Hydroxylamine hydrochloride

Iupac Name：hydroxylamine;hydrochloride

Molecular Weight：69.488

Modify Date.: 2022-11-16 19:21

Introduction: Colorless or off-white crystalline solid. pH (0.1 molar aqueous solution) 3.4. pH (0.2 molar aqueous solution) 3.2. View more+

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1. Names and Identifiers

1.1 Name: Hydroxylamine hydrochloride
1.2 Synonyms: Ammonium, hydroxy-, chloride (1:1) EINECS 226-798-2 hydroxyaminehydrochloride hydroxylamine,hydrochloride hydroxylaminechloride hydroxylaminechloride(1:1) HydroxyLamine-Hydrochioride Hydroxylammonium chloride HYDROXYLAMMONIUM CHLORIDE REAGENT (ACS), LOW MERCURY MFCD00051089 OXAMMONIUM HCL OXAMMONIUM HYDROCHLORIDE

1.3 CAS No.: 5470-11-1

1.4 CID: 443297

1.5 EINECS(EC#): 226-798-2

1.6 Molecular Formula: ClH4NO (isomer)

1.7 Inchi: InChI=1S/ClH.H3NO/c;1-2/h1H;2H,1H2

1.8 InChkey: WTDHULULXKLSOZ-UHFFFAOYSA-N

1.9 Canonical Smiles: NO.Cl

1.10 Isomers Smiles: NO.Cl

2. Properties

2.1 Density: 1.67

2.1 Melting point: 155-158℃

2.1 Boiling point: 304° F (Decomposes) (NTP, 1992)

2.1 Flash Point: 152

2.1 Precise Quality: 68.99810

2.1 PSA: 46.25000

2.1 logP: 0.83660

2.1 Solubility: 470g/l

2.2 Appearance: Colorless or off-white crystalline solid

2.3 Storage: Hygroscopic. Ambient temperatures.

2.4 Chemical Properties: White crystals

2.5 Color/Form: White to off-white

2.6 Contact Allergens: Hydroxylamine and its salts are used in variousbranches of industry, as reducing agents in color filmdevelopers or as reagents in laboratories.

2.7 PH: 2.5-3.5 (25℃, 50mg/mL in H2O)

2.8 Water Solubility: 560 g/L (20 oC)

2.9 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.

2.10 StorageTemp: Store at +15°C to +25°C.

3. Use and Manufacturing

3.1 General Description: Colorless or off-white crystalline solid. pH (0.1 molar aqueous solution) 3.4. pH (0.2 molar aqueous solution) 3.2.

3.2 Purification Methods: Crystallise 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 materials

3.3 Usage: Organic synthesis, photographic developer,medicine, controlled reduction reactions, nondiscoloring short-stopper for synthetic rubbers, antioxidant for fatty acids.

4. Safety and Handling

4.1 Symbol: GHS05;GHS07;GHS08;GHS09;

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22;R36/38;R43;R48/22;R50

4.1 Safety Statements: S22;S24;S37;S61

4.1 Packing Group: III

4.1 Fire Hazard: Flash point data for Hydroxylamine hydrochloride are not available; however, Hydroxylamine hydrochloride is probably combustible.

4.2 Hazard Class: 8

4.2 Hazard Declaration: H290; H302 + H312; H315; H317; H319; H351; H373; H410

4.2 RIDADR: UN 2923

4.2 Caution Statement: P273-P280-P305 + P351 + P338-P501

4.2 WGK Germany: 3

4.2 RTECS: NC3675000

4.2 Report: Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

4.3 Safety: Poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of HCl and NO_x.
Safety Information of Hydroxylamine hydrochloride (CAS NO.5470-11-1):
Hazard Codes:?Xn,N
Risk Statements: 22-36/38-43-48/22-50?
R22:Harmful if swallowed.?
R36/38:Irritating to eyes and skin.?
R43:May cause sensitization by skin contact.?
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed.?
R50:Very toxic to aquatic organisms.
Safety Statements: 22-24-37-61?
S22:Do not breathe dust.?
S24:Avoid contact with skin.?
S37:Wear suitable gloves.?
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2923 8/PG 2
WGK Germany: 3
RTECS: NC3675000
F: 21
HazardClass: 8
PackingGroup: III

4.4 Sensitive: Hygroscopic

4.5 Specification: ?Hydroxylamine hydrochloride (CAS NO.5470-11-1), its Synonyms are Hydroxyamine hydrochloride ; Hydroxyammonium chloride ; Hydroxylamine chloride ; Hydroxylamine chloride (1:1) ; Hydroxylamine-1-hydrochloride ; Hydroxylammonium chloride ; Oxammonium hydrochloride .

