1923-70-2

Basic information

• Product Name: Tetrabutylammonium perchlorate
• Synonyms: n,n,n-tributyl-1-butanaminiuperchlorate;TETRABUTYLAMMONIUM PERCHLORATE ELECTRO-C HEMICAL GRADE;Tetrabutylammonium perchlorate, contains max. 10% water, 99%;TETRABUTYLAMMONIUM PERCHLORATE REAGENT;Tetrabutylammoniumperchlorate,min.98%;1-Butanaminium, N,N,N-tributyl-, perchlorate;tetra-n-butylammonium perchlorate, electrochemical grade;Tetra-n-butylammonium perchlorate, 99+%
• CAS NO: 1923-70-2
• Molecular Formula: C₁₆H₃₆N*ClO₄
• Molecular Weight: 341.91
• EINECS: 217-655-5
• Product Categories: Ammonium Polyhalides, etc. (Quaternary);Oxidation;Quaternary Ammonium Compounds;Synthetic Organic Chemistry;Detergents A to ZSynthetic Reagents;Detergents;Perchlorates;Ammonium SaltsSynthetic Reagents;Greener Alternatives: Catalysis;Phase Transfer Catalysts;Ammonium SaltsAnalytical Reagents;Electrochemistry;Supporting Electrolytes for Electrochemistry;metal perchlorate salt
• Mol File: 1923-70-2.mol
• Article Data: 19

Chemical Properties

• Melting Point: 211-215 °C
• Appearance: White/Crystalline Powder
• Density: 1.0387 (rough estimate)
• Refractive Index: 1.6800 (estimate)
• Solubility: acetonitrile: 0.1 g/mL, clear, colorless
• Water Solubility: Soluble in acetonitrile and ethanol. Very slightly soluble in water.
• Sensitive: Hygroscopic
• Stability: Stable. Strong oxidizer - contact with combustible material may cause fire. Incompatible with strong reducing agents, combustibl
• BRN: 3579274
• CAS DataBase Reference: Tetrabutylammonium perchlorate(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrabutylammonium perchlorate(1923-70-2)
• EPA Substance Registry System: Tetrabutylammonium perchlorate(1923-70-2)

Safety Data

• Hazard Codes: O,Xi
• Statements: 5-8-36/37/38
• Safety Statements: 17-26-36-36/37/39
• RIDADR: UN 1479 5.1/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 5.1
• PackingGroup: II
• Hazardous Substances Data: 1923-70-2(Hazardous Substances Data)

Usage

Chemical Description

Tetrabutylammonium perchlorate is a salt commonly used as a supporting electrolyte in electrochemical experiments.

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 1923-70-2 differently. You can refer to the following data:
1. Tetrabutylammonium perchlorate is a polarographic supporting electrolyte.
2. Suitable for use as a polarographic supporting electrolyteTetra-n-butylammonium perchlorate is used as a supporting electrolyte in polarographic measurements.
3. Tetrabutylammonium perchlorate is a tetraalkylammonium salt that can be used in phase-transfer catalysis.

General Description

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Purification Methods

Crystallise the perchlorate from EtOH ethyl acetate, from n-hexane or diethyl ether/acetone mixture, ethyl acetate or hot CH2Cl2. Dry it in a vacuum at room temperature over P2O5 for 24hours. [Anson et al. J Am Chem Soc 106 4460 1984, Ohst & Kochi J Am Chem Soc 108 2877 1986, Collman et al. J Am Chem Soc 108 2916 1986, Blau & Espenson J Am Chem Soc 108 1962 1986, Gustowski et al. J Am Chem Soc 108 1986, Ikezawa & Kutal J Org Chem 52 3299 1987, Beilstein 4 IV 557.]

