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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

Different sources of media describe the Description of 7803-49-8 differently. You can refer to the following data:
1. 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.
2. 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.

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

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

Different sources of media describe the Uses of 7803-49-8 differently. You can refer to the following data:
1. 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.
2. 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.
3. Reducing agent, organic synthesis.

Definition

Different sources of media describe the Definition of 7803-49-8 differently. You can refer to the following data:
1. ChEBI: The simplest hydroxylamine, consisting of ammonia bearing a hydroxy substituent. It is an intermediate in the biological nitrification by microbes like bacteria.
2. hydroxylamine: A colourless solid,NH2OH, m.p. 33°C. It explodes onheating and may be employed as anoxidizing agent or reducing agent. Itis made by the reduction of nitratesor nitrites, and is used in makingnylon. With aldehydes and ketones itforms oximes.

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.

General Description

Odorless white crystalline solid. Sinks and mixes with water.

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

7803-49-8 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (B22202)  Hydroxylamine, 50% aq. soln.   

  • 7803-49-8

  • 100ml

  • 482.0CNY

  • Detail
  • Alfa Aesar

  • (B22202)  Hydroxylamine, 50% aq. soln.   

  • 7803-49-8

  • 500ml

  • 1521.0CNY

  • Detail
  • Aldrich

  • (467804)  Hydroxylaminesolution  50 wt. % in H2O, 99.999%

  • 7803-49-8

  • 467804-10ML

  • 458.64CNY

  • Detail
  • Aldrich

  • (438227)  Hydroxylaminesolution  50 wt. % in H2O

  • 7803-49-8

  • 438227-250ML

  • 720.72CNY

  • Detail

7803-49-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name hydroxylamine

1.2 Other means of identification

Product number -
Other names HYDROXYLAMINE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7803-49-8 SDS

7803-49-8Synthetic route

hydroxylamine hemisulfate

hydroxylamine hemisulfate

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
With sodium hydroxide; 8-quinolinol; water at 20℃; for 3.66667h; Product distribution / selectivity;98%
With 8-quinolinol; water; calcium oxide at 10 - 40℃; for 3.66667h; pH=3.8 - 12.3; Product distribution / selectivity;50%
Nitrite

Nitrite

tin(ll) chloride

tin(ll) chloride

A

hydroxylamine
7803-49-8

hydroxylamine

B

dinitrogen monoxide
10024-97-2

dinitrogen monoxide

C

trans-hyponitrous acid
19467-31-3, 173728-04-6

trans-hyponitrous acid

Conditions
ConditionsYield
In waterA n/a
B 90%
C n/a
cis-nitrous acid
7782-77-6

cis-nitrous acid

tin(ll) chloride

tin(ll) chloride

A

hydroxylamine
7803-49-8

hydroxylamine

B

dinitrogen monoxide
10024-97-2

dinitrogen monoxide

C

trans-hyponitrous acid
19467-31-3, 173728-04-6

trans-hyponitrous acid

Conditions
ConditionsYield
In waterA n/a
B 90%
C n/a
nitric acid
7697-37-2

nitric acid

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
With sulfuric acid Electrolysis; max. temp.:15°C;24 A,40 min,cooling,mixing;84%
With sulfuric acid Electrolysis; 15-20 °C,cathode:Pb (amalgam surface);2.4 A,3.25 h;71.3%
With sulfuric acid Electrolysis; mercury cathode,6 A,room temp.;66.1%
Nitrite

Nitrite

A

nitrogen
7727-37-9

nitrogen

B

ammonia
7664-41-7

ammonia

C

hydroxylamine
7803-49-8

hydroxylamine

D

dinitrogen monoxide
10024-97-2

dinitrogen monoxide

Conditions
ConditionsYield
In dichloromethane Electrochem. Process; electrocatalytic redn. at Fe(III)(H2O)(TPPS)(3-)-modified electrode, pH 2.1, -0.9 V, 7.5 h;A <1
B 84%
C <1
D 8%
With alkali metal amalgam In not given byproducts: alkali hydroxide; in dild. soln.,cooling,optimal yield for NH2OH;
With alkali metal amalgam In not given byproducts: alkali hydroxide; formation of N2O best at low temp., formation of N2 best at high temp., independent of the dilution; high yield of NH3 (and N2O2(2-)) obtained by agitation in a closed vessel or by dropping concd. nitrite soln. on excess aolid amalgame;;
sodium nitrate
7631-99-4

