Misplaced Pages

Halazone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Halazone
Names
Preferred IUPAC name 4-(Dichlorosulfamoyl)benzoic acid
Other names
  • Pantocide
  • p-Sulfondichloramidobenzoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.140 Edit this at Wikidata
EC Number
  • 201-253-1
PubChem CID
UNII
UN number 1479
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H5Cl2NO4S/c8-10(9)15(13,14)6-3-1-5(2-4-6)7(11)12/h1-4H,(H,11,12)Key: XPDVQPODLRGWPL-UHFFFAOYSA-N
SMILES
  • C1=CC(=CC=C1C(=O)O)S(=O)(=O)N(Cl)Cl
Properties
Chemical formula C7H5Cl2NO4S
Molar mass 270.08 g·mol
Appearance Fine white powder with an odor of chlorine
Melting point 213 °C (415 °F; 486 K); 196 °C with decomposition.
Solubility in water Less than 1 g/L at 70 °F
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319
Precautionary statements P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N (what is  ?) Infobox references
Chemical compound

Halazone (4-(dichlorosulfamoyl)benzoic acid) is a chemical compound whose formula can be written as either C
7H
5Cl
2NO
4S or (HOOC)(C
6H
4)(SO
2)(NCl
2). It has been widely used to disinfect drinking water.

Other names for this compound include p-sulfondichloramidobenzoic acid, 4-benzoic acid, and Pantocide.

Uses

Halazone tablets have been used to disinfect water for drinking, especially where treated tap water is not available. A typical dosage is 4 mg/L.

Halazone tablets were commonly used during World War II by U.S. soldiers for portable water purification, even being included in accessory packs for C-rations until 1945.

Halazone was widely used by Marine infantry units during the Vietnam War. Halazone has largely been replaced in that use by sodium dichloroisocyanurate. The primary limitation of halazone tablets was the very short usable life of opened bottles, typically three days or less, unlike iodine-based tablets which have a usable open bottle life of three months.

Dilute halazone solutions (4 to 8 ppm of available chlorine) has also been used to disinfect contact lenses, and as a spermicide.

Mechanism of action

Halazone's disinfecting activity is mainly due to the hypochlorous acid (HClO) released by hydrolysis of the chlorine-nitrogen bonds when the product is dissolved in water:

(R1)(R2)NCl + H
2O → HOCl + (R1)(R2)NH

The hypochlorous acid is a powerful oxidizer and chlorinating agent that destroys or denatures many organic compounds.

Production

Halazone can be prepared by chlorination of p-sulfonamidobenzoic acid.

Another synthesis route is the oxidation of dichloramine-T with potassium permanganate in a mild alkaline medium.

See also

References

  1. ^ PubChem: "Halazone". Accessed on 2018-06-18.
  2. ^ NTP (1992), cited by PubChem
  3. Jean-Claude Bradley: Open Melting Point Dataset. Quoted by Chemspider.
  4. ^ Saljoughian, M.; Sadeghi, M. T. (1986). "An improved procedure for the synthesis ofp-(dichlorosulfamoyl)benzoic acid (Halazone)". Monatshefte für Chemie. 117 (4): 553. doi:10.1007/BF00810903.
  5. Gripo Laboratories: "Water purification range: Halazone USP based Chlorine Tablets Archived 2020-06-27 at the Wayback Machine". Product page, accessed on 2018-06-18
  6. Precise Health Care PVT LTD: "Halazone tablets Archived 2021-09-01 at the Wayback Machine". Product page, accessed on 2018-06-18
  7. Hlavatá, L; Aguilaniu, H; Pichová, A; Nyström, T (2003). "The oncogenic RAS2val19 mutation locks respiration, independently of PKA, in a mode prone to generate ROS". The EMBO Journal. 22 (13): 3337–3345. doi:10.1093/emboj/cdg314. PMC 165639. PMID 12839995.
  8. ^ Rosenthal, Ruth Ann; Schlitzen, Ronald L; McNamee, Linda S; Dassanayake, Nissanake L; Amass, Roger (1992). "Antimicrobial activity of organic chlorine releasing compounds". Journal of the British Contact Lens Association. 15 (2): 81. doi:10.1016/0141-7037(92)80044-Z.
Antiseptics and disinfectants (D08)
Acridine derivatives
Biguanides and amidines
Phenol and derivatives
Nitrofuran derivatives
Iodine products
Quinoline derivatives
Quaternary ammonium compounds
Mercurial products
Silver compounds
Alcohols
Other
Categories: