56-34-8

Basic information

• Product Name: Tetraethylammonium Chloride
• Synonyms: ETAMON CHLORIDE;TETRAETHYLAMMONIUM CHLORIDE;TEA CHLORIDE;Ethanaminium,N,N,N-triethyl-,chloride;n,n,n-triethyl-ethanaminiuchloride;n,n,n-triethylethanaminiumchloride;teac;tetraethyl-ammoniuchloride
• CAS NO: 56-34-8
• Molecular Formula: C₈H₂₀N*Cl
• Molecular Weight: 165.7
• EINECS: 200-267-5
• Product Categories: quarternary ammonium salts;Ammonium Chlorides (Quaternary);Quaternary Ammonium Compounds;Ion Channels;Quaternary ammonium salt
• Mol File: 56-34-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 39°C
• Boiling Point: 273.32°C (rough estimate)
• Appearance: white to light yellow/Crystalline Powder
• Density: 1.08
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: Store at RT
• Solubility: methanol: 0.1 g/mL, clear, colorless
• Water Solubility: Soluble in water, ethanol, chloroform, or acetone
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents. Protect from moisture.
• Merck: 14,9200
• BRN: 3563247
• CAS DataBase Reference: Tetraethylammonium Chloride(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraethylammonium Chloride(56-34-8)
• EPA Substance Registry System: Tetraethylammonium Chloride(56-34-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: BS6125000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 56-34-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 56-34-8 differently. You can refer to the following data:
1. Medicine (nerve-blocking agent).
2. Tetraethylammonium Chloride can be used as a source of tetraethylammonium ions for various pharmaceutical studies and has the ability to block K+ channels in various tissues. Tetraethylammonium Chloride can also block the transmission of nervous impulses across autonomic ganglions.
3. Tetraethylammonium chloride (TEAC) has been used:used for inhibition of peroxynitrite induced relaxation in rat aorta ringsas a pharmacological blocker of K+ current and Ca2+ induced K+ current in antennal lobe neuronsfor the induction of TEAC sensitive currents in cochlear inner hair cells digested with proteolytic enzymes and analyze its properties

Definition

ChEBI: A quarternary ammonium chloride salt in which the cation has four ethyl substituents around the central nitrogen.

General Description

Visit our Sensor Applications portal to learn more.

Biological Activity

Non-selective K + channel blocker.

Biochem/physiol Actions

Tetraethylammonium chloride (TEAC) blocks K+ channels non-specifically. In rat aorta rings, tetraethylammonium inhibits relaxation induced by peroxynitrite. It blocks nicotinic acetylcholine neurotransmission by blocking the receptor-mediated K+ currents. TEAC can increase the contractility and mobility of colon and rectum and is a therapeutic option for Hirschsprung′s disease patients. TEAC reduces the inflammatory responses, improves cardiac, vascular and hemodynamic properties during early sepsis in animals. TEAC has cytotoxic and anti-proliferative potential and induces apoptosis in glioma cells by downregulating B-cell lymphoma-2 (Bcl-2) and upregulating Bcl-2 associated X (Bax).

in vitro

tetraethylammonium (tea) is a small ion that is thought to block open k channels by binding either to an internal or to an external site. for this reason, it has been used to probe the ion conduction pathway or pore of k channel mutants and a k channel chimera. tea blocks k+ channels at two sites, which define the inner and outer mouths of the channel pores [1].

in vivo

vasorelaxant effect of taurine can be diminished by tea in rat isolated arteries [2]

Purification Methods

Crystallise the chloride from EtOH by adding diethyl ether, from warm water by adding EtOH and diethyl ether, from dimethylacetamide or from CH2Cl2 by addition of diethyl ether. Dry it over P2O5 in vacuum for several days. It also crystallises from acetone/CH2Cl2/hexane (2:2:1) [Blau & Espenson J Am Chem Soc 108 1962 1986, White & Murray J Am Chem Soc 109 2576 1987]. [Beilstein 4 IV 332.]

references

[1] taglialatela m, vandongen am, drewe ja, joho rh, brown am, kirsch ge. patterns of internal and external tetraethylammonium block in four homologous k+ channels. mol pharmacol. 1991 aug;40(2):299-307.[2] niu lg, zhang ms, liu y, xue wx, liu db, zhang j, liang yq. vasorelaxant effect of taurine is diminished by tetraethylammonium in rat isolated arteries. eur j pharmacol. 2008 feb 2;580(1-2):169-74. epub 2007 oct 25.[3] shea pa, dunklee pe, et al. preliminary clinical investigation of tetraethylammonium chloride with particular reference to disorders of the circulatory system. calif med. 1948 sep;69(3):193-6.