sodium nitrate

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
With hydrogenchloride Electrolysis; lead cathode,coal anode,cooling of the anode surface,2.75 h,24 A;81%
With sulfuric acid byproducts: Na2SO4; Electrolysis; lead electrodes,5 A,3.7-3.6 V,cooling; neutralization with NaOH,heating with acetone at 70-80°C,crystn. of Na2SO4 in 12 h,mixing with benzene,decompn. of the formed acetoxime with HCl,evapn.;
In water Electrolysis; Cu-cathode;;0%
Nitrite

Nitrite

A

nitrogen
7727-37-9

nitrogen

B

ammonia
7664-41-7

ammonia

C

hydroxylamine
7803-49-8

hydroxylamine

D

dinitrogen monoxide
10024-97-2

dinitrogen monoxide

E

hydrazine
302-01-2

hydrazine

Conditions
ConditionsYield
In dichloromethane Electrochem. Process; electrocatalytic redn. at Fe(III)(PP)Cl-modified electrode, pH 2.1, -0.8 V, 1.0 h;A 30%
B 63%
C 13%
D <1
E <1
In dichloromethane Electrochem. Process; electrocatalytic redn. at Fe(III)(PP)Cl-modified electrode, pH 2.1, -0.9 V, 2.5 h;A 35%
B 52%
C 13%
D <1
E <1
In dichloromethane Electrochem. Process; electrocatalytic redn. at Fe(III)(PP)Cl-modified electrode, pH 2.1, -0.7 V, 4.0 h;A 39%
B 34%
C 13%
D 12%
E 2%
In dichloromethane Electrochem. Process; electrocatalytic redn. at Fe(III)(PP)Cl-modified electrode, pH 2.1, -0.6 V, 3.0 h;A 35%
B 31%
C 16%
D 18%
E <1
In dichloromethane Electrochem. Process; electrocatalytic redn. at Fe(III)(H2O)(TMPyP)(5+)-modified electrode, pH 2.1, -0.9 V, 4.0 h;A 14%
B 27%
C 13%
D 32%
E <1
Nitrite

Nitrite

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
Electrolysis; 0°C,cylindrical zinc cathode,0.02 A/cm^2,from nitrite soln.;59.7%
In water Electrolysis; with zinc cathode;various yields for various temp.;
With water In water byproducts: K2N2O2, NH3, N2; shaking of cold concd. nitrite soln. with K amalgam (39 g K + 2800 g Hg);; main product is K2N2O2;;
In water Electrolysis; with zinc cathode;various yields for various temp.;
With H2O; K amalgam In water
hydroxylamine hydrochloride
5470-11-1

hydroxylamine hydrochloride

sodium butanolate
2372-45-4

sodium butanolate

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
In butan-1-ol byproducts: NaCl; heating; crystn. at -10°C;50%
hydroxylamine hydrochloride
5470-11-1

hydroxylamine hydrochloride

sodium ethanolate
141-52-6

sodium ethanolate

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
In ethanol byproducts: NaCl; 1.5-2 h; washing with waterfree ethanol,filtering,crystn.,filtering at -18°C;40%
In ethanol byproducts: NaCl; outfreezing;
In ethanol byproducts: NaCl; reaction of suspn. of hydroxylammonium chloride with sodium ethoxide in abs. ethanol, NaCl pptn.; NaCl ppt. filtration off (glass filter);
nitrogen(II) oxide
10102-43-9

nitrogen(II) oxide

A

ammonia
7664-41-7

ammonia

B

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
In N,N-dimethyl-formamide Electrolysis; bulk electrolysis of soln. containing NO, with CoTSPc-modified glassy carbon electrode, in the presence of TEAP as electrolyte, pH = 4-7; not isolated;A 25%
B n/a
hydroxylamine hydrochloride
5470-11-1

