7803-49-8 Usage
Chemical Description
Hydroxylamine is a reactive compound that is commonly used as a reducing agent and in the synthesis of oximes.
Description
Hydroxylamine is the hydroxyl derivative of ammonia, a versatile chemical compound with a wide range of applications across various industries. It is used as a nucleophile in aromatic substitution reactions and as a reducing agent. Hydroxylamine can be converted into hydroxylamine-O-sulphonic acid, which is a good aminating agent. It is also used as an intermediate in nitrification and in the semiconductor industry for cleaning formations, such as aluminum interconnects.
Uses
Used in Photographic Processing:
Hydroxylamine is used as a reducing agent in photographic processing, helping to stabilize the development process and improve image quality.
Used in Leather Tanning:
In the leather industry, hydroxylamine serves as a stabilizer for natural rubber and is used as a dehairing agent for hides, contributing to the production of high-quality leather products.
Used in Polymer and Plastics Production:
Hydroxylamine is used in the manufacturing of nylon and other polymers, such as polyamide plastics. It forms oximes through its reaction with aldehydes, which are intermediates in the commercial production of these materials.
Used in Pharmaceutical, Pesticide, and Varnish Industries:
Some hydroxylamine-converted oximes are used in smaller amounts as pharmaceuticals, pesticides, and varnishes to prevent the formation of a skin, indicating its diverse applications in these fields.
Used in Antioxidant Applications:
Hydroxylamine acts as an antioxidant in photographic developers, stabilizes polymerization monomers, and reduces Cu2+ in the dyeing of acrylic fibers, showcasing its importance in various chemical processes.
Used in Semiconductor Industry:
In the semiconductor industry, hydroxylamine is a component of a solution that dissolves photoresist following lithography, playing a crucial role in the manufacturing of electronic components.
Used in Organic Synthesis:
Hydroxylamine is utilized as a reducing agent in organic synthesis, enabling the production of various organic compounds and contributing to the advancement of chemical research and development.
Used in Analytical Chemistry:
Hydroxylamine is employed as a reducing agent in synthetic and analytical chemistry, facilitating the analysis and synthesis of different chemical compounds.
Used in Fatty Acids and Soaps:
Hydroxylamine serves as an antioxidant for fatty acids and soaps, preventing the development of objectionable tastes and odors during the refining of fatty materials.
Used in Selective Cleavage of Peptide Bonds:
Hydroxylamine can be used to selectively cleave asparaginyl-glycine peptide bonds, which is an important application in the field of biochemistry and pharmaceuticals.
References
Stephen A. Lawrence, Amines: Synthesis, Properties and Applications, 2004, ISBN 0521782848
Howard Lees, Hydroxylamine as an intermediate in nitrification, Nature, 1951, vol. 169, 156-157
Egon Wiberg and Nils Wiberg, Inorganic Chemistry, 2001, ISBN 0123526515
https://www.britannica.com/science/hydroxylamine
Karen A. Reinhardt and Richard F. Reidy, Handbook for Cleaning for Semiconductor Manufacturing: Fundamentals and Applications, 2011, ISBN 9780470625958
Preparation
Hydroxylamine is unstable as a free base. It is prepared from hydroxy-lamine hydrochloride, NH2OH?HCl, which is obtained by electrolytic reduc-tion of ammonium chloride solution. The hydrochloride undergoes alkalinedecomposition to hydroxylamine, which is collected by vacuum distillation.
Air & Water Reactions
Decomposes rapidly at room temperature or when dissolved in hot water by internal oxidation-reduction. Reacts with water or steam to produce heat and corrosive liquids.
Reactivity Profile
HYDROXYLAMINE is a white solid, thermally unstable, decomposes rapidly at room temperature or when dissolved in hot water by internal oxidation-reduction. HYDROXYLAMINE should be stored below 10° C [Bailar, 1973, vol. 2, p. 272]. Explosive reaction with strong oxidizers (chromium trioxide, potassium dichromate) or powdered zinc upon heat. Reaction with zinc or calcium produces explosive bishydroxylamides. HYDROXYLAMINE ignites on contact with cupric sulfate, alkali metals (sodium, potassium), oxidants (e.g., barium oxide, barium peroxide, lead dioxide, potassium permanganate, chlorine), phosphorus trichloride and pentachloride. HYDROXYLAMINE reacts vigorously with hypochlorites, pyridine, carbonyls [Sax, 9th ed., 1996, p. 1875]. On contact with organic materials in thin layer (e.g., crystals on filter paper), HYDROXYLAMINE may ignite spontaneously in air. HYDROXYLAMINE explodes when heated above 70° C [Brauer, 1963, vol. 1, p. 502]. During a distillation process, an explosion occurred. Potassium hydroxide is thought to be involved in the explosion. Employees in the plant complained of chest pains and suffered chemical burns. Five people were killed by the explosion.
