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208930

Sigma-Aldrich

Tin(IV) chloride

98%

Synonym(s):

Stannic chloride fuming

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About This Item

Linear Formula:
SnCl4
CAS Number:
7646-78-8
Molecular Weight:
260.52
EC Number:
231-588-9
MDL number:
MFCD00011242
UNSPSC Code:
12352106
PubChem Substance ID:
24852219
NACRES:
NA.22
Pricing and availability is not currently available.

vapor density

9 (vs air)

Quality Level

200

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

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.[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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335,H412

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX1895
MKCW5762
MKCW5761
MKCW7984
MKCV2491

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Sigma-Aldrich

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Tin (IV) chloride-promoted synthesis of 4-aminopyridines and 4-aminoquinolines.
Veronese A C, et al.
Tetrahedron, 51(45), 12277-12284 (1995)
A Highly Stereoselective Synthesis of α-Glucosides from 1-O-Acetyl Glucose by Use of Tin (IV) Chloride?Silver Perchlorate Catalyst System.
Mukaiyama T, et al.
Chemistry Letters (Jpn), 20(4), 533-536 (1991)
Tin (IV) chloride catalyzed cycloaddition reactions between 3-ethoxycyclobutanones and allylsilanes.
Matsuo J I, et al.
Organic Letters, 11(17), 3822-3825 (2009)
Jian Zhi et al.
Nature communications, 12(1), 445-445 (2021-01-21)
Realizing transparent and energy-dense supercapacitor is highly challenging, as there is a trade-off between energy storing capability and transparency in the active material film. We report here that interstitial boron-doped mesoporous semiconductor oxide shows exceptional electrochemical capacitance which rivals other
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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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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