hydroxylamine hydrochloride

sodium methylate
124-41-4

sodium methylate

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
In methanol byproducts: NaCl; filtering,distn. at reduced pressure;17%
hydrogenchloride
7647-01-0

hydrogenchloride

4-hydroxyimino-5-oxo-2-oxy-4,5-dihydro-1H-pyrazole-3-carbaldehyde-oxime

4-hydroxyimino-5-oxo-2-oxy-4,5-dihydro-1H-pyrazole-3-carbaldehyde-oxime

hydroxylamine
7803-49-8

hydroxylamine

hydrogenchloride
7647-01-0

hydrogenchloride

3-(β-hydroxyimino-3-methyl-phenethyl)-3H-benz[de]isochromen-1-one

3-(β-hydroxyimino-3-methyl-phenethyl)-3H-benz[de]isochromen-1-one

hydroxylamine
7803-49-8

hydroxylamine

hydrogenchloride
7647-01-0

hydrogenchloride

3,4-bis((hydroxyimino)methyl)-1,2,5-oxadiazole 2-oxide
153309-81-0

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

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
α-isocyanilic acid;
hydrogenchloride
7647-01-0

hydrogenchloride

2-(hydroxyimino)-γ-butyrolactone
5400-68-0

2-(hydroxyimino)-γ-butyrolactone

A

hydroxylamine
7803-49-8

hydroxylamine

B

α-oxo-butyrolactone

α-oxo-butyrolactone

Conditions
ConditionsYield
higher-melting form;
hydrogenchloride
7647-01-0

hydrogenchloride

furan-2,4-dione-4-oxime

furan-2,4-dione-4-oxime

A

tetrahydrofuran-2,4-dione
4971-56-6

tetrahydrofuran-2,4-dione

B

hydroxylamine
7803-49-8

hydroxylamine

hydrogenchloride
7647-01-0

hydrogenchloride

4-hydroxyamino-pyridine-2,6-diol

4-hydroxyamino-pyridine-2,6-diol

A

piperidine-2,4,6-trione
5768-12-7

piperidine-2,4,6-trione

B

hydroxylamine
7803-49-8

hydroxylamine

hydrogenchloride
7647-01-0

hydrogenchloride

1,3-dimethylvioluric acid
5417-13-0

1,3-dimethylvioluric acid

A

1,3-dimethylalloxan
2757-85-9

1,3-dimethylalloxan

B

hydroxylamine
7803-49-8

hydroxylamine

hydrogenchloride
7647-01-0

hydrogenchloride

1-methyl-2-thioxo-imidazolidine-4,5-dione-4-oxime

1-methyl-2-thioxo-imidazolidine-4,5-dione-4-oxime

A

hydroxylamine
7803-49-8

hydroxylamine

B

1-methyl-2-thio-parabanic acid

1-methyl-2-thio-parabanic acid

hydrogenchloride
7647-01-0

hydrogenchloride

N-hydroxycamphorimide
98919-82-5

N-hydroxycamphorimide

A

D-(+)-camphoric acid
124-83-4

D-(+)-camphoric acid

B

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
at 140℃;
tris-benzonitrile oxide

tris-benzonitrile oxide

A

3,5-diphenyl-1,2,4-oxadiazole-4-oxide
20594-92-7

3,5-diphenyl-1,2,4-oxadiazole-4-oxide

B

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
With hydrogenchloride
6-methoxy-benzofuran-2,3-dione-2-oxime
60795-23-5

