71-91-0

Basic information

• Product Name: Tetraethylammonium bromide
• Synonyms: TETRAETHYLAMMONIUM BROMIDE;TEAB;TEA BROMIDE;Ammonium, tetraethyl-, bromide;Beparon;Bromethyl;Bromure de tetraethylammonium;tmd10
• CAS NO: 71-91-0
• Molecular Formula: Br*C₈H₂₀N
• Molecular Weight: 210.16
• EINECS: 200-769-4
• Product Categories: quarternary ammonium salts;Ammonium Bromides (Quaternary);Quaternary Ammonium Compounds;Ammonium Salts;Greener Alternatives: Catalysis;Phase Transfer Catalysts;Ion-pair Reagents;Pharmaceutical intermediates;surfactant
• Mol File: 71-91-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 285 °C (dec.)(lit.)
• Appearance: White to cream/Liquid
• Density: 1,397 g/cm3
• Vapor Density: 5.3 (vs air)
• Refractive Index: 1,442-1,444
• Storage Temp.: Store at room temperature.
• Solubility: acetonitrile: 0.1 g/mL warm, clear, colorless
• Water Solubility: 2795 g/L (25 º C)
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,9199
• BRN: 3563430
• CAS DataBase Reference: Tetraethylammonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraethylammonium bromide(71-91-0)
• EPA Substance Registry System: Tetraethylammonium bromide(71-91-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: BS5950000
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 71-91-0(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystalline solid

Uses

Different sources of media describe the Uses of 71-91-0 differently. You can refer to the following data:
1. Tetraethylammonium Bromide, can be used as a source of tetraethylammonium ions for various pharmaceutical studies. It has also the ability to block K+ channels in various tissues.
2. Tetraethylammonium bromide (TEAB) catalyzes the synthesis of thioesters by the oxidative coupling of aldehydes or alcohols with thiols or disulfides.It is used as a catalyst, along with o-iodoxybenzoic acid (IBX), in the oxidation of sulfides to sulfoxides and primary carboxamides to one-carbon dehomologated nitriles.TEAB can also be used as an organic template to synthesize zeolite beta.

General Description

The use of ion-pairing reagents as mobile phase additives allows the separation of ionic and highly polar substances on reversed phase HPLC columns. The purity of mobile phase additives is of utmost importance to their successful application. Sigma-Aldrich offers an outstanding range of tailor-made reagents for anionic (quaternary ammonium and phosphonium salts) and cationic (alkanesulfonates) determination. All mobile phase additives are subject to rigorous testing with special emphasis on the requirements of modern reversed phase HPLC:

Purification Methods

Recrystallise the bromide from EtOH, CHCl3 or diethyl ether, or recrystallise it from acetonitrile and dry it over P2O5 under reduced pressure for several days. It also recrystallises from EtOH/diethyl ether (1:2), EtOAc, water or boiling MeOH/acetone (1:3) or by adding an equal volume of acetone and allowing to cool. Dry it at 100o in vacuo for 12 days, and store over P2O5. [Beilstein 4 IV 332.]

InChI:InChI=1/C8H20N.BrH/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H/q+1;/p-1

Synthetic route

trans-2-bromobutenedioic acid dimethyl ester (2509-16-2) + triethylamine (121-44-8) → tetraethylammonium bromide (71-91-0) + dimethyl diethylaminofumarate (996-85-0, 98033-35-3)

Conditions	Yield
In acetonitrile for 7h; Heating;	A 98.6% B 87%

ethyl bromide (74-96-4) + triethylamine (121-44-8) → tetraethylammonium bromide (71-91-0)

Conditions	Yield
In acetonitrile at 60℃; for 72h;	98%

(Et4N)2{Mo3(μ3-S)(μ2-S2)3Br6} → (PPh3)3Mo3(μ3-S)(μ2-S)3Br4 + tetraethylammonium bromide (71-91-0) + triphenylphosphine sulfide (3878-45-3)

