dibutylstannanone

• ChemBase ID: 126970
• Molecular Formular: C8H18OSn
• Molecular Mass: 248.92892
• Monoisotopic Mass: 250.0379592
• SMILES: CCCC[Sn](=O)CCCC
• Canonical SMILES: CCCC[Sn](=O)CCCC
• InChI: InChI=1S/2C4H9.O.Sn/c2*1-3-4-2;;/h2*1,3-4H2,2H3
• InChIKey: JGFBRKRYDCGYKD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dibutylstannanone
• IUPAC Traditional name: dibutyltin oxide
• Synonyms: Dibutyltin oxide; Dibutyloxotin; Dibutyltin(IV) oxide; Di-n-butyltin oxide; 二丁基氧化锡; 氧化二丁基锡; 二正丁基氧化锡

Database IDs

• CAS Number: 818-08-6
• EC Number: 212-449-1
• MDL Number: MFCD00001992
• Beilstein Number: 4126243
• PubChem SID: 24851031; 162221293; 24861710
• PubChem CID: 61221
• Chemspider ID: 55164
• Wikipedia Title: Dibutyltin_oxide

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5452
• LogD (pH = 7.4): 1.5452
• Log P: 1.5452
• Molar Refractivity: 40.6947 cm^3
• Polarizability: 20.808336 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white solid
• Melting Point: >300 °C (decomp. 210 °C); >300°C; ≥300 °C(lit.)
• Auto Ignition Point: 279 °C; 534 °F
• Density: 1.6 g/cm^3

Safety Information

• RTECS: WH7175000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 3146; UN3146
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 25-36-51/53; 25-41-48/25-51/53; R: 21-25-36/38-48/23/25-50/53
• Safety Statements: 26-36/37-45-61; 26-39-45-61; S: 1/2-35-36/37/39-45-60-61
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H318-H372-H411; H301-H319-H411-H401
• GHS Precautionary statements: P264-P273-P280-P301 + P310-P305 + P351 + P338-P314; P280-P301+P310-P305+P351+P338-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3146 6.1/PG 2

Product Information

• Purity: 98%
• Grade: purum
• Linear Formula: (CH3CH2CH2CH2)2SnO

DETAILS

Sigma Aldrich - 183083

Packaging
100 g in poly bottle
500 g in glass bottle

REFERENCES

• Reacts with 1,2-diols to form 5-membered cyclic dibutylstannoxane derivatives. For use in the glycoside field, see: Synthesis, 409 (1995). Formation of these derivatives is greatly accelerated by microwave irradiation: Synlett, 89 (1994). The stannylene derivatives are activated to electrophilic attack:
• With bromine, the ɑ-hydroxy ketone is formed: J. Chem. Soc., Perkin 1, 1568 (1979). With acyl or sulfonyl chlorides, overall regioselective monoacylation of the diol at the more substituted hydroxyl can be achieved: Tetrahedron Lett., 21, 221 (1980); J. Chem. Soc., Chem. Commun., 1457 (1985); J. Org. Chem., 55, 5132 (1990); 61, 5257 (1996). Selective monotosylation of 1,2-diols has also been achieved catalytically: Tetrahedron Lett., 41, 3773 (2000).
• Catalyst for lactonization and lactamization reactions: J. Am. Chem. Soc., 102, 7578 (1980), particularly useful in the formation of macrolides: J. Am. Chem. Soc., 105, 7130 (1983). For catalysis of N-acylation of hydroxy alcohols with microwave irradiation, see: J. Org. Chem., 61, 5264 (1996).
• Promotes the cycloaddition of Trimethylsilyl azide, L00173 to nitriles to give 5-aryltetrazoles, some of which are important as angiotensin II inhibitors: J. Org. Chem., 58, 4139 (1993):
  
• Catalyst for the dehydration of amides to nitriles under neutral conditions: Synthesis, 1724 (1999); for use of microwave irradiation, see: J. Org. Chem., 64, 1713 (1999).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 1847 (2004).