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Merck
CN
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Key Documents

Safety Information

208930

Sigma-Aldrich

Tin(IV) chloride

98%

Synonym(s):

Stannic chloride fuming

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CN¥4,211.00

About This Item

Linear Formula:
SnCl4
CAS Number:
Molecular Weight:
260.52
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.22

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vapor density

9 (vs air)

Quality Level

vapor pressure

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

Assay

98%

form

liquid

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

Cl[Sn](Cl)(Cl)Cl

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This Item
259950B12695801809
苄氯 ReagentPlus®, 99%, contains ≤1% propylene oxide as stabilizer

185558

苄氯

assay

99%

assay

98.0-100.5%, 99%

assay

≥99%

assay

≥99.0% (GC)

solubility

0.46 g/L at 30 °C (Decomposes in contact with water)

solubility

-

solubility

-

solubility

460 mg/L

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

refractive index

n20/D 1.538 (lit.)

refractive index

n20/D 1.553 (lit.)

refractive index

n20/D 1.553 (lit.)

refractive index

-

bp

177-181 °C (lit.)

bp

198 °C (lit.)

bp

198 °C (lit.)

bp

179.3 °C/1013 hPa

mp

−43 °C (lit.)

mp

−1 °C (lit.)

mp

−1 °C (lit.)

mp

-39 °C

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.[1]

Application

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


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.[6]
  • 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.[7]
  • SnCl4-silver perchlorate forms an effective catalytic system for the stereoselective of glycosylation 1-O-acetyl glucose.[8]

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Tin (IV) Chloride.
Castellino S, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis null
Facile Syntheses of C-Glycosides of Aromatic Compounds.
Ohrui H, et al.
Agricultural and Biological Chemistry, 36(9), 1651-1653 (1972)
Tin (IV) chloride-chiral pyrogallol derivatives as new Lewis acid-assisted chiral Br?nsted acids for enantioselective polyene cyclization.
Kumazawa K, et al.
Organic Letters, 6(15), 2551-2554 (2004)
Synthesis of (?)-norambreinolide by cyclization of trans-?-monocyclohomofarnesic acid.
Saito A, et al.
Chemistry Letters (Jpn), 10(6), 757-760 (1981)
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)

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