InChI:InChI=1/C16H36N.ClHO4/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;2-1(3,4)5/h5-16H2,1-4H3;(H,2,3,4,5)/q+1;/p-1

Synthetic route

tetrabutylammomium bromide (1643-19-2) → tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
With trimethyl phosphite; perchloric acid at 0 - 60℃; for 15h; Inert atmosphere; neat (no solvent);	95%
With perchloric acid
With perchloric acid
With perchloric acid

(NBu4)2{palladium(μ-Br)bis(pentafluorophenyl)}2 (74436-10-5) + silver perchlorate → cis-[Pd(pentafluorophenyl)2(THF)2] + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In tetrahydrofuran byproducts: AgCl; Addn. of AgClO4 to soln. of Pd-complex under N2, stirring (room temp., 20 min).; Evapn. of suspn. to dryness, extg. of residue (diethyl ether), evapn., addn. of n-hexane.;	A 90% B n/a

N-n-Bu4{Au(C6Cl5)2} + silver perchlorate → [{Au(C6Cl5)2}Ag]n + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane AgClO4 added to (NBu4)(Au(C6Cl5)2) in dichloromethane and stirred at room temp. for 6 h;; ppt. filtered off and washed with diethylether; elem. anal.;	A 90% B n/a

NBu4[Ag(C6F5)2] + {Ag(CH2P(C6H5)3)2}(1+)*ClO4(1-)={Ag(CH2P(C6H5)3)2}ClO4 → {Ag(C6F5)(CH2P(C6H5)3)} + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In diethyl ether stirred at room temp. for 8 h; filtered off (N(C4H9)4)(ClO4), soln. concd., addn. of n-hexane, pptn.; elem. anal.;	A 85% B n/a

(NBu4)2{palladium(μ-Br)bis(pentachlorophenyl)}2 (86392-02-1) + silver perchlorate → cis-[Pd(C6Cl5)2(thf)2] + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In tetrahydrofuran byproducts: AgCl; Addn. of AgClO4 to soln. of Pd-complex under N2, stirring (room temp., 20 min).; Evapn. of suspn. to dryness, extg. of residue (diethyl ether), evapn., addn. of n-hexane.;	A 80% B n/a

{NBu4}{Pt(pentafluorophenyl)4} + [Ag(OClO3)(tetrahydrothiophene)] (1020072-44-9, 132018-77-0) → tetrabutylammonium tetrakis(pentafluorophenyl)-1κ4C1-tetrahydrothiophene-2κS-platinumargentate (Ag-Pt) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, room temp., 5 min; evapn. to dryness, treated with Et2O, filtration, evapn. to dryness, washeed with hexane, dried in vac.;	A 80% B n/a

{NBu4}{Pt(pentafluorophenyl)4} + {Ag(tetrahydrothiophene)}ClO4 (137400-80-7) → tetrabutylammonium tetrakis(pentafluorophenyl)-1κ4C1-tetrahydrothiophene-2κS-platinumargentate (Ag-Pt) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, room temp., 5 min; evapn. to dryness, treated with Et2O, filtration, evapn. to dryness, washed with hexane, elem. anal.;	A 79% B n/a

perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) + {(C4H9)4N}{cis-Pt(C6F5)2(C6Cl5)(tetrahydrothiophene)} → (C4H8S)(C6Cl5)(C6F5)2PtAg(P(C6H5)3) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, 0°C, 30 min; evapn. to dryness, washing with i-PrOH, elem. anal.;	A 78% B n/a

(NBu4)2{trans-PtCl2(C6Cl5)2} + perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) → N(C4H9)4(1+)*PtAgCl2(C6Cl5)2(P(C6H5)3)(1-) = (N(C4H9)4){PtAgCl2(C6Cl5)2(P(C6H5)3)} + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane exclusion of light; addn. of Ag-compd. to soln. of Pt-compd. in CH2Cl2 (molar ratio Pt-compd./Ag-compd. 1:1), stirring (room temp., 1 h); evapn., treatment with cold MeOH (0°C), filtn., washing (MeOH); elem. anal.;	A 77% B n/a

perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) + {(C4H9)4N}{cis-Pt(C6F5)(C6Cl5)2(triphenylphosphine)} → ((C6H5)3P)(C6Cl5)2(C6F5)PtAg(P(C6H5)3) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, 0°C, 30 min; evapn. to dryness, extn. with Et2O, filtration, evapn. to dryness, treated with hexane, elem. anal.;	A 77% B n/a

(NBu4)2{platinum2(μ-pentafluorophenyl)2(pentafluorophenyl)4} (116349-58-7) + silver perchlorate → (NBu4){platinum2(silver)(μ-pentafluorophenyl)2(pentafluorophenyl)4(diethyl ether)} (95674-06-9) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In diethyl ether; dichloromethane Addn. of AgClO4 to a CH2Cl2 soln. of Pt-complex (molar ratio 1:1) and stirring of mixt. (exclusion of light, room temp., 1 h).; Evapn. of soln. to dryness and treatment of resulting oily residue with O(C2H5)2 to separate the insoluble org. compd. Evapn. of ether soln. to dryness gives a solid.;	A 76% B n/a

(NBu4)2{platinum(pentafluorophenyl)3Cl} (90621-02-6) + silver perchlorate → (NBu4)2{platinum2(μ-pentafluorophenyl)2(pentafluorophenyl)4} (116349-58-7) + tetrabutylammonium perchlorate (1923-70-2) + silver(I) chloride

Conditions	Yield
In dichloromethane Addn. of AgClO4 to a CH2Cl2 soln. of Pt-complex and stirring of mixt. (exclusion of light, room temp., 2 h).; Filtn. of formed AgCl, evapn. of resulting yellow soln. to dryness and treatment of obtained oily residue with O(C2H5)2 to separate the insoluble org. compd. Evapn. of ether soln. to dryness gives a solid.;	A 76% B n/a C n/a

perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) + {(C4H9)4N}{Pt(C6Cl5)3(pyridine)} → {(pyridine)(C6Cl5)3PtAg(triphenylphosphine)} + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, 0°C, 30 min; evapn. to dryness, extn. with Et2O, filtration, evapn. to dryness, treated with hexane, elem. anal.;	A 75% B n/a

perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) + {(C4H9)4N}{cis-Pt(C6F5)2(C6Cl5)(triphenylphosphine)} → ((C6H5)3P)(C6Cl5)(C6F5)2PtAg(P(C6H5)3) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, 0°C, 30 min; evapn. to dryness, extn. with Et2O, filtration, evapn. to dryness, treated with hexane, elem. anal.;	A 73% B n/a

(NBu4)2{platinum(pentafluorophenyl)3Cl} (90621-02-6) + silver perchlorate → (NBu4){platinum2(silver)(μ-pentafluorophenyl)2(pentafluorophenyl)4(diethyl ether)} (95674-06-9) + tetrabutylammonium perchlorate (1923-70-2) + silver(I) chloride

Conditions

Yield

In diethyl ether; dichloromethane Addn. of AgClO4 to a CH2Cl2 soln. of Pt-complex (molar ratio 2:1) and stirring of mixt. (exclusion of light, room temp., 2 h).; Filtn. of formed AgCl and of excess of AgClO4, evapn. of resulting yellow soln. to dryness and washing of obtained oily residue with O(C2H5)2 to separate the insoluble org. compd. Partial evapn. of yellow soln. and addn. of n-hexane gives a solid.;

A 72% B n/a C n/a

perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) + {(C4H9)4N}{cis-Pt(C6F5)2(C6Cl5)(pyridine)} → (C5H5N)(C6Cl5)(C6F5)2PtAg(P(C6H5)3) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, 0°C, 30 min; evapn. to dryness, extn. with Et2O, filtration, evapn. to dryness, treated with hexane, elem. anal.;	A 72% B n/a

perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) + {(C4H9)4N}{Pt(C6Cl5)3(triphenylphosphine)} → (triphenylphosphine)(C6Cl5)3PtAg(triphenylphosphine) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, 0°C, 30 min; evapn. to dryness, extn. with Et2O, filtration, evapn. to dryness, treated with hexane, elem. anal.;	A 70% B n/a

triphenylphosphinesilver perchlorate + (NBu4)2{platinum2(μ-pentafluorophenyl)2(pentafluorophenyl)4} (116349-58-7) → (NBu4){platinum2(silver)(μ-pentafluorophenyl)2(pentafluorophenyl)4(PPh3)} (116349-60-1) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane Addn. of O3ClOAgPPh3 to a soln. of Pt-compd. (CH2Cl2, -30°C) and stirring of mixt. (30 min, -30°C, exclusion of light).; Pumping of soln. to dryness (-30°C) and treatment of residue with O(C2H5)2 (-30°C). Evapn. of soln. to dryness and addn. of n-hexane after sepn. of insoluble NBu4ClO4.;	A 69% B n/a

{NBu4}{Pt(pentafluorophenyl)4} + perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) → tetrabutylammonium tetrakis(pentafluorophenyl)-1κ4C1-triphenylphosphine-2κP-platinumargentate (Ag-Pt) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, room temp., 5 min; evapn. to dryness, addn. of Et2O, filtration, evapn. to dryness, treated with hexane, drying in vac., elem. anal.;	A 68% B n/a

perchlorato(triphenylphosphane)silver(I) (73165-02-3, 623171-38-0) + {(C4H9)4N}{Pt(C6Cl5)3(tetrahydrothiophene)} → (tetrahydrothiophene)(C6Cl5)3PtAg(triphenylphosphine)} + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, 0°C, 30 min; evapn. to dryness, extn. with Et2O, filtration, evapn. to dryness, treated with hexane, elem. anal.;	A 68% B n/a

trans-dichlorobis(pyridine)platinum(II) (14024-97-6, 14872-21-0, 15227-42-6) + {NBu4}{Pt(C6F5)3(OCMe2)} → [NBu4]2[Pt2(μ-pentafluorophenyl)2(pentafluorophenyl)4] + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane; acetone addn. of trans-(PtCl2(py)2) to soln. of Pt-complex in CH2Cl2/acetone (2:1), stirring (1 h); evapn. to dryness, washing (diethyl ether, 2.product solid), evapn. of washings to dryness, treatment with i-PrOH/hexane;	A 58% B n/a

[μ-nitrido-bis(triphenylphosphorus)][Au(2,4,6-CC6F3H2)2] + silver perchlorate → Au(1+)*Ag(1+)*2C6F3H2(1-)=AuAg(C6F3H2)2 + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In diethyl ether equimolar amt. of AgClO4 was added to soln. of Au-compound in Et2O, stirred for 1 h; filtered, filtrate evapd., hexane added; elem. anal.;	A 56% B >99

O3ClOAg(P(C2H5)3) (107556-35-4) + (NBu4)2{trans-PtCl2(C6Cl5)2} → Pt(C6Cl5)2((μ-Cl)Ag(PEt3))2 + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane exclusion of light; addn. of Ag-compd. to soln. of Pt-compd. in CH2Cl2 (molar ratio Pt-compd./Ag-compd. 1:2), stirring (room temp., 2 h); evapn., treatment with MeOH, filtn., washing (MeOH); elem. anal.;	A 51% B n/a

{NBu4}{Pt(pentafluorophenyl)4} + Ag(OClO3)(O(C2H5)2) → tetrabutylammonium tetrakis(pentafluorophenyl)-1κ4C1-diethyl ether-2κO-platinumargentate (Ag-Pt) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, room temp., 5 min; evapn. to dryness, addn. of Et2O, filtration, evapn. to dryness, treated with hexane, drying in vac., elem. anal.;	A 50% B n/a

{NBu4}{Pt(pentafluorophenyl)4} + silver perchlorate → tetrabutylammonium tetrakis(pentafluorophenyl)-1κ4C1-diethyl ether-2κO-platinumargentate (Ag-Pt) + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
With diethyl ether In dichloromethane with exclusion of light, molar ratio of starting materials is 1:1, room temp., 5 min; evapn. to dryness, addn. of Et2O, filtration, evapn. to dryness, treated with hexane, drying in vac., elem. anal.;	A 50% B n/a

perchlorato(methyldiphenylphosphane)silver(I) (110373-27-8) + (NBu4)2{trans-PtCl2(C6Cl5)2} → Pt(C6Cl5)2((μ-Cl)Ag(PPh2Me))2 + tetrabutylammonium perchlorate (1923-70-2)

Conditions	Yield
In dichloromethane exclusion of light; addn. of Ag-compd. to soln. of Pt-compd. in CH2Cl2 (molar ratio Pt-compd./Ag-compd. 1:1), stirring (room temp., 1 h); filtn., evapn., treatment with MeOH; elem. anal.;	A 39% B n/a
In dichloromethane exclusion of light; addn. of Ag-compd. to soln. of Pt-compd. in CH2Cl2 (molar ratio Pt-compd./Ag-compd. 1:2), stirring (room temp., 1 h); filtn., evapn., treatment with MeOH; elem. anal.;	A 73-77 B n/a

Didodecyl-(3-methyl-2-butenyl)-sulfonium perchlorate + tetrabutylammonium dihydrogen phosphate → didodecyl sulfide (2469-45-6) + tetrabutylammonium perchlorate (1923-70-2) + (methyl-2 butene-3 yl-2) phosphate de potassium (110071-93-7)

