2-INDANONE OXIME

PRODUCT IDENTIFICATION

CAS NO. 3349-63-1

2-INDANONE OXIME

EINECS NO. 222-105-2
FORMULA C9H9NO
MOL WT. 147.18

H.S. CODE

 

TOXICITY

 

SYNONYMS 1,3-Dihydro-2H-inden-2-one oxime;
DERIVATION

 

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white powder
MELTING POINT 152 - 154 C
BOILING POINT  
SPECIFIC GRAVITY  
SOLUBILITY IN WATER  
pH  
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AUTOIGNITION

 

NFPA RATINGS

 

REFRACTIVE INDEX

 
FLASH POINT  
STABILITY

Stable under ordinary conditions

GENERAL DESCRIPTION & APPLICATIONS

Indene is a clear to yellowish liquid ; boils at 181C and melts at -2 C. It is a polynuclear hydrocarbon compound with a five-membered ring fused to benzene ring. Indan, 2,3-dihydroindene, is a clear to yellowish liquid; boiling point 177 C;  insoluble in water; soluble in alcohol and ether. They are obtained from coal tar distillation; used as solvents, raw material for synthetic resins and to make other organic compounds such as pharmaceutical ingredients and agrochemicals especially plant growth regulators. Some indane compounds have the characteristic odour and  are used for the preparation of perfumes and flavouring agents. A main industrial application of indene is the production of indene/cumarone thermoplastic resin. Indanone is a ketone form of indane. There are position isomers, 1-indanone and 2-indanone. Indanone is known as an important drug intermediate for serotonin reuptake inhibitors and others. Oxime is any compound with the general formula R\R'/C=N-OH, where R and R' are hydrogen atoms or organic groups derived by removal of a hydrogen atom from an organic compound.

Indanedione is the nucleus of synthetic anticoagulants for the treatment of disorders in which there is excessive or undesirable clotting, such as thrombophlebitis, pulmonary embolism, and certain cardiac conditions. They inhibits the hepatic synthesis of the vitamin K–dependent coagulation factors. Anticoagulants act as rodenticide by causing massive hemorrhaging. Indanedione class anticoagulants or rodenticides include diphenadione, phenindione,  pindone, and valone. Indane class compounds show various functions such as light and temperature sensitivity, heat resistance, conductivity, emittability, corrosion resistance and detection of amino groups. They are used in the applications of  thermo and light sensitizer, liquid crystal chemistry, optical brightening agents, luminescence chemistry, spectrophotometric analysis, molecular chemistry, organometallic-complexes and biochemorphology industry. Indane class compounds can create perfumes, aroma chemicals or fragrance enhancers. They also contribute to the development of drugs having analgesic, anaesthetic and sedative properties, and antibiotics.

Oxime is any compound with the general formula R\R'/C=N-OH, where R and R' are hydrogen atoms or organic groups. Oximes are condensation products of hydroxylamines with aldehydes (forming aldoxime), ketones (forming ketoxime), or quonone. Aldoximes exist only as a syn isomer. But benzaldoxime (aromatic aldoximes) exist in syn- and anti isomers: the syn form melts at 34C, antiisomeric form at 130 C; both forms are soluble in ethanol and ether. 

There are two geometrical isomer: syn and anti isomer (the term syn-anti isomerism is for stereoisomers by other atoms' unsaturated bond rather than carbon). Two isomers have very different properties. The conversion of oximes into corresponding amides, known as Beckmann rearrangement (usually using sulphuric acid as a catalyst), is used to make synthetic fiber monomers. Cyclhexanone oxime is converted into its isomer epsilon-caprolactam which is the raw material to make nylon-6. The amides obtained by Beckmann rearrangement can be converted into amines by hydrolysis, which are useful in the manufacture of dyes, plastics, synthetic fibres, and pharmaceuticals.

Oximes are used as a peel-preventing additive in paints and lacquers. It acts as an antioxidant against oxidative drying materials which forms sticky skin with air oxygen. The another effect of anti-skinning offers drying time delay which can be used in formulating paints.

Oximes are used as chemical building block for the synthesis of agrochemicals and pharmaceuticals. In medicine application, Oxime structure is effective in cholinesterase reactivators to treat the poisoning by organophosphates. Example of these drugs are pralidoxime, obidoximine, methoxime, asoxime, and trimedoxime. Oxime moiety is found in some cephalosporin antibiotics. Diacetyl monoxime is used as an inhibitor of ATP-sensitive potassium ion channels.

Diacetyl (dimethylglyoxal) reacts with hydroxylamine to produce diacetyldioxime (dimethylglyoxime). The characteristic property of oxime is the scavenging free radical and oxygen. Diacetyl oxime is used as a chelating agent. An application example is the spectrophotometric determination of Co(II), Fe(II), Ni(II), Pd(II) and Re(VII)1. Dimethylglyoxime reacts with a nickel salt in a green solution to generate a red colored insoluble tetradentate coordinate complex of nickel. It is used as a reagent for the colorimetric determination of urea and ureido compounds.

Oxime is used as a ligand in transition-metal complex catalyst chemistry. Oxime acts as an antioxidant, radical scavenger which find applications in textile, plastic, paint, detergent, and rubber industry.

SALES SPECIFICATION

APPEARANCE

white powder
PURITY

99.0% min

MELTING POINT

152 - 154 C

TRANSPORTATION
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OTHER INFORMATION