3338-24-7

Basic information

• Product Name: sodium O,O-diethyl dithiophosphate
• Synonyms: sodium O,O-diethyl dithiophosphate;Phosphorodithioic acid, O,O-diethyl ester, sodium salt;O,O-DIETHYLPHOSPHORODITHIOATE,SODIUMSALT;Natrium-O,O-diethyldithiophosphat;ethyl sodium phosphorodithioate;hostaflot let;o,o-diethyldithiofosforecnan sodny;Dithiophosphoric acid O,O-diethyl ester sodium salt
• CAS NO: 3338-24-7
• Molecular Formula: C₄H₁₀NaO₂PS₂
• Molecular Weight: 208.214531
• EINECS: 222-079-2
• Product Categories: Dithiophosphate
• Mol File: 3338-24-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 193-194 °C
• Boiling Point: 232.7 °C at 760 mmHg
• Flash Point: 94.5 °C
• Appearance: /
• Density: (20oC)1.18
• Vapor Pressure: 0.0887mmHg at 25°C
• PKA: 8.86[at 20 ℃]
• Water Solubility: 1000g/L at 20℃
• CAS DataBase Reference: sodium O,O-diethyl dithiophosphate(CAS DataBase Reference)
• NIST Chemistry Reference: sodium O,O-diethyl dithiophosphate(3338-24-7)
• EPA Substance Registry System: sodium O,O-diethyl dithiophosphate(3338-24-7)

Safety Data

• Hazardous Substances Data: 3338-24-7(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C4H11O2PS2.Na/c1-3-5-7(8,9)6-4-2;/h3-4H2,1-2H3,(H,8,9);/q;+1/p-1

Synthetic route

antimony(III) tris(O,O-diethylphosphorodithioate) (875827-00-2, 74153-83-6) → sodium O,O-diethyl phosphorodithioate (3338-24-7)

Conditions	Yield
With sodium pyrrolide In tetrahydrofuran for 2h; Ambient temperature;	70%

ethanol (64-17-5) → sodium O,O-diethyl phosphorodithioate (3338-24-7)

Conditions	Yield
Stage #1: ethanol With tetraphosphorus decasulfide In benzene at 60℃; for 1h; Stage #2: With sodium hydroxide

O,O-Diethyl hydrogen phosphorodithioate (298-06-6) → sodium O,O-diethyl phosphorodithioate (3338-24-7)

Conditions	Yield
With sodium hydroxide In water at 26 - 32℃; for 5.33333h; pH=9;
With sodium hydroxide In water; toluene

[RuCl(η(5)-C5H4Me)(PPh3)2] (55272-36-1) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Ru(C5H4CH3)(P(C6H5)3)S2P(OC2H5)2

Conditions	Yield
In methanol byproducts: NaCl, P(C6H5)3; refluxing under N2, 10-20 min; immediate pptn.; filtration; washing (methanol, water, methanol); drying (vac.); elem. anal.;	100%

chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) (32993-05-8) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Ru(C5H5)(P(C6H5)3)S2P(OC2H5)2

Conditions	Yield
In methanol byproducts: NaCl, P(C6H5)3; refluxing under N2, 10-20 min; immediate pptn.; filtration; washing (methanol, water, methanol); drying (vac.); elem. anal.;	100%

methyl 5-(chloromethyl)-2-furoate (2144-37-8) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → O,O-diethyl S-<5-(methoxycarbonyl)furfuryl> phosphorodithioate

Conditions	Yield
Ambient temperature;	98.7%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + titanium tetrachloride (7550-45-0) → ClTi(S2P(OEt)2)3 (111720-14-0)

Conditions	Yield
In benzene byproducts: sodium chloride; TiCl4 in benzene added to suspn. NaS2P(OEt)2 in benzene (molar ratio 1:3), react. mixt. refluxed for 3 h; ppt. filtered, solvent removed under reduced pressure, product washed with n-hexane and dried; elem. anal.;	98%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → 2,4,6-tris-diethoxythiophosphorylsulfanyl-[1,3,5]triazine (18895-90-4)

Conditions	Yield
In acetone for 24h; Ambient temperature;	95%

lanthanum(III) chloride hydrated + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Na[La(OO'-diethyl phosphorodithioate)4]