Conditions	Yield
With Potassium benzoate; copper(I) bromide In dichloromethane	A n/a B n/a C 17%

tetrabutylammonium perchlorate (1923-70-2) + boron trichloride (10294-34-5) → tetrabutylammonium trichloroperchloratoborate (54775-46-1)

Conditions	Yield
In chloroform introducing of gaseous BCl3 to soln. of <(C4H9)4N> in CHCl3 at 20°C; distn. and drying in vac.;	100%
In neat (no solvent) Bu4NClO4 reacted slowly with excess of BCl3 at 20°C; elem. anal.;
In chloroform Bu4NClO4 reacted slowly with BCl3 in CHCl3 at 20°C; elem. anal.;
In chloroform

4,5-dimethylethylene (trans,trans) sulphate (4440-89-5) + tetrabutylammonium perchlorate (1923-70-2) → trans-2-Butene (624-64-6) + C4H8O8S2(2-)*2K(1+) + 2C16H36N(1+)*C6H12O8S2(2-)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; Product distribution; electrolysis, oth. solvent, var. cathodes;	A 99% B 42% C n/a

boron trifluoride (7637-07-2) + tetrabutylammonium perchlorate (1923-70-2) → tetrabutylammonium trifluoroperchloratoborate

Conditions	Yield
In chloroform Bu4NClO4 reacted with BF3 in CHCl3 at 20°C;	99%

Ru(2,6-(C6H5NCO)2C5H3N)(2,2',2''-terpyridine) (1007838-83-6) + tetrabutylammonium perchlorate (1923-70-2) → [Ru(2,6-(C6H5NCO)2C5H3N)(2,2',2''-terpyridine)]ClO4 (1007838-97-2)

Conditions	Yield
In dichloromethane; acetonitrile Electrolysis; 1:9 CH2Cl2:MeCN (0.1 M TBAP), 0.4 V vs. SCE, 298 K; layering over toluene, slow diffusion, elem. anal.;	99%

Ru(2,6-(4-CH3C6H4NCO)2C5H3N)(2,2',2''-terpyridine) (1007838-80-3) + tetrabutylammonium perchlorate (1923-70-2) → [Ru(2,6-(4-CH3C6H4NCO)2C5H3N)(2,2',2''-terpyridine)]ClO4 (1007838-95-0)

Conditions	Yield
In dichloromethane; acetonitrile Electrolysis; 1:9 CH2Cl2:MeCN (0.1 M TBAP), 0.4 V vs. SCE, 298 K; layering over toluene, slow diffusion, elem. anal.;	99%

Ru(2,6-(4-CH3OC6H4NCO)2C5H3N)(2,2',2''-terpyridine) (1007838-78-9) + tetrabutylammonium perchlorate (1923-70-2) → [Ru(2,6-(4-CH3OC6H4NCO)2C5H3N)(2,2',2''-terpyridine)]ClO4 (1007838-91-6)

Conditions	Yield
In dichloromethane; acetonitrile Electrolysis; 1:9 CH2Cl2:MeCN (0.1 M TBAP), 0.4 V vs. SCE, 298 K; layering over toluene, slow diffusion, elem. anal.;	99%

Ru(N,N'-bis(4'-chlorophenyl)pyridine-2,6-dicarboxamide)(2,2',2''-terpyridine) (1007838-85-8) + tetrabutylammonium perchlorate (1923-70-2) → [Ru(2,6-(ClC6H4NCO)2C5H3N)(2,2',2''-terpyridine)]ClO4 (1007838-99-4)

Conditions	Yield
In dichloromethane; acetonitrile Electrolysis; 1:9 CH2Cl2:MeCN (0.1 M TBAP), 0.4 V vs. SCE, 298 K; layering over toluene, slow diffusion, elem. anal.;	99%

Ru(2,6-(O2NC6H4NCO)2C5H3N)(2,2',2''-terpyridine) (1007838-88-1) + tetrabutylammonium perchlorate (1923-70-2) → [Ru(2,6-(O2NC6H4NCO)2C5H3N)(2,2',2''-terpyridine)]ClO4 (1007839-01-1)

Conditions	Yield
In dichloromethane; acetonitrile Electrolysis; 1:9 CH2Cl2:MeCN (0.1 M TBAP), 0.4 V vs. SCE, 298 K; layering over toluene, slow diffusion, elem. anal.;	99%

Au3(MeN=COMe)3 + tetrabutylammonium perchlorate (1923-70-2) → [Au3(MeN=COMe)3](ClO4)0.34

Conditions	Yield
In dichloromethane Electrolysis;	99%

pyridine (110-86-1) + Vanadium (III) chloride-(tris-tetrahydrofuran) (131063-11-1, 16997-51-6, 19559-06-9) + tetrabutylammonium perchlorate (1923-70-2) + water (7732-18-5) + sodium acetate (127-09-3) → [V3O(O2CMe)6(pyridine)3](ClO4) (178882-95-6)

Conditions	Yield
In pyridine; acetic acid; acetonitrile byproducts: NaCl; N2-atmosphere; stirring V-complex with AcONa in MeCN/AcOH/pyridine=2:1:2v/v/v for 24 h, filtration off of NaCl, Bu4NClO4 addn.; further educt: acetic acid; vol. reduction (vac.), pptn. on Et2O addn., collection (filtration), washing (Et2O), drying (vac.); elem. anal.;	95%

ammonium thiocyanate + ammonium hexabromotechnetate + tetrabutylammonium perchlorate (1923-70-2) → {(n-C4H9)4N}3{Tc(NCS)6}

Conditions	Yield
With N2H4*H2O In methanol NH4SCN and (NH4)2TcBr6 refluxed in methanol under N2 or Ar for 24 h, system cooled to room temp., N2H4*H2O added, mixt. filtered under inert atm., filtrate treated with n-Bu4NClO4 in methanol; solid filtered under inert atm., washed with water, methanol, dried in vac.; elem. anal.;	93%

picoline (108-89-4) + Vanadium (III) chloride-(tris-tetrahydrofuran) (131063-11-1, 16997-51-6, 19559-06-9) + tetrabutylammonium perchlorate (1923-70-2) + water (7732-18-5) + sodium acetate (127-09-3) → [V3O(O2CMe)6(4-picoline)3](ClO4)

Conditions	Yield
In acetic acid; acetonitrile N2-atmosphere; stirring V-complex with AcONa in MeCN/AcOH/4-picoline=2:1:2.2 v/v/v for 24 h, filtration off of NaCl, Bu4NClO4 addn.; further educt: acetic acid; vol. reduction (vac.), pptn. on Et2O addn., collection (filtration), washing (Et2O), drying (vac.); elem. anal.;	91%

(tetrahydrothiophene)gold(I) chloride (39929-21-0) + tetrabutylammonium perchlorate (1923-70-2) + lithium-2,4,6-trifluorophenyl (53732-49-3) → [μ-nitrido-bis(triphenylphosphorus)][Au(2,4,6-CC6F3H2)2]

Conditions	Yield
In diethyl ether byproducts: Au; mixing soln. of Au-complex and ligand (-78°C), stirring for 20 min, warming to room temp., stirring (30 min), filtration, addn. to Bu4N(ClO4) soln. (pptn.); recrystn. (CH2Cl2/EtOH);	90%

osmium(2,2'-bipyridine)2(3,5-di-tert-butylcatechol) (129264-47-7) + tetrabutylammonium perchlorate (1923-70-2) → {osmium(2,2'-bipyridine)2(3,5-di-tert-butylcatechol)}perchlorate

Conditions	Yield
In methanol; dichloromethane stirred in air at room temp. for 24h; cooled in a refrigerator; elem. anal.;	90%

potassium cyanide + [platinum(II)(μ-chloride)(2-( p-tolyl)-pyridine(-H))]2 (400654-03-7) + tetrabutylammonium perchlorate (1923-70-2) + acetonitrile (75-05-8) → [(n-butyl)4N][platinum(II)(CN)2(2-( p-tolyl)-pyridine(-H))]*0.5(acetonitrile)

Conditions	Yield
Stage #1: [platinum(II)(μ-chloride)(2-( p-tolyl)-pyridine(-H))]2 With silver perchlorate In acetonitrile for 7h; Darkness; Stage #2: potassium cyanide In methanol for 2h; Stage #3: tetrabutylammonium perchlorate; acetonitrile Further stages;	90%

2-(1,8-naphthyridin-2-yl)thiazole (170439-30-2) + tetraacetatodiruthenium chloride + tetrabutylammonium perchlorate (1923-70-2) + water (7732-18-5) → cis-[Ru2(2-(2-thiazolyl)-1,8-naphthyridine)2(OAc)2][ClO4]2(H2O)0.5

