Hydroxylamine Hydrochloride CAS#: 5470-11-1 - ChemicalBook

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Hydroxylamine hydrochloride Basic information
Product Name:Hydroxylamine hydrochloride
Synonyms:OXAMMONIUM HCL;OXAMMONIUM HYDROCHLORIDE;hydroxyaminehydrochloride;hydroxylaminechloride;hydroxylaminechloride(1:1);HydroxyLamine-Hydrochioride;HYDROXYLAMMONIUM CHLORIDE REAGENT (ACS), LOW MERCURY;HYDROXYLAMMONIUM CHLORIDE SOLUTION 50% AQUEOUS W/V
CAS:5470-11-1
MF:NH2OH·HCl
MW:69.49
EINECS:226-798-2
Product Categories:Amination;Hydroxylamines;Anilines, Aromatic Amines and Nitro Compounds;Inorganics;Hydroxylamines (Unsubstituted);Synthetic Organic Chemistry;Pharmaceutical Intermediates;Pharma material;5470-11-1
Mol File:5470-11-1.mol
Hydroxylamine hydrochloride Structure
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 +15°C to +25°C.
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.
InChIKeyWTDHULULXKLSOZ-UHFFFAOYSA-N
LogP-0.810 (est)
CAS DataBase Reference5470-11-1(CAS DataBase Reference)
EPA Substance Registry SystemHydroxylamine hydrochloride (5470-11-1)
Safety Information
Hazard Codes Xn,N,E
Risk Statements 22-36/38-43-48/22-50-40-21/22-2
Safety Statements 22-24-37-61-36/37
RIDADR UN 2923 8/PG 2
WGK Germany 3
RTECS NC3675000
F 21
TSCA Yes
HazardClass 8
PackingGroup III
HS Code 28251000
ToxicityLD50 orally in mice: 408 mg/kg (Riemann)
MSDS Information
ProviderLanguage
Hydroxylammonium chloride English
ACROS English
SigmaAldrich English
ALFA English
Hydroxylamine hydrochloride Usage And Synthesis
DescriptionHydroxylamine hydrochloride is a reducing agent that is routinely used for the deacetylation of SATA to form free sulfhydryls (Figure 1), for cleavage of protein cross‐linkers that contain carbonyl groups (i.e. EGS) and for mutagenesis of plasmid DNA.Generation of free sulfhydryls with SATA and hydroxylamine.Hydroxylamine converts aldehydes and ketones (carbonyls) to their oxime derivative in weak bases, therefore cross‐linkers and other compounds with carbonyl groups are cleavable with Hydroxylamine hydrochloride.SATA and SATP are modification reagents that add a sulfhydryl group to primary amines on biomolecules. The initial modification results in the addition of an acetyl‐protected sulfur enabling storage of the biomolecule. To generate a free sulfhydryl the biomolecule is treated with hydroxylamine to remove the protecting acetyl group (see figure).EGS and sulfo‐EGS are homobifunctional, succinimidyl ester, amine reactive crosslinkers that are resistant to cleavage by denaturants used in SDS‐PAGE conditions, but may be cleaved with hydroxylamine.
Chemical PropertiesHydroxylamine Hydrochloride(NH2OH.HCl) is an inorganic compound that is the hydrochloric acid salt of hydroxylamine. It is highly hygroscopic and decomposes when exposed to dampness above 151℃. This compound is primarily used as a reducing agent and imaging agent and is instrumental in the preparation of oximes in organic synthesis. It can convert aldehydes and ketones to oximes and acid chlorides to hydroxamic acids. However, This product is highly toxic and irritating to the skin.
Physical propertiesIt is a colorless monoclinic crystal that is hygroscopic and decomposes slowly in moist air. It has a density of 1.67 g/cm3 at a temperature of 17°C and melts at 151°C with decomposition. It is highly soluble in water, with a solubility of 84g/100g at 20°C, and is also soluble in lower alcohols and glycols. A 0.1 molar solution of this substance has a pH of 3.4.
