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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
En este momento no podemos mostrarle ni los precios ni la disponibilidad

grado

for analytical purposes

Nivel de calidad

200

densidad de vapor

4.7 (vs air)

presión de vapor

100 mmHg ( 17.8 °C)
105 mmHg ( 20 °C)

Ensayo

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.[1] Its chlorination reaction with dimethyl sulfide has been studied.[2] Sulfuryl chloride may be used as an efficient reagent for the p-chlorination of phenols.[3]

Aplicación

Sulfuryl chloride (SO2Cl2) may be used in the following studies:
  • Synthesis of α-chloroketones.[4]
  • Regioselective (ortho-selective) chlorination of phenols.[3][5]
  • Conversion of monocyclic allylic cis-1,2-diols to the corresponding trans-1,2-chlorohydrins.[6]
  • Preparation of β-chlorotetrahydrofuran derivatives.[7]

Sulfuryl chloride may be used as an efficient reagent for the p-chlorination of phenols.[3]

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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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)
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
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)
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    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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