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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/REAXYS Number:
3539763
EC Number:
226-798-2
MDL number:
MFCD00051089
UNSPSC Code:
12352300
PubChem Substance ID:
329751008
NACRES:
NA.21

vapor pressure

0.001 hPa ( 50 °C)

Quality Level

100

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.)

SMILES string

Cl.NO

InChI

1S/ClH.H3NO/c;1-2/h1H;2H,1H2

InChI key

WTDHULULXKLSOZ-UHFFFAOYSA-N

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General description

Hydroxylamine hydrochloride (Hydroxylammonium chloride) participates in the synthesis of 1,2,4-oxadiazoles, secondary amides and tertiary amides.
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

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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

4.1A - Other explosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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