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2950-43-8 - Hydroxylamine-O-sulfonic acid, 97% - A12560 - Alfa Aesar

A12560 Hydroxylamine-O-sulfonic acid, 97%

Numéro CAS
2950-43-8
Synonymes

Dimensions Prix ($) Quantité Disponibilité
25g 73,50
100g 209,00
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Hydroxylamine-O-sulfonic acid, 97%

MDL
MFCD00011604
EINECS
220-971-6

Propriétés chimiques

Formule
NH2OSO3H
Poids formulaire
113.09
Point de fusion
ca 210° dec.
Sensibilité
Hygroscopic
Solubilité
Soluble in water and methanol. Slightly soluble in ethanol. Insoluble in ether and chloroform.

Applications

Hydroxylamine-O-sulfonic acid is used in the synthesis of quinolones for the benzodiazepine site of GABAA receptors. It is also used as a polymerization catalyst and an amination reagent. It is involved in the preparation of diazene by reacting with an alkali. It is also used in the inhibition of polychlorinated dibenzo-p-dioxins (PCDD) as well as (polychlorinated biphenyl) PCB formation in co-combustion.

Notes

Moisture sensitive and hygroscopic. Store in cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents, strong bases, acid chlorides, acid anhydrides and corrodes metal.

Références bibliographiques

Aminating agent for nucleophiles. For a review of chemistry, see: Org. Prep. Proced. Int., 14, 265 (1982).

Primary and secondary amines are converted to hydrazines: J. Org. Chem., 14, 813 (1949); Chem. Ber., 92, 2521 (1959); pyridine to 1-aminopyridinium salts: Org. Synth. Coll., 5, 43 (1977); benzotriazole to the benzyne precursor 1-aminobenzotriazole: J. Chem. Soc., Chem. Commun., 192, 193 (1965); for preparation of the bis(aminotriazolobenzene), a precursor of "1,4-dibenzyne", see: Tetrahedron Lett., 25, 2073 (1984).

Aromatic rings can be aminated in the presence of AlCl3: J. Am. Chem. Soc., 83, 221 (1961). Reaction is more successful with certain heterocycles, N,N'-dimethyluracil giving the 5-amino-derivative almost quantitatively: Tetrahedron Lett., 2751 (1973).

Reaction with ketones results in oxime sulfates which undergo the Beckmann rearrangement to amides on heating: J. Org. Chem. USSR, 17, 2284 (1981); the conversion of cyclic ketones to lactams can conveniently be carried out as a one-step operation: Synthesis, 537 (1979); J. Org. Chem., 54, 4419 (1989); Org. Synth. Coll., 7, 254 (1988).

Aldehydes are converted directly to nitriles: Tetrahedron Lett., 3187 (1974): Helv. Chim. Acta, 59, 2786 (1976).

A one-pot synthesis of aryl or heteroaryl amines from carboxylic acids (as their chlorides) has been reported, equivalent to the Schmidt or Hofmann reactions: Synthesis, 1143 (1990).

Can also provide a source of the reducing agent diimide: Liebigs Ann. Chem., 645, 1 (1962); 721, 240 (1969). For examples of the use of diimide in the reduction of alkenes, see Hydrazine monohydrate, A14005.

With aqueous NaOH, hydrodeamination of primary amines to alkanes is possible for simple aliphatic amines, amino acids or even peptides: J. Am. Chem. Soc., 100, 341 (1978).

Abe, M.; Nakano, M.; Kosaka, A.; Miyoshi, H. Syntheses of photoreactive cardiolipins for a photoaffinity labeling study. Tetrahedron Lett. 2015, 56 (17), 2258-2261.

Yang, T.; Liu, Z.; Li, X. D. Developing diazirine-based chemical probes to identify histone modification ‘readers’ and ‘erasers’. Chem. Sci. 2015, 6 (2), 1011-1017.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H314-H318-H341-H317

Causes severe skin burns and eye damage. Causes serious eye damage. Suspected of causing genetic defects. May cause an allergic skin reaction.

Mentions de prudence: P260-P201-P261-P280-P281-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Use personal protective equipment as required. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
956566
Classe de danger
8
Groupe d'emballage
III
Code tarifaire harmonisé
2825.10
TSCA
Yes
RTECS
NC5427000

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Analytique et matériel de laboratoire