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Sigma-Aldrich

Thionyl chloride

Thionyl chloride

ReagentPlus®, ≥99%

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5 ML
$42.20
100 ML
$73.70
500 ML
$120.00
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$213.00
4 X 100 ML
$228.00
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$400.00

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5 ML
$42.20
100 ML
$73.70
500 ML
$120.00
1 L
$213.00
4 X 100 ML
$228.00
2.5 L
$400.00

About This Item

Linear Formula:
SOCl2
CAS Number:
Molecular Weight:
118.97
Beilstein/REAXYS Number:
1209273
EC Number:
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
NACRES:
NA.21
assay:
≥99%
form:
liquid

$42.20


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vapor pressure

97 mmHg ( 20 °C)

Quality Level

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.[1]

Application

Thionyl chloride may be used in the following processes:
  • To facilitate the synthesis of indenones from 3-hydroxyindanones via dehydroxylation.[2]
  • Surface modification of amorphous carbon nanotubes (α-CNTs) in stearic acid-dichloromethane solution.[3]
  • To functionalize silica gel for thioacetalization of aldehydes.[4]
  • Conversion of tert-butyl esters to acid chlorides.[5]
  • Conversion of aliphatic and aromatic sulfoxides to sulfides in the presence of triphenylphosphine.[6]
  • As an activator to generate ketenes in-situ for preparing 2-azetidinones.[7]

Legal Information

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

pictograms

Skull and crossbonesCorrosion

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

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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Customers Also Viewed

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1 of 1

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)
Fox MA and Whitesell JK
Organic Chemistry, 607-607 null
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)
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)

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    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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  2. 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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