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467804

Sigma-Aldrich

Hydroxylamine solution

50 wt. % in H2O, 99.999%

Synonym(s):

HDA

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About This Item

Linear Formula:
NH2OH
CAS Number:
7803-49-8
Molecular Weight:
33.03
EC Number:
232-259-2
MDL number:
MFCD00044522
UNSPSC Code:
12352116
PubChem Substance ID:
24870439
NACRES:
NA.22

Assay

99.999%

concentration

50 wt. % in H2O

bp

107 °C

density

1.078 g/mL at 25 °C

SMILES string

NO

InChI

1S/H3NO/c1-2/h2H,1H2

InChI key

AVXURJPOCDRRFD-UHFFFAOYSA-N

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General description

Hydroxylamine solution is widely used as a reducing agent and antioxidant in organic synthesis, polymer industry and water treatment.

Application

Hydroxylamine solution (NH2OH) can be used as a reactant for the preparation of:
  • Primary amides from aldehydes catalyzed by an arene–ruthenium(II) complex.
  • Hydroxyaminoguanidines and carboxamide derivatives of ofloxacin for biological studies.
  • Fe3O4/Au (GoldMag) nanoparticles for antibody immobilization.

Reactant for preparation of:
  • Prodrug for cardiovascular agent Nω-hydroxy-L-arginine (NOHA, nitric oxide precursor)
  • Hydroxyaminoguanidines as anti-cancer agents
  • Nonsteroidal 2,3-dihydroquinoline glucocorticoid receptor agonists with reduced phosphoenolpyruvate caboxykinase (PEPCK) transactivation
  • Carboxamide derivatives of ofloxacin with improved antimicrobial properties
  • Analogues of coumarin based TNF-α converting enzyme (TACE) inhibitors
  • HIV integrase inhibitors

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Carc. 2 - Desen. Expl. 4 - Eye Dam. 1 - Met. Corr. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 - STOT SE 3

Target Organs

Blood, Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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N-Hydroxy-N′-aminoguanidines as anti-cancer lead molecule: QSAR, synthesis and biological evaluation
Basu A, et al.
Bioorganic & Medicinal Chemistry Letters, 21(11), 3324-3328 (2011)
Ruthenium-catalyzed one-pot synthesis of primary amides from aldehydes in water
Garcia-Alvarez R, et al.
Royal Society of Chemistry Advances, 3(17), 5889-5894 (2013)
The synthesis of GoldMag nano-particles and their application for antibody immobilization
Cui Y, et al.
Biomedical Microdevices, 7(2), 153-156 (2005)
Sequential α-ketoacid-hydroxylamine (KAHA) ligations: synthesis of C-terminal variants of the modifier protein UFM1.
Ayodele O Ogunkoya et al.
Angewandte Chemie (International ed. in English), 51(38), 9693-9697 (2012-08-24)
Rika Goda et al.
Drug metabolism and disposition: the biological fate of chemicals, 34(5), 828-835 (2006-03-02)
Flutamide (2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-propanamide), a nonsteroidal antiandrogen, is used in the treatment of prostate cancer but is occasionally associated with hepatic dysfunction. In the present study, the metabolism of flutamide including the formation of the possible reactive toxic metabolites was investigated using
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