1197-58-6

Basic information

• Product Name: 4-METHOXYBENZYL ISOCYANIDE
• Synonyms: 4-METHOXYBENZYL ISOCYANIDE;HANSA ISN-0033;BIO-FARMA BF001956;1-Isocyanomethyl-4-methoxy-benzene
• CAS NO: 1197-58-6
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• Mol File: 1197-58-6.mol

Chemical Properties

• Boiling Point: 90-95 °C(Press: 0.005 Torr)
• Appearance: /
• CAS DataBase Reference: 4-METHOXYBENZYL ISOCYANIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXYBENZYL ISOCYANIDE(1197-58-6)
• EPA Substance Registry System: 4-METHOXYBENZYL ISOCYANIDE(1197-58-6)

Safety Data

• Hazardous Substances Data: 1197-58-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Methoxybenzyl isocyanide is used as a building block in organic synthesis for the preparation of complex organic molecules. Its ability to react with various functional groups makes it a versatile reagent in chemical reactions.
Used in Pharmaceutical Industry:
4-Methoxybenzyl isocyanide is used as an intermediate in the synthesis of pharmaceutical compounds. Its reactivity with different functional groups allows for the creation of a wide range of drug molecules.
Used in Agrochemical Industry:
4-Methoxybenzyl isocyanide is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its versatility in reacting with various functional groups enables the development of effective crop protection products.
Used in Research and Development:
4-Methoxybenzyl isocyanide is used as a research chemical in academic and industrial laboratories. Its unique reactivity and properties make it a valuable tool for studying various chemical reactions and processes.

InChI:InChI=1/C9H9NO/c1-10-7-8-3-5-9(11-2)6-4-8/h3-6H,7H2,2H3

Upstream product

• 67-66-3 chloroform 
• 2393-23-9 4-methoxy-benzylamine 
• 1895-39-2 sodium chlorodifluoroacetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 6343-93-7 2-(4-methoxyphenyl)acetamide 
• 2746-25-0 p-Methoxybenzyl bromide 
• 17061-63-1 N-(4-methoxybenzyl)formamide 

Downstream Products

• 104-47-2 p-methoxybenzylnitrile 
• 1025964-23-1 5-tert-Butyl-3-(4-methoxy-phenyl)-5H-imidazo[1,5-a]quinoxalin-4-one 
• 183986-42-7 3-Isocyano-1,3-bis-(4-methoxy-phenyl)-propan-1-one O-methyl-oxime 
• 180588-22-1 1-(4-Methoxy-benzyl)-4-[(Z)-4-methoxy-benzylimino]-1,3-diaza-spiro[4.4]nonane-2-thione 
• 588708-21-8 N-acetyl-N-(4-methoxybenzyl)-α,α-diethylglycine 4-methoxybenzyl amide 
• 588708-25-2 N-acetyl-N-(4-methoxybenzyl)-α,α-dipropylglycine 4-methoxybenzyl amide 
• 588708-30-9 N-acetyl-N-(4-methoxybenzyl)-α,α-dibenzylglycine 4-methoxybenzyl amide 
• 658044-04-3 N-benzoyl-N-(4-methoxybenzyl)-α,α-dibenzylglycine 4-methoxybenzyl amide 
• 1033514-10-1 C₃₇H₃₈N₄O₃ 
• 1033514-27-0 C₂₆H₃₄N₄O₂S 
• 1033514-23-6 C₂₄H₂₈N₄O₂ 
• 1033514-24-7 2-[allyl(5,6-diphenylpyrazin-2-yl)amino]-N-(4-methoxybenzyl)-4-methylpentanethioamide 
• 1033514-06-5 C₃₃H₃₆N₄O₂ 
• 1178564-08-3 C₂₃H₂₉N₃O₄ 

Relevant articles and documents

(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors

(o-Phenylenediamino)borylstannanes were newly synthesized to achieve radical boryl substitutions of a variety of alkyl radical precursors. Dehalogenative, deaminative, decharcogenative, and decarboxylative borylations proceeded in the presence of a radica

Anodic Oxidation of Aminotetrazoles: A Mild and Safe Route to Isocyanides

A new electrochemical method for the preparation of isocyanides from easily accessible aminotetrazole derivatives has been developed, which tolerates an unprecedented range of functional groups. The use of chemical, rather than electrochemical, oxidation to afford isocyanides was also demonstrated, which provides access to these compounds for those without electrosynthesis equipment. The practicality of scale-up using flow electrochemistry has been demonstrated, in addition to the possibility of using electrochemically generated isocyanides in further reactions.

Synthesis of isocyanides by reacting primary amines with difluorocarbene

A general, convenient, and friendly route for preparing a versatile building block of isocyanides from primary amines is developed. Difluorocarbene, generated in situ from decarboxylation of chlorodifluoroacetate, reacts efficiently with primary amines to produce isocyanides. Various primary amines are well tolerated, including aryl, heteroaryl, benzyl, and alkyl amines, as well as amine residues in amino acids and peptides. Late-stage functionalization of biologically active amines is demonstrated, showing its practical capacity in drug design and peptide modification.

