204722

Sigma-Aldrich

Tin(II) chloride

≥99.99% trace metals basis

Synonym(s):
Stannous chloride
Linear Formula:
SnCl2
CAS Number:
Molecular Weight:
189.62
EC Number:
MDL number:
eCl@ss:
38140204
PubChem Substance ID:
NACRES:
NA.21

Quality Level

vapor pressure

33 hPa (~429 °C)

assay

≥99.99% trace metals basis

form

crystalline powder
flakes

reaction suitability

reagent type: catalyst
core: tin

pH

2.18 (20 °C)

bp

652 °C (lit.)

mp

246 °C (lit.)

SMILES string

Cl[SnH2]Cl

InChI

1S/2ClH.Sn/h2*1H;/q;;+2/p-2

InChI key

AXZWODMDQAVCJE-UHFFFAOYSA-L

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General description

Tin(II) chloride (Stannous chloride, SnCl2) is widely employed as reducing reagent. It plays significant role in diverse fields of science. Since it exhibits superior catalytic action in molten state, it is employed for the hydroliquefaction of coals. It is a promising raw material for the chemical vapour deposition (CVD) of semiconducting layers. It can be prepared by reacting its dihydrate form with acetic anhydride. It exhibits reducing properties in acidic media. It participates in the reduction of the following compounds:
  • aromatic nitro compounds
  • nitriles
  • cyanosilyl ethers
  • organic azides
On mixing sodium cyanoborohydride with SnCl2 in a 2:1 ratio, a reducing reagent mixture is obtained. This reagent is useful for the reduction of tertiary, allyl and benzyl halides.

Application

Tin(II) chloride has been used for the reduction of hydroperxoxides to the corresponding alcohols in a study.
Tin(II) chloride may be used:
  • To catalyze the addition of diazo sulfones, diazo phosphine oxides and diazo phosphonates to aldehydes to form β-keto sulfones, β-keto phosphine oxides and β-keto phosphonates, respectively.
  • Along with trityl chloride, to catalyze the aldol reaction of silyl enol ethers with acetals or aldehydes and the Michael reaction of silyl enol ethers with α,β-unsaturated ketones.
  • As a promoter in the allylic amination of allylic alcohols with amines in the presence of palladium catalyst.

Packaging

10, 50 g in glass bottle

Signal Word

Danger

Target Organs

Cardio-vascular system, Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN3260 - class 8 - PG 2 - EHS - Corrosive solid, acidic, inorganic, n.o.s., HI: all

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Tin (II) Chloride.
Faul MM and Thiel OR.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (1995)
Quantitative assays for esterified oxylipins generated by immune cells.
Morgan AH, et al.
Nature Protocols, 5(12), 1919-1931 (2010)
Palladium-catalyzed allylic amination of allylic alcohols with tin (II) chloride and triethylamine.
Masuyama Y, et al.
Chemistry Letters (Jpn), 24(12), 1121-1122 (1995)
Transformation of molten SnCl2 to SnO2 nano-single crystals.
Kamali AR, et al.
Ceramics International, 40(6), 8533-8538 (2014)
Tin (II) chloride catalyzed addition of diazo sulfones, diazo phosphine oxides, and diazo phosphonates to aldehydes.
Holmquist CR and Roskamp EJ.
Tetrahedron Letters, 33(9), 1131-1134 (1992)

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