97522-06-0

Basic information

• Product Name: methyl (3-chloro-4-nitrophenyl)acetate
• Synonyms: methyl (3-chloro-4-nitrophenyl)acetate
• CAS NO: 97522-06-0
• Molecular Weight: 229.62
• Mol File: 97522-06-0.mol

Chemical Properties

• CAS DataBase Reference: methyl (3-chloro-4-nitrophenyl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3-chloro-4-nitrophenyl)acetate(97522-06-0)
• EPA Substance Registry System: methyl (3-chloro-4-nitrophenyl)acetate(97522-06-0)

Safety Data

• Hazardous Substances Data: 97522-06-0(Hazardous Substances Data)

Upstream product

• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 121-73-3 3-Nitrochlorobenzene 
• 2916-76-9 methyl (trimethylsilyl)acetate 
• 88-73-3 2-Chloronitrobenzene 
• 53088-68-9 methyl 3-chlorophenylacetate 
• 1878-65-5 3-chlorophenylacetic acid 

Downstream Products

• 163395-25-3 3-chloro-4-nitrophenylacetic acid 
• 101349-30-8 methyl 4-amino-3-chlorobenzene-1-acetate 
• 163395-23-1 2-(3-Chloro-4-nitro-phenyl)-N-[(3-hydroxy-benzylcarbamoyl)-methyl]-acetamide 
• 317356-69-7 methyl 4-[N'-(2bromophenyl)ureido]-3-chlorophenylacetate 
• 317364-40-2 methyl 3-chloro-4-[N'-(2-chlorophenyl) ureido]phenylacetate 
• 317364-37-7 methyl 3-chloro-4-[N'-(2-methylphenyl)ureido]phenylacetate 
• 317356-70-0 (4-[N'-(2-bromophenyl)ureido]-3-chlorophenyl)acetic acid 
• 317364-41-3 (3-chloro-4-[N'-(2-chlorophenyl)ureido]phenyl)acetic acid 
• 317364-38-8 (3-chloro-4-[N'-(2-methylphenyl)ureido]phenyl)acetic acid 
• 317356-71-1 C₂₈H₂₆BrClFN₃O₅ 
• 317364-42-4 C₂₈H₂₆Cl₂FN₃O₅ 
• 317364-39-9 methyl 4-[(2S,4S)-1-[(3-chloro-4-[N'-(2-methylphenyl)ureido]phenyl)acetyl]-4-fluoro-2-pyrrolidinylmethoxy]benzoate 

Relevant articles and documents

Synthesis and biological evaluation of benzoic acid derivatives as potent, orally active VLA-4 antagonists

A series of benzoic acid derivatives was synthesized as VLA-4 antagonists. Introduction of chlorine or bromine into the 3-position on the central benzene of the diphenylurea portion as in lead compound 2 led to improvement in the pharmacokinetic properties. In particular, 12l demonstrated an acceptable plasma clearance and bioavailability in mice and rats as well as dogs (mice, CL = 18.5 ml/min/kg, F = 28 %; rats, CL = 5.2 ml/min/kg, F = 36 %; dogs, CL = 3.6 ml/min/kg, F = 55 %). Additionally, 12l exhibited potent activity with an IC50 value of 0.51 nM and efficacy by oral administration at a dosage of 10 mg/kg in a rat pleurisy model.

VLA-4 inhibitor compounds

Compounds that selectively inhibit the binding of ligands to alpha4beta1 integrin (VLA-4) and methods for their preparation are disclosed. In one embodiment, compounds of the invention are represented by Formula I: As selective inhibitors of VLA-4 mediated cell adhesion, compounds of the present invention are useful in the treatment of conditions associated with such adhesion, including, but not limited to, such conditions as inflammatory and autoimmune responses, diabetes, asthma, psoriasis, inflammatory bowel disease, transplantation rejection, and tumor metastasis. Also disclosed are pharmaceutical compositions, methods of inhibiting VLA-4 mediated cell adhesion and methods of treating conditions associated with LA-4 mediated cell adhesion, which involve compounds of Formula I.

IMIDAZOLINYLMETHYL ARALKYLSULFONAMIDES

Compounds of the Formula: where R1-R6 are those defined herein and methods for producing the same. Also provided are pharmaceutical compositions comprising a Compound of Formula I and methods for their use as therapeutic agents.

A Convergent Synthesis of 14-Membered F-O-G Ring Analogs of the Teicoplanin Binding Pocket via Intramolecular SNAr Reaction

An intramolecular SNAr reaction for efficient macrocyclization via biaryl ether formation was developed for syntheses of the 14-membered macrocycles 2 and 3 related to F-O-G ring of teicoplanin 1.Chloride as well as fluoride could be used as the leaving group in this reaction.However, the latter was prefered since it required milder conditions.Both ortho and para nitro, fluoro disubstituted aromatic rings were suitable for the macrocyclization reaction with tethered aryl oxides.The nonproteinogenic α-amino acid 23, required for the synthesis of 3, was prepared via an asymmetric Strecker synthesis using (R)-phenylglycinol as a chiral auxiliary.The overall synthetic strategy was convergent, and the cyclization could be performed in the presence of the highly sensitive arylglycine unit without racemization.

Nucleophilic Addition of Silyl Enol Ethers to Aromatic Nitro Compounds: Scope and Mechanism of Reaction

In sharp contrast to alkali-metal enolates, silyl enol ethers and ketene silyl acetals add to aromatic nitro compounds in the presence of a fluoride ion source to give the intermediate dihydroaromatic nitronates, which can be observed by NMR.In situ oxidation of the intermediate with bromine or DDQ yields α-nitroaryl carbonyl compounds in moderate-to-high yields.The reaction is applicable to alkyl-, alkoxy-, and halogen-substituted nitrobenzenes as well as to heterocyclic and condensed nitroaromatic compounds.While substitution ortho to the nitro group predominates with sterically undemanding silyl reagents, para-substitution products are exclusively obtained with bulky reagents.However, by blocking the para position with an appropriate group such as chlorine, the addition can be directed to the ortho position.Halogen atoms of halogenated nitroaromatics and p-nitrocumenyl chloride are not displaced in the reaction, suggesting the absence of radical ion intermediates.Dihydroaromatic nitro derivatives ca be isolated in some cases, such as anthracene and naphthalene systems which are less prone to rearomatize.