447285

Sigma-Aldrich

Thionyl chloride

ReagentPlus®, 99.5%, low iron

Linear Formula:
SOCl2
CAS Number:
Molecular Weight:
118.97
Beilstein/REAXYS Number:
1209273
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

vapor pressure

97 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99.5%

form

liquid

contains

<5 ppm iron

refractive index

n20/D 1.518 (lit.)

bp

79 °C (lit.)

mp

−105 °C (lit.)

density

1.631 g/mL at 25 °C (lit.)

cation traces

Fe: ≤ 5.0 ppm

SMILES string

ClS(Cl)=O

InChI

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

InChI key

FYSNRJHAOHDILO-UHFFFAOYSA-N

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Application

Thionyl chloride was used to produce graphene-based hybrid transparent conductive electrodes (TCEs).
It may be used in the following processes:
  • Synthesis of indenones from 3-hydroxyindanones via dehydroxylation.
  • Modification of amorphous carbon nanotubes (a-CNTs) in stearic acid-dichloro methane solution.
  • To functionalize silica gel for thioacetalization of aldehydes.
It may be used in the synthesis of:
  • substituted stilbene derivatives
  • tert-butyl ((S)-1-((R)-oxiran-2-yl)-2-phenylethyl)carbamate
  • optically active chloroalkanes

Packaging

100, 500 mL in glass bottle
5 mL in ampule

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

hazcat

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

Target Organs

Respiratory system

Supp Hazards

EUH014 - EUH029

storage_class_code

8A - Combustible, corrosive hazardous materials

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Eagleson M.
Concise Encyclopedia Chemistry, 7-7 (1994)
The electron diffraction investigation of sulfur monochloride, sulfur dichloride, sulfur trioxide, thionyl chloride, sulfuryl chloride, vanadium oxytrichloride, and chromyl chloride.
Palmer KJ.
Journal of the American Chemical Society, 60(10), 2360-2369 (1938)
High-resolution synchrotron far infrared spectroscopy of thionyl chloride: Analysis of the ν3 and ν6 fundamental bands.
Martin-Drumel MA, et al.
Journal of Molecular Spectroscopy (2015)
CaF2 catalyzed SN2 type chlorodehydroxylation of chiral secondary alcohols with thionyl chloride: a practical and convenient approach for the preparation of optically active chloroalkanes.
Zhang J, et al.
Tetrahedron Letters, 54(18), 2261-2263 (2013)
Thionyl Chloride-Mediated Synthesis of tert-Butyl ((S)-1-((R)-Oxiran-2-yl)-2-phenylethyl) carbamate with Boc-Involved Neighboring Group Participation.
Li T, et al.
Synthetic Communications, 45(10), 1183-1189 (2015)

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