(aminooxy)sulfonic acid

• ChemBase ID: 69664
• Molecular Formular: H3NO4S
• Molecular Mass: 113.09312
• Monoisotopic Mass: 112.97827858
• SMILES: NOS(=O)(=O)O
• Canonical SMILES: NOS(=O)(=O)O
• InChI: InChI=1S/H3NO4S/c1-5-6(2,3)4/h1H2,(H,2,3,4)
• InChIKey: DQPBABKTKYNPMH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (aminooxy)sulfonic acid
• IUPAC Traditional name: aminooxysulfonic acid
• Synonyms: Hydroxylamine-O-sulfonic acid; Hydroxylamine-O-sulfonic acid; (Aminooxy)(hydroxy)sulphane dioxide; Amino hydrogen sulphate; (aminooxy)sulfonic acid; 羟胺-O-磺酸

Database IDs

• CAS Number: 2950-43-8
• EC Number: 220-971-6
• MDL Number: MFCD00011604
• Beilstein Number: 956566
• PubChem SID: 24852769; 162035390; 24853666; 24871729
• PubChem CID: 76284

CALCULATED PROPERTIES

• Acid pKa: -4.0278726
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.3434331
• LogD (pH = 7.4): -3.359927
• Log P: -2.1056616
• Molar Refractivity: 17.8405 cm^3
• Polarizability: 7.9683447 Å^3
• Polar Surface Area: 89.62 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~225 °C (dec.); 208-211°C; 210 °C (dec.)(lit.); ca 210°C dec.

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Corrosive/Carcinogenic/Mutagenic/Harmful/Hygroscopic/Keep Cold/Store under Argon; Hygroscopic; IRRITANT
• RTECS: NC5427000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3260; UN3260
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; III
• Risk Statements: 34; 34-43-68
• Safety Statements: 20-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: false; 是
• GHS Pictograms: GHS05; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318-H341-H317
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3260 8/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (RT); ≥95.0% (RT); 90%; 95%; 95+%; 97%; 99.999%
• Grade: purum; technical; technical grade
• Linear Formula: H2NOSO3H

DETAILS

MP Biomedicals - 02157458

Purity: 95%
Light tan crystals.

Sigma Aldrich - 480975

Packaging
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 55495

General description
may contain isopropyl ether

Sigma Aldrich - 213136

Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 227978

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 55493

General description
may contain isopropyl ether
Other Notes
Review of its use in organic chemistry1

REFERENCES

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