Hazard
Decomposes rapidly at room temperature,
violently when heated, detonates in flame-heated
test tube. Irritant to tissue.
Health Hazard
INHALATION: Moderately toxic by inhalation and oral routes with the following symptoms possible: headache, vertigo, tinnitus, dyspnea, nausea and vomiting, cyanosis, proteinuria and hematuria, jaundice, restlessness, and convulsion. Methemoglobinemia has been reported. EYES: Corrosive - highly irritating. SKIN: Irritating or corrosive to skin. INGESTION: Moderately toxic by inhalation and oral routes with the following symptoms possible; headache, vertigo, tinnitus, dyspnea, nausea and vomiting, cyanosis, proteinuria and hematuria, jaundice, restlessness, and convulsion. Methemoglobinemia has been reported.
Carcinogenicity
Carcinogenicity of hydroxylamine and
its salts has not been demonstrated. Several
studies have shown a decreased incidence of
spontaneous mammary tumors in mice exposed
to the sulfate and hydrochloride.3–7 There was
some indication of an increase in the incidence
of spontaneous mammary tumors when the
sulfate was administered to older animals
whose mammary glands were already well
developed.
Environmental Fate
The large-scale production and use of hydroxylamine may
result in its release to the environment through various waste
streams. Hydroxylamine will exist solely as a vapor in the
ambient atmosphere, and will be degraded in the atmosphere
by reaction with photochemically produced hydroxyl radicals;
the half-life for this reaction in air is estimated to be 18 h.
Abiotic degradation of hydroxylamine by photochemically
produced peroxy radicals is an important environmental fate
process in surface waters, with the half-life of the reaction
measured at approximately 2 h. An estimated bioconcentration
factor of 3 suggests that the potential for bioconcentration in
aquatic organisms is low. If released terrestrially, hydroxylamine
will most likely exist in its protonated form due to its
pKa of 5.94; the protonated form is nonvolatile. Koc estimates
of 14 for hydroxylamine suggest that it may have very high
mobility in soil.
Purification Methods
Crystallise it from n-butanol at -10o, collect it by vacuum filtration and wash it with cold diethyl ether. Harmful vapours. [Hurd Inorg Synth I 87 1939, Semon in Org Synth Coll Vol I 318 1932.]
Toxicity evaluation
Hydroxylamine acts as a reducing agent when absorbed
systemically, producing methemoglobin and the formulation
of Heinz bodies in the blood. It can induce hemolytic anemia.
It inhibits platelet aggregation and is a nitric oxide vasodilator.
Oxylamines such as hydroxylamine and methoxylamine
disturb DNA replication and act as potent mutagens, causing
nucleotide transition from one purine to another or one
pyrimidine to another.
Allergic reactions of the skin following dermal exposure to
hydroxylamine resemble contact eczema, or possibly urticaria
of Quincke’s edema. The pathogenesis of this reaction appears
to be mediated by a delayed type T-lymphocyte reaction.
Check Digit Verification of cas no
The CAS Registry Mumber 7803-49-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,8,0 and 3 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 7803-49:
(6*7)+(5*8)+(4*0)+(3*3)+(2*4)+(1*9)=108
108 % 10 = 8
So 7803-49-8 is a valid CAS Registry Number.
InChI:InChI=1/H3NO/c1-2/h2H,1H2
7803-49-8Relevant articles and documents
Divers, E.,Haga, T.
, p. 203 (1885)
Witt-Hurd, C. de,Brownstein, H. J.
, p. 67 (1925)
Electrocatalytic Multielectron Nitrite Reduction in Water by an Iron Complex
Stroka, Jesse R.,Kandemir, Banu,Matson, Ellen M.,Bren, Kara L.
, p. 13968 - 13972 (2020)
Catalytic reduction of nitrite by an iron complex in water near neutral pH to form hydroxylamine and ammonium is reported. The catalyst is an iron center coordinated by the pentadentate macrocycle 2,13-dimethyl-3,6,9,12,18-pentaazabicyclo[12.3.1]octadeca-1(18),2,12,14,16-pentaene (FeN5H2). Catalysis is observed by cyclic voltammetry at a half-wave potential of Ep/2 = -0.98 V vs Ag/AgCl (1 M KCl) when FeN5H2, nitrite, and a buffer (pH 7.2) are present. Controlled potential electrolysis of FeN5H2 and nitrite in pH 7.2 buffer at -0.98 V produces hydroxylamine (faradaic efficiency > 90%). FeN5H2 catalyzes ammonium production by disproportionation of hydroxylamine with concomitant formation of nitrous oxide and dinitrogen. These results are a rare example of multielectron electrocatalytic nitrite reduction by an iron complex near neutral pH.