Conditions	Yield
In ethanol molar ratio Ln : P = 1 : 4, boiling and stirring (10 min); hot filtration, evapn. to dryness, extn. into hot C6H6, filtration, concn., crystn. on cooling, collection, washing (C6H6), drying (vac.);	95%
In diethyl ether molar ratio Ln : P = 1 : 4, boiling and stirring (10 min); hot filtration, evapn. to dryness, extn. into Et2O, filtration, concn., crystn. on cooling, collection, washing (C6H6), drying (vac.);

lanthanumtrichloridehydrate + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Na[La(OO'-diethyl phosphorodithioate)4]

Conditions	Yield
In ethanol molar ratio of chloride:phosphinate=1:4, boiling for 10 min, manipulations were carried out rapidly in air; filtration, drying, extraction with hot benzene, filtration, concentration, cooling, crystallization, washing with benzene, drying in vac.;	95%
In ethanol molar ratio of chloride:phosphinate=1:4, boiling for 10 min, manipulations were carried out rapidly in air; filtration, drying, extraction with hot benzene, filtration, concentration, cooling, crystallization, washing with benzene, drying in vac.;	95%

Methyltrichlorosilane (75-79-6) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → C13H33O6P3S6Si

Conditions	Yield
In benzene for 5h; Reflux;	95%

aqueous cadmium chloride + sodium O,O-diethyl phosphorodithioate (3338-24-7) → bis(O,O-diethyldithiophosphato)cadmium(II) (17165-77-4)

Conditions	Yield
In ethanol adding of educts to ethanol, refluxing for 1 h; cooling, filtration, recrystn. (ethanol);	93%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + titanium tetrachloride (7550-45-0) → Cl2Ti(S2P(OEt)2)2 (111720-13-9)

Conditions	Yield
In benzene byproducts: sodium chloride; TiCl4 in benzene added to suspn. NaS2P(OEt)2 in benzene (molar ratio 1:2), react. mixt. refluxed for 3 h; ppt. filtered, solvent removed under reduced pressure, product washed with n-hexane and dried; elem. anal.;	93%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + titanium tetrachloride (7550-45-0) → ClTi(S2P(OEt)2)4

Conditions	Yield
In benzene byproducts: sodium chloride; TiCl4 in benzene added to suspn. NaS2P(OEt)2 in benzene (molar ratio 1:4 , react. mixt. refluxed for 3 h; ppt. filtered, solvent removed under reduced pressure, product washed with n-hexane and dried; elem. anal.;	93%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + tri-n-butylchlorogermane (2117-36-4) → tributylgermanium(IV) diethyldithiophosphate (82515-67-1)

Conditions	Yield
In benzene Ge compd. added to suspn. of Na salt in C6H6, mixture refluxed for 2 h; filtration, concg., distn.; elem. anal.;	93%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + 1,3-dibromotetra-n-butyldistannoxane (28520-97-0) → 1-bromo-3-diethyldithiophosphatotetrabutyldistanoxane

Conditions	Yield
In benzene byproducts: NaBr; moisture free atmosphere; addn. of suspn. of dithiophosphate to soln. ofstannoxane, refluxing with stirring (4 h); filtration, solvent removal (vac.), washing (n-hexane); elem. anal.;	92%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + Chloroarsenic(III) (95641-46-6) → dithiophosphoric acid O,O'-diethyl ester S-(5-methyl-benzo[1,3,2]dithiarsol-2-yl) ester

Conditions	Yield
In benzene for 4h; Heating;	91%

C10H20AsClN2S4 + sodium O,O-diethyl phosphorodithioate (3338-24-7) → C14H30AsN2O2PS6

Conditions	Yield
In benzene Heating;	91%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + diphenylantimony(III) chloride (2629-47-2) → diphenylantimony(III) O,O-(C2H5)2-dithiophosphate (126443-50-3)

Conditions	Yield
In benzene byproducts: NaCl; addn. of Na-salt in benzene to Ph2SbCl, refluxing for 2 h; filtn. of NaCl, removing of the volatile fraction under vac. gives a liquid, dissoln. in petroleum ether and keeping in a deep freezer overnight, solvent removal in vac., elem. anal.;	91%

lanthanum(III) chloride heptahydrate + Dibenzyl sulfoxide (621-08-9) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → bis(dibenzyl sulfoxide)tris(O,O'-diethyl dithiophosphato)lanthanum(III)

Conditions	Yield
In ethanol dissolving LaCl3*7H2O, Na(Et2dtp) and dibenzyl sulfoxide in warm ethanol; filtn., removal of the solvent in a vacuum evaporator at 80°C, dissolving the residue in warm benzene, cooling, standing in contact with petroleum ether vapour at room temp. for several days, filtn.;	90%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + Gallium trichloride (13450-90-3) → gallium(III) diethyldithiophosphate (96029-97-9)

