Triphenyl tin hydroxide

Structural formula
General
Surname	Triphenyl tin hydroxide
other names	Fentin hydroxide; TPTH; Brestan liquid;
Molecular formula	C 18 H 16 OSn
Brief description	white solid with a slightly aromatic odor
External identifiers / databases
EC number	200-990-6
ECHA InfoCard	100,000,901
PubChem	327657
Wikidata	Q7843285
properties
Molar mass	367.03 g mol −1
Physical state	firmly
density	1.54 g cm −3
Melting point	122-123.5 ° C
Vapor pressure	4.7 · 10 −7 hPa (25 ° C)
solubility	1.2 mg l −1 (at 20 ° C); 4 mg l −1 (at 25 ° C);
safety instructions
H and P phrases	H: 301 + 311-330-315-318-335-351-361d-371-372-410
	P: 201-260-273-280-304 + 340 + 310
Toxicological data	46 mg kg −1 ( LD 50 , rat , oral ) ; 1600 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triphenyltin hydroxide is a chemical compound from the group of organotin compounds . When heated above 45 ° C it dehydrates to bis (triphenyltin) oxide , which is stable up to 250 ° C.

Extraction and presentation

Triphenyltin hydroxide can be obtained by reacting chlorobenzene with magnesium , tin (IV) chloride in a Grignard reaction and subsequent reaction with sodium hydroxide solution .

{\ displaystyle \ mathrm {C_ {6} H_ {5} Cl \ + \ Mg \ {\ xrightarrow {}} \ C_ {6} H_ {5} MgCl}}

{\ displaystyle \ mathrm {SnCl_ {4} \ + \ 3 \ C_ {6} H_ {5} MgCl \ {\ xrightarrow {}} \ (C_ {6} H_ {5}) _ {3} SnCl \ + \ 3 \ MgCl_ {2}}}

{\ displaystyle \ mathrm {(C_ {6} H_ {5}) _ {3} SnCl \ + \ NaOH \ {\ xrightarrow {}} \ (C_ {6} H_ {5}) _ {3} SnOH \ + \ NaCl}}

use

Triphenyltin hydroxide was used as a fungicide , especially against late blight . It was approved in Germany between 1971 and 2001.

The EU Commission decided in 2002 not to include triphenyltin hydroxide in the list of permissible active ingredients in plant protection products because of the possible risk to users and non-target organisms. In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

safety instructions

In the past, triphenyltin compounds have been used in agriculture as fungicides and as algicides and molluscicides in anti-fouling paints . In the EU, the use of phenyltin compounds in agriculture has been banned since 1998 in the manufacture of paints since 2003. Triphenyltin hydroxide is extremely irritating to corrosive to the conjunctiva; skin irritation was also observed. No skin sensitizing effect was found in animal experiments. Organotin compounds are classified as toxic to very toxic. When absorbed, they accumulate in the liver, kidneys and adrenal glands. The toxicity to mammals is LC ₅₀ (inhalation - rat) 60.3 mgkg ⁻¹ , LD ₅₀ (oral - rat) 160 - 360 mgkg ⁻¹ and LD ₅₀ (dermal - rat) 1600 mgkg ^{- 1} .

Based on the analogy to the effect of triphenyltin hydroxide, a MAK value of 0.002 mg tin · m ^{−3 was} established for all phenyltin compounds .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on fentin hydroxide in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f ^g phenyltin compounds [MAK Value Documentation in German language, 2010] . In: The MAK Collection for Occupational Health and Safety . January 31, 2012, doi : 10.1002 / 3527600418.mb240668verd0048 .
↑ Entry on Fentin hydroxide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
^ Müfit Bahadir, H. Parlar, M. Spiteller: Springer Umweltlexikon . Springer-Verlag, July 2, 2013, ISBN 978-3-642-56998-2 , p. 426.
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 402 ( limited preview in Google Book search).
↑ Decision of the Commission of June 20, 2002 (PDF) on the non-inclusion of fentin hydroxide in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products containing this active substance (2002/479 / EC).
↑ General Directorate Health and Food Safety of the European Commission: Entry on Fentin hydroxide in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on fentin hydroxide in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[The_MAK_Collection-2] ↑ ^a ^b ^c ^d ^e ^f ^g phenyltin compounds [MAK Value Documentation in German language, 2010] . In: The MAK Collection for Occupational Health and Safety . January 31, 2012, doi : 10.1002 / 3527600418.mb240668verd0048 .

[CLP_100.000.901-3] Entry on Fentin hydroxide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[BahadirParlar2013-4] Müfit Bahadir, H. Parlar, M. Spiteller: Springer Umweltlexikon . Springer-Verlag, July 2, 2013, ISBN 978-3-642-56998-2 , p. 426.

[Thomas_A._Unger-5] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 402 ( limited preview in Google Book search).

[6] Decision of the Commission of June 20, 2002 (PDF) on the non-inclusion of fentin hydroxide in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products containing this active substance (2002/479 / EC).

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on Fentin hydroxide in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.