Salicylaldoxime

Salicylaldoxime
Names
	IUPAC name Salicylaldehyde oxime
	Other names Saldox
Identifiers
CAS Number	94-67-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	10446269 ;
ECHA InfoCard	100.002.140
PubChem CID	5359280;
CompTox Dashboard (EPA)	DTXSID9052638 ;
	InChI InChI=1S/C7H7NO2/c9-7-4-2-1-3-6(7)5-8-10/h1-5,9-10H/b8-5- Key: ORIHZIZPTZTNCU-YVMONPNESA-N ; InChI=1/C7H7NO2/c9-7-4-2-1-3-6(7)5-8-10/h1-5,9-10H/b8-5- Key: ORIHZIZPTZTNCU-YVMONPNEBT;
	SMILES Oc1ccccc1/C=N\O;
Properties
Chemical formula	C7H7NO2
Molar mass	137.13598
Appearance	white to off-white crystals
Melting point	59-61 °C
Solubility in water	25 g L-1
Hazards
NFPA 704 (fire diamond)	2 1 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Salicylaldoxime is a chemical compound described by the formula C₆H₄CH=NOH-2-OH. It is the oxime of salicylaldehyde. This crystalline solid is a chelator and sometimes used in the analysis of samples containing transition metal ions, with which it often forms brightly-coloured coordination complexes.^[1]

In the era when metals were analysed by spectrophotometry, many chelating ligands were developed that selectively formed brightly coloured complexes with particular metal ions. This methodology has been eclipsed with the introduction of inductively coupled plasma methodology. Salicylaldoxime can be used to selectively precipitate metal ions for gravimetric determination. It forms a greenish-yellow precipitate with copper at a pH of 2.6 in the presence of acetic acid. Under these conditions, this is the only metal that precipitates; at pH 3.3, nickel also precipitates. Iron (III) will interfere. ^[2]

Adsorbed or chemically bonded to a solid support such as silica gel, it can be used to preconcentrate or extract metals from a dilute solution such as seawater.^[3] It has been used as an ionophore in ion selective electrodes, with good response to Pb²⁺ and Ni²⁺.^[4]

Salicylaldoxime has also been used to probe ion channels in muscle tissue^[5] and as a probe in photosystem I.^[6]

External links

Chemical data at NIST Chemistry WebBook

References

^ P Sedwick (1984). "The Separation Of Metals From Treated Deep-Sea Ferromanganese Nodules By Adsorptive Bubble Techniques Using Salicylaldoxime And Sodium Diethyldithiocarbamate As Organic Precipitating Reagents". Separation Science and Technology. 19 (2–3): 183–190. doi:10.1080/01496398408060654. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
^ SH Simonsen (1955). "Spectrophotometric Determination Of Copper With Salicylaldoxime - Application To Analysis Of Aluminum Alloys". Analytical Chemistry. 27 (8): 1336–1339. doi:10.1021/ac60104a039. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
^ AR Sarkar (1996). "Sorption Recovery of Metal Ions Using Silica Gel Modified with Salicylaldoxime". Talanta. 43 (11): 1857–1862. doi:10.1016/0039-9140(96)01953-4. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
^ EK Quagraine (1992). "Studies Of Spectrophotometric Reagents In Some Transition-Metal And Lead Ion-Selective Electrodes". Analyst. 117 (12): 1899–1903. doi:10.1039/an9921701899. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
^ H Chunlei (1995). "Multiple Effects Of Salicylaldoxime On Rat Cardiac Action-Potentials". Pharmacology & Toxicology. 77 (6): 386–390. doi:10.1111/j.1600-0773.1995.tb01047.x. PMID 8835364. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)
^ S Katoh (1966). "Inhibitory Effect Of Salicylaldoxime On Chloroplast Photooxidation-Reduction Reactions". Biochemical and Biophysical Research Communications. 24 (6): 903. doi:10.1016/0006-291X(66)90335-4. PMID 5970525. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

[1] P Sedwick (1984). "The Separation Of Metals From Treated Deep-Sea Ferromanganese Nodules By Adsorptive Bubble Techniques Using Salicylaldoxime And Sodium Diethyldithiocarbamate As Organic Precipitating Reagents". Separation Science and Technology. 19 (2–3): 183–190. doi:10.1080/01496398408060654. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

[2] SH Simonsen (1955). "Spectrophotometric Determination Of Copper With Salicylaldoxime - Application To Analysis Of Aluminum Alloys". Analytical Chemistry. 27 (8): 1336–1339. doi:10.1021/ac60104a039. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

[3] AR Sarkar (1996). "Sorption Recovery of Metal Ions Using Silica Gel Modified with Salicylaldoxime". Talanta. 43 (11): 1857–1862. doi:10.1016/0039-9140(96)01953-4. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

[4] EK Quagraine (1992). "Studies Of Spectrophotometric Reagents In Some Transition-Metal And Lead Ion-Selective Electrodes". Analyst. 117 (12): 1899–1903. doi:10.1039/an9921701899. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

[5] H Chunlei (1995). "Multiple Effects Of Salicylaldoxime On Rat Cardiac Action-Potentials". Pharmacology & Toxicology. 77 (6): 386–390. doi:10.1111/j.1600-0773.1995.tb01047.x. PMID 8835364. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |month= ignored (help)

[6] S Katoh (1966). "Inhibitory Effect Of Salicylaldoxime On Chloroplast Photooxidation-Reduction Reactions". Biochemical and Biophysical Research Communications. 24 (6): 903. doi:10.1016/0006-291X(66)90335-4. PMID 5970525. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)

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