Conditions	Yield
Stage #1: 2-(2-thiazolyl)-1,8-naphthyridine; tetraacetatodiruthenium chloride; tetrabutylammonium perchlorate In methanol Inert atmosphere; Schlenk technique; Reflux; Stage #2: water Inert atmosphere; Schlenk technique;	90%

tetrabutylammonium perchlorate (1923-70-2) + C78H55Co5N24O(3+)*3BF4(1-)*3.75C2H3N*0.33H2O + acetonitrile (75-05-8) → C78H55Co5N24O(2+)*2ClO4(1-)*2C2H3N

Conditions	Yield
Glovebox; Inert atmosphere; Electrochemical reaction;	90%

tris(pentafluorophenyl)(tetrahydrothiophene)gold(III) + tetrabutylammonium perchlorate (1923-70-2) + sodium N,N-dimethyldithiocarbamate dihydrate (128-04-1) → N(C4H9)4(1+)*Au(C6F5)3(S2CN(CH3)2)(1-) = {N(C4H9)4}{Au(C6F5)3(S2CN(CH3)2)}

Conditions	Yield
In dichloromethane; acetone byproducts: NaClO4; to soln. of Au complex in acetone added Na(S2CNMe2)*2H2O, stirred for 2 h at room temp., evapd. to dryness, soln. of (NBu4)ClO4 in CH2Cl2 added, stirred for 1h at room temp.; filtered, washed with CH2Cl2, filtrate and washings were evapd. in vac. to ca. 5 ml, upon addition of n-hexane pptd. product; elem. anal.;	89%

tris(pentafluorophenyl)(tetrahydrothiophene)gold(III) + tetrabutylammonium perchlorate (1923-70-2) + sodium N,N-dimethyldithiocarbamate dihydrate (128-04-1) → N(C4H9)4(1+)*{Au(C6F5)3}2(S2CN(CH3)2)(1-) = {N(C4H9)4}{{Au(C6F5)3}2(S2CN(CH3)2)}

Conditions	Yield
In dichloromethane; acetone to soln. of Au complex in acetone added Na(S2CNMe2)*2H2O, stirred for 2 h at room temp., evapd. to dryness, soln. of (NBu4)ClO4 in CH2Cl2 added, stirred for 1h at room temp.; filtered, washed (2*5 ml) with CH2Cl2, filtrate and washings were evapd. in vac. to ca. 5 ml, upon addition of n-hexane pptd. product; elem. anal.;	89%

1,4,8,11-Tetraazacyclotetradecane (295-37-4) + tetrabutylammonium perchlorate (1923-70-2) + iron (7439-89-6) + acetonitrile (75-05-8) → [Fe(1,4,8,11-tetraazacyclotetradecane)(CH3CN)2](ClO4)2

Conditions	Yield
With trifluorormethanesulfonic acid In acetonitrile Ar-atmosphere; refluxing excess Fe with CF3SO3H for 4 h, filtration, mixing with cyclam, refluxing for 30 min, addn. of Bu4NClO4, refluxing for 30 min; cooling in ice bath, Et2O addn. (pptn.);	88%

potassium cyanide + [Pt(2-phenylpyridinate)(NCMe)2]ClO4 (1048673-03-5) + tetrabutylammonium perchlorate (1923-70-2) → tetrabutylammonium dicyano[(2-pyridyl)phenyl-2-ido]platinate(II) (167647-56-5)

Conditions	Yield
In methanol KCN was added to suspn. Pt complex in MeOH at room temp. and stirred for1 h, soln. was filtered through Celite and evapd. to dryness, Bu4NClO4 and acetone were added and stirred for 1 h; soln. was filtered through Celite, soln. was evapd. to dryness, residue was treated with water, filtered, dried (110°C) and recrystd. from CH2Cl2-Et2O; elem. anal.;	88%

[2,2]bipyridinyl (366-18-7) + [NBu4]2[Pd4(μ-Cl)4(μ-PPh2)2(C6F5)4] + tetrabutylammonium perchlorate (1923-70-2) → [Pd2(μ-PPh2)(C6F5)4(bipy)2][ClO4] (195203-54-4)

