3717-24-6

Basic information

• Product Name: (NE)-N-[(4-chlorophenyl)methylidene]hydroxylamine
• Synonyms: (NE)-N-[(4-chlorophenyl)methylidene]hydroxylamine;(E)-4-Chlorobenzaldehyde oxime;(E)-4-Chlorobenzaldoxime;Benzaldehyde, 4-chloro-, oxime, (E)-;Benzaldehyde, p-chloro-, oxime, (E)-;Nsc74;p-Chloro-syn-benzaldoxime;Syn-p-chlorobenzaldoxime
• CAS NO: 3717-24-6
• Molecular Formula: C₇H₆ClNO
• Molecular Weight: 155.58
• Mol File: 3717-24-6.mol
• Article Data: 34

Chemical Properties

• Melting Point: 142-143 °C
• Boiling Point: 233.2°Cat760mmHg
• Flash Point: 94.8°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 0.0314mmHg at 25°C
• Refractive Index: 1.55
• PKA: 10.45±0.10(Predicted)
• CAS DataBase Reference: (NE)-N-[(4-chlorophenyl)methylidene]hydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: (NE)-N-[(4-chlorophenyl)methylidene]hydroxylamine(3717-24-6)
• EPA Substance Registry System: (NE)-N-[(4-chlorophenyl)methylidene]hydroxylamine(3717-24-6)

Safety Data

• Hazardous Substances Data: 3717-24-6(Hazardous Substances Data)

Usage

General Description

(NE)-N-[(4-chlorophenyl)methylidene]hydroxylamine is a chemical compound with the molecular formula C7H7ClNO. It is a hydroxylamine derivative, containing a nitroso group. (NE)-N-[(4-chlorophenyl)methylidene]hydroxylamine is used in various chemical reactions, such as in the synthesis of pharmaceuticals and agrochemicals. It also has potential applications in the development of new materials and in research studies. The presence of the chlorophenyl and hydroxylamine groups makes this compound a versatile building block for the preparation of diverse organic molecules with potential biological and industrial significance. Its unique structure and reactivity make it an important intermediate in the synthesis of various chemical compounds.

InChI:InChI=1/C7H6ClNO/c8-7-3-1-6(2-4-7)5-9-10/h1-5,10H/b9-5+

Upstream product

• 87-91-2 diethyl (2R,3R)-tartrate 
• 3717-23-5 (Z)-p-chlorobenzaldehyde oxime 
• 80055-48-7 syn-p-Chlor-benzaldoxim-acetat 
• 104-88-1 4-chlorobenzaldehyde 
• 880143-18-0 (E)-4-chlorobenzaldehyde-O-ethoxycarbonyloxime 
• 96-29-7 ethyl methyl ketone oxime 
• 104-86-9 4-chlorobenzylamine 
• 1867-38-5 4-chlorobenzylidenemalonodinitrile 
• 873-76-7 para-Chlorobenzyl alcohol 
• 2168-82-3 dithio-4-chlorobenzoic acid 

Downstream Products

• 3717-23-5 (Z)-p-chlorobenzaldehyde oxime 
• 158042-17-2 3,5-bis(4-chlorophenyl)-1,2,4-oxadiazole 
• 117041-95-9 p-chlorobenzonitrolic acid 
• 880143-18-0 (E)-4-chlorobenzaldehyde-O-ethoxycarbonyloxime 
• 18802-67-0 4-chloro-benzaldehyde-(O-benzoyl oxime ) 
• 141891-21-6 4-Chloro-benzaldehyde O-ethyl-oxime 
• 23879-15-4 4-chlorophenylaldazine di-N-oxide 
• 7304-76-9 1-chloro-4-(dinitromethyl)benzene 
• 104-88-1 4-chlorobenzaldehyde 
• 203861-66-9 N-(4-chlorobenzylidene)methylamine N-oxide 
• 21913-13-3 N,N-bis(4-chlorobenzyl)amine 
• 104-86-9 4-chlorobenzylamine 
• 623-03-0 4-Cyanochlorobenzene 
• 1227841-18-0 (E)-4-chlorobenzaldehyde O-3-phenylpropioloyl oxime 

Relevant articles and documents

Visible-Light-Mediated Strategies for the Preparation of Oxime Ethers Derived from O-H Insertions of Oximes into Aryldiazoacetates

Two visible-light-mediated O-H insertion protocols involving oximes and aryldiazoacetates leading to different products depending on the solvent employed are reported. In DCM, direct O-H insertion takes place. In THF, there is the additional incorporation of the ring-opened form of this solvent into the structure of the product. These metal-free protocols are mild and tolerant to air and moisture. The preparation of an acaricide has been developed as an example of synthetic application.

Identification of morpholine based hydroxylamine analogues: Selective inhibitors of MARK4/Par-1d causing cancer cell death through apoptosis

Microtubule affinity-regulating kinase 4 (MARK4) is a serine/threonine kinase involved in the phosphorylation of MAP proteins that regulates microtubule dynamics and abets tumor progression by participating in oncogenic signaling pathways. It is overexpressed in multiple human malignancies and no drug is available for this potential therapeutic target at present. Therefore, using the structure based drug design strategy, a library of hydroxylamine derivatives of morpholine were designed and synthesized as small molecule inhibitors of MARK4. Compound 32 having the CF3 group at the ortho position of the phenyl ring tethered with the >CNOH core and the hinge binder morpholine component was found to be a potent and selective inhibitor of MARK4 over thirty other serine-threonine kinases. Study of cell viability and compound induced morphological changes in MCF-7 cancer cells discovered that molecule 32 caused death of cancerous cells through the mechanism of apoptosis. Compound 32 may be transported and delivered to the target site through the blood stream, and has promising antioxidant potential. Such bio-active molecules could serve as optimized lead candidates in drug discovery for cancer treatment through MARK4 inhibition.

Novel access to 2-substituted quinolin-4-ones by nickel boride-mediated reductive ring transformation of 5-(2-nitrophenyl)isoxazoles

Reductive ring transformation of 3-substituted 5-(2-nitrophenyl)isoxazoles, readily accessible via 1,3-dipolar cycloaddition of 2-ethinylnitrobenzene with nitrile oxides, opens a novel access to 2-substituted quinolin-4-ones. Nickel boride, generated in situ from nickel chloride and sodium borohydride, allows, via simultaneous reduction of the nitro group and reductive cleavage of the isoxazole ring, the one-step conversion into the target quinolin-4-ones. This protocol tolerates various functional groups, except olefins, and thus is complementary to the reductive ring transformation with iron/acetic acid, which predominantly tolerates olefins.