Conditions	Yield
In benzene byproducts: NaCl; Na salt was added to the soln. of Ga salt in molar ratio 3:1, the mixt.was refluxed for 2 h; NaCl was filtered, the solvent was removed in vac., elem. anal.;	89%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + triethylchlorogermane (994-28-5) → triethylgermanium(IV) diethyldithiophosphate (60899-40-3)

Conditions	Yield
In benzene Ge compd. added to suspn. of Na salt in C6H6, mixture refluxed for 2 h; filtration, concg., distn.; elem. anal.;	89%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + phenyltin trichloride (1124-19-2) → PhSn(S2P(OEt)2)3 (152408-52-1)

Conditions	Yield
In benzene byproducts: sodium chloride; PhSnCl3 in benzene added to suspn. (EtO)2PS2Na in benzene (molar ratio 1:3) and mixt. refluxed for 3 h; NaCl filtered off, solvent removed under reduced pressure; elem. anal.;	88%

Ni[(OCNHC6H4SCO)C6H4]2(NO3)2 (864763-82-6) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Ni[(OCNHC6H4SCO)C6H4]2[S2P(OC2H5)2]2 (864763-75-7)

Conditions	Yield
In tetrahydrofuran; methanol byproducts: NaNO3; mixed Ni-compd. in THF and Na-compd. in CH3OH in 1:2 molar ratio, refluxed for ca. 2 h; filtered, washed with CH3OH, dried in vac., crystallized with a THF/EtOHmixture (1:1), elem. anal.;	88%

2,4-Dichloro-6-methoxy-1,3,5-triazine (3638-04-8) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Dithiophosphoric acid S-[4-(diethoxy-thiophosphorylsulfanyl)-6-methoxy-[1,3,5]triazin-2-yl] ester O,O'-diethyl ester

Conditions	Yield
In acetone for 24h;	87%

Ni[(OCNHC6H4SCO)(CH2)3]2(NO3)2 (864763-80-4) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Ni[(OCNHC6H4SCO)(CH2)3]2[S2P(OC2H5)2]2 (864763-69-9)

Conditions	Yield
In tetrahydrofuran; methanol byproducts: NaNO3; mixed Ni-compd. in THF and Na-compd. in CH3OH in 1:2 molar ratio, refluxed for ca. 2 h; filtered, washed with CH3OH, dried in vac., crystallized with a THF/EtOHmixture (1:1), elem. anal.;	87%

Ni[(OCNHC6H4SCO)(CH2)4]2(NO3)2 (864763-81-5) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Ni[(OCNHC6H4SCO)(CH2)4]2[S2P(OC2H5)2]2 (864763-72-4)

Conditions	Yield
In tetrahydrofuran; methanol byproducts: NaNO3; mixed Ni-compd. in THF and Na-compd. in CH3OH in 1:2 molar ratio, refluxed for ca. 2 h; filtered, washed with CH3OH, dried in vac., crystallized with a THF/EtOHmixture (1:1), elem. anal.;	87%

Ni[(OCNHC6H4SCO)CH2]2(NO3)2 (864763-78-0) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Ni[(OCNHC6H4SCO)CH2]2[S2P(OC2H5)2]2 (864763-63-3)

Conditions	Yield
In tetrahydrofuran; methanol byproducts: NaNO3; mixed Ni-compd. in THF and Na-compd. in CH3OH in 1:2 molar ratio, refluxed for ca. 2 h; filtered, washed with CH3OH, dried in vac., crystallized with a THF/EtOHmixture (1:1), elem. anal.;	86%

bis(N,N-dimethyldithiocarbamato)arsenic(III) chloride + sodium O,O-diethyl phosphorodithioate (3338-24-7) → C10H22AsN2O2PS6

Conditions	Yield
In benzene for 4h; Heating;	85%

di-μ-chloro-bis(1,5-cyclooctadiene)dirhodium (12092-47-6) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → {(η-cycloocta-1,5-diene)-rhodium(I)-(S2P(OC2H5)2)} (85253-22-1)

Conditions	Yield
In benzene byproducts: NaCl; addition of a solution of the Rh(I) compound (0.51 mmol) in benzene to a suspension of the sodium salt (1.02 mmol) in benzene, stirring (2 - 3 hours), filtration and evaporation;; drying, recrystallization from benzene-hexane; elem. anal.;;	85%

sodium O,O-diethyl phosphorodithioate (3338-24-7) + thallium(I) acetate (563-68-8) → Tl(1+)*(S2P(OC2H5)2)(1-)=Tl(S2P(OC2H5)2)