Conditions	Yield
In isopropyl alcohol; acetone stirring Pd-complex with bipy (in Me2CO) for 10 min, partial evapn., add. if i-PrOH and Bu4NClO4; pptn. on partial evapn.., collection (filtration), washing (i-PrOH), drying in air; elem. anal.;	87%

[NBu4]2[Pd4(μ-Cl)4(μ-PPh2)2(C6F5)4] + tetrabutylammonium perchlorate (1923-70-2) + 1,10-phenanthroline hydrate (5144-89-8) → [Pd2(μ-PPh2)(C6F5)4(phen)2][ClO4] (195203-56-6)

Conditions	Yield
In isopropyl alcohol; acetone stirring Pd-complex with phen (in Me2CO) for 10 min, partial evapn., add. if i-PrOH and Bu4NClO4; pptn. on partial evapn.., collection (filtration), washing (i-PrOH), drying in air; elem. anal.;	87%

potassium cyanide + [(C6F5)2Pt(μ-PPh2)2Pt(μ-PPh2)2Pt(CH3CN)2] + tetrabutylammonium perchlorate (1923-70-2) → [NBu4]2[(RF)2Pt(μ-PPh2)2Pt(μ-PPh2)2Pt(CN)2]

Conditions	Yield
In acetone at 20℃; for 12h;	87%

tris(pentafluorophenyl)(tetrahydrothiophene)gold(III) + tetrabutylammonium perchlorate (1923-70-2) + sodium diethyldithiocarbamate trihydrate (20624-25-3) → N(C4H9)4(1+)*{Au(C6F5)3}2(S2CN(C2H5)2)(1-) = {N(C4H9)4}{{Au(C6F5)3}2(S2CN(C2H5)2)}

Conditions	Yield
In dichloromethane; acetone appropriated choice of molar ratio of educts; to soln. of Au complex in acetone added Na(S2CNEt2)*3H2O, stirred for 2 h at room temp., evapd. to dryness, soln. of (NBu4)ClO4 in CH2Cl2 added, stirred for 1h at room temp.; filtered, washed (2*5 ml) with CH2Cl2, filtrate and washings were evapd. in vac. to ca. 5 ml, upon addition of n-hexane pptd. product; elem. anal.;	84%

1,4-diiodo-2,3,5,6-tetrafluorobenzene (392-57-4) + tetrabutylammonium perchlorate (1923-70-2) → 1.5C6F4I2*C16H36N(1+)*ClO4(1-)

Conditions	Yield
In methanol at 20℃;	84%

Upstream product

• 1643-19-2 tetrabutylammomium bromide 
• 14999-75-8 Triethylammonium perchlorate 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 
• 73165-02-3 perchlorato(triphenylphosphane)silver(I) 
• 228118-52-3 tetrabutylammonium dimethylaurate(I) 
• 1020072-44-9 [Ag(OClO₃)(tetrahydrothiophene)] 
• 137400-80-7 {Ag(tetrahydrothiophene)}ClO₄ 

Downstream Products

• 624-64-6 trans-2-Butene 
• 110315-78-1 {(CH₃C(CH₂P(C₆H₅)2)3)Co(O₂C₆Cl₄)}⁽¹⁺⁾*ClO₄^(1-)={(CH₃C(CH₂P(C₆H₅)2)3)Co(O₂C₆Cl₄)}ClO₄ 
• 92999-16-1 (C₄H₉)4N⁽¹⁺⁾*[Au(C₆F₅)2(CN)2]^(1-)=(C₄H₉)4N[Au(C₆F₅)2(CN)2] 
• 202535-07-7 Cr₄O₂(O₂CCH₃)7(C₁₀H₈N₂)2⁽¹⁺⁾*ClO₄^(1-)=[Cr₄O₂(O₂CCH₃)7(C₁₀H₈N₂)2](ClO₄) 
• 7647-14-5 sodium chloride 
• 1227952-97-7 chloro(N,N'-di-tert-butyl-2,11-diaza[3.3](2,6)pyridinophane)phenylpalladium(III) perchlorate 
• 1626-24-0 chlorotriphenylgermane 
• 914-45-4 tetra-n-butylammonium picrate 
• 14999-75-8 Triethylammonium perchlorate 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 1643-19-2 tetrabutylammomium bromide 
• 311-28-4 tetra-(n-butyl)ammonium iodide 
• 10442-39-4 tetra-n-butylammonium cyanide 

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