InChI:InChI=1/C6H15N.ClH/c1-4-7(5-2)6-3;/h4-6H2,1-3H3;1H/p-1

Synthetic route

cis-(3,5-bis(ethoxycarbonyl)-4,6-diphenyl-2H-pyran-2-ylidene)dichloro(triphenylphosphine)platinum + tetraethylammonium iodide (68-05-3) → (Pt(CC(CO2C2H5)C(C6H5)C(CO2C2H5)C(C6H5)O)(P(C6H5)3)I2) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In methanol under N2 atm. to soln. NEt4I in CH3OH added (Pt(CC(CO2Et)=C(Ph)C(CO2Et)=C(Ph)O)(PPh3)Cl2) and stirred at room temp. for 24 h; solid filtered off, washed with methanol and dried; elem. anal.;	A 83% B n/a

(tetraethylammonium)(CpFe(carbonyl)2) (57812-16-5) + (η6-p-(CH3O2C)ClC6H4)chromium tricarbonyl (12241-54-2) → cyclopentadienyl iron(II) dicarbonyl dimer (38117-54-3) + (η6-p-(CH3O2C)CpFe(carbonyl)2C6H4)chromium tricarbonyl (114636-10-1) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In tetrahydrofuran Dissolution of reactants in THF (protective gas), swirling.; Filtn., evapn., extn. with Et2O followed by extn. with hot toluene, filtn., concg., refrigeration at -20°C, elem. anal.;	A n/a B 63% C n/a

(tetraethylammonium)(CpFe(carbonyl)2) (57812-16-5) + (η6-m-(CF3)ClC6H4)chromium tricarbonyl (114636-07-6) → cyclopentadienyl iron(II) dicarbonyl dimer (38117-54-3) + (η6-m-(CF3)(CpFe(carbonyl)2)C6H4))chromium tricarbonyl (114636-09-8) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In tetrahydrofuran Dissolution of reactants in THF (protective gas), swirling.; Filtn., evapn., extn. with Et2O followed by extn. with hot toluene, filtn., concg., refrigeration at -20°C, elem. anal.;	A n/a B 60% C n/a

triethylamine hydrochloride (554-68-7) + Diethyl carbonate (105-58-8) → tetraethylammonium chloride (56-34-8)

Conditions	Yield
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;	54%

(tetraethylammonium)(CpFe(carbonyl)2) (57812-16-5) + tricarbonyl(p-(trifluoromethyl)chlorobenzene)chromium (107067-36-7) → cyclopentadienyl iron(II) dicarbonyl dimer (38117-54-3) + (η6-p-(CF3)(CpFe(carbonyl)2)C6H4))chromium tricarbonyl (114636-08-7) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In tetrahydrofuran Dissolution of reactants in THF (protective gas), swirling for 8 h.; Opening flask in air, filtn., evapn., extn. with cold Et2O followed by extn. with hot toluene, filtn., concg., refrigeration at -20°C for 8 h, elem. anal.;	A n/a B 39% C n/a

di-(tetraethylammonium) hexachlororhenate → tetraethylammonium decachlorodirhenate(IV) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In trifluoroacetic acid heating Re-compd. with mixt. of trifluoroaceti acid and trifluoroacetic anhydride (1:1) (Ar atmosphere); partial evapn., washing (solvents), drying (vac., KOH); elem. anal.;	A 35% B n/a

quinoline (91-22-5) + tetraethyl ammonium [Rh(cyclooctadiene)(C10H9N3)2] (120782-55-0) → {Rh(Cl)(1,5-cyclooctadiene)(quinoline)} (120782-62-9) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In dichloromethane addn. of methanol, elimination of CH2Cl2, pptn. filtered off, washed with methanol, air-dried; elem. anal.;	A 31% B n/a

diethyl sulfate (64-67-5) + triethylamine (121-44-8) → tetraethylammonium chloride (56-34-8)

