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Hydroxylamine hydrochloride

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Hydroxylamine hydrochloride Basic information
Hydroxylamine hydrochloride Chemical Properties
  • Melting point:155-157 °C (dec.)(lit.)
  • Density 1.67 g/mL at 25 °C(lit.)
  • vapor pressure 0.054 Pa (50 °C)
  • storage temp. Store at RT.
  • solubility 470g/l
  • form Liquid
  • color White to off-white
  • PH2.5-3.5 (25℃, 50mg/mL in H2O)
  • Water Solubility 560 g/L (20 ºC)
  • Sensitive Hygroscopic
  • Merck 14,4828
  • BRN 3539763
  • Stability:Substances to be avoided include strong oxidizing agents. Heating above 115 C may cause explosion; do not store above 65C. Moisture and air sensitive.
  • CAS DataBase Reference5470-11-1(CAS DataBase Reference)
  • EPA Substance Registry SystemHydroxylamine hydrochloride (5470-11-1)
Safety Information
Hydroxylamine hydrochloride Usage And Synthesis
  • Chemical PropertiesWhite crystals
  • Physical propertiesColorless monoclinic crystals; hygroscopic; decomposes slowly in moist air;density 1.67 g/cm3at 17°C; melts at 151°C (decomposes); highly soluble inwater (84g/100g at 20°C); soluble in lower alcohols and glycols; pH of 0.1molar solution 3.4.
  • UsesOrganic synthesis, photographic developer, medicine, controlled reduction reactions, nondiscoloring short-stopper for synthetic rubbers, antioxidant for fatty acids.
  • UsesHydroxylammonium-chloride is a reducing agent in photography; in synthetic and analytical chemistry; as an antioxidant for fatty acids and soaps; in textiles; in medicine; controlled reduction reactions; non-discoloring short stoppers for synthetic rubbers; reagent for enzyme reactivation; powerful reducing agent; converts aldehydes and ketones to oximes and acid chlorides to hydroxamic acids; catalyst, swelling agent, and copolymerization inhibitor in polymerization processes; in floor lacquers and as an antioxidant for fatty acids and soaps.
  • PreparationHydroxylamine hydrochloride is prepared by electrolytic reduction ofammonium chloride.
  • Biotechnological ApplicationsHydroxylamine hydrochloride is a strong reducing agent that is useful in biochemical crosslinking applications, including the deacetylation of SATA and chemical cleavage of EGS and Sulfo-EGS. Hydroxylamine converts carbonyl compounds (aldehydes and ketones) to their oxime derivatives in the presence of a weak base. Therefore, crosslinkers and other compounds that contain a carbonyl within their structure are cleavable with hydroxylamine•HCl.
    EGS  and its water-soluble analog, Sulfo-EGS, are homobifunctional, succinimidyl ester, amine-reactive crosslinkers useful for covalent stabilization of polypeptide multimers and protein:protein interactions. Unlike disulfidecontaining crosslinkers, EGS and Sulfo-EGS will not cleave by reducing SDS-PAGE conditions but may be cleaved when necessary with hydroxylamine.
    SATA  and SATP are modification reagents for addition of sulfhydryl groups to proteins and other molecules containing primary amines. Such sulfhydryl addition is an important step in one popular method for preparing protein conjugates such as antibodies with horseradish peroxidase enzyme. The initial modification results in addition of an acetyl-protected sulfur, enabling storage of the modified protein; to make the sulfur available as a sulhydryl group (-SH) for the final conjugation reaction, hydroxylamine is used to remove the protecting acetyl group.
    Hydroxylamine•HCl is more stable to oxidation than the free base form of hydroxylamine; nevertheless, always prepare hydroxylamine solutions immediately before use and store the product desiccated. Hydroxylamine•HCl is soluble in polar solvents such as water, ethanol, methanol, glycerol and propylene glycol.
  • General DescriptionColorless or off-white crystalline solid. pH (0.1 molar aqueous solution) 3.4. pH (0.2 molar aqueous solution) 3.2.
  • Air & Water ReactionsHygroscopic. Sensitive to prolonged exposure to air. Water soluble. Reacts slowly with water.
  • Reactivity ProfileA powerful reducing agent. Reacts with bases and oxidizing agents.
  • HazardToxic by ingestion, strong irritant to tissue.
  • Fire HazardFlash point data for Hydroxylamine hydrochloride are not available; however, Hydroxylamine hydrochloride is probably combustible.
  • Contact allergensHydroxylamine and its salts are used in various branches of industry, as reducing agents in color film developers or as reagents in laboratories.
  • Purification MethodsCrystallise the salt from aqueous75% ethanol or boiling methanol, and dry it under vacuum over CaSO4 or P2O5. It has also been dissolved in a minimum of water and saturated with HCl; after three such crystallisations, it is dried under a vacuum over CaCl2 and NaOH. Its solubility at 20o is 85% in H2O, 6% in EtOH and 12% in MeOH. [Hurd Inorg Synth I 87 1939, Semon in Org Synth Coll Vol I 318 1941.]
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