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Merck
CN

88950

Thionyl chloride

puriss., ≥99.0%

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About This Item

Linear Formula:
SOCl2
CAS Number:
7719-09-7
Molecular Weight:
118.97
EC Number:
231-748-8
UNSPSC Code:
12352300
PubChem Substance ID:
329769678
Beilstein/REAXYS Number:
1209273
MDL number:
MFCD00011449

Key Documents

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InChI key

FYSNRJHAOHDILO-UHFFFAOYSA-N

InChI

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

SMILES string

ClS(Cl)=O

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.)

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General description

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

Application

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

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

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

监管及禁止进口产品
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Eagleson M.
Concise Encyclopedia Chemistry, 1056-1056 (1994)
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, 118-118 (1994)
High-resolution synchrotron far infrared spectroscopy of thionyl chloride: Analysis of the ?3 and ?6 fundamental bands.
Martin-Drumel MA, et al.
Journal of Molecular Spectroscopy (2015)
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
View All Related Papers

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