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Thiophosphoryl chloride
Ball-and-stick model of thiophosphoryl chloride Space-filling model of thiophosphoryl chloride
Names
IUPAC name
Phosphorothioic trichloride
Other names
Phosphoric sulfochloride (1:3)[1]
Phosphorus(V ) sulfochloride
Thiophosphoryl chloride
Identifiers
CAS Number
3D model (JSmol )
ChemSpider
ECHA InfoCard 100.021.476
EC Number
PubChem CID
RTECS number
UNII
UN number
1837
CompTox Dashboard (EPA )
InChI=1S/Cl3PS/c1-4(2,3)5 Y
Key: WQYSXVGEZYESBR-UHFFFAOYSA-N Y
Key: WQYSXVGEZYESBR-UHFFFAOYAE
Properties
Chemical formula
PSCl3
Molar mass
−1
Appearance
Colorless liquid
Density
1.67 g/cm3
Melting point
−35 °C (−31 °F; 238 K )
Boiling point
125 °C (257 °F; 398 K )
Solubility in water
Reacts
Solubility
Soluble in benzene , chloroform , CS 2 CCl4
Structure
Molecular shape
Tetrahedral at the P
Hazards
Occupational safety and health
Main hazards
Violent hydrolysis; releasing HCl on contact with water,[2]
GHS labelling[4]
Pictograms
Signal word
Danger
Hazard statements
H302 , H314 , H330
Precautionary statements
P260 , P264 , P270 , P271 , P280 , P284 , P301+P317 , P301+P330+P331 , P302+P361+P354 , P304+P340 , P305+P354+P338 , P316 , P320 , P321 , P330 , P363 , P403+P233 , P405 , P501
Flash point
none[3]
Related compounds
Related compounds
Thiophosphoryl fluoride
Thiophosphoryl bromide
Thiophosphoryl iodide
Phosphorothioic chloride difluoride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Thiophosphoryl chloride is an inorganic compound with the chemical formula P S Cl 3 [5] phosphorus chloride and used to thiophosphorylate organic compounds, such as to produce insecticides .
Synthesis [ edit ]
Thiophosphoryl chloride can be generated by several reactions starting from phosphorus trichloride . The most common and practical synthesis, hence used in industrial manufacturing, is directly reacting phosphorus trichloride with excess sulfur at 180 °C.[6]
PCl3 3
Using this method, yields can be very high after purification by distillation. Catalysts facilitate the reaction at lower temperatures, but are not usually necessary.
Alternatively, it is obtained by combining phosphorus pentasulfide and phosphorus pentachloride.[7]
3 PCl5 2 S 5 3
Structure [ edit ]
Thiophosphoryl chloride has tetrahedral molecular geometry and C3v molecular symmetry , with the structure S=PCl3 . According to gas electron diffraction , the phosphorus–sulfur bond length is 189 pm Cl−P−Cl bond angle is 102°.[8]
Reactions [ edit ]
PSCl3 is soluble in benzene , carbon tetrachloride , chloroform , and carbon disulfide .[5] hydrolyzes rapidly in basic or hydroxylic solutions, such as alcohols and amines , to produce thiophosphates .[6] PSCl3 reacts, and contingent on the reaction conditions, produces either phosphoric acid , hydrogen sulfide , and hydrochloric acid or dichlorothiophosphoric acid and hydrochloric acid.[9]
PSCl3 2 3 PO 4 2 HCl
PSCl3 2 2
PSCl3 is used to thiophosphorylate organic compounds (to add thiophosphoryl group, P=S, with three free valences at the P organic compounds ).[6] aminoalcohols , diols , and diamines .[5] PSCl3 is used to produce insecticides , like parathion .[9]
PSCl3 3 CH 2 CH 3 CH 2 2
(CH 3 CH 2 2 + [− O−C6 H 4 2 CH 3 CH 2 2 6 H 4 2 NaCl
PSCl3 reacts with tertiary amides to generate thioamides .[5]
C 6 H 5 3 2 3 6 H 5 3 2 POCl3
When treated with methylmagnesium iodide , it give tetramethyldiphosphine disulfide (H 3 2 3 2 .[10]
References [ edit ]
^ Thiophosphoryl chloride: trade names
^ Thiophosphoryl chloride: main hazards
^ Thiophosphoryl chloride: flash point
^ "Thiophosphoryl chloride" . pubchem.ncbi.nlm.nih.gov .
^ a b c d Spilling, C. D. "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
^ a b c Betterman G, Krause W, Riess G, Hofmann T (2005). "Phosphorus Compounds, Inorganic". Ullmann’s Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi :10.1002/14356007.a19_527 . ISBN 3527306730
^ Martin, D. R.; Duvall, W. M. “Phosphorus(V ) Sulfochloride” Inorganic Syntheses, 1953, Volume IV, p73. doi :10.1002/9780470132357.ch24 .
^ Kuchitsu, Kozo; Moritani, Tohei; Morino, Yonezo (1971). "Molecular structures of phosphoryl fluoride, phosphoryl chloride, and thiophosphoryl chloride studied by gas electron diffraction". Inorganic Chemistry (journal) 10 2 ): 344–350. doi :10.1021/ic50096a025 .
^ a b Fee, D. C.; Gard, D. R.; Yang, C. “Phosphorus Compounds” Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons: New York, 2005 doi :10.1002/0471238961.16081519060505.a01.pub2
^ G. W. Parshall "Tetramethylbiphosphine Disulfide" Org. Synth. 1965, volume 45, p. 102. doi :10.15227/orgsyn.045.0102
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Thiophosphoryl_chloride&oldid=1222003189 " C a t e g o r i e s : ● P h o s p h o r u s h a l i d e s ● T h i o p h o s p h o r y l c o m p o u n d s ● T h i o c h l o r i d e s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h o u t E B I s o u r c e ● A r t i c l e s w i t h o u t K E G G s o u r c e ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 3 M a y 2 0 2 4 , a t 0 8 : 1 9 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