Conditions	Yield
With Petroleum ether durch Zerlegung des entstandenen Aethylsulfats mit wss. Ba(OH)2;

tri-tert-butoxy-chloro-silane (18105-64-1) + tetraethylammoniumcyanide (13435-20-6) → tetraethylammonium chloride (56-34-8) + tri(tert-butoxy)silyl cyanide (110473-67-1) + tri(tert-butoxy)silyl isocyanide (110473-68-2)

Conditions	Yield
In acetonitrile for 1h; Yield given. Yields of byproduct given;

chloroethane (75-00-3) + ammonia (7664-41-7) → tetraethylammonium chloride (56-34-8) + ethylamine (75-04-7) + diethylamine (109-89-7) + triethylamine (121-44-8)

diethyl ether (60-29-7) + ethyl chlorosulfate (625-01-4) + diethylamine (109-89-7) → N,N-diethylamino-sulfonic acid (42731-89-5) + tetraethylammonium chloride (56-34-8) + hydrochloride of triethylamine

Conditions	Yield
at 0℃;

tetraethyl-ammonium; chloride , compound with bromine + lime/chalk/ → tetraethylammonium chloride (56-34-8)

Conditions	Yield
beim Aufbewahren im Exsiccator;

tetraethylammonium tetrachloroborate → tetraethylammonium chloride (56-34-8) + boron trichloride (10294-34-5)

Conditions	Yield
at 100℃;

C18H30N4OS2*C8H20N(1+)*Cl(1-) → tetraethylammonium chloride (56-34-8) + 1-butyl-3-{3-[(3-butyl-thioureido)-methyl]-2-hydroxy-benzyl}-thiourea (321898-65-1)

Conditions	Yield
In chloroform-d1 at 20℃; Equilibrium constant;

N-phenyl methyl carbamate (2603-10-3) → tetraethylammonium chloride (56-34-8)

Conditions	Yield
With aniline In nitrobenzene

nitrosylchloride (2696-92-6) + tetraethylammonium; [36Cl]chloride → nitrosyl chloride + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In neat (no solvent) Kinetics; at -36 - -5°C with or without light;;	A >99 B n/a

tetraethyl ammonium [Rh(cyclooctadiene)(C10H9N3)2] (120782-55-0) → Rh(Cl)(1,5-cyclooctadiene)(ethylenediamine) (108786-85-2) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
With ethylenediamine In dichloromethane pptn. filtered off, washed with CH2Cl2, air-dried;

tetraethylammonium azide (993-20-4) + cyanogen chloride (506-77-4) → cyanogen azide (764-05-6) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In acetonitrile at 0-12°C, in soln. free from water;	A >99 B >99
at 0-12°C, in excess of ClCN;	A >99 B >99
In pentane at 0-12°C, in soln. free from water;	A >99 B >99

sodium benzoate (532-32-1) + bis(1-methyl-2-imidazolyl)hydroxymethane (67319-03-3) + (Et4N)2(Fe2OCl6) (87495-23-6) → {Fe4O2(bis(N-methylimidazol-2-yl)carbinol)2(bis(N-methylimidazol-2-yl)carbinolate)2(O2CPh)4}Cl2*5H2O*2CH3CN (111410-35-6) + tetraethylammonium chloride (56-34-8) + triethylamine hydrochloride (554-68-7) + sodium chloride (7647-14-5)

Conditions	Yield
In dichloromethane; triethylamine; acetonitrile mixt. of the Fe complex in CH3CN and Na benzoate stirred for 0.5 h; mixt. of BICOH in CH3CN/CH2Cl2 and Et3N stirred for 1 h and added to first mixt.; reaction mixt. stirred for 1 h; filtration, solvents removed in vac.; solid washed with hexane/CHCl3; resulting oil dried overnight under vac.; recrystn. from CH3CN; elem. anal.;	A 10-25 B n/a C n/a D n/a

tetraethyl ammonium [Rh(cyclooctadiene)(C10H9N3)2] (120782-55-0) → RhCl(1,5-cyclooctadiene)(PPh3) (31781-57-4) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
With P(C6H5)3 In methanol; dichloromethane CH2Cl2/MeOH 1:1; elimination of CH2Cl2, filtered off, washed with methanol, air-dried;

bis(tetraethylammonium) oxopentachlorotechnetate(V) → tetraethylammonium oxotetrachlorotechnetate(V) + tetraethylammonium chloride (56-34-8)

