Thiophosphoryl trichloride

Structural formula
General
Surname	Thiophosphoryl trichloride
other names	Phosphorus sulfochloride Thiophosphoryl chloride Phosphorothiochloride
Molecular formula	PSCl 3
Brief description	volatile, colorless liquid with a pungent odor
External identifiers / databases
CAS number 3982-91-0 EC number 223-622-6 ECHA InfoCard 100,021,476 PubChem 19883 ChemSpider 18729 Wikidata Q419792
properties
Molar mass	169.40 g mol −1
Physical state	liquid
density	1.67 g cm −3
Melting point	−40.8 ° C (alpha form) −36.2 ° C (beta form)
boiling point	125 ° C
Vapor pressure	16 hPa (20 ° C)
solubility	decomposes in water soluble in many organic solvents such as benzene and chloroform
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 302-330-314-335 EUH: 029 P: 280-260-309 + 310-304 + 341-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-402
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Thiophosphoryl trichloride is an inorganic chemical compound from the group of phosphorus halides and sulfur compounds .

Extraction and presentation

Thiophosphoryl trichloride can be prepared from phosphorus trichloride by various reactions . The most common practical synthesis used in industrial production is the reaction of phosphorus trichloride with excess sulfur at 180 ° C.

${\displaystyle \mathrm {PCl_{3}+S\rightarrow PSCl_{3}} }$

Alternatively, the production by reaction of phosphorus pentasulphide and phosphorus pentachloride is possible with a yield of about 70%.

${\displaystyle \mathrm {3\ PCl_{5}+P_{2}S_{5}\rightarrow 5\ PSCl_{3}} }$

properties

Thiophosphoryl trichloride is a volatile, colorless liquid with a pungent odor. It is chemically unstable at elevated temperature and slowly hydrolyzes in water to form orthophosphoric acid , hydrochloric acid and hydrogen sulfide . The compound is readily soluble in benzene , carbon tetrachloride , carbon disulfide and chloroform , among others .

use

Thiophosphoryl trichloride is used for the production of organic thiophosphorus compounds (such as insecticides e.g. parathion ) and thioamides .

${\displaystyle \mathrm {PSCl_{3}+2\ C_{2}H_{5}OH\rightarrow (C_{2}H_{5}O)_{2}PSCl+2\ HCl} }$

${\displaystyle \mathrm {(C_{2}H_{5}O)_{2}PSCl+NaOC_{6}H_{4}NO_{2}\rightarrow } }$ ${\displaystyle \mathrm {(C_{2}H_{5}O)_{2}PSOC_{6}H_{4}NO_{2}+NaCl} }$

safety instructions

The gases produced during the hydrolysis of thiophosphoryl trichloride (see above) can ignite or explode when heated in air.

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on thiophosphoryl trichloride in the GESTIS substance database of the IFA , accessed on February 1, 2016 (JavaScript required)
2. ↑ Spilling, CD: Thiophosphoryl Chloride , in Encyclopedia of Reagents for Organic Synthesis John Wiley & Sons, Weinheim, 2001. doi : 10.1002 / 047084289X.rt104 . Article Online Posting Date: April 15, 2001.
3. ↑ ^{a b} Data sheet Thiophosphoryl chloride from Sigma-Aldrich , accessed on April 19, 2013 ( PDF ).
4. ↑ Betterman, G .; Krause, W .; Riess, G .; Hofmann, T. “Phosphorus Compounds, Inorganic” Ullman's Encyclopedia of Industrial Chemistry. John Wiley & Sons: New York, 2005. doi : 10.1002 / 14356007.a19_527 .
5. ↑ Martin, DR; Duvall, WM “Phosphorus (V) Sulfochloride” Inorganic Syntheses, Volume IV. McGraw-Hill, 1953. doi : 10.1002 / 9780470132357.ch24 .
6. ↑ Donald Ray Martin and Wilmer M. Duvall: Phosphorus (V) sulfochloride (Thiophosphoryl chloride) . In: JC Bailar, Jr. (Ed.): Inorganic Syntheses . tape 4 . McGraw-Hill, Inc., 1953, pp. 71-74 (English).
7. ^ Fee, DC; Gard, DR; Yang, C. "Phosphorus Compounds" Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons: New York, 2005. doi : 10.1002 / 0471238961.16081519060505.a01.pub2 .