6-methoxy-benzofuran-2,3-dione-2-oxime

acid

acid

A

(2-hydroxy-4-methoxy-phenyl)-glyoxylic acid
120240-70-2

(2-hydroxy-4-methoxy-phenyl)-glyoxylic acid

B

hydroxylamine
7803-49-8

hydroxylamine

4,5-dichloro-2-hydroxy-isoindoline-1,3-dione
859952-63-9

4,5-dichloro-2-hydroxy-isoindoline-1,3-dione

diluted mineral acid

diluted mineral acid

A

3,4-dichloro-phthalic acid
56962-06-2

3,4-dichloro-phthalic acid

B

hydroxylamine
7803-49-8

hydroxylamine

pyrrole-2,5-dione monooxime
74230-05-0

pyrrole-2,5-dione monooxime

water
7732-18-5

water

acid

acid

A

ammonia
7664-41-7

ammonia

B

hydroxylamine
7803-49-8

hydroxylamine

hydrogenchloride
7647-01-0

hydrogenchloride

pyrrolo[3,4-c]pyridine-1,3-dione-1-oxime

pyrrolo[3,4-c]pyridine-1,3-dione-1-oxime

A

3,4-pyridinecarboxylic acid
490-11-9

3,4-pyridinecarboxylic acid

B

ammonia
7664-41-7

ammonia

C

hydroxylamine
7803-49-8

hydroxylamine

Conditions
ConditionsYield
at 150℃;
hydrogenchloride
7647-01-0

hydrogenchloride

Metafulminuric acid
42526-20-5

Metafulminuric acid

A

formic acid
64-18-6

formic acid

B

hydrogen cyanide
74-90-8

hydrogen cyanide

C

ammonia
7664-41-7

ammonia

D

hydroxylamine
7803-49-8

hydroxylamine

Metafulminuric acid
42526-20-5

Metafulminuric acid

sulfuric acid
7664-93-9

sulfuric acid

A

formic acid
64-18-6

formic acid

B

hydrogen cyanide
74-90-8

hydrogen cyanide

C

ammonia
7664-41-7

ammonia

D

hydroxylamine
7803-49-8

hydroxylamine

metafulminuric acid
188686-50-2

metafulminuric acid

hydrochloric acid /20percent/

hydrochloric acid /20percent/

A

formic acid
64-18-6

formic acid

B

carbonic-acid
463-79-6

carbonic-acid

C

ammonia
7664-41-7

ammonia

D

hydroxylamine
7803-49-8

hydroxylamine

hydrogenchloride
7647-01-0

hydrogenchloride

(E)-2H-chromen-2-one oxime

(E)-2H-chromen-2-one oxime

A

hydroxylamine
7803-49-8

hydroxylamine

B

coumarin
91-64-5

coumarin

hydroxylamine
7803-49-8

hydroxylamine

nitrogen
7727-37-9

nitrogen

Conditions
ConditionsYield
silver (I) ion In water catalytic oxydation in presence of AgCl at pH=7.2;;100%
silver (I) ion In water catalytic oxydation in presence of AgI at pH=12.7;;91%
silver (I) ion In water catalytic oxydation in presence of (Ag(S2O3)2)(3-) at pH=12.7;;89%
2-formylbenzene boronic acid
40138-16-7

2-formylbenzene boronic acid

hydroxylamine
7803-49-8

hydroxylamine

1-hydroxy-1H-2,3,1,-benzoxazaborine
17067-02-6

1-hydroxy-1H-2,3,1,-benzoxazaborine

Conditions
ConditionsYield
In not given according to Dewar, M. J. S.; Dougherty, R. C. J. Am. Chem. Soc. 1964, 86, 433-436;99%
formaldehyd
50-00-0

formaldehyd

hydroxylamine
7803-49-8

hydroxylamine

potassium carbonate
584-08-7

potassium carbonate

phenylboronic acid
98-80-6

phenylboronic acid

potassium 3-phenyl-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo[3.3.1.1(3,7)]decan-3-uide

potassium 3-phenyl-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo[3.3.1.1(3,7)]decan-3-uide

Conditions
ConditionsYield
Stage #1: formaldehyd; hydroxylamine; phenylboronic acid In methanol; water at 0 - 20℃; for 18.1667h;
Stage #2: potassium carbonate In methanol; water at 20℃; for 5h;
99%
formaldehyd
50-00-0

formaldehyd

dihydroxy-methyl-borane
13061-96-6

dihydroxy-methyl-borane

hydroxylamine
7803-49-8

hydroxylamine

potassium carbonate
584-08-7

potassium carbonate

potassium 3-methyl-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo[3.3.1.1(3,7)]decan-3-uide

potassium 3-methyl-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo[3.3.1.1(3,7)]decan-3-uide