Conditions	Yield
In not given Tc-complex was dissolved in MeOH or abs. EtOH with decompn.;;

tetraethylammonium chloride (56-34-8) + 2,4,6-Trinitrophenol (88-89-1) → tetraethylammonium picrate (741-03-7)

Conditions	Yield
With 2-chloropyridine In acetonitrile Product distribution; without reagent;	100%

pentaamminetrifluoromethanesulfonato ruthenium(III) trifluoromethanesulfonate (84278-98-8) + tetraethylammonium chloride (56-34-8) → {Ru(NH3)5(pyrazine)}Cl2 (104626-96-2)

Conditions	Yield
With mercury; zinc In acetone addn. of Zn(Hg) to {Ru(NH3)5(OSO2CF3)}(CF3SO3)2 soln. (in degassed acetone), 30 min., addn. to pyrazine soln. (acetone) over 15 min, immediately deep purple soln., react. 30 min (over Zn(Hg)), removal of Zn(Hg), addn. of Et4NCl (in acetonitrile), pptn.; filtration, washing (degassed CH3CN, acetone), drying (vac.); elem. anal.;	100%

pentaamminetrifluoromethanesulfonato ruthenium(III) trifluoromethanesulfonate (84278-98-8) + tetraethylammonium chloride (56-34-8) → {Ru(NH3)5(pyrazine)}(BF4)2 (41481-91-8)

Conditions	Yield
With mercury; zinc In acetone addn. of Zn(Hg) to {Ru(NH3)5(OSO2CF3)}(CF3SO3)2 soln. (in degassed acetone), 30 min., addn. to pyrazine soln. (acetone) over 15 min, react. 30 min (over Zn(Hg)), removal of Zn(Hg), addn. of Et4NCl (in acetonitrile), pptn., recrystn. as BF4(1-) salt; elem. anal.;	100%

iron pentacarbonyl (13463-40-6) + di(rhodium)tetracarbonyl dichloride + tetraethylammonium chloride (56-34-8) → Fe5RhC(CO)16(1-)*(C2H5)4N(1+)={Fe5RhC(CO)16}((C2H5)4N)

Conditions

Yield

With sodium amalgam In diethylene glycol Ar, soln. of Fe(CO)5 treated with Na#Hg, Fe(CO)5 added, stirred and heated to 150-160°C, continued for 3-4 h at 130-140°C, cooledto about 20°C, Rh-compound added, stirred for 30-40 min, filtered, 3-fold excess hexane added; decanted; ppt. washed (hexane); extd. (water); Et4NCl in H2O added; pptfiltered; washed (water); dried (vac., 20°C); recrystd. (CH2Cl2); elem. anal.;

100%

Cl4(OEt2)W(NPh) + tetra-t-butoxy(phenylimido)tungsten(VI) + tetraethylammonium chloride (56-34-8) → tetraethylammonium {tetrachloro(phenylimido)(tert-butoxido)tungsten(VI)}

Conditions	Yield
In dichloromethane W(NCPh)Cl4(Et2O) and org. compd. codissolved in CH2Cl2 under N2, after a few min W(NPh)(OCMe3)4 added (molar ratio 2.9:3.8:0.95), mixture stirred for 8 h; evapn. in vac., recrystn. (CH2Cl2, -30°C);	100%

tetraethylammonium chloride (56-34-8) + tungsten tris(neopentyl)neopentylidyne (68490-69-7) → [Et4N][W(#CtBu)Cl4] (78251-20-4)

Conditions	Yield
With hydrogenchloride In diethyl ether elem. anal.;	100%
With HCl In diethyl ether; dichloromethane ether soln. of HCl was added to CH2Cl2 soln. of W compd. and Et4NCl (N2)at 0°C; 20 min at 0°C, then 30 min at room temp.; filtration, recrystn. from CH2Cl2; elem. anal.;	90%
With HCl In not given W compd. treated with 3 equiv of HCl in presence of N(C2H5)4Cl;