THE FORMATION OF HYDROXYLAMINE BY INSERTION OF THE NH(1Δ) RADICAL INTO THE O-H BOND OF WATER
Kawai, Jun,Tsunashima, Shigeru,Sato, Shin
, p. 823 - 826 (1983)
The photolysis of hydrogen azide was examined in water.The main products were nitrogen and hydroxylamine.Hydroxylamine formed was converted into acetoxime by the reaction with acetone which was added after irradiation.The amount of acetoxime was analyzed
Versatility and trends in the interaction between Pd(ii) and peptide hydroxamic acids
Ozsváth, András,Farkas, Etelka,Diószegi, Róbert,Buglyó, Péter
, p. 8239 - 8249 (2019)
Primary and secondary di- and tripeptide hydroxamic acids, Ala-Ala-NHOH, Ala-Ala-N(Me)OH, Ala-Gly-Gly-NHOH and Ala-Gly-Gly-N(Me)OH were synthesized and their interaction with Pd(ii) (as a Pt(ii) model but with faster ligand exchange reactions) was studied in aqueous solution in the presence of the Cl- competitor ion by pH-potentiometric and 1H NMR methods. To the best of our knowledge, this is the first detailed solution study on Pd(ii)-peptide hydroxamate systems revealing that, except for Ala-Gly-Gly-NHOH, the other three ligands act not only as coordination compounds, but also the hydrolysis of the coordinated ligands and formation of the protonated hydroxylamine and Pd(ii) complexes of the corresponding peptides under acidic conditions occurred. The hydrolysis was rather slow with Ala-Gly-Gly-N(Me)OH (more than one week), and just a bit faster with Ala-Ala-NHOH, so speciation studies could also be performed successfully on the systems containing one of the latter two ligands. This was, however, hindered for the Pd(ii)-Ala-Ala-N(Me)OH system, where, in addition to the quite fast hydrolysis of the ligand, the reduction of Pd(ii) to elementary metal by the N(Me)-hydroxylamine formed was also observed. Speciation studies with Ala-Gly-Gly-NHOH revealed the predominance of a very stable 4N-donor complex, (NH2, 2Namide, Nhydr.) over a wide pH range. This ligand is also capable of binding the metal ion excess with the hydroxymate (O,O) set in dinuclear species. The formation of this latter type of complex is hindered with the secondary analogue, Ala-Gly-Gly-N(Me)OH, where, in addition to the 3N donor atoms, the hydroxamate-O is also involved in the coordination of the most stable complex. However, the formation of mixed hydroxo species at high pH and a bis-complex in a rather slow process with (NH2, Namide)2 bonding mode in the presence of ligand excess was proven. Although the 3N coordination (NH2, Namide, Nhydx) results in a highly stable complex with the dipeptide derivative, Ala-Ala-NHOH, the fourth coordination site remains free for accepting an NH2 moiety from the excess ligand, or a hydroxide ion at high pH. Likewise, the hydroxymate (O,O) set remains free to bind the metal ion excess in a trinuclear species. The results of this study may also contribute to the design and synthesis of novel Pt(ii) complexes with anticancer potential.
Polizzi, S.,Benedetti, A.,Fagherazzi, G.,Goatin, C.,Strozzi, R.,et al.
, p. 494 - 499 (1987)
Application of an immobilized ionic liquid for the preparation of hydroxylamine via hydrolysis of cyclohexanone oxime
Wang, Shuangyu,Liu, Jiaqi,Cheng, Peng,Li, Zhihui,Zhang, Dongsheng,Yang, Qiusheng,Zhao, Xinqiang,Wang, Yanji
, p. 742 - 750 (2021/02/05)
Preparation of hydroxylamine via hydrolysis of cyclohexanone oxime was studied over porous SiO2 supported acid ionic liquid catalyst. The catalyst [SPIPTES]CF3SO3@SiO2 was prepared through sol-gel method and characterized by elemental analysis, IR and TG, etc. Various parameters such as reaction temperature and time, catalyst amount were investigated systematically. The optimized reaction conditions investigated were catalyst:cyclohexanone oxime (mass ratio) 4 : 1, conducted at 60 °C for 1 h. Since the present hydrolysis reaction is controlled by thermodynamics, the conversion of cyclohexanone oxime could not be very high. However, reasonable result was achieved under the optimized reaction conditions. Cyclohexanone oxime conversion was 38.41 % and NH2OH yield was 37.65 %. Additionally, combining experiments with density functional theory calculations, a possible catalyst structure and reaction pathway involved protonated cyclohexanone oxime mechanism was proposed for the present hydrolysis in this study.
INHIBITORS OF RNA-BINDING PROTEINS, COMPOSITIONS THEREOF, AND THERAPEUTIC USES THEREOF
-
Paragraph 0109, (2020/12/11)
The present technology is directed to compounds that inhibit of the interaction of RNA-binding protiens with RNA, intermediaes thereof, compositions thereof, and methods of treatment utilizing such compounds, where the compounds are of Formula (I).