Conditions
ConditionsYield
Stage #1: formaldehyd; dihydroxy-methyl-borane; hydroxylamine In methanol; water at 0 - 20℃; for 18.1667h;
Stage #2: potassium carbonate In methanol; water at 20℃; for 5h;
97%
O{AuP(C6H4CH3)3}3(1+)*BF4(1-) = O{AuP(C6H4CH3)3}3BF4

O{AuP(C6H4CH3)3}3(1+)*BF4(1-) = O{AuP(C6H4CH3)3}3BF4

hydroxylamine
7803-49-8

hydroxylamine

[(P(o-tolyl)3Au)3(μ-NOH)]BF4
259853-62-8

[(P(o-tolyl)3Au)3(μ-NOH)]BF4

Conditions
ConditionsYield
In dichloromethane (N2); for 10 min; pptd. (Et2O);93%
formaldehyd
50-00-0

formaldehyd

hydroxylamine
7803-49-8

hydroxylamine

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

3-(pyridin-3-yl)-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo-[3.3.1.1(3,7)]decan-1-ium-3-uide

3-(pyridin-3-yl)-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo-[3.3.1.1(3,7)]decan-1-ium-3-uide

Conditions
ConditionsYield
In methanol; water at 0 - 20℃; for 18.1667h;92%
formaldehyd
50-00-0

formaldehyd

hydroxylamine
7803-49-8

hydroxylamine

potassium carbonate
584-08-7

potassium carbonate

3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

potassium 3-(pyridin-3-yl)-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo[3.3.1.1(3,7)]decan-3-uide hydrate

potassium 3-(pyridin-3-yl)-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo[3.3.1.1(3,7)]decan-3-uide hydrate

Conditions
ConditionsYield
Stage #1: formaldehyd; hydroxylamine; 3-pyridylboronic acid In methanol; water at 0 - 20℃; for 18.1667h;
Stage #2: potassium carbonate In methanol; water at 20℃; for 5h;
92%
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

hydroxylamine
7803-49-8

hydroxylamine

ethyl 2-(hydroxyimino)acetate
31767-14-3, 31767-15-4, 37858-07-4

ethyl 2-(hydroxyimino)acetate

Conditions
ConditionsYield
In toluene at 20℃; for 2h; Molecular sieve;90%
[(IrCl(μ-SC6H3MeCH2)(PPh3))2(μ-XySSXy)]*2CH2Cl2

[(IrCl(μ-SC6H3MeCH2)(PPh3))2(μ-XySSXy)]*2CH2Cl2

hydroxylamine
7803-49-8

hydroxylamine

[Ir(μ-SC6H3MeCH2)Cl(PPh3)(NH2OH)]2

[Ir(μ-SC6H3MeCH2)Cl(PPh3)(NH2OH)]2

Conditions
ConditionsYield
In dichloromethane; water under N2 atm. to soln. Ir complex in CH2Cl2 was added aq. hydroxylamine and stirred at room temp. for 2 h; soln. was evapd. to dryness in vacuo, residue was recrystd. from CH2Cl2-Et2O and dried; elem. anal.;90%
hydroxylamine
7803-49-8

hydroxylamine

malononitrile
109-77-3

malononitrile

4-amino-N-hydroxy-furazan-3-carboxamidine
13490-32-9

4-amino-N-hydroxy-furazan-3-carboxamidine

Conditions
ConditionsYield
Stage #1: malononitrile With hydrogenchloride; sodium nitrite In water Cooling with ice;
Stage #2: hydroxylamine In water Reflux;
90%
2-acetyl benzo[b]thiophene
22720-75-8