[3+2] Anionic Cycloaddition of Isocyanides to Acyclic Enamines and Enaminones: A New, Simple, and Convenient Method for the Synthesis of 2,4-Disubstituted Pyrroles

We herein demonstrate a new approach for the synthesis of 2,4-disubstituted pyrroles by [3+2] cycloaddition reaction of isocyanides to the activated double bond of various enamines and enaminones. This process paved the way for the synthesis a series of 2,4-disubstituted pyrroles, which are known to be intermediates in the synthesis of biologically active compounds, in good to excellent yields from simple and commercially available starting materials. The process is carried out efficiently using a strong base, tBuOK, at low temperatures (0 °C). The described method is simple, proceeds in one step, does not require additional catalysts and hence, has a wide scope.

Nonacidic Farnesoid X Receptor Modulators

As a cellular bile acid sensor, farnesoid X receptor (FXR) participates in regulation of bile acid, lipid and glucose homeostasis, and liver protection. Clinical results have validated FXR as therapeutic target in hepatic and metabolic diseases. To date, potent FXR agonists share a negatively ionizable function that might compromise their pharmacokinetic distribution and behavior. Here we report the development and characterization of a high-affinity FXR modulator not comprising an acidic residue.

Enantioselective Synthesis of Quaternary Δ4- and Δ5-Dehydroprolines Based on a Two-Step Formal [3+2] Cycloaddition of α-Aryl and α-Alkyl Isocyano(thio)acetates with Vinyl Ketones

A divergent synthesis of optically active quaternary Δ4- and Δ5-dehydro prolines is developed based on the first catalytic enantioselective conjugate addition of α-substituted isocyano(thio)acetates to vinyl ketones that is general for both α-aryl and α-alkyl isocyano(thio)acetates. The new tetrasubstituted C?N stereocenter is formed without the need of any metal salt due to a bifunctional tertiary amine/squaramide catalyst, featuring a bulky polyaryl sidearm and an unusually short squaramide diamide H???H interatomic distance in the solid state.

Synthesis of imidazo[1,2-a]pyridines in a sequential one-pot Groebke-Blackburn modification using 2-aminopyridines, aldehydes and amines

Herein we present a novel synthetic procedure for the synthesis of imidazo[1,2-a]pyridines in a modified Groebke-Blackburn fashion. In a sequential three-step one-pot protocol the commercially hardly available isocyanide-component is formed in situ using standard reagents. Cyclization to the desired products can be afforded in the same reaction mixture. The absent need of isolation of the isocyanide in this protocol eases its handling considerably and workup is only needed to finally furnish the imidazo[1,2-a]pyridines via coloumn chromatography. This protocol is a convenient way to more diverse libraries of imidazo[1,2-a]pyridines extending the functionality of the Groebke-Blackburn synthesis.

Synthesis of isocyanides through dehydration of formamides using XtalFluor-E

The formation of isocyanides from formamides using XtalFluor-E, [Et2NSF2]BF4, is presented. A wide range of formamides can be used to produce the corresponding isocyanides in up to 99% yield. In a number of cases, the crude products showed good purity (generally >80% by NMR) allowing to be used directly in multi-component reactions.

Novel ultrasound-promoted parallel synthesis of trifluoroatrolactamide library via a one-pot passerini/hydrolysis reaction sequence and their fungicidal activities

An ultrasound-promoted one-pot Passerini/hydrolysis reaction sequence has been developed for the synthesis of trifluoroatrolactamide derivatives using a diverse range of trifluoroacetophenones and isonitriles in acetic acid. Parallel synthesis in a centrifuge tube using a noncontact ultrasonic cell crusher was used in this study as an efficient method for the rapid generation of combinatorial trifluoroatrolactamide libraries, and subsequent biochemical evaluation of the resulting compounds indicated that they possessed excellent broad-spectrum fungicidal activities. N-(4-chlorophenyl)-2-(4-ethylphenyl)-3,3, 3-trifluoro-2-hydroxypropanamide and N-(4-chlorophenyl)-3,3,3-trifluoro-2- hydroxy-2-(4-methoxyphenyl)propanamide, in particular, showed significant fungicidal activities against all of the fungal species tested in the current study.

Catalytic enantioselective Michael addition of α-aryl-α- isocyanoacetates to vinyl selenone: Synthesis of α,α-disubstituted α-amino acids and (+)- and (-)-trigonoliimine A

Be like Mike: The title reaction in the presence of the catalyst 1 afforded Michael adducts in excellent yields and enantioselectivities. The adducts were readily converted into α,α′-disubstituted α-amino acids. The enantioselective total synthesis of bot