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159417

Sigma-Aldrich

Hydroxylamine hydrochloride

ReagentPlus®, 99%

Synonym(s):

Hydroxylammonium chloride

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About This Item

Linear Formula:
NH2OH · HCl
CAS Number:
5470-11-1
Molecular Weight:
69.49
Beilstein:
3539763
EC Number:
226-798-2
MDL number:
MFCD00051089
UNSPSC Code:
12352300
PubChem Substance ID:
329751008
NACRES:
NA.21
grade:
reagent
form:
crystalline
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grade

reagent

Quality Level

100

vapor pressure

0.001 hPa ( 50 °C)

product line

ReagentPlus®

Assay

99%

form

crystalline

technique(s)

inhibition assay: suitable

pH

2.5-3.5 (20 °C, 50 g/L)

mp

155-157 °C (dec.) (lit.)

density

1.67 g/mL at 25 °C (lit.)

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A9045A0701A4718
Agarose, low gelling temperature

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Agarose, low gelling temperature BioReagent, suitable for cell culture, suitable for insect cell culture, suitable for plant cell culture

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A4718

Agarose

form

powder

form

powder

form

powder

form

powder

gel strength

≥200 g/cm2 (1% gel)

gel strength

≥200 g/cm2 (1% gel)

gel strength

≥250 g/cm2 (1% gel)

gel strength

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

transition temp

congealing temperature 26-30 °C

transition temp

congealing temperature 26-30 °C

transition temp

gel point 26 °C ±2 °C (1.5% gel)

transition temp

gel point ≤35 °C (3% gel)

technique(s)

cell culture | mammalian: suitable

technique(s)

cell culture | insect: suitable, cell culture | mammalian: suitable, cell culture | plant: suitable

technique(s)

electrophoresis: suitable

technique(s)

electrophoresis: suitable

General description

Hydroxylamine hydrochloride (Hydroxylammonium chloride) participates in the synthesis of 1,2,4-oxadiazoles,[1] secondary amides and tertiary amides.[2]
Hydroxylamine hydrochloride (NH2OH.HCl) is a hygroscopic salt widely used as a reactant in electrophilic substitution reactions, oxidation, and reduction reactions. It is also used in the synthesis of nitriles, pyrazoles, isoxazoles, nitrones, and pyridine.

Application

Hydroxylamine hydrochloride can be used as a reactant:
  • in the synthesis of primary amides from aldehydes in the presence of cesium carbonate (Cs2CO3) as a catalyst.
  • in the conversion of alicyclic /aliphatic carbonyl compounds and the aromatic aldehydes into corresponding oximes.
  • in the one-pot synthesis of nitriles from aldehydes in the presence of sodium sulfate (anhyd) and sodium bicarbonate catalysts.
  • It can also be used as a reducing agent in the preparation of single-layer reduced graphene oxide (RGO) sheets and films.

Biochem/physiol Actions

MAO inhibitor; inhibits platelet aggregation.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Met. Corr. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 Oral

Target Organs

spleen

Storage Class Code

4.1A - Other explosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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    Certificates of Analysis (COA)

    Lot/Batch Number
    MKCW6772
    MKCX0792
    MKCV9098
    MKCV5161
    MKCV2672

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    Susie Suh et al.
    Nature biomedical engineering, 5(2), 169-178 (2020-10-21)
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    Cell host & microbe, 28(5), 660-668 (2020-08-19)
    Eradication of pathogens from the bloodstream is critical to prevent disseminated infections and sepsis. Kupffer cells in the liver form an intravascular firewall that captures and clears pathogens from the blood. Here, we show that the catching and killing of
    Dongwoo Kim et al.
    Analytical chemistry, 81(21), 9183-9187 (2009-10-31)
    We report the use of electroless gold deposition as a light scattering signal enhancer in a multiplexed, microarray-based scanometric immunoassay using gold nanoparticle probes. The use of gold development results in greater signal enhancement than the typical silver development, and
    Magnesia-supported hydroxylamine hydrochloride in the presence of sodium carbonate as an efficient reagent for the synthesis of 1, 2, 4-oxadiazoles from nitriles.
    Kaboudin B and Saadati F.
    Tetrahedron Letters, 48(16), 2829-2832 (2007)
    Simbarashe Ngwerume et al.
    The Journal of organic chemistry, 78(3), 920-934 (2012-12-29)
    A novel gold-catalyzed method for the regioselective synthesis of highly substituted pyrroles directly from oximes and alkynes was developed via independent optimization of two key steps of the process. Importantly, a cationic gold(I) species was shown to activate multiple steps
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