Conditions	Yield
In water aq. soln. of ligand was added to aq. soln. of TlOCOCH3; ppt. was filtered, dried under reduced pressure, crystd. from toluene; elem. anal.;	85%

(C4H9)2GeCl + sodium O,O-diethyl phosphorodithioate (3338-24-7) → (C4H9)2Ge[S2P(OC2H5)2]2 (82515-70-6)

Conditions	Yield
In benzene Ge compd. added to suspn. of Na salt in C6H6, mixture refluxed for 2 h; filtration, concg., distn.; elem. anal.;	85%

Ni[(OCNHC6H4SCO)(CH2)2]2(CH3COO)2 (864763-84-8) + sodium O,O-diethyl phosphorodithioate (3338-24-7) → Ni[(OCNHC6H4SCO)(CH2)2]2[S2P(OC2H5)2]2 (864763-66-6)

Conditions	Yield
In tetrahydrofuran; methanol byproducts: CH3COONa; mixed Ni-compd. in THF and Na-compd. in CH3OH in 1:2 molar ratio, refluxed for ca. 2 h; filtered, washed with CH3OH, dried in vac., crystallized with a THF/EtOHmixture (1:1), elem. anal.;	85%

Upstream product

• 875827-00-2 antimony(III) tris(O,O-diethylphosphorodithioate) 
• 64-17-5 ethanol 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 

Downstream Products

• 25795-00-0 diethyl S-(phenylthio)methyl phosphorodithioate 
• 2275-18-5 prothoate 
• 6873-73-0 dithiophosphoric acid O,O'-diethyl ester-S-(p-tolylsulfanyl-methyl ester) 
• 786-19-6 carbophenothion 
• 108878-79-1 diethoxythiophosphorylsulfanyl-acetic acid-(4-nitro-phenyl ester) 
• 37602-94-1 O,O-diethyl S-(2-phenyl)ethyl phosphorodithioate 
• 2279-84-7 dithiophosphoric acid O,O'-diethyl ester-S-(dimethylcarbamoyl-methyl ester) 
• 2901-90-8 bis(diethoxyphosphoryl)disulphide 
• 117997-27-0 Di-O-ethyl 3-chloro-5-methoxy-2-<5H>-furanon-4-yl dithiophosphate 
• 298-04-4 disulfoton 
• 21312-72-1 Pd(II) diethyldithiophosphate 
• 126443-50-3 diphenylantimony(III) O,O-(C₂H₅)2-dithiophosphate 
• 2117-78-4 (C₆H₅)3SnS₂P(OC₂H₅)2 

Relevant articles and documents

Method for preparing O,O-dialkyl S-[2-(alkylthio)alkyl] phosphorodithioates

The invention relates to a method of preparing O,O-dialkyl S-[2-(alkylthio)alkyl]phosphorodithioates by treating -O,O-dialkyl dithiophosphoric acids with a base in the substantial absence of organic solvent to obtain O,O-dialkyl dithiophosphoric acid salts that are in turn treated with thioalcohol derivatives to form the O,O-dialkyl S-[2-(alkylthio)alkyl]phosphorodithioates.

NUCLEOPHILIC SUBSTITUTION REACTIONS ON ANTIMONY(III) 0,0-DISUBSTITUTED PHOSPHORODITHIOATES

Antimony(III) tris(O,O-diisobutyl phosphorodithioate), 1 (R=i-Bu) has been found to undergo a nucleophilic displacement reaction with sodium 1-propanethiolate to give antimony(III) tris-(1-propanethiolate), 4, and sodium O,O-diisobutyl phosphorodithioate (8, R=i-Bu).Reaction of 1 (R=i-Bu) with phenyllithium gave triphenylstibine and lithium O,O-diisobutyl phosphorodithioate.Similar reactions of various compounds of type 1 with the sodium salts of carboxylic acids and with the sodium salt of pyrrole were also found to occur.Furthermore, antimony tris(O,O-diisobutyl phosphorodithioate), 1 (R=i-Bu), was found to undergo solvolysis with n- propyl mercaptan to give 4 and O,O-diisobutyl phosphorodithioic acid 5.Compounds of type 1 are used as passivating agents in petroleum refining, and reactions of the types described for 1 with n-propyl mercaptan and with the salts of carboxylic acids probably occur when "Phil-Ad CA" is added to the feedstock of a fluid catalytic cracking unit.