74903-79-0

Basic information

• Product Name: N-hydroxy-4-methoxybenzenecarboximidoyl chloride
• Synonyms: N-hydroxy-4-methoxybenzenecarboximidoyl chloride
• CAS NO: 74903-79-0
• Molecular Weight: 185.61
• Mol File: 74903-79-0.mol

Chemical Properties

• CAS DataBase Reference: N-hydroxy-4-methoxybenzenecarboximidoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-4-methoxybenzenecarboximidoyl chloride(74903-79-0)
• EPA Substance Registry System: N-hydroxy-4-methoxybenzenecarboximidoyl chloride(74903-79-0)

Safety Data

• Hazardous Substances Data: 74903-79-0(Hazardous Substances Data)

Upstream product

• 3717-21-3 (E)-4-methoxybenzaldoxime 
• 123-11-5 4-methoxy-benzaldehyde 
• 70286-37-2 4-methoxy-benzaldehyde-(O-methyl-seqtrans-oxime ) 
• 54582-27-3 (Z)-2-methoxybenzaldehyde oxime 
• 3717-21-3 p-methoxyl benzaldoxime 

Downstream Products

• 5311-71-7 methyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl ether 
• 132906-68-4 (3aR,9aS)-3-(4-Methoxy-phenyl)-9-methyl-3a,4,9,9a-tetrahydro-isoxazolo[5,4-b]quinoline-4-carbonitrile 
• 161064-07-9 3-(4-methoxyphenyl)-5-vinylisoxazoline 
• 188118-29-8 3,5-bis(4-methoxyphenyl)-1,2,4-oxadiazole 4-oxide 
• 188118-33-4 3-anisyl-5-phenyl-1,2,4-oxadiazole-4-oxide 
• 125674-28-4 [3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphonic acid diethyl ester 
• 473253-52-0 thiopropionic acid S-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-ylmethyl]ester 
• 473253-50-8 methyl-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphinic acid 2-chloro-ethyl ester 
• 140946-63-0 3-(4-methoxyphenyl)-4,5-dihydroisoxazole-5-carboxylic acid methyl ester 

Relevant articles and documents

Isocyanide-mediated multicomponent synthesis of C-oximinoamidines

By capitalizing on the different reactivity of nitrile N-oxides with isocyanides and amine, α-oximinoamidines, a so far elusive class of compounds, have been synthesized in a straightforward way by reacting isocyanides, syn-chlorooximes, and amines in a multicomponent fashion.

Decarboxylative Borylation of Stabilized and Activated Carbon Radicals

Redox-active esters (RAEs) as active radical precursors have been extensively studied for C?B bond formations. However, the analogous transformations of stabilized radicals from the corresponding acid precursors remain challenging owing to the strong preference towards single-electron oxidation to the stable carbocations. This work describes a general strategy for rapid access to various aliphatic and aromatic boronic esters by mild photoinduced decarboxylative borylation. Both aryl and alkyl radicals could be generated from the leaving group-assisted N-hydroxybenzimidoyl chloride esters, even α-CF3 substituted substrates could be activated for further elaboration.

Reaction between (Z)-Arylchlorooximes and α-Isocyanoacetamides: A procedure for the synthesis of Aryl-α-ketoamide amides

(Z)-Arylchlorooximes and α-isocyanoacetamides undergo a smooth reaction to produce 1,3-oxazol-2-oxime derivatives in good yields. Opening of the oxazole ring and deoximation reaction give a facile access to aryl-α-ketoamide amides, a class of privileged s

Stereospecific synthesis of syn -α-oximinoamides by a three-component reaction of isocyanides, syn -chlorooximes, and carboxylic acids

A stereospecific multicomponent reaction among isocyanides, syn-chlorooximes, and carboxylic acids provides an efficient synthesis of biologically relevant syn-α-oximinoamides.

Diastereoselective cycloadditions of a soluble polymer-supported substituted allyl alcohol derived from Baylis-Hillman reaction with nitrile oxides

A diastereoselective cycloaddition of a soluble polymer-supported Baylis-Hillman adduct with nitrile oxides is described. The reaction has shown to proceed with moderate diastereoselectivity, favoring the syn isomer of the resulting 3,5-substituted isoxazolines. The stereochemistry of the products has been assigned using 1H NMR studies. The structure of one of the diastereomers has been determined by single-crystal X-ray crystallographic analysis.

PTP-1B inhibitors: Cyclopenta[d][1,2]-oxazine derivatives

A series of novel cyclopenta[d][1,2]-oxazine derivatives was prepared and evaluated for their inhibitory activity toward protein tyrosine phosphatase 1B (PTP-1B). Compound 6s was found to be an inhibitor of PTP-1B with nanomolar IC50 value and

Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates

Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted isoxazoles, respectively. The process is highly reliable and exhibits an unusually wide scope with respect to both components. Computational studies revealed a stepwise mechanism involving unprecedented metallacycle intermediates, which appear to be common for a variety of dipoles.

Inhibition of the antibacterial target UDP-(3-O-acyl)-N-acetylglucosamine deacetylase (LpxC): Isoxazoline zinc amidase inhibitors bearing diverse metal binding groups

UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase (LpxC) is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram negative bacteria. Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-position,

Unusual Regioselectivity of the Dipolar Cycloaddition Reactions of Nitrile Oxides and Tertiary Cinnamides and Crotonamides

Benzonitrile oxides undergo 1,3-dipolar cycloaddition reactions with methyl cinnamate to produce the 5-phenyl and 4-phenyl regioisomers in approximately an 80:20 ratio. However, use of N,N-diethylcinnamide as the dipolarophile unexpectedly resulted in the formation of the 5-phenyl and 4-phenyl regioisomers in a 23:77 ratio. Studies have shown that this phenomena occurs only for tertiary cinnamides. In addition, it has been demonstrated that the phenyl group of tertiary cinnamides is not essential for the reversal of regioselectivity since crotonamides produce the same results and trends as the cinnamides. However, since acrylates and acrylamides both produce the 5-carbonyl regioisomers, it can be concluded that the β-substituent is playing a key role for the unexpected results by possibly increasing steric interactions between the dipole and dipolarophile in the transition state. Transition state energies were calculated for the regioisomeric cycloadduct pairs derived from several crotonamides as well as methyl crotonate. These calculations indicate that steric factors are indeed responsible for the reversal of regioselectivity.

Conformationally restrained β-blocking oxime ethers. 2. Synthesis and β-adrenergic properties of diastereoisomeric anti and syn 2-(5'-(3'-aryl-substituted)isoxazolidinyl)-N-alkylethanolamines

The diastereoisomeric 2-(5'-(3'-aryl)isoxazolidinyl)ethaolamines 1c-h-4c-h were synthesized as analogs of the corresponding P-blocking isoxazolines unsubstituted on the aromatic ring 1a-4a, with the aim of checking the effects on the adrenergic properties