4.6 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	subcutaneous	70mg/kg (70mg/kg)	?	"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
mouse	LD50	intraperitoneal	10mg/kg (10mg/kg)	?	National Technical Information Service. Vol. AD277-689,
mouse	LD50	oral	408mg/kg (408mg/kg)	?	Acta Pharmacologica et Toxicologica. Vol. 6, Pg. 285, 1950.
mouse	LD50	subcutaneous	125mg/kg (125mg/kg)	?	Acta Biologica et Medica Germanica. Vol. 21, Pg. 635, 1968.
rat	LD50	oral	141mg/kg (141mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	National Technical Information Service. Vol. OTS0555279,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Corrosive to metals, Category 1

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Skin sensitization, Category 1

Carcinogenicity, Category 2

Specific target organ toxicity \u2013 repeated exposure, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H290 May be corrosive to metals H302 Harmful if swallowed H312 Harmful in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H317 May cause an allergic skin reaction H351 Suspected of causing cancer H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention	P234 Keep only in original packaging. P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P273 Avoid release to the environment.
Response	P390 Absorb spillage to prevent material damage. P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P308+P313 IF exposed or concerned: Get medical advice/ attention. P314 Get medical advice/attention if you feel unwell. P391 Collect spillage.
Storage	P406 Store in a corrosion resistant/...container with a resistant inner liner. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

IR : KBr disc

IR : nujol mull

7. Synthesis Route

5470-11-1Total: 1 Synthesis Route

7647-01-0

7632-00-0 234 Suppliers

5470-11-1 402 Suppliers

7647-14-5 844 Suppliers

Literatures:
Journal of the Chemical Society, , vol. 51, p. 660
Yield: null

8. Other Information

8.0 Usage: Hydroxylamine 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.

8.1 Description: Hydroxylamine hydrochloride is an inorganic substance, a colorless crystalline, easily deliquescence, white chemical substance, mainly used as a reducing agent and an imaging agent, used in the preparation of oximes in organic synthesis, and also used in the synthesis of anticancer drugs (hydroxylamine hydrochloride). urea), sulfonamides (trimoxazole) and pesticides (methomyl). It has strong hygroscopicity and will decompose when it is damped above 151℃. At 17°C, 83.8g can be dissolved in 100g of water. This product is highly toxic and irritating to the skin. The production equipment should be sealed to prevent running, running, dripping and leaking, and operators should wear protective equipment. When splashed on the skin, rinse with plenty of water.

8.2 Preparation: Sodium nitrite synthesis method (oximation method) Add water to the reaction kettle, add sodium nitrite under stirring, add sodium metabisulfite in stages, and then acidify with sulfuric acid. The acidified material is sent to the hydrolysis kettle, acetone is added, neutralized with liquid caustic soda, and the neutralized liquid is distilled to obtain acetone oxime. Acetone oxime and hydrochloric acid are added to the salt-forming kettle for reaction to generate hydroxylamine hydrochloride and acetone. Acetone is recovered and used; hydroxylamine hydrochloride is concentrated, crystallized by cooling, centrifuged and dried to obtain the finished product. Raw material consumption quota: sodium nitrite (95%) 1970kg/t, sodium metabisulfite (64% as SO2) 5418kg/t, acetone (98%) 1175kg/t. 2. Nitromethane method Nitromethane reacts with hydrochloric acid and water to obtain hydroxylamine hydrochloride. According to HGB3044-76, the hydroxylamine hydrochloride product is white crystal, the content of the second-grade product is ≥98.5, and the content of the third-grade product is ≥97%. Raw material consumption quota: nitromethane 1200kg/t, hydrochloric acid (30%) 1500kg/t. Or by the action of nitromethane with hydrochloric acid and water to obtain hydroxylamine hydrochloride.

8.3 Flammability and Explosibility: Notclassified

8.4 Merck: 14,4828

8.5 BRN: 3539763

8.6 Description: Hydroxylamine 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.

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.

8.7 Chemical Properties: White crystals

8.8 Physical properties: Colorless 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.

8.9 Uses: Organic synthesis, photographic developer, medicine, controlled reduction reactions, nondiscoloring short-stopper for synthetic rubbers, antioxidant for fatty acids.

8.10 Uses: Hydroxylammonium-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.

8.11 Preparation: Hydroxylamine hydrochloride is prepared by electrolytic reduction ofammonium chloride.

8.12 Biotechnological Applications: Hydroxylamine 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.

8.13 General Description: Colorless or off-white crystalline solid. pH (0.1 molar aqueous solution) 3.4. pH (0.2 molar aqueous solution) 3.2.

8.14 Air & Water Reactions: Hygroscopic. Sensitive to prolonged exposure to air. Water soluble. Reacts slowly with water.

8.15 Reactivity Profile: A powerful reducing agent. Reacts with bases and oxidizing agents.

8.16 Hazard: Toxic by ingestion, strong irritant to tissue.

8.17 Fire Hazard: Flash point data for Hydroxylamine hydrochloride are not available; however, Hydroxylamine hydrochloride is probably combustible.

8.18 Biochem/physiol Actions: MAO inhibitor; inhibits platelet aggregation.

8.19 Contact allergens: Hydroxylamine and its salts are used in various branches of industry, as reducing agents in color film developers or as reagents in laboratories.

8.20 Purification Methods: Crystallise 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.]

9. Computational chemical data

Molecular Weight: 69.488g/mol
Molecular Formula: ClH₄NO
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 68.9981414
Monoisotopic Mass: 68.9981414
Complexity: 2
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 46.2
Heavy Atom Count: 3
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADcYACIAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAUCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

Preparing a solution of hydroxylamine hydrochloride in HCl, struggling Oct 18 2021
I recently came across a paper with a methodology description i cant seem to get the grasp of. I need to make a particular solution for Fe extraction. The protocol's description is from this paper . Take a 100 μL aliquot of X (a soil sample previously mixed with 0.5M HCl) and mix it with 2 mL of a...

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