157767
Sulfuryl chloride
97%
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About This Item
Linear Formula:
SO2Cl2
CAS Number:
Molecular Weight:
134.97
NACRES:
NA.21
PubChem Substance ID:
UNSPSC Code:
12352302
EC Number:
232-245-6
MDL number:
Assay:
97%
Form:
liquid
InChI key
YBBRCQOCSYXUOC-UHFFFAOYSA-N
InChI
1S/Cl2O2S/c1-5(2,3)4
SMILES string
ClS(Cl)(=O)=O
vapor density
4.7 (vs air)
vapor pressure
100 mmHg ( 17.8 °C), 105 mmHg ( 20 °C)
assay
97%
form
liquid
Quality Level
bp
68-70 °C (lit.)
mp
−54 °C (lit.)
density
1.665 g/mL at 20 °C (lit.)
Related Categories
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. Its chlorination reaction with dimethyl sulfide has been studied. Sulfuryl chloride may be used as an efficient reagent for the p-chlorination of phenols.
Application
Sulfuryl chloride (SO2Cl2) may be used in the following studies:
Sulfuryl chloride may be used as an efficient reagent for the p-chlorination of phenols.
- 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.
signalword
Danger
hcodes
target_organs
Respiratory system
supp_hazards
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Classifications
Acute Tox. 2 Inhalation - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3
Storage Class
6.1B - Non-combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
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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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