2-acetyl benzo[b]thiophene

hydroxylamine
7803-49-8

hydroxylamine

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
Stage #1: hydroxylamine; methyl carbamate With sodium hydroxide In water at 5 - 30℃;
Stage #2: 2-acetyl benzo[b]thiophene With methanol; sodium tetrahydroborate In tetrahydrofuran; water at 10 - 40℃;
Stage #3: With hydrogenchloride; acetic acid at 40 - 45℃; for 3h;
88%
1-(2-chloroisonicotinyl)-1,3-butanedione
1101064-65-6

1-(2-chloroisonicotinyl)-1,3-butanedione

(3-methylphenyl)hydrazine hydrochloride
637-04-7

(3-methylphenyl)hydrazine hydrochloride

hydroxylamine
7803-49-8

hydroxylamine

2-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine
250263-25-3

2-chloro-4-[1-(3-methylphenyl)-3-methyl-1H-pyrazol-5-yl]pyridine

Conditions
ConditionsYield
In ethanol87%
hydroxylamine
7803-49-8

hydroxylamine

A

nitrogen
7727-37-9

nitrogen

B

dinitrogen monoxide
10024-97-2

dinitrogen monoxide

Conditions
ConditionsYield
With Hg2(NO3)2 In not given byproducts: Hg; addn. of 0.04 M NH2OH to 0.005 M Hg2(NO3)2 soln. buffered with acetate at 20°C, autocatalysis of reaction by Hg;;A 13%
B 87%
With Hg2(NO3)2; silver In not given byproducts: Hg; addn. of 0.04 M NH2OH to 0.005 M Hg2(NO3)2 soln. buffered with acetate at 20°C, autocatalysis of reaction by Hg, further catalysis by addn. of collodial Ag soln.;;A 63%
B 34%
With oxygen In not given byproducts: water; Electrolysis; N2O formed on cathode, N2 formed on anode;
1-(benzothiazol-2-yl)-3-(N,N-dimethylamino)-2-(phenylsulfonyl)prop-2-en-1-one

1-(benzothiazol-2-yl)-3-(N,N-dimethylamino)-2-(phenylsulfonyl)prop-2-en-1-one

hydroxylamine
7803-49-8

hydroxylamine

3-(benzothiazol-2-yl)-4-(phenylsulfonyl)isoxazole

3-(benzothiazol-2-yl)-4-(phenylsulfonyl)isoxazole

Conditions
ConditionsYield
With ammonium acetate In ethanol at 100℃; under 12901.3 Torr; for 0.25h; Temperature; Microwave irradiation;87%
formaldehyd
50-00-0

formaldehyd

hydroxylamine
7803-49-8

hydroxylamine

boric acid
11113-50-1

boric acid

potassium carbonate
584-08-7

potassium carbonate

potassium 3-hydroxy-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo[3.3.1.1(3,7)]decan-3-uide

potassium 3-hydroxy-2,4,10-trioxa-1,5,7-triaza-3-boratricyclo[3.3.1.1(3,7)]decan-3-uide

Conditions
ConditionsYield
Stage #1: formaldehyd; hydroxylamine; boric acid In water at 0 - 20℃; for 18.1667h;
Stage #2: potassium carbonate In methanol; water at 20℃; for 5h;
86%
dichloromethane
75-09-2

dichloromethane

[Ru(CO)(OSO2CF3)((C2H5)2NCS2)(P(C6H5)3)2]
261001-82-5

[Ru(CO)(OSO2CF3)((C2H5)2NCS2)(P(C6H5)3)2]

hydroxylamine
7803-49-8

hydroxylamine

[Ru(CO)(NH2OH)((C6H5)3P)2((C2H5)2NCS2)](1+)*(OSO2CF3)(1-)*CH2Cl2=[Ru(CO)(NH2OH)((C6H5)3P)2((C2H5)2NCS2)](OSO2CF3)*CH2Cl2

[Ru(CO)(NH2OH)((C6H5)3P)2((C2H5)2NCS2)](1+)*(OSO2CF3)(1-)*CH2Cl2=[Ru(CO)(NH2OH)((C6H5)3P)2((C2H5)2NCS2)](OSO2CF3)*CH2Cl2

Conditions
ConditionsYield
In dichloromethane (N2); all manipulations were carried out using Schlenk techniques; addn. of 1 equiv. of hydroxylamine to soln. of (Ru(CO)(OTf)(Et2NCS2)(PPh3))in CH2Cl2, stirring at room temp. for 2 h; removal of solvent, recrystn. from CH2Cl2-hexane; elem. anal.;85%
mer,trans-Re(η1-OSO2CF3)(CO)3(PPh3)2
136921-71-6, 186672-59-3

