33512-94-6

Basic information

• Product Name: ALPHA-CHLORO-3-NITROBENZALDOXIME
• Synonyms: ALPHA-CHLORO-3-NITROBENZALDOXIME;M-NITROBENZOHYDROXIMOYL CHLORIDE;a-Chloro-3-nitrobenzaldoxime;-Chloro-3-nitrobenzaldoxime;Benzenecarboximidoyl chloride, N-hydroxy-3-nitro-
• CAS NO: 33512-94-6
• Molecular Formula: C₇H₅ClN₂O₃
• Molecular Weight: 200.58
• Mol File: 33512-94-6.mol
• Article Data: 48

Chemical Properties

• Melting Point: 93-95 °C
• Boiling Point: 367.2 °C at 760 mmHg
• Flash Point: 175.9 °C
• Appearance: /
• Density: 1.5 g/cm³
• Vapor Pressure: 4.87E-06mmHg at 25°C
• Refractive Index: 1.612
• PKA: 9.98±0.70(Predicted)
• CAS DataBase Reference: ALPHA-CHLORO-3-NITROBENZALDOXIME(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-CHLORO-3-NITROBENZALDOXIME(33512-94-6)
• EPA Substance Registry System: ALPHA-CHLORO-3-NITROBENZALDOXIME(33512-94-6)

Safety Data

• Hazardous Substances Data: 33512-94-6(Hazardous Substances Data)

Usage

General Description

ALPHA-CHLORO-3-NITROBENZALDOXIME, also known as chlorodinitrobenzaldoxime, is a chemical compound that is primarily used as a reagent in analytical chemistry and in the production of pharmaceuticals. It is a pale yellow crystalline solid with a molecular formula of C7H4ClN3O3. ALPHA-CHLORO-3-NITROBENZALDOXIME is often used as a GC derivatization reactant in the analysis of aliphatic amines and as a reagent for the determination of cobalt. It is also employed in the synthesis of various pharmaceutical drugs and is an important intermediate in organic synthesis. ALPHA-CHLORO-3-NITROBENZALDOXIME is known to have low toxicity and is relatively stable under normal conditions.

InChI:InChI=1/C7H5ClN2O3/c8-7(9-11)5-2-1-3-6(4-5)10(12)13/h1-4,11H/b9-7+

Upstream product

• 3717-29-1 E-3-nitrobenzaldoxime 
• 99-61-6 3-nitro-benzaldehyde 
• 619-24-9 3-nitrobenzonitrile 
• 5023-94-9 m-nitrobenzamide oxime 
• 3431-62-7 3-nitrobenzaldoxime 
• 3717-30-4 3-nitrobenzaldoxime 

Downstream Products

• 65623-50-9 1-[hydroxyimino-(3-nitro-phenyl)-methyl]-piperidine 
• 5023-94-9 m-nitrobenzamide oxime 
• 51003-63-5 3,4-bis(3-nitrophenyl)furoxan 
• 619-24-9 3-nitrobenzonitrile 
• 25284-11-1 5-methyl-2-(3-nitro-phenyl)-benzooxazole 
• 29095-12-3 3-(3-nitro-phenyl)-6-phenyl-[1,4,2,5]dioxadiazine 
• 21172-10-1 3-(3-nitro-phenyl)-isoxazole-4-carbonitrile 
• 14659-72-4 3-(3-nitro-phenyl)-4,5-dihydro-isoxazole 
• 21172-09-8 3-(3-nitro-phenyl)-isoxazole-5-carbonitrile 
• 21125-33-7 (5-methylsulfanyl-[1,3,4]thiadiazol-2-yl)-(3-nitro-phenyl)-amine 
• 21125-34-8 2-methylsulfanyl-5-(3-nitro-phenyl)-[1,3,4]thiadiazole 
• 61191-65-9 3-(3-nitro-phenyl)-3a,4,5,9b-tetrahydro-naphtho[2,1-d]isoxazole 
• 61191-66-0 1-(3-nitro-phenyl)-3a,4,5,9b-tetrahydro-naphtho[1,2-d]isoxazole 
• 72590-54-6 3'-(3-nitro-phenyl)-4'H-spiro[adamantane-2,5'-isoxazole] 

Relevant articles and documents

Design and synthesis of sinomenine isoxazole derivatives via 1,3-dipolar cycloaddition reaction

A novel structure of sinomenine isoxazole derivatives is synthesised from sinomenine hydrochloride and aromatic aldehydes and requires six steps. 19 target compounds have been obtained in good yields. The sinomenine hydrochloride transforms to 4-alkynyl sinomenine, which is a key intermediate product to synthesise the target sinomenine isoxazole compounds, after a neutralisation reaction with ammonia and substitution reaction with 3-chloropropyne. Another key intermediate product is 1,3-dipole, which can be obtained from aromatic aldehyde. After treatment with hydroxylamine hydrochloride and then sodium carbonate solution, aromatic aldehyde is converted to aldehyde oxime, which reacts with N-chlorosuccinimide (NCS) to afford aryl hydroximino chloride. 1,3-Dipole is eventually formed in situ while triethylamine (TEA) in DMF is added dropwise. Then 4-alkynyl sinomenine is added to provide the sinomenine isoxazole derivative via 1,3-dipolar cycloaddition reaction as the key step. All the target compounds are characterised by melting point, 1H NMR, 13C NMR, HRMS and FT-IR spectroscopy.

Dibenzazepine-linked isoxazoles: New and potent class of α-glucosidase inhibitors

α-Glucosidase inhibition is a valid approach for controlling hyperglycemia in diabetes. In the current study, new molecules as a hybrid of isoxazole and dibenzazepine scaffolds were designed, based on their literature as antidiabetic agents. For this, a series of dibenzazepine-linked isoxazoles (33–54) was prepared using Nitrile oxide-Alkyne cycloaddition (NOAC) reaction, and evaluated for their α-glucosidase inhibitory activities to explore new hits for treatment of diabetes. Most of the compounds showed potent inhibitory potency against α-glucosidase (EC 3.2.1.20) enzyme (IC50 = 35.62 ± 1.48 to 333.30 ± 1.67 μM) using acarbose as a reference drug (IC50 = 875.75 ± 2.08 μM). Structure-activity relationship, kinetics and molecular docking studies of active isoxazoles were also determined to study enzyme-inhibitor interactions. Compounds 33, 40, 41, 46, 48–50, and 54 showed binding interactions with critical amino acid residues of α-glucosidase enzyme, such as Lys156, Ser157, Asp242, and Gln353.

Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs

Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.