4589-97-3 Usage
Preparation
To a solution of 50 gm (0.34 mole) of ω-oximinoacetophenone (ω-isonitrosoacetophenone) in 150 ml of ethanol is added to a solution of 48 gm (0.595 mole) of sodium acetate and 24 gm (0.345 mole) of hydrox-ylamine hydrochloride in 75 ml of water. The mixture is heated at reflux for 4 hr. After cooling, a large portion of the Solvent is evaporated off under reduced pressure. The mixed crude product, which precipitates, is filtered off, washed with water, and air-dried to afford 51 gm (92%), m.p. 150-158°C.
The separation of the three isomers by fractional crystallization pro-cedures depends on the relative ratio of the components in the mixture, the concentration of the components in the solvent, the length of time the solvent-product mixture is heated, etc. It is therefore important that the progress of the crystallization be followed by thin-layer chromatography using freshly prepared tic plates [Merck (Darmstadt) silica gel G is recom-mended as the coating]. The suggested tic solvent is benzene-ethyl acetate (7:3), detection by iodine vapor; 0.45 Rf for phenyl-amphi-glyoxime (I), 0.40 Rf for phenyl-anti-glyoxime (II), and 0.35 Rf for phenyl-syn-glyoxime(III).
Anti-glyoxime (II), and 0.35 Rf for phenyl-syn-glyoxime(III). Anti-phenyl-amphi-glyoxime (I) is separated from the mixed product by repeated recrystallization from acetone-chloroform (or alcohol-water), m.p. 178-180°C; UV, λmax (95% ethanol) 230 mμ (ε 14,800).
Phenyl-anti-glyoxime (II) is isolated from the mother liquor of the first crystallization in the separation of (I). The residue from the evaporation of this mother liquor is crystallized repeatedly from acetone-chloroform. After sublimation, the properties of the material are as follows: sublima-tion temperature, 90°C (0.2 mm Hg); m.p. 166-168°C; UV, λmax (95% ethanol) 228 mμ (ε 14,380). Only about 1% of pure isomer is isolated from the starting product.
Phenyl-syn-glyoxime (III) is isolated by crystallizing the starting product from a dilute solution of ethyl acetate, m.p. 168-170°C; UV, λmax (95% ethanol) 252 mμ (ε 12,200).
Check Digit Verification of cas no
The CAS Registry Mumber 4589-97-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,5,8 and 9 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 4589-97:
(6*4)+(5*5)+(4*8)+(3*9)+(2*9)+(1*7)=133
133 % 10 = 3
So 4589-97-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H8N2O2/c11-9-6-8(10-12)7-4-2-1-3-5-7/h1-6,10,12H/b8-6+
4589-97-3Relevant articles and documents
Manning,Stansbury
, p. 4885,4888 (1959)
Green and highly selective protocol for the synthesis of oximes
Ghosh, Pranab,Subba, Raju
, p. 529 - 532 (2013/11/06)
A green and efficient protocol has been developed for the synthesis of either exclusively a monoxime or exclusively a dioxime from a host of 1,2-dicarbonyl compounds on silica.
One-pot synthesis of 3-amino-4-aryl- and 3-amino-4-hetarylfurazans
Sheremetev
, p. 1057 - 1059 (2007/10/03)
A "one pot" method for the synthesis of 3-amino-4-aryl- and 3-amino-4-hetarylfurazans from β-aryl- and 4-β-hetaryl-β-oxo acid esters was developed.
