carbamimidoylsulfinic acid

• ChemBase ID: 89368
• Molecular Formular: CH4N2O2S
• Molecular Mass: 108.11966
• Monoisotopic Mass: 107.99934838
• SMILES: NC(=N)S(=O)O
• Canonical SMILES: NC(=N)S(=O)O
• InChI: InChI=1S/CH4N2O2S/c2-1(3)6(4)5/h(H3,2,3)(H,4,5)
• InChIKey: FYOWZTWVYZOZSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: carbamimidoylsulfinic acid
• IUPAC Traditional name: formamidine sulfinic acid; thiourea dioxide
• Synonyms: carbamimidoylsulfinic acid; Aminoiminomethanesulfinic acid; Formamidinesulfinic acid; Thiourea dioxide; Formamidinesulphinic acid; amino(imino)methanesulfinic acid; 二氧化硫脲; 氨基亚氨基甲亚磺酸; 甲脒亚磺酸

Database IDs

• CAS Number: 1758-73-2
• EC Number: 217-157-8
• MDL Number: MFCD00002397
• Beilstein Number: 506653
• PubChem SID: 24894787; 162076248
• PubChem CID: 61274

CALCULATED PROPERTIES

• Acid pKa: -2.3398976
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.965675
• LogD (pH = 7.4): -0.9657384
• Log P: -0.9656744
• Molar Refractivity: 31.4 cm^3
• Polarizability: 8.693216 Å^3
• Polar Surface Area: 87.17 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 124-127 °C (dec.)(lit.); 124-127°C; 126 - 128°C; ca 126°C dec.
• Density: 1.68
• Hydrophobicity(logP): -2.358

Safety Information

• Storage Warning: Moisture Sensitive
• RTECS: PB0372500
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 3341; UN3341
• German water hazard class: 1
• Hazard Class: 4.2
• Packing Group: 2; III
• Risk Statements: 5-22-36/37/38
• Safety Statements: 26; 26-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H251-H302-H315-H319-H335; H301-H315-H319-H335-H252
• GHS Precautionary statements: P235 + P410-P261-P305 + P351 + P338; P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3341 4.2/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%; ≥98.0% (RT); 95%; 98%
• Grade: purum
• Linear Formula: NH2C(=NH)SO2H

DETAILS

Sigma Aldrich - F16001

Application
Convenient reagent for the reduction of ketones to secondary alcohols.
Packaging
100 g in poly bottle
5 g in glass bottle

REFERENCES

• Disulfides and N-tosylsulfimines are reduced, under phase-transfer conditions, to thiols and sulfides respectively: Synthesis, 529 (1975). In the presence of iodine as a catalyst, sulfoxides are reduced to sulfides in high yield: Synthesis, 542 (1978).
• For use in the reductive cyclization of nitro ketones to pyrroles, see 2-Benzylidenecyclohexanone, L13434 and 3-Penten-2-one, L13031.
• Has been used to reduce ketones to secondary alcohols: Tetrahedron Lett., 343 (1972), and aldehydes to primary alcohols: J. Chin. Chem. Soc., 21, 235 (1973).