Disulfur dichloride

Disulfur dichloride
Disulfur dichloride
Identifiers
CAS number 10025-67-9 YesY, 85408-26-0 (isobutenate)
PubChem 24807 YesY, 174464 (isobutenate) YesY
ChemSpider 23192 YesY, 152167 (isobutenate) YesY
EC number 233-036-2
UN number 3390
MeSH Sulfur+monochloride
RTECS number WS4300000
Jmol-3D images Image 1
Properties
Molecular formula S2Cl2
Molar mass 135.04 g/mol
Appearance yellow liquid
Density 1.688 g/cm3
Melting point

-80 °C, 193 K, -112 °F

Boiling point

137.1 °C, 410 K, 279 °F

Solubility in water decomp with loss of HCl
Solubility soluble in ethanol, benzene, ether, chloroform, CCl4 [1]
Refractive index (nD) 1.658
Structure
Coordination
geometry
gauche
Dipole moment 1.60 D [1]
Hazards
MSDS ICSC 0958
EU Index 016-012-00-4
EU classification Toxic (T)
Harmful (Xn)
Corrosive (C)
Dangerous for the environment (N)
R-phrases R14, R20, R25, R29, R35, R50
S-phrases (S1/2), S26, S36/37/39, S45, S61
NFPA 704
NFPA 704.svg
1
2
1
Flash point 118.5 °C
Autoignition
temperature
234 °C
Related compounds
Related sulfur chlorides Sulfur dichloride
Thionyl chloride
Sulfuryl chloride
Related compounds Disulfur difluoride
Disulfur dibromide
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Disulfur dichloride is the chemical compound with the formula S2Cl2 [2][3][4] [5] . Some alternative names for this compound are sulfur monochloride (the name implied by its empirical formula, SCl), disulphur dichloride (British English Spelling) and sulphur monochloride (British English Spelling). S2Cl2 has the structure implied by the formula Cl-S-S-Cl, wherein the angle between the Cla-S-S and S-S-Clb planes is 90°. This structure is referred to as gauche, and is akin to that for H2O2. A different isomer of S2Cl2 is S=SCl2; this isomer forms transiently when S2Cl2 is exposed to UV-radiation (see thiosulfoxides).

Synthesis and basic properties

Disulfur dichloride is an orange/yellow liquid that smokes in air due to reaction with water:

2 S2Cl2 + 2 H2O → SO2 + 4 HCl + 3/8 S8

It is synthesized by partial chlorination of elemental sulfur:

S8 + 4 Cl2 → 4 S2Cl2 ΔH = −58.2 kJ/mol

Excess chlorine gives sulfur dichloride:

S2Cl2 + Cl2 → 2 SCl2 ΔH = −40.6 kJ/mol

Both reactions are reversible, and upon standing, SCl2 releases chlorine to revert to the disulfur dichloride. It has the ability to dissolve sulfur, which reflects in part the formation of polysulfanes:

S2Cl2 + n S → S2+nCl2

S2Cl2 also arises from the chlorination of CS2 as in the synthesis of thiophosgene.

Applications

S2Cl2 has been used to introduce C-S bonds. In the presence of AlCl3, S2Cl2 reacts with benzene to give diphenyl sulfide:

S2Cl2 + 2 C6H6 → (C6H5)2S + 2 HCl + 1/8 S8

Anilines react with S2Cl2 in the presence of NaOH via the so-called Herz reaction to give ortho-aminothiophenolates. These species are precursors to thioindigo dyes. It is also used to prepare the sulfur mustard "gas" by reaction with ethylene:

S2Cl2 + 2 C2H4 → (ClC2H4)2S + 1/8 S8

Other uses include manufacturing sulfur dyes, insecticides, synthetic rubbers. Also used in cold vulcanization of rubbers, as polymerization catalyst for vegetable oils and for hardening soft woods.

References

  1. ^ a b Pradyot Patnaik. Handbook of Inorganic Chemicals. McGraw-Hill, 2002, ISBN 0070494398
  2. ^ Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
  3. ^ Hartman, W. W.; Smith, L. A.; Dickey, J. B. (1934), "Diphenylsulfide", Org. Synth. 14: 36, http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv2p0242 ; Coll. Vol. 2: 242 
  4. ^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4
  5. ^ Garcia-Valverde M., Torroba T. (2006). "Heterocyclic chemistry of sulfur chlorides - Fast ways to complex heterocycles". European J. Org. Chem. 4 (4): 849–861. doi:10.1002/ejoc.200500786. 

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