Cl4(OEt2)W(NPh) + tetraethylammonium chloride (56-34-8) → [W(NC6H5)Cl5](1-)*(N(C2H5)4)(1+)=[W(NC6H5)Cl5](N(C2H5)4) (83634-27-9)

Conditions	Yield
In dichloromethane org. compd. added to soln. of W complex in CH2Cl2 under N2, kept for 5 min; cooling to -30°C, filtration, washing with pentane, drying in vac.;	100%

[Co4(CO)3(μ3-CO)3(μ3-C8H8)(η4-C8H8)] + tetraethylammonium chloride (56-34-8) → N(C2H5)4(1+)*Co3(CO)6(C8H8)(1-)=N(C2H5)4Co3(CO)6(C8H8)

Conditions	Yield
With LiHBEt3 In tetrahydrofuran; water inert atm.; LiHBEt3 in THF was added to Co-complex in THF, mixt. was stirred for 0.5 h at room temp., solvent was removed under reduced pressure, redissolved in THF, NEt4Cl in water was added dropwise, stirred for 1 h; pptn. by addn. of n-heptane, ppt. was collected, washed with water and pentane; elem. anal.;	100%

H2N(CH(CH3)2)2(1+)*Os4(CO)12(PO)(1-)=[H2N(CH(CH3)2)2][Os4(CO)12(PO)] + tetraethylammonium chloride (56-34-8) → (C2H5)4N(1+)*Os4(CO)12(PO)(1-)=[(C2H5)4N][Os4(CO)12(PO)]

Conditions	Yield
In dichloromethane N2-atmosphere; crystn. (CH2Cl2 / hexane); elem. anal.;	100%

H2N(CH(CH3)2)2(1+)*Ru4(CO)12(PO)(1-)=[H2N(CH(CH3)2)2][Ru4(CO)12(PO)] + tetraethylammonium chloride (56-34-8) → (C2H5)4N(1+)*Ru4(CO)12(PO)(1-)=[(C2H5)4N][Ru4(CO)12(PO)]

Conditions	Yield
In not given N2-atmosphere; crystn. (CH2Cl2 / hexane); elem. anal.;	100%

Ru(C14H21C15H10N3)(N2C36H38O8(C6H4CN)(C2H4SOCH3))(2+)*2PF6(1-)=[Ru(C29H31N3)(N2C36H38O8(C6H4CN)(C2H4SOCH3))](PF6)2 + tetraethylammonium chloride (56-34-8) → RuCl(C14H21C15H10N3)(N2C36H38O8(C6H4CN)(C2H4SOCH3))(1+)*PF6(1-)=[RuCl(C29H31N3)(N2C36H38O8(C6H4CN)(C2H4SOCH3))]PF6 (888940-16-7, 889103-60-0)

Conditions	Yield
With potassium hexafluorophosphate In dichloromethane-d2 Irradiation (UV/VIS); soln. of Ru complex and Et4NCl in CD2Cl2 irradiated (xenon 1000 W lamp fitted with water filter and Andover 470FS10-50 interference filter) at 25°C for 2 h, aq. KPF6 added; ppt. filtered off, washed with water, recovered with acetone and dried under vac.;	100%

(CH2)18(O(C6H4)2C5H2N(C5H4N)2)Ru(C5H5N)(NC5H2(C6H4O)CHCHC5H2(C6H2(CH3)3)N)(2+)*2PF6(1-)=C77H80N6O2RuP2F12 + tetraethylammonium chloride (56-34-8) → (CH2)18(O(C6H4)2C5H2N(C5H4N)2)RuCl(NC5H2(C6H4O)CHCHC5H2(C6H2(CH3)3)N)(2+)*2PF6(1-)=C72H75N5O2ClRuP2F12

Conditions	Yield
In dimethyl sulfoxide soln. of Ru complex in DMSO was heated at 140°C for 2 h in dark under Ar; KPF6 added; filtered; washed (H2O); recovered with acetone; dried; Et4NCl and acetone were added; refluxed under Ar for 3 h; cooled to room temp.; KPF6 added; filtered; washed (H2O); recovered withacetone; dried; chromd. (silica gel, acetone/H2O/KNO3, 80/5/0.5);	100%

