Hydroxylamine

Base Information

• Chemical Name: Hydroxylamine
• CAS No.: 7803-49-8
• Molecular Formula: H3N O
• Molecular Weight: 33.0299
• Hs Code.: 28251090
• European Community (EC) Number: 232-259-2
• ICSC Number: 0661
• UN Number: 2735
• UNII: 2FP81O2L9Z
• DSSTox Substance ID: DTXSID7041043
• Nikkaji Number: J941E
• Wikipedia: Hydroxylamine
• Wikidata: Q259997,Q27110260,Q27110261
• Metabolomics Workbench ID: 49803
• ChEMBL ID: CHEMBL1191361
• Mol file: 7803-49-8.mol

Synonyms:Hydroxylamine;Hydroxylamine Hydrochloride;Hydroxylammonium Chloride

Chemical Property of Hydroxylamine

Chemical Property:

• Appearance/Colour: white needles or flakes
• Vapor Pressure: 9 mm Hg ( 40 °C)
• Melting Point: 7°C
• Refractive Index: n20/D 1.393
• Boiling Point: 56.5 °C at 760 mmHg
• PKA: pK (20°) 7.97
• Flash Point: °C
• PSA: 46.25000
• Density: 1.078
• LogP: 0.03460
• Storage Temp.: Store below +30°C.
• Solubility.: Water
• Water Solubility.: Miscible with water, liquid ammonia and methanol. Slightly miscible with ether, benzene, carbon disulfide and chloroform.
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 33.021463719
• Heavy Atom Count: 2
• Complexity: 2
• Transport DOT Label: Corrosive

Purity/Quality:

99.9% ^*data from raw suppliers

HydroxylamineSolution(50?wt.%inH2O) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,N
• Statements: 5-22-37/38-41-43-48/22-50-40-21/22
• Safety Statements: 23-26-36/37/39-47-61-22-46

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Compounds
• Canonical SMILES: NO
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is corrosive to the eyes. The substance is irritating to the skin and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in the formation of methaemoglobin and consequent anaemia. Tumours have been detected in experimental animals but may not be relevant to humans.
• Description: Hydroxylamine is the hydroxyl derivative of ammonia. Hydroxylamine is used as a nucleophile in aromatic substitution reactions and as a reducing agent. By the reaction with aldehydes, hydroxylamine forms oximes, which are intermediates in the commercial production of polyamide plastics. Some hydroxylamine converted oximes are used in smaller amounts as pharmaceuticals, pesticides, and varnishes to prevent formation of a skin. With it is reduction ability, hydroxylamine is used as an antioxidant in photographic developers, to stabilize polymerization monomers, and to reduce Cu2+ in the dyeing of acrylic fibers. Hydroxylamine can be converted into hydroxylamine-O-sulphonic acid, which is a good aminating agent. Hydroxylamine can also be used as an intermediate in nitrification. It is further used in semiconductor industry in the cleaning formations, such as for aluminum interconnect. Hydroxylamine was first synthesized by Wilhem Clemens Lossen in 1865 in the laboratory of Wilhelm Heinrich Heintz while working in Halle. The Lossen synthesis originally generated hydroxylamine in aqueous solution. Anhydrous hydroxylamine was prepared later by Lobry de Bruyn and Crismer in 1891. The free base is extremely volatile, and industrial-scale production has been fraught with problems, including large explosions at facilities in the United States and Japan. Much of the hydroxylamine produced and transported is in salt form or as a dilute aqueous solution.
• Physical properties: White crystalline solid; orthogonal plates or needles; unstable; density 1.21g/cm3at 20°C; melts at 33°C; vaporizes at 58°C; very soluble in water, liquidammonia and lower alcohols; sparingly soluble in most other organic solvents;decomposes in hot water; pKa5.94 at 25°C.
• Uses: Reducing agent used in photographic processing, leather tanning, manufacturing of nylon and other polymers; as a stabilizer for natural rubber; to prevent the development of objectionable tastes and odors during the refining of fatty materials. Hydroxylamine is used as a reducing agent in photography, in synthetic and analytical chemistry, as an antioxidant for fatty acids and soaps, and as a dehairing agent for hides. In addition, hydroxylamine is used in the production of cyclohexanone oxime, an isomer of caprolactam, which is an intermediate in the production of nylon-6. In the semiconductor industry, hydroxylamine can be a component of a solution that dissolves a photoresist following lithography. Hydroxylamine can also be used to selectively cleave asparaginyl-glycine peptide bonds. Reducing agent, organic synthesis.

Technology Process of Hydroxylamine

There total 391 articles about Hydroxylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

Nitrite + tin(ll) chloride → hydroxylamine (7803-49-8) + dinitrogen monoxide (10024-97-2) + trans-hyponitrous acid (19467-31-3,173728-04-6)

Guidance literature:

In water;

Reference yield: 90.0%

cis-nitrous acid (7782-77-6) + tin(ll) chloride → hydroxylamine (7803-49-8) + dinitrogen monoxide (10024-97-2) + trans-hyponitrous acid (19467-31-3,173728-04-6)

Guidance literature:

In water;

Reference yield: 32.0%

Nitrite → nitrogen (7727-37-9) + ammonia (7664-41-7) + hydroxylamine (7803-49-8) + dinitrogen monoxide (10024-97-2) + hydrazine (302-01-2,78206-91-4,119775-10-9,75013-58-0)

Guidance literature:

In dichloromethane; Electrochem. Process; electrocatalytic redn. at Fe(III)(PP)Cl-modified electrode, pH 2.1, -0.8 V, 1.0 h;

upstream raw materials:

hydrogenchloride

3,4-bis((hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxide

2-(hydroxyimino)-γ-butyrolactone

1,3-dimethylvioluric acid

Downstream raw materials:

2-(4-Butoxy-phenoxy)-N-hydroxy-acetamide

9H-xanthen-9-one oxime

2,6-diamino-3-nitro-pyridine

N'-hydroxy-2-phenylethanimidamide

Refernces

• 1、 Luckhaus, David,Scott, Jacqueline L.,Crim, F. Fleming. "An experimental and theoretical study of the vibrationally mediated photodissociation of hydroxylamine". . p. 1533 - 1541. Retrieved 1999.
• 2、 Plymale, Noah T.,Dassanayake, Rohan S.,Hassanin, Hanaa A.,Brasch, Nicola E.. "Kinetic and mechanistic studies on the reactions of the reduced vitamin B12 complex cob(I)alamin with nitrite and nitrate". . p. 913 - 921. Retrieved 2012.
• 3、 Birk, Helmut,Jones, Harold. "". . p. 333 - 347. Retrieved 1988.
• 4、 Moskalenko,Boeva,Boev. "A feature of reaction of 1,1′-diacetylferrocene with dimethylformamide dimethyl acetal leading to a new strategy of the synthesis of asymmetrical 1,1′-disubstituted ferrocene". . p. 529 - 534. Retrieved 2011.
• 5、 Moskalenko,Boeva,Boev. "Reaction of acetylferrocene with dimethylformamide dimethyl acetal and some transformations of the reaction product". . p. 521 - 528. Retrieved 2011.
• 6、 Gaisford, Simon,Hills, Andrew K.,Beezer, Anthony E.,Mitchell, John C.. "Thermodynamic and kinetic analysis of isothermal microcalorimetric data: Applications to consecutive reaction schemes". . p. 39 - 45. Retrieved 1999.
• 7、 Bagger, Alexander,Rossmeisl, Jan,Wan, Hao. "Electrochemical Nitric Oxide Reduction on Metal Surfaces". supporting information. p. 21966 - 21972. Retrieved 2021/09/02.