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88950

Sigma-Aldrich

Thionyl chloride

puriss., ≥99.0%

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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:
329769678

vapor pressure

97 mmHg ( 20 °C)

grade

puriss.

assay

≥99.0%

form

liquid

color

APHA: ≤50

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 a sulfur containing acid halide.[1] It participates in the preparation of butadiyne (diacetylene).[2] On reaction with benzaldehyde, it affords benzylidene dichloride.[3] It is widely employed for the transformation of alcohols into reactive alkyl chlorides.[4]

Application

Thionyl chloride may be employed for the sulfonation of aromatic compounds.[5] It may be used in the synthesis of following:
  • cyclooctasulfur oxide[6]
  • disulfuroxide[6]
  • acetylchloride[1]
  • organochlorine compounds[7]
  • G-series nerve agents such as phosgene or chloropicrine[7]
  • 1-(chloromethyl)-3,5-dimethylbenzene[8]

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pictograms

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GHS06,GHS05

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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

6.1C - 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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Meng Zhou et al.
Molecules (Basel, Switzerland), 20(6), 10122-10130 (2015-06-04)
Pincer (Phebox)Ir(mesityl)(OAc) (2) (Phebox = 3,5-dimethylphenyl-2,6-bis(oxazolinyl)) complex, formed by benzylic C-H activation of mesitylene (1,3,5-trimethylbenzene) using (Phebox)Ir(OAc)2OH2 (1), was treated with thionyl chloride to rapidly form 1-(chloromethyl)-3,5-dimethylbenzene in 50% yield at 23 °C. A green species was obtained at the
Eagleson M.
Concise Encyclopedia Chemistry, 1056-1056 (1994)
Eagleson M.
Concise Encyclopedia Chemistry, 118-118 (1994)
Jinjian Zheng et al.
Analytica chimica acta, 891, 255-260 (2015-09-22)
Thionyl chloride is often used to convert alcohols into more reactive alkyl chloride, which can be easily converted to many compounds that are not possible from alcohols directly. One important reaction of alkyl chloride is nucleophilic substitution, which is typically
Eagleson M.
Concise Encyclopedia Chemistry, 1049-1049 (1994)
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