2,5,8-tri-tert-butyl-1,3,4,6,7,9-hexaazaphenalene (1178510-98-9) + tetraethylammonium chloride (56-34-8) → 2,5,8-tri-tert-butyl-1,3,4,6,7,9-hexaazaphenalenyl tetraethylammonium (1254106-85-8)

Conditions	Yield
Stage #1: 2,5,8-tri-tert-butyl-1,3,4,6,7,9-hexaazaphenalene With sodium hydroxide In 1,4-dioxane; water at 80℃; for 1h; Stage #2: tetraethylammonium chloride In 1,4-dioxane; water at 20℃; for 0.5h;	100%

K3Mo(NCS)6 + tetraethylammonium chloride (56-34-8) → 3C8H20N(1+)*C6H6MoN6S6(3-)

Conditions	Yield
Stage #1: K3Mo(NCS)6; tetraethylammonium chloride In water Inert atmosphere; Stage #2: In water; acetonitrile Inert atmosphere;	100%

2F6P(1-)*2C2H3N*C76H60Co2N4S4(2+) + tetraethylammonium chloride (56-34-8) → C38H30ClCoN2S2 (1610803-43-4)

Conditions	Yield
In dichloromethane at 20℃;	100%

[tetra-n-butylammonium][diethylaminonium]4[V12O32]Cl + tetraethylammonium chloride (56-34-8) → [tetra-n-butylammonium]3[tetraethylmmonium][NH3C2H4NH3]0.5[V12O32]Cl

Conditions	Yield
In chloroform at 29.84℃; for 72h; Inert atmosphere;	100%

tetraethylammonium chloride (56-34-8) → tetraethyl-ammonium; chloride , compound with iodine trichloride (6735-56-4)

Conditions	Yield
With I2Cl6 Schlenk technique; Inert atmosphere;	100%
With Iodine monochloride In dichloromethane; acetonitrile at 0℃; for 1h; Inert atmosphere; Schlenk technique;	82%

iron(III) chloride hexahydrate + nitrilotriacetic acid, trisodium salt monohydrate + tetraethylammonium chloride (56-34-8) → [Et4N]2[dichloronitrilotriacetatoiron(III)]

Conditions	Yield
In N,N-dimethyl-formamide FeCl3*6H2O dissolved in DMF, ligand and (CH3CH2)4NCl added, overnight, diluted with acetone; ppt. filtered, recrystd. from MeCN/acetone;	99.8%

{2,6-i-Pr2C6H3NH3}{Re(C-t-Bu)(2,6-i-Pr2C6H3NH)Cl4} + tetraethylammonium chloride (56-34-8) → {NEt4}{Re(C-t-Bu)(2,6-i-Pr2C6H3NH)Cl4}

Conditions	Yield
In dichloromethane N2-filled drybox or Schlenk techniques; Et4NCl added over 1 h under vigorous stirring; soln. filtered, concd., Et2O added until most of ppt. formed, flask left overnight at -40°C; elem. anal.;	99%

(Ti((CH3)2C6H2OCH2)2C4H9C6H2OCl)2 (458525-04-7) + dichloromethane (75-09-2) + tetraethylammonium chloride (56-34-8) → N(C2H5)4(1+)*Ti2((C8H8OCH2)2C4H9C6H2O)2Cl3(1-)*0.5CH2Cl2=N(C2H5)4Ti2(((CH3)2C6H2OCH2)2C4H9C6H2O)2Cl3*0.5CH2Cl2

Conditions	Yield
In tetrahydrofuran the mixt. in THF was stirred at room temp. for 22 h (Ar); solvent was removed in vac.; elem. anal.;	99%

[AlCl(2,2'-methylenebis(6-tert-butyl-4-methylphenoxido))]2 (345196-68-1) + tetraethylammonium chloride (56-34-8) → [[(CH3)(O)C6H2[C(CH3)3]]2CH2]AlCl2(1-)*(C2H5)4N(1+)=[[(CH3)(O)C6H2[C(CH3)3]]2CH2]AlCl2[(C2H5)4N] (503536-09-2)

