CAS NO: 1591-37-3
• Molecular Formula: C₈H₈N₂O
• Molecular Weight: 148.17
• Mol File: 1591-37-3.mol

Chemical Properties

• Melting Point: 141 °C
• Boiling Point: 339.4°C at 760 mmHg
• Flash Point: 159.1°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 9.22E-05mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 1.39±0.10(Predicted)
• CAS DataBase Reference: 2-amino-6-methoxybenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-6-methoxybenzonitrile(1591-37-3)
• EPA Substance Registry System: 2-amino-6-methoxybenzonitrile(1591-37-3)

Safety Data

• Hazardous Substances Data: 1591-37-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-amino-6-methoxybenzonitrile is used as an intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs and therapeutic agents. Its unique structure allows for the creation of diverse chemical entities with potential medicinal properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-amino-6-methoxybenzonitrile serves as an intermediate in the synthesis of agrochemicals, including pesticides and herbicides. Its reactivity and structural features enable the production of effective compounds for agricultural applications.
Used in Medicinal Chemistry and Drug Discovery:
2-amino-6-methoxybenzonitrile is utilized as a building block in medicinal chemistry and drug discovery due to its unique structure and reactivity. Researchers leverage its properties to design and synthesize novel compounds with potential therapeutic effects, contributing to the advancement of pharmaceutical research.
Used in the Development of New Materials and Organic Compounds:
This chemical compound is also used as a building block for the development of new materials and organic compounds, showcasing its versatility and applicability in various scientific and industrial fields. Its unique structural features make it a valuable component in the creation of innovative materials with diverse applications.

InChI:InChI=1/C8H8N2O/c1-11-8-4-2-3-7(10)6(8)5-9/h2-4H,10H2,1H3

Upstream product

• 38469-85-1 2-methoxy-6-nitrobenzonitrile 
• 77326-36-4 2-amino-6-fluorobenzonitrile 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 606-21-3 1-chloro-2,6-dinitrobenzene 
• 35213-00-4 2,6-dinitrobenzonitrile 

Downstream Products

• 54166-67-5 2'-Cyano-3'-methoxyoxanilic acid ethyl ester 
• 1591-38-4 2-amino-6-methoxybenzamide 
• 27018-21-9 5-methoxy-2,4-diaminoquinazoline 
• 66195-38-8 2-Jod-6-methoxybenzonitril 
• 66195-40-2 2-iodo-6-methoxybenzamide 
• 190011-78-0 2-amino-N'-hydroxy-6-methoxybenzimidamide 
• 1012369-79-7 (2-cyano-3-methoxy-phenyl)-carbamic acid ethyl ester 
• 74897-46-4 3-amino-1-(p-tosyl)indole-2-carbonitrile 
• 103204-98-4 S-<2-Carboxy-3-methoxy-phenyl>-thioglykolsaeure 
• 61948-86-5 5-methoxy-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 
• 61948-59-2 2,4-dichloro-5-methoxy-quinazoline 

Relevant articles and documents

Superacidic Cyclization of Activated Anthranilonitriles into 2-Unsubstituted-4-aminoquinolines

4-Aminoquinolines were prepared in a three-step synthesis starting from substituted anthranilonitriles. The condensation on 1,1,1-trichloro-4-ethoxybut-3-enone proceeded efficiently either neat or in refluxing EtOH. Cyclization in superacidic trifluoromethanesulfonic acid provided unstable intermediate, which upon treatment with NaOEt in ethanol, afforded the expected esters. Theoretical investigations pointed out a monoprotonated nitrilium as the reactive species during the cyclization process.

On the Synthesis and Reactivity of 2,3-Dihydropyrrolo[1,2- a ]quinazolin-5(1 H)-ones

An improved, scalable synthetic route to the quinazolinone natural product 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one is reported. The applicability of this method to analogue synthesis and the synthesis of related natural products is explored. Finally, reactivity of the scaffold to a variety of electrophilic reagents, generating products stereoselectively, is reported.

Synthesis and biological evaluation of novel 2,4-diaminoquinazoline derivatives as SMN2 promoter activators for the potential treatment of spinal muscular atrophy

Proximal spinal muscular atrophy (SMA) is an autosomal recessive disorder characterized by death of motor neurons in the spinal cord that is caused by deletion and/or mutation of the survival motor neuron gene (SMN1). Adjacent to SMN1 are a variable number of copies of the SMN2 gene. The two genes essentially differ by a single nucleotide, which causes the majority of the RNA transcripts from SMN2 to lack exon 7. Although both SMN1 and SMN2 encode the same Smn protein amino acid sequence, the loss of SMN1 and incorrect splicing of SMN2 have the consequence that Smn protein levels are insufficient for the survival of motor neurons. The therapeutic goal of our medicinal chemistry effort was to identify small-molecule activators of the SMN2 promoter that, by up-regulating gene transcription, would produce greater quantities of full-length Smn protein. Our initial medicinal chemistry effort explored a series of C5 substituted benzyl ether based 2,4-diaminoquinazoline derivatives that were found to be potent activators of the SMN2 promoter; however, inhibition of DHFR was shown to be an off-target activity that was linked to ATP depletion. We used a structure-guided approach to overcome DHFR inhibition while retaining SMN2 promoter activation. A lead compound 11a was identified as having high potency (EC50 = 4 nM) and 2.3-fold induction of the SMN2 promoter. Compound 11a possessed desirable pharmaceutical properties, including excellent brain exposure and long brain half-life following oral dosing to mice. The piperidine compound 11a up-regulated expression of the mouse SMN gene in NSC-34 cells, a mouse motor neuron hybrid cell line. In type 1 SMA patient fibroblasts, compound 11a induced Smn in a dose-dependent manner when analyzed by immunoblotting and increased the number of intranuclear particles called gems. The compound restored gems numbers in type I SMA patient fibroblasts to levels near unaffected genetic carriers of SMA.

