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

A12560 Hydroxylamine-O-sulfonic acid, 97%

Codice CAS
2950-43-8
Sinonimi

Dimensioni Prezzo ($) Quantità Disponibilità
25g 73,50
100g 209,00
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Hydroxylamine-O-sulfonic acid, 97%

MDL
MFCD00011604
EINECS
220-971-6

Proprietà chimiche

Formula
NH2OSO3H
Peso formula
113.09
Punto di fusione
ca 210° dec.
Sensibilità
Hygroscopic
Solubilità
Soluble in water and methanol. Slightly soluble in ethanol. Insoluble in ether and chloroform.

Applicazioni

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.

Note

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.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H314-H318-H317-H341

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

Dichiarazioni precauzionali: P260u-P201-P280g-P304+P340-P405-P501a

Obtain special instructions before use. Wear protective gloves. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
956566
Classe di rischio
8
Gruppo di imballaggio
III
Codice tariffe armonizzato
2825.10
TSCA
Yes
RTECS
NC5427000

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