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157767

Sigma-Aldrich

Sulfuryl chloride

97%

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25 ML
¥9,800
1 L
¥23,900

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25 ML
¥9,800
1 L
¥23,900

About This Item

Linear Formula:
SO2Cl2
CAS Number:
7791-25-5
Molecular Weight:
134.97
EC Number:
232-245-6
MDL number:
MFCD00011451
UNSPSC Code:
12352302
PubChem Substance ID:
57647521
NACRES:
NA.21
form:
liquid

¥9,800

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vapor density

4.7 (vs air)

Quality Level

200

vapor pressure

100 mmHg ( 17.8 °C)
105 mmHg ( 20 °C)

Assay

97%

form

liquid

refractive index

n20/D 1.443 (lit.)

bp

68-70 °C (lit.)

mp

−54 °C (lit.)

density

1.665 g/mL at 20 °C (lit.)

SMILES string

ClS(Cl)(=O)=O

InChI

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

InChI key

YBBRCQOCSYXUOC-UHFFFAOYSA-N

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General description

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]

Application

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]

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H314,H330,H335

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

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

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

157767-1KG:
157767-1L:
157767-25G-PW:
157767-25ML:
157767-VAR:
157767-1KG-PW:
157767-1L-PC:
157767-25G:
157767-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4240
STBL2022
STBL3226
STBK9649
STBK3652

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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)
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)
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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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