mer,trans-Re(η1-OSO2CF3)(CO)3(PPh3)2

hydroxylamine
7803-49-8

hydroxylamine

[mer,trans-Re-(CO)3(NH2OH)(PPh3)2][SO3CF3]
201141-14-2

[mer,trans-Re-(CO)3(NH2OH)(PPh3)2][SO3CF3]

Conditions
ConditionsYield
In dichloromethane elem. anal.;85%
(hydrotris(3,5-dimeth-ylpyrazolyl)borate)Ir(η4-CH2=C(CH3)CH=CH2)

(hydrotris(3,5-dimeth-ylpyrazolyl)borate)Ir(η4-CH2=C(CH3)CH=CH2)

hydroxylamine
7803-49-8

hydroxylamine

C20H31BIrN7

C20H31BIrN7

Conditions
ConditionsYield
In tetrahydrofuran; water at 120℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;85%
[1-acetyl-1'-(2-aminopyrimidin-4-yl)]ferrocene
1309386-08-0

[1-acetyl-1'-(2-aminopyrimidin-4-yl)]ferrocene

hydroxylamine
7803-49-8

hydroxylamine

(C5H4C(CH3)NOH)Fe(C5H4C4H2N2(NH2))
1309386-18-2

(C5H4C(CH3)NOH)Fe(C5H4C4H2N2(NH2))

Conditions
ConditionsYield
In ethanol; water to soln. of Fe complex in EtOH was added aq. soln. of hydroxylamine; mixt. was refluxed for 4 h with stirring; mixed with H2O; solvent removed (vac.); residue dissolved in water; extd. (ethyl acetate); org. layer washed (H2O); dried (anhyd. Na2SO4); concd.; subjected to chromy. (benzene-CHCl3. (2:1) as eluent); elem. anal.;84%
1-(1-methyl-1H-benzimidazol-2-yl)-3-(N,N-dimethylamino)-2-(phenylsulfonyl)prop-2-en-1-one

1-(1-methyl-1H-benzimidazol-2-yl)-3-(N,N-dimethylamino)-2-(phenylsulfonyl)prop-2-en-1-one

hydroxylamine
7803-49-8

hydroxylamine

3-(1-methyl-1H-benzimidazol-2-yl)-4-(phenylsulfonyl)isoxazole

3-(1-methyl-1H-benzimidazol-2-yl)-4-(phenylsulfonyl)isoxazole

Conditions
ConditionsYield
With ammonium acetate In ethanol at 100℃; under 12901.3 Torr; for 0.25h; Temperature; Microwave irradiation;84%
iron(III)octaethylporphyrin chloride
28755-93-3

iron(III)octaethylporphyrin chloride

hydroxylamine
7803-49-8

hydroxylamine

octaethylporphyrin iron(II) nitrosyl
55917-58-3

octaethylporphyrin iron(II) nitrosyl

Conditions
ConditionsYield
In methanol; dichloromethane at 20℃; for 0.5h; Schlenk technique;84%
In methanol; dichloromethane at 20℃; for 0.5h; Inert atmosphere;83%
furfural
98-01-1

furfural

nickel(II)

nickel(II)

hydroxylamine
7803-49-8

hydroxylamine

Ni(C4H3OCHNO)2
36501-90-3, 60351-84-0

Ni(C4H3OCHNO)2

Conditions
ConditionsYield
In ethanol Electrolysis; anodic dissolution of nickel electrodes, supporting salt: Et4NBr; evapn. of most of the solvent, filtered off, washed with CHCl3, dried under vac.;82%

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).

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