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Xylenol orange information


Xylenol orange
Names
Preferred IUPAC name
2,2′,2′′,2′′′-{(1,1-Dioxo-2,1λ6-benzoxathiole-3,3(1H)-diyl)bis[(6-hydroxy-5-methyl-3,1-phenylene)methylenenitrilo]}tetraacetic acid
Other names
XO[1]
Identifiers
CAS Number
  • 1611-35-4 checkY
  • 3618-43-7 (tetrasodium salt) checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 65838 checkY
ECHA InfoCard 100.015.049 Edit this at Wikidata
EC Number
  • 216-553-8
PubChem CID
  • 73041
UNII
  • S2VDY878QD checkY
  • 0549U815B1 (tetrasodium salt) checkY
CompTox Dashboard (EPA)
  • DTXSID1061819 Edit this at Wikidata
InChI
  • InChI=1S/C31H32N2O13S/c1-17-7-21(9-19(29(17)42)11-32(13-25(34)35)14-26(36)37)31(23-5-3-4-6-24(23)47(44,45)46-31)22-8-18(2)30(43)20(10-22)12-33(15-27(38)39)16-28(40)41/h3-10,42-43H,11-16H2,1-2H3,(H,34,35)(H,36,37)(H,38,39)(H,40,41) checkY
    Key: ORZHVTYKPFFVMG-UHFFFAOYSA-N checkY
SMILES
  • O=C(O)CN(CC(=O)O)Cc1c(O)c(cc(c1)C3(OS(=O)(=O)c2ccccc23)c4cc(c(O)c(c4)CN(CC(=O)O)CC(=O)O)C)C
Properties
Chemical formula
 C31H32N2O13S
Molar mass 672.66 g·mol−1
Melting point 195 °C (383 °F; 468 K)
Solubility in water
 200 mg/mL
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H315, H319, H335
Precautionary statements
 P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazards (white): no code
2
1
2
Flash point > 93 °C (199 °F; 366 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Xylenol orange is an organic reagent, most commonly used as a tetrasodium salt as an indicator for metal titrations. When used for metal titrations, it will appear red in the titrand and become yellow once it reaches its endpoint. Historically, commercial preparations of it have been notoriously impure,[2] sometimes consisting of as little as 20% xylenol orange, and containing large amounts of semi-xylenol orange and iminodiacetic acid. Purities as high as 90% are now available.

It is fluorescent, and has excitation maximums of 440 & 570 nm and an emission maximum of 610 nm.[3]

  1. ^ Li, Zhong-Guang (2019-01-01), Khan, M. Iqbal R.; Reddy, Palakolanu Sudhakar; Ferrante, Antonio; Khan, Nafees A. (eds.), "Chapter 5 - Measurement of Signaling Molecules Calcium Ion, Reactive Sulfur Species, Reactive Carbonyl Species, Reactive Nitrogen Species, and Reactive Oxygen Species in Plants", Plant Signaling Molecules, Woodhead Publishing, pp. 83–103, ISBN 978-0-12-816451-8, archived from the original on 2023-11-11, retrieved 2023-11-11
  2. ^ Gay, Craig; Collins, James; Gebicki, Janusz M. (1999), "Determination of Iron in Solutions with the Ferric–Xylenol Orange Complex", Analytical Biochemistry, 273 (2): 143–148, doi:10.1006/abio.1999.4207, PMID 10469483
  3. ^ "Fluorescence - Fluorochrome Data Tables". Molecular Expressions Microscopy Primer: Specialized Microscopy Techniques. 2018-09-11. Retrieved 2020-01-30.

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