208930

Sigma-Aldrich

Tin(IV) chloride

98%

Synonym(s):
Stannic chloride fuming
Linear Formula:
SnCl4
CAS Number:
Molecular Weight:
260.52
EC Number:
MDL number:
PubChem Substance ID:
Pricing and availability is not currently available.

vapor density

9 (vs air)

Quality Level

vapor pressure

10 mmHg ( 10 °C)
18.6 mmHg ( 20 °C)
20 mmHg ( 22 °C)

assay

98%

reaction suitability

core: tin
reagent type: Lewis acid
reagent type: catalyst

bp

114 °C (lit.)

mp

−33 °C (lit.)

density

2.226 g/mL at 25 °C (lit.)

SMILES string

ClSn(Cl)(Cl)Cl

InChI

1S/4ClH.Sn/h4*1H;/q;;;;+4/p-4

InChI key

HPGGPRDJHPYFRM-UHFFFAOYSA-J

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General description

Stannic chloride (SnCl4) is a strong Lewis acid widely used as a promoter or catalyst in organic synthesis. It is soluble in most organic solvents.

Application

Stannic chloride can be used to catalyze:
  • Cyclization of trans β-monocyclohomofarnesic acid to form norambreinolide.
  • Formation of C-glycosides of aromatic compounds such as thiophene, naphthalene and phloroglucinol trimethyl ether.
  • Formal 4+2 cycloaddition of 3-ethoxycyclobutanones and allyltrialkylsilanes to form 3-ethoxy-5-(trialkylsilyl)methylcyclohexan-1-ones.
  • Diastereoselective reaction of δ-alkoxyallylstannanes with aldehydes to form 1,5-diol derivatives.


Other applications of SnCl4:
  • The SnCl4-2,6-dialkoxyphenols complexes can catalyze cyclization of poylenes, such as 4-(homogeranyl)toluene to form trans-fused tricyclic compound.
  • SnCl4 can act as a promoter during the reaction of ortho-aminobenzonitriles with β-ketoesters and β-enaminonitriles to form 4-aminoquinolines and 4-aminopyridines, respectively.
  • SnCl4-silver perchlorate forms an effective catalytic system for the stereoselective of glycosylation 1-O-acetyl glucose.

Packaging

250 g in Sure/Seal™
2 kg in Sure/Seal™

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

C

Risk Statement

34-52/53

Safety Statement

7/8-26-45-61

RIDADR

UN 1827 8 / PGII

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

1, 5-Asymmetric induction in reactions between δ-alkoxyallylstannanes and aldehydes induced by tin (IV) chloride.
McNeill A H and Thomas E J
Tetrahedron Letters, 31(43), 6239-6242 (1990)
Min Huang et al.
International journal of biological macromolecules, 162, 220-228 (2020-06-17)
In this work, we present Co3S4-SnO2 supported polyvinylpyrrolidone-cellulose (PVPCS) nano-structure for Lidocaine degradation. The nanostructure was characterized by various techniques i.e. morphological and optical ones. The results have demonstrated that Co3S4-SnO2 nanocomposites were evenly supported on the PVPCS. Moreover, the...
Synthesis of (?)-norambreinolide by cyclization of trans-?-monocyclohomofarnesic acid.
Saito A, et al.
Chemistry Letters (Jpn), 10(6), 757-760 (1981)
Tin (IV) chloride-promoted synthesis of 4-aminopyridines and 4-aminoquinolines.
Veronese A C, et al.
Tetrahedron, 51(45), 12277-12284 (1995)
Tin (IV) chloride catalyzed cycloaddition reactions between 3-ethoxycyclobutanones and allylsilanes.
Matsuo J I, et al.
Organic Letters, 11(17), 3822-3825 (2009)

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