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230464

Sigma-Aldrich

Thionyl chloride

ReagentPlus®, ≥99%

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About This Item

Linear Formula:
SOCl2
CAS Number:
7719-09-7
Molecular Weight:
118.97
Beilstein/REAXYS Number:
1209273
EC Number:
231-748-8
MDL number:
MFCD00011449
UNSPSC Code:
12352300
PubChem Substance ID:
24853806
NACRES:
NA.21

vapor pressure

97 mmHg ( 20 °C)

Quality Level

200

product line

ReagentPlus®

assay

≥99%

form

liquid

refractive index

n20/D 1.518 (lit.)

bp

79 °C (lit.)

mp

−105 °C (lit.)

density

1.631 g/mL at 25 °C (lit.)

anion traces

chloride (Cl-): 59.0-60.2%

SMILES string

ClS(Cl)=O

InChI

1S/Cl2OS/c1-4(2)3

InChI key

FYSNRJHAOHDILO-UHFFFAOYSA-N

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General description

Thionyl chloride is an inorganic acid chloride mainly used to prepare carboxylic acid chlorides from carboxylic acids.

Application

Thionyl chloride may be used in the following processes:
  • To facilitate the synthesis of indenones from 3-hydroxyindanones via dehydroxylation.
  • Surface modification of amorphous carbon nanotubes (α-CNTs) in stearic acid-dichloromethane solution.
  • To functionalize silica gel for thioacetalization of aldehydes.
  • Conversion of tert-butyl esters to acid chlorides.
  • Conversion of aliphatic and aromatic sulfoxides to sulfides in the presence of triphenylphosphine.
  • As an activator to generate ketenes in-situ for preparing 2-azetidinones.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1A - STOT SE 3

target_organs

Respiratory system

supp_hazards

EUH014,EUH029

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
CDBG4645
SDBB0867
SDBB1283
SHBQ3023
STBL3375

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Thionyl chloride (or oxalyl chloride) as an efficient acid activator for one-pot synthesis of [Beta]-lactams.
Ebrahimi E & Jarrahpour A.
Iranian Journal of Science and Technology, 38(A1), 49-49 (2014)
Fox MA and Whitesell JK
Organic Chemistry, 607-607 null
The Conversion of tert-Butyl Esters to Acid Chlorides Using Thionyl Chloride.
Greenberg JA & Sammakia T
The Journal of Organic Chemistry, 82(6), 3245-3251 (2017)
Deoxygenation of sulfoxides to sulfides with thionyl chloride and triphenylphosphine: Competition with the Pummerer reaction
Jang Y, et al.
The Journal of Organic Chemistry, 78(12), 6328-6331 (2013)
Thionyl chloride assisted functionalization of amorphous carbon nanotubes: A better field emitter and stable nanofluid with better thermal conductivity.
Sarkar SK, et al.
Mat. Res. Bul., 1-8 (2015)
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