Conditions	Yield
With P(C6H5)3 In methanol Stirring of a suspn. of Mo-compd. and PPh3 (MeOH, 1 h).; Filtn. of pptd. green solid, washing with hot MeOH and benzene, drying (vac.), elem. anal.;	A 60% B n/a C >99

quinoline (91-22-5) + Et4N{Rh(1,5-cyclooctadiene)Br2} (120782-58-3) → {Rh(Br)(1,5-cyclooctadiene)(quinoline)} (120782-61-8) + tetraethylammonium bromide (71-91-0)

Conditions	Yield
In dichloromethane addn. of methanol, elimination of CH2Cl2, pptn. filtered off, washed with methanol, air-dried; elem. anal.;	A 53% B n/a

(Et4N)2{Mo3(μ3-S)(μ2-S2)3Br6} → Mo3(μ3-S)(μ2-S)3(dppe)3Br4 + tetraethylammonium bromide (71-91-0)

Conditions	Yield
With C2H4(P2(C6H5)4) In methanol byproducts: (dppe)S2; Boiling of Mo-compd. with dppe (MeOH, 1 h).; Recrystn. of bright green ppt. from a CH2Cl2/hexane mixt., elem. anal.;	A 48% B n/a

diethyl sulfate (64-67-5) + triethylamine (121-44-8) → tetraethylammonium bromide (71-91-0)

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

cis+trans-dibromoethylene (540-49-8) + triethylamine (121-44-8) → tetraethylammonium bromide (71-91-0) + diethylamine (109-89-7)

triethylamine (121-44-8) + toluene (108-88-3) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → ethyl 2-diethylaminopropanoate (82614-48-0) + tetraethylammonium bromide (71-91-0) + triethylamine hydrobromide (636-70-4)

Conditions	Yield
at 50℃;

triethylamine (121-44-8) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → ethyl 2-diethylaminopropanoate (82614-48-0) + tetraethylammonium bromide (71-91-0) + triethylamine hydrobromide (636-70-4)

Conditions	Yield
at 107℃;

dimethyl 2-bromofumarate (20688-29-3) + triethylamine (121-44-8) → tetraethylammonium bromide (71-91-0) + dimethyl diethylaminofumarate (996-85-0, 98033-35-3)

Conditions	Yield
In acetonitrile for 7h; Heating;

dimethyl 2,3-dibromobutane-1,4-dicarboxylate (51575-86-1) + triethylamine (121-44-8) → tetraethylammonium bromide (71-91-0) + dimethyl diethylaminofumarate (996-85-0, 98033-35-3)

Conditions	Yield
In acetonitrile for 7h; Heating;

triethylamine (121-44-8) + 2-bromobutyric acid ethyl ester (533-68-6) → crotonic acid pin-2-en-10-yl ester + butyric acid pin-2-en-10-yl ester (79433-52-6) + tetraethylammonium bromide (71-91-0) + ester of/the/ α-oxy-butyric acid

Conditions	Yield
at 100℃;

triethylamine (121-44-8) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → LACTIC ACID (849585-22-4) + tetraethylammonium bromide (71-91-0) + triethylammonium hydroxidepropionic acid

Conditions	Yield
nachfolgende Verseifung;

piperazine (110-85-0) + tetraethylammonium hydroxide (77-98-5) + bromoacetic acid (79-08-3) → 2C8H20N(1+)*C8H12N2O4(2-) + tetraethylammonium bromide (71-91-0)

Conditions	Yield
In water at 80℃; Title compound not separated from byproducts;

2C8H20N(1+)*C8H12N2O4(2-) + Benzyl bromoacetate (5437-45-6) → (4-benzyloxycarbonylmethoxycarbonylmethyl-piperazin-1-yl)-acetic acid benzyloxycarbonylmethyl ester + tetraethylammonium bromide (71-91-0)

Conditions	Yield
In acetonitrile for 8h; Heating; Title compound not separated from byproducts;	A 216 mg B n/a

tetraethylammonium hexabromorhenate(IV) → tetraethylammonium decabromodirhenate(IV) + tetraethylammonium bromide (71-91-0)

Conditions	Yield
In trifluoroacetic acid heating Re-compd. with mixt. of trifluoroaceti acid and trifluoroacetic anhydride (1:1) (Ar atmosphere); washing (solvents), drying (vac., KOH); elem. anal.;	A 75-85 B n/a