Conditions	Yield
	99%

trichlorotris(tetrahydrofuran)chromium(III) (10170-68-0, 16997-54-9) + nitrido{bis-N,N'-(salicylaldehyde)ethylenediiminato}manganese(V) (142021-25-8) + tetraethylammonium chloride (56-34-8) + acetonitrile (75-05-8) → N,N'-ethylenebis(salicylideneiminato)manganese(III) chloride*acetonitrile (105241-53-0) + [Cr(N)Cl4](2-)*2N(C2H5)4(1+)=[N(C2H5)4]2[Cr(N)Cl4]

Conditions	Yield
In acetonitrile (N2); dissolving of CrCl3(THF)3 in CH3CN, addn. of Mn(N)(salen), stirring for 1 h, filtration, addn. of soln. of Et4NCl in CH3CN/C2H5OH/H2O (15:14:1) to filtrate; concn., cooling to -5°C, crystn., washing with acetone/water (20:1), elem. anal.;	A 99% B 52%

benzo[1,2,5]thiadiazole (273-13-2, 22706-22-5) + OsH(CS)(NCCH3)2(P(C6H5)3)2(1+)*ClO4(1-) = [OsH(CS)(NCCH3)2(P(C6H5)3)2]ClO4 (218795-12-1) + tetraethylammonium chloride (56-34-8) → [OsHCl(CS)(C6H4N2S)(P(C6H5)3)2] (218794-73-1)

Conditions	Yield
In ethanol; dichloromethane addn. of 2,1,3-benzothiadiazole and Et4NCl in EtOH to the Os complex in CH2Cl2, reflux (1 h); addn. of EtOH, concn. (rotavapor), filtration, washing (EtOH; light petroleum), drying (vac.); elem. anal.;	99%

[Mo(acetylacetonate)(H2O)(η7-cycloheptatrienyl)]BF4 + tetraethylammonium chloride (56-34-8) → [Mo(acetylacetonate)(Cl)(η7-cycloheptatrienyl)]

Conditions	Yield
In acetone N2-atmosphere; excess Et4NCl, refluxing for 1.5 h; filtration, evapn., extn. into hot THF, filtration, evapn., crystn. (CH2Cl2/Et2O, -23°C); elem. anal.;	99%

[(C,N-1-(6-mesityl-2-picolyl)-3-mesitylimidazol-2-ylidene)Rh(1,5-cyclooctadiene)]BF4 + tetraethylammonium chloride (56-34-8) → [(C-1-(6-mesityl-2-picolyl)-3-mesitylimidazol-2-ylidene)Rh(1,5-cyclooctadiene)Cl]

Conditions	Yield
In not given	99%

[(2,6-dimesitylphenyl)(2,6-diethylphenyl)Ge(μ-S)(μ-OH)Ru(PPh3)](B(3,5-(CF3)2C6H3)4) (912672-52-7) + tetraethylammonium chloride (56-34-8) → [(2,6-dimesitylphenyl)(2,6-diethylphenyl)(OH)Ge(μ-S)RuCl(PPh3)] (912672-58-3)

Conditions	Yield
In tetrahydrofuran (N2); std. Schlenk technique; Et4NCl was added to soln. of Ge-Ru complexin THF; mixt. was stirred at room temp. for 1 h; evapd.; chromd. (silica gel, ether); elem. anal.;	99%

dichloromethane (75-09-2) + 3,5-bis(bis[(N'-tert-butylureayl)-N-ethyl]aminomethyl)-1H-pyraze (887280-10-6) + tetraethylammonium chloride (56-34-8) + water (7732-18-5) + cobalt(II) chloride (7646-79-9) → tetraethylammonium μ-hydroxo-μ-(3,5-bis(bis[(N'-tert-butylureaylato)-N-ethyl]aminatomethyl)-1H-pyrazolato)dicobaltate(II) dichloromethane adduct (2/1)

Conditions	Yield
With KH In N,N-dimethyl acetamide byproducts: KCl; (Ar); a soln. of ligand treated with KH, CoCl2 added, stirred for 30 min, H2O added, stirred for 30 min, N(C2H5)4Cl added, stirred for 1 h; evapd. (vac., at room temp.), washed (Et2O), dried (vac.), dissolved in CH2Cl2, filtered, evapd. (vac.); elem. anal.;	99%

