532-54-7

Basic information

• Product Name: 2-Isonitrosoacetophenone
• Synonyms: 1-phenyl-glyoxa2-oxime;2-hydroxyimino-acetophenon;alpha-oxo-benzeneacetaldehydaldoxime;phenylglyoxalaldoxime;OMEGA-(HYDROXYIMINO)ACETOPHENONE;OMEGA-ISONITROSOACETOPHENONE;PHENYLGLYOXALDOXIME;Phenylglyoxal 2-oxime
• CAS NO: 532-54-7
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.15
• EINECS: 208-539-5
• Product Categories: Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Oximes
• Mol File: 532-54-7.mol
• Article Data: 31

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 270.21°C (rough estimate)
• Flash Point: 138.699 °C
• Appearance: beige to yellowish crystalline powder
• Density: 1.2517 (rough estimate)
• Vapor Pressure: 0.000352mmHg at 25°C
• Refractive Index: 1.5320 (estimate)
• Storage Temp.: 2-8°C
• PKA: 8.49±0.10(Predicted)
• Water Solubility: SOLUBLE IN COLD WATER
• Merck: 14,5191
• BRN: 2041691
• CAS DataBase Reference: 2-Isonitrosoacetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isonitrosoacetophenone(532-54-7)
• EPA Substance Registry System: 2-Isonitrosoacetophenone(532-54-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-24/25
• RIDADR: 2811
• WGK Germany: 3
• RTECS: MD3325000
• TSCA: Yes
• Hazardous Substances Data: 532-54-7(Hazardous Substances Data)

Usage

Description

2-Isonitrosoacetophenone is a beige to yellowish crystalline powder that is known for its unique chemical properties and various applications across different industries. It is a compound that has garnered interest due to its potential uses in chemical and pharmaceutical research.

Uses

Used in Chemical Analysis:
2-Isonitrosoacetophenone is used as a reagent for the detection of ferrous ions, with which it forms a blue color soluble in chloroform. This property makes it a valuable tool in chemical analysis and research, particularly in the identification and quantification of ferrous ions in various samples.
Used in Pharmaceutical Industry:
2-Isonitrosoacetophenone is used to create complexes with copper and amino acids. These complexes have demonstrated enhanced antimicrobial activities, particularly against gram-positive bacteria, and also possess antioxidant properties. This makes them potentially useful in the development of new antimicrobial agents and therapies, as well as in the field of antioxidant research.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 2558, 1974 DOI: 10.1021/jo00931a022

Purification Methods

Crystallise it from water. [Beilstein 7 IV 2132.]

InChI:InChI=1/C8H7NO2/c10-8(6-9-11)7-4-2-1-3-5-7/h1-6,11H/b9-6-

Upstream product

• 5492-70-6 phenyl-glyoxal-2-(N-phenyl oxime ) 
• 64-17-5 ethanol 
• 127-09-3 sodium acetate 
• 532-54-7 hydroxyiminoacetophenone 
• 540-80-7 tert.-butylnitrite 
• 98-86-2 acetophenone 
• 110-46-3 isopentyl nitrite 
• 2439-92-1 4-phenylisoxazole 
• 1816-88-2 2-azido-1-phenylethan-1-one 
• 541-42-4 i-propyl nitrite 
• 100-52-7 benzaldehyde 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 108488-77-3 1-phenyl-3-piperidino-propane-1,2-dione-2-oxime 
• 411211-25-1 phenyl-glyoxal-2-oxime-1-semicarbazone 
• 32464-52-1 3-methyl-1-oxy-5-phenyl-pyrazin-2-ylamine 
• 63324-73-2 1-(2-methyl-4-phenyl-1H-pyrrol-3-yl)ethan-1-one 
• 59009-58-4 3-benzoyl-2-methyl-4-phenylpyrrole 
• 109068-42-0 1-(2-dimethylamino-ethyl)-3-phenyl-quinoxalinium; chloride-hydrochloride 
• 136440-21-6 4-Phenyl-2,2-dipropyl-2H-imidazole 1-oxide 
• 138000-88-1 2,2-Dioctyl-4-phenyl-2H-imidazole 1-oxide 
• 136440-17-0 2-Methyl-2-octyl-4-phenyl-2H-imidazole 1-oxide 
• 107046-75-3 1-Cyclohexyl-2-phenyl-ethane-1,2-dione 1-oxime 
• 50627-20-8 2-amino-3-cyano-5-phenylpyrazine-1-N-oxide 
• 113120-64-2 2-amino-3-benzyloxycarbonyl-5-phenylpyrazine 1-oxide 
• 125989-50-6 4-Oxy-6-phenyl-[1,2,4]triazin-3-ylamine 
• 50627-56-0 2-amino-3-ethoxycarbonyl-5-phenylpyrazine 1-oxide 

Relevant articles and documents

Discovery of Hydroxyamidine Derivatives as Highly Potent, Selective Indoleamine-2,3-dioxygenase 1 Inhibitors

In this study, a series of novel hydroxyamidine derivatives were identified as potent and selective IDO1 inhibitors by structure-based drug design. Among them, compounds 13-15 and 18 exhibited favorable enzymatic and cellular activities. Compound 18 showed improved bioavailability in mouse, rat, and dog (F% = 44%, 58.8%, 102.1%, respectively). With reasonable in vivo pharmacokinetic properties, compound 18 was further evaluated in a transgenic MC38 xenograft mouse model. The combination of compound 18 with PD-1 monoclonal antibody showed a synergistic antitumor effect. These data indicated that compound 18 as a potential cancer immunotherapy agent should warrant further investigation.

Site-selective conversion of azido groups at carbonyl α-positions into oxime groups leading triazide to a triple click conjugation scaffold

This paper reports the selective conversion of alkyl azido groups at the carbonyl α-position into oximes through β-elimination of dinitrogen, followed by transoximation. With this method and diazo conversion, a triazido molecule was transformed into a triple click conjugation scaffold allowing one-pot four-component coupling.

Single-Step Modular Synthesis of Unsaturated Morpholine N-Oxides and Their Cycloaddition Reactions

A single-flask procedure for the generation of α-keto-N-alkenylnitrones through a Chan–Lam coupling and subsequent spontaneous 6π electrocyclization of these intermediates for the synthesis of 2H-1,4-oxazine N-oxides has been developed for a variety of α-ketooximes and alkenylboronic acids. This transformation provides a new approach to C-substituted unsaturated morpholine derivatives that are poised to undergo further functionalization for the preparation of a diverse array of novel heterocyclic structures. The scope of the new method for the synthesis of 2H-1,4-oxazine N-oxides is discussed, in addition to initial studies describing the cycloaddition reactivity of these new heterocyclic intermediates.