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Sigma-Aldrich

Sulfuryl chloride

97%

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About This Item

Fórmula lineal:
SO2Cl2
Número de CAS:
7791-25-5
Peso molecular:
134.97
Número CE:
232-245-6
Número MDL:
MFCD00011451
Código UNSPSC:
12352302
ID de la sustancia en PubChem:
57647521
NACRES:
NA.21

densidad de vapor

4.7 (vs air)

Nivel de calidad

200

presión de vapor

100 mmHg ( 17.8 °C)
105 mmHg ( 20 °C)

Análisis

97%

formulario

liquid

índice de refracción

n20/D 1.443 (lit.)

bp

68-70 °C (lit.)

mp

−54 °C (lit.)

densidad

1.665 g/mL at 20 °C (lit.)

cadena SMILES

ClS(Cl)(=O)=O

InChI

1S/Cl2O2S/c1-5(2,3)4

Clave InChI

YBBRCQOCSYXUOC-UHFFFAOYSA-N

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Descripción general

Sulfuryl chloride is a sulfur containing reagent. It is widely used for chlorination of various compounds, as it dissociates into sulfur dioxide and chlorine during reaction. Thus, it acts as a source of molecular chlorine for various aromatic chlorination reactions. Its chlorination reaction with dimethyl sulfide has been studied. Sulfuryl chloride may be used as an efficient reagent for the p-chlorination of phenols.

Aplicación

Sulfuryl chloride (SO2Cl2) may be used in the following studies:
  • Synthesis of α-chloroketones.
  • Regioselective (ortho-selective) chlorination of phenols.
  • Conversion of monocyclic allylic cis-1,2-diols to the corresponding trans-1,2-chlorohydrins.
  • Preparation of β-chlorotetrahydrofuran derivatives.

Sulfuryl chloride may be used as an efficient reagent for the p-chlorination of phenols.

Pictogramas

Skull and crossbonesCorrosion
GHS06,GHS05

Palabra de señalización

Danger

Frases de peligro

H314,H330,H335

Clasificaciones de peligro

Acute Tox. 2 Inhalation - Eye Dam. 1 - Skin Corr. 1C - STOT SE 3

Órganos de actuación

Respiratory system

Riesgos supl.

EUH014

Código de clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Clase de riesgo para el agua (WGK)

WGK 1

Equipo de protección personal

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
STBL4240
STBL2022
STBL3226
STBK9649
STBK3652

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Sigma-Aldrich

230464

Thionyl chloride

Derek R Boyd et al.
Organic & biomolecular chemistry, 12(13), 2128-2136 (2014-02-27)
Monocyclic allylic cis-1,2-diols reacted with sulfuryl chloride at 0 °C in a regio- and stereo-selective manner to give 2-chloro-1-sulfochloridates, which were hydrolysed to yield the corresponding trans-1,2-chlorohydrins. At -78 °C, with very slow addition of sulfuryl chloride, cyclic sulfates were
Chlorinations with sulfuryl chloride. I. The peroxide-catalyzed chlorination of hydrocarbons.
Kharasch MS and Brown HC.
Journal of the American Chemical Society, 61(8), 2142-2150 (1939)
Application of Sulfuryl Chloride for the Quick Construction of β-Chlorotetrahydrofuran Derivatives from Homoallylic Alcohols under Mild Conditions.
Zeng X, et al.
Synthesis, 45(17), 2391-2396 (2013)
The chlorination of active hydrogen compounds with sulfuryl chloride. I. Ketones.
Wyman DP and Kaufman PR.
The Journal of Organic Chemistry, 29(7), 1956-1960 (1964)
Noam I Saper et al.
The Journal of organic chemistry, 79(2), 809-813 (2013-12-18)
2,2,6,6-Tetramethylpiperidine (TMP)-catalyzed (1-10%) chlorinations of phenols by SO2Cl2 in aromatic solvents are more ortho selective than with primary and less hindered secondary amine catalysts. Ortho-selective chlorination is successful even with electron deficient phenols such as 2-hydroxybenzaldehyde and 2'-hydroxyacetophenone. Notably, ortho
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