CharacteristicsFeatures of Hydroxylamine hydrochloride: Quench amine-labeling or crosslinking reactions (e.g., with NHS esters)Expose protected sulfhydryl groups on SATA-modified moleculesCleave carbonyl-containing crosslinkers such as EGS and Sulfo-EGS
UsesHydroxylamine hydrochloride is a monomoamine oxidase inhibitor. It is used to prepare oximes and hydroxmic acids in organic synthesis. It acts as a copolymerization inhibitor. It can be used to remove bromine and polybromide from a solution during extraction of lignin from lignocellulosic biomass. It is key starting material for the preparation of pharmaceuticals and agrochemicals. It plays a vital role in rubber and plastic industries as an antioxidant, a vulcanization accelerator and a radical scavenger. It is also used as a color stabilizer and emulsion additive in color films.
PreparationHydroxylamine hydrochloride is prepared by electrolytic reduction of ammonium chloride. Or by the action of nitromethane with hydrochloric acid and water to obtain hydroxylamine hydrochloride.
DefinitionChEBI: Hydroxylamine hydrochloride is an organic molecular entity. It is a colorless inorganic compound (HONH2) used in organic synthesis and as a reducing agent, due to its ability to donate nitric oxide.
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.MAN0011201_HydroxylamineHCl_UG.pdf
General DescriptionHydroxylamine hydrochloride appears as colorless or off-white crystalline solid. pH (0.1 molar aqueous solution) 3.4. pH (0.2 molar aqueous solution) 3.2. (NTP, 1992)
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.
Biochem/physiol ActionsMAO inhibitor; inhibits platelet aggregation.
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.]
Hydroxylamine hydrochloride Preparation Products And Raw materials
Raw materialsSodium nitrite-->Dimethyl sulfate-->Water-->Sodium metabisulfite-->Nitromethane-->Acetone oxime
Preparation Products2-AMINO-5,6-DICHLOROBENZOIC ACID-->ETHYL 5-METHYLISOXAZOLE-3-CARBOXYLATE-->5-METHYL-4-ISOXAZOLESULFONYL CHLORIDE-->5-AMINOISOXAZOLE-4-CARBOXYLIC ACID ETHYL ESTER-->4-Aminotetrahydropyran hydrochloride-->6-Bromoisatin-->3,4,5-Trimethoxybenzylamine-->Methyl 3-amino-4-methylthiophene-2-carboxylate-->4-AMINO-1,2,5-OXADIAZOLE-3-CARBONITRILE-->3-(2,6-Dichlorophenyl)-5-methylisoxazole-4-carboxylic acid-->ETHYL 3-(2,6-DICHLORO-PHENYL)-5-METHYL-ISOXAZOLE-4-CARBOXYLATE-->Epiandrosterone acetate-->6-AMINO-2-METHYL-2-HEPTANOL-->5-Methyl-3-phenylisoxazole-->2,6-Dicyano-4-Nitroaniline-->(2,6-DIMETHYLPHENOXY)ACETOXIME-->2-Butanone oxime-->3-METHYL-5-PHENYL-4-ISOXAZOLECARBOXYLIC ACID-->4-(METHYLTHIO)BENZYLAMINE-->heptanal oxime-->3-(2-Chlorophenyl)-5-methylisoxazole-4-carbonyl chloride-->BENZAMIDOXIME HYDROCHLORIDE-->2-Pyridylamid oxime-->NEMONAPRIDE-->3-(2-Chlorophenyl)-5-methylisoxazole-4-carboxylic acid-->Adrafinil-->17-Ethinylandrost-5-ene-3,17-diol-->5-Methyl-3-phenylisoxazole-4-carbonyl chloride-->4-Pyridylamidoxime-->3-PYRIDYLAMIDOXIME-->3-METHYL-5-PHENYLISOXAZOLE-->3-METHYLTHIOPHENE-2-CARBONITRILE-->N-Hydroxysulfosuccinimide sodium salt-->DIPHENYLGLYOXIME-->5-Chloro-3,6-dihydroxy-5-androstan-17-one 3-acetate-->2,3-DIMETHOXYBENZONITRILE-->5 A-CHLORO-6 B,19-EPOXY-3 B -HYDROXY-5 A-ANDROSTAN-17-ONE-->2-CHLOROBENZALOXIME-->Pyrazole-1,3-dimethyl-5-phenoxy-4-carboxaldehyde oxime-->Ethyl 5-methyl-3-phenylisoxazole-4-carboxylate
Tag:Hydroxylamine hydrochloride(5470-11-1) Related Product Information
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