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Thiophosgene information


Thiophosgene
Thiophosgene
Thiophosgene
Thiophosgene
Thiophosgene
Names
IUPAC name
Carbonothioyl dichloride
Other names
Thiophosgene; Thiocarbonyl chloride; Carbonothioic dichloride
Identifiers
CAS Number
  • 463-71-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:29366 checkY
ChemSpider
  • 9645 checkY
ECHA InfoCard 100.006.675 Edit this at Wikidata
PubChem CID
  • 10040
RTECS number
  • XN2450000
UNII
  • 067FQP576P checkY
CompTox Dashboard (EPA)
  • DTXSID2060046 Edit this at Wikidata
InChI
  • InChI=1S/CCl2S/c2-1(3)4 checkY
    Key: ZWZVWGITAAIFPS-UHFFFAOYSA-N checkY
  • InChI=1/CCl2S/c2-1(3)4
    Key: ZWZVWGITAAIFPS-UHFFFAOYAH
SMILES
  • ClC(Cl)=S
Properties
Chemical formula
CSCl2
Molar mass 114.97 g·mol−1
Appearance Red liquid
Odor Persistent, choking odor
Density 1.50 g/cm3
Boiling point 70 to 75 °C (158 to 167 °F; 343 to 348 K)
Solubility in water
Decomposes
Solubility in other solvents Reacts with amines and alcohols, soluble in polar organic solvents
Magnetic susceptibility (χ)
-50.6·10−6 cm3/mol
Refractive index (nD)
1.558
Structure
Molecular shape
planar, sp2, C2v
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic
Flash point 62 °C (144 °F; 335 K)
Related compounds
Related compounds
  • Phosgene
  • Thiocarbonyl fluoride
  • Thiocarbonyl bromide
  • Sulfur dichloride
  • Thionyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.[1]

  1. ^ Manchiu D. S. Lay, Mitchell W. Sauerhoff And Donald R. Saunders "Carbon Disulfide" in Ullmann's Encyclopedia Of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_185

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Thiophosgene

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Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to...

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Thiocarbonyldiimidazole

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commercially available but can also be prepared via the reaction of thiophosgene with two equivalents of imidazole. The imidazole groups on TCDI can be...

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Phosgene

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contaminating the Ohio River. Carbonyl bromide Carbonyl fluoride Oxalyl chloride Thiophosgene Thionyl chloride Perfluoroisobutene Bis(trifluoromethyl) disulfide Merck...

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Disulfur dichloride

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S2Cl2 also arises from the chlorination of CS2 as in the synthesis of thiophosgene or carbon tetrachloride. S2Cl2 hydrolyzes to sulfur dioxide and elemental...

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Carbon disulfide

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Cl2 → CCl4 + S2Cl2 This conversion proceeds via the intermediacy of thiophosgene, CSCl2. CS2 is a ligand for many metal complexes, forming pi complexes...

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Organosulfur chemistry

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include the important compounds carbon disulfide, carbonyl sulfide, and thiophosgene. Thioketones (RC(=S)R′) are uncommon with alkyl substituents, but one...

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Thioacyl chloride

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+ COCl2 → PhC(S)Cl + HCl + COS The most common thioacyl chloride is thiophosgene. Hermann Staudinger; Siegwart, J. (1920). "Ueber Thiobenzoylchlorid"...

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Carbon tetrachloride

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{2CCl4 + 2CO -> 2COCl2 + C2Cl4}}} Reaction with hydrogen sulfide gives thiophosgene: CCl 4 + H 2 S ⟶ CCl 2 S + 2 HCl {\displaystyle {\ce {CCl4 + H2S -> CCl2S...

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Dithietane

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4,4-tetrachloro-1,3-dithietane, the photochemically-formed dimer of thiophosgene, and tetrakis(trifluoromethyl)-1,3-dithietane, [(CF3)2CS]2. Oxidized...

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Dimethyl trithiocarbonate

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of trithiocarbonic acid with methanethiol. One synthesis starts from thiophosgene as described in this simplified equation: CSCl2 + 2 CH3SH → CS(SCH3)2...

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List of inorganic compounds

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chloride – TlCl Thallium(III) chloride – TlCl3 Thionyl chloride – SOCl2 Thiophosgene – CSCl2 Thorium(IV) chloride – ThCl4 Thulium(III) chloride – TmCl3 Tin(II)...

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Thiocarbonate

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which has C2v symmetry. Monothiocarbonate arises by the hydrolysis of thiophosgene or the reaction of base with carbonyl sulfide: COS + 2 NaOH → Na2CO2S...

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Thioureas

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N′-disubstituted thioureas can be prepared by coupling two amines with thiophosgene: HNR2 + S=CCl2 → 2 S=C(NR2)2 + 2 HCl Amines also condense with organic...

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Diafenthiuron

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2,6-diisopropyl-4-phenoxyaniline will then undergo a reaction with thiophosgene and form N-(2,6-diisopropyl-4-phenoxyphenyl)isothiocyanate. This in turn...

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Tricarbon monoxide

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silver acetylide derivative of sodium propiolate (AgC≡CCOONa), and then thiophosgene. AgC≡CCOONa in turn is made from silver ions and sodium propiolate. The...

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Organic photochemistry

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truxillic acid. Many photodimers are now recognized, e.g. pyrimidine dimer, thiophosgene, diamantane. Another example was uncovered by Egbert Havinga in 1956...

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Metal carbonyl

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indirect routes, such as the reaction of disodium tetracarbonylferrate with thiophosgene: Na2Fe(CO)4 + CSCl2 → Fe(CO)4CS + 2 NaCl Complexes of CSe and CTe have...

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Perchloromethyl mercaptan

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performing the reaction in the presence of diketones. Another byproduct is thiophosgene. The more volatile byproducts such as carbon tetrachloride and sulfur...

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List of UN numbers 2401 to 2500

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(UN No. no longer in use) UN 2473 6.1 Sodium arsanilate UN 2474 6.1 Thiophosgene UN 2475 8 Vanadium trichloride UN 2476 ? (UN No. no longer in use) Warfarin...

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Altanserin

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[83763-22-8] (2). The reaction of the terminal amino group with thiophosgene [463-71-8] leads to the corresponding isothiocyanate derivative, 4-fluorophenyl...

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Difluoroamino sulfur pentafluoride

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dinitrogen tetrafluoride are disulfur decafluoride or sulfur dioxide or thiophosgene in an electric discharge. A corona discharge in a sulfur hexafluoride...

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