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Merck

320536

Sigma-Aldrich

Thionyl chloride

reagent grade, 97%

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About This Item

Fórmula lineal:
SOCl2
Número de CAS:
Peso molecular:
118.97
Beilstein/REAXYS Number:
1209273
EC Number:
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
NACRES:
NA.21
assay:
97%
grade:
reagent grade
form:
liquid
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grade

reagent grade

Quality Level

vapor pressure

97 mmHg ( 20 °C)

assay

97%

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.)

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 as a reagent 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]
  • To functionalize silica gel for thioacetalization of aldehydes.[3]
  • Conversion of tert-butyl esters to acid chlorides.[4]
  • Conversion of aliphatic and aromatic sulfoxides to sulfides in the presence of triphenylphosphine.[5]

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

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which 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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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)
Mojtaba Taseidifar
Ecotoxicology and environmental safety, 206, 111389-111389 (2020-09-29)
An improved method has been developed for the efficient synthesis of octanoyl-cysteine in single-chain form (N-octanoyl-cys) which operates as a surfactant over a wide pH range, is easily decomposed into natural products and has a high product yield. The compound
Selective protection of carbonyl compounds. Silica gel treated with thionyl chloride as an effective catalyst for thioacetalization.
Kamitori Y, et al.
The Journal of Organic Chemistry, 51(9), 1427-1431 (1986)

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Questions

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  1. 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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  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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