NOVEL 2-CYANO-3-(HALO)ALKOXY-BENZENESULFONAMIDE COMPOUNDS FOR COMBATING ANIMAL PESTS

The invention relates to 2-cyano-3-(halo)alkoxy-benzenesulfonamide compounds (I), where the variables Alk and R1 to R5 are as defined in claim 1, and/or to their agriculturally useful salts. Moreover, the present invention relates to: the use of compounds (I) and/or their salts for combating animal pests; agricultural compositions comprising such an amount of at least one compound of the general formula (I) and/or at least one agriculturally useful salt of (I) and at least one inert liquid and/or solid agronomically acceptable carrier that it has a pesticidal action and, if desired, at least one surfactant; and a method of combating animal pests which comprises contacting the animal pests, their habit, breeding ground, food supply, plant, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the formula (I) and/or at least one agriculturally acceptable salt thereof; a method for the for the protection of seeds from soil insects and of the resulting plant's roots and shoots from soil and foliar insects comprising contacting the seeds before sowing and/or after pregermination with a 2-cyano-3-(halo)alkoxy-benzenesulfonamide compound of the general formula (I).

2-CYANOBENZENESULFONAMIDES FOR COMBATING ANIMAL PESTS

The invention relates to 2-cyanobenzenesulfonamide compounds of the formula (I) where the variables R1 to R5 are as defined in claim 1 and/or to their agriculturally use-ful salts. Moreover, the present invention relates to the use of compounds (I) and/or

Antifolate and Antibacterial Activities of 5-Substituted 2,4-Diaminoquinazolines

A series of 5-substituted 2,4-diaminoquinazolines (3) has been synthesized and evaluated as inhibitors of the enzyme dihydrofolate reductase (DHFR) from both bacterial and mammalian sources.The best compounds (e.g. 53) show good activity against Escherichia coli DHFR, but there is no significant selectivity for the bacterial over the mammalian enzyme.The structure-activity relationships for enzyme inhibition appear to be complex and not amenable to simple analysis; a hypotesis to explain the observed qualitative structure-activity relationships is proposed.The inhibitory activities of the compounds against the growth of intact bacterial cells in vitro closely parallel those for the inhibition of the isolated bacterial enzymes, suggesting that their antifolate action is responsible for their antibacterial effects.Five of the compounds were tested for their ability to cure a systemic E. coli infection in the mouse, but they showed no therapeutic effects at their maximum tolerated doses.

Substituted benzoxazin-2-ones and pharmaceutical compositions containing them

This invention is directed to novel benzoxazin-2-ones of the formula STR1 wherein A is a sulfur atom or an SO, SO2, R--N=S, or R--N=SO2 group where R is a hydrogen atom or an acyl group; D is an alkylene group; R1 is an al

4-Hydroxy-1,2-Benzisothiazol-3(2H)-one-1,1-dioxides and salts thereof

Compounds of the formula STR1 wherein R1 is hydrogen or hydroxyl, and non-toxic, pharmacologically acceptable salts thereof formed with inorganic or organic bases. The compounds as well as their salts are useful as sweetening agents.

N-(Aminophenyl)oxamic Acids and Esters as Potent, Orally Active Antiallergy Agents

A series of N-(2-cyano-substituted-phenyl)oxamates was prepared by acylation of the appropriate anthranilonitrile with ethyloxalyl chloride.Hydrolysis with sodium hydroxide gave the corresponding oxamic acid sodium salts.These compounds were extremely potent when tested in the rat passive cutaneous anaphylaxis (PCA assay either by the ip or the po route of administration).One of the sodium salts, oxoacetic acid sodium salt (11a, Wy-41 195), has ED50 value of 0.07 mg/kg po and has been selected for further evaluation.

Compositions and process of treatment

This invention relates to pharmaceutical compositions containing known compounds of the formula SPC1 Wherein M is selected from the group consisting of hydrogen, aluminum, ammonium, sodium, potassium, calcium, tris(hydroxymethyl)methylammonium and lower alkyl of 1 through 4 carbon atoms, R is selected from the group consisting of hydrogen and lower alkyl of 1 through 4 carbon atoms, and R1 and R2 are selected from the group consisting of hydrogen, fluorine, chlorine, bromine, trifluoromethyl, lower alkoxy of 1 through 4 carbon atoms and lower alkyl of 1 through 4 carbon atoms. The compounds (1) above are formulated with pharmaceutical carriers for inhalation or for oral, parenteral or rectal administration, with insufflation being the preferred method. The compositions are useful in the prophylactic treatment of sensitized humans and mammals for allergic and all anaphylactic reactions of a reaginmediated and non-reagin-mediated nature.