[(o-(diphenylphosphino)(N-benzylidene)aniline(-1H))Ir(1,5-cyclooctadiene)H]BF4 + carbon monoxide (201230-82-2) + tetraethylammonium chloride (56-34-8) → [(o-(diphenylphosphino)(N-benzylidene)aniline(-1H))IrHCl(CO)]

Conditions	Yield
In not given	99%

7,7,10,10,19,19,22,22-octamethyl-5,12,17,24-tetrahydro-8,9,20,21-tetrathia-5,12,17,24-tetraaza-dibenzo[a,k]cycloeicosene-6,11,18,23-tetraone (933452-60-9) + tetraethylammonium iron(tetraethylthiolate) (959926-16-0) + tetraethylammonium chloride (56-34-8) → 2N(CH2CH3)4(1+)*FeCl(SC(CH3)2CONC6H4NCOC(CH3)2S)(2-)=(N(CH2CH3)4)2FeCl(SC(CH3)2CONC6H4NCOC(CH3)2S)

Conditions	Yield
In N,N-dimethyl-formamide (under Ar); Fe-complex and N(CH2CH3)4Cl added to DMF soln. of ligand, stirred for 5 h; solvent removed;	99%

Upstream product

• 554-68-7 triethylamine hydrochloride 
• 105-58-8 Diethyl carbonate 
• 64-67-5 diethyl sulfate 
• 121-44-8 triethylamine 
• 68-05-3 tetraethylammonium iodide 
• 120782-55-0 tetraethyl ammonium [Rh(cyclooctadiene)(C₁₀H₉N₃)2] 
• 532-32-1 sodium benzoate 
• 67319-03-3 bis(1-methyl-2-imidazolyl)hydroxymethane 
• 87495-23-6 (Et₄N)2(Fe₂OCl₆) 
• 57812-16-5 (tetraethylammonium)(CpFe(carbonyl)2) 
• 114636-07-6 (η6-m-(CF3)ClC6H4)chromium tricarbonyl 
• 12241-54-2 (η6-p-(CH3O2C)ClC6H4)chromium tricarbonyl 
• 993-20-4 tetraethylammonium azide 
• 506-77-4 cyanogen chloride 

Downstream Products

• 741-03-7 tetraethylammonium picrate 
• 14307-38-1 tetraethylammonium 2-nitrophenolate 
• 13435-20-6 tetraethylammoniumcyanide 
• 7758-95-4 lead(II) chloride 
• 10199-34-5 cis-dichlorobis(triphenylphosphine)platinum(II) 
• 132108-60-2 ((C₂H₅)4N)⁽¹⁺⁾*(Pt(C₆H₅CN)Cl₃)^(1-)=((C₂H₅)4N)(Pt(C₆H₅CN)Cl₃) 
• 23273-29-2 tetraethylammonium(trichloro)phenylborate 
• 118773-91-4 tetraethylammonium pentachloro(pyridine)iridate(IV) 
• 628-13-7 pyridine hydrochloride 
• 59246-46-7 bis(triphenylphosphine)carbonyliridium(I) chloride 
• 80907-59-1 ruthenium(2,2'-bipyrazine)2Cl₂ 
• 13536-48-6 PBrCl₂ 
• 13550-32-8 PClBr₂ 
• 7789-60-8 phosphorus tribromide 

Relevant articles and documents

Process for preparing tetrafluoroborate salt and intermediates thereof

There is provided a process for preparing tetraalkyl ammonium halide utilizing a catalytic amount of acetonitrile in a reaction under pressure and at an elevated temperature of an alkyl halide and a trialkyl halide and in which tetrafluoroborate can be subsequently prepared.

Intermediates useful in a synthesis of 2-chloro-2'-deoxyadenosine

This invention relates to a novel process for preparing 2-chloro-2'-deoxyadenosine (2-CdA) having the following formula STR1 from a compound of the following formula STR2 The invention also relates to intermediates which are useful in preparing 2-CdA. The compound 2-CdA is useful as an antileukemic agent, i.e., in treating leukemias, such as hairy cell leukemia.