Et4N{Rh(1,5-cyclooctadiene)Br2} (120782-58-3) → Rh(Br)(1,5-cyclooctadiene)(ethylenediamine) (120782-68-5) + tetraethylammonium bromide (71-91-0)

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

Et4N{Rh(1,5-cyclooctadiene)Br2} (120782-58-3) → Rh(Br)(1,5-cyclooctadiene)(triphenylphosphine) (33136-93-5) + tetraethylammonium bromide (71-91-0)

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

C6H5O(1-)*C6H6O*C8H20N(1+) (1392488-19-5) + benzyl bromide (100-39-0) → (benzyloxy)benzene (946-80-5) + tetraethylammonium bromide (71-91-0) + phenol (108-95-2)

Conditions	Yield
In acetonitrile at 20℃;

Br(1-)*C8H20N(1+)*C4H10O2 → tert.-butylhydroperoxide (75-91-2) + tetraethylammonium bromide (71-91-0)

Conditions	Yield
In [D3]acetonitrile at 24.84℃; Equilibrium constant;

tetraethylammonium bromide (71-91-0) + trans-3-Brom-5-(phenylsulfonyl)cyclopenten → Tetraethylammonium-phenylsulfonylcyclopentadienid

Conditions	Yield
With sodium hydride 1.) THF, 2.) CH2Cl2;	100%

tetraethylammonium bromide (71-91-0) + trans-3-Brom-5-(p-tolylsulfonyl)cyclopenten → Tetraethylammonium-(4-methylphenylsulfonyl)cyclopentadienid

Conditions	Yield
With sodium hydride 1.) THF, 1 h, 2.) CH2Cl2;	100%

1-benzyloxymethyl-9-(4'-β-(dibenzylphosphono)methoxy-2',3'-dideoxy-2',3'-didehydro-β-D-erythrofuranosyl)hypoxanthine (1232003-43-8) + tetraethylammonium bromide (71-91-0) → 9-(2',3'-dideoxy-4'-β-phosphonomethoxy-β-D-erythrofuranosyl)hypoxanthine di(triethylammonium) salt

Conditions	Yield
With 5% Pd(II)/C(eggshell); hydrogen In methanol under 760.051 Torr;	100%

C32H33N4O9P (1232003-54-1) + tetraethylammonium bromide (71-91-0) → 9-(4'-β-phosphonomethoxy-β-D-erythrofuranosyl)hypoxanthine di(triethylammonium) salt

Conditions	Yield
With 5% Pd(II)/C(eggshell); hydrogen In methanol under 760.051 Torr;	100%

2-pyridylphenyl-biphenyl-2,2'-silane + tetraethylammonium bromide (71-91-0) + methyllithium (917-54-4) → tetraethylammonium methyl 2-pyridylphenyl-biphenyl-2,2'-silicate

Conditions	Yield
Stage #1: 2-pyridylphenyl-biphenyl-2,2'-silane; methyllithium In tetrahydrofuran; diethyl ether at -78 - 20℃; for 0.5h; Stage #2: tetraethylammonium bromide In tetrahydrofuran; diethyl ether at 20℃;	100%

tetraethylammonium bromide (71-91-0) + dimethyl sulfate (77-78-1) → tetraethylammonium methyl sulfate (20648-49-1)

Conditions	Yield
In acetonitrile at 20℃; for 0.583333h;	100%

tetraethylammonium bromide (71-91-0) + methyl trifluoromethanesulfonate (333-27-7) → methyl bromide (74-83-9) + tetraethylammonium trifluoromethanesulphonate (35895-69-3)

Conditions	Yield
In acetonitrile at 20℃; for 0.583333h; Temperature;	A n/a B 100%

tetraethylammonium bromide (71-91-0) + methyl p-toluene sulfonate (80-48-8) → tetraethylammonium tosylate (733-44-8)

Conditions	Yield
In acetonitrile at 20℃; for 0.583333h;	100%

Methyl methanesulfonate (66-27-3) + tetraethylammonium bromide (71-91-0) → tetraethylammonium methanesulfonate (16909-18-5)

Conditions	Yield
In acetonitrile at 20℃; for 0.583333h;	100%

tin (7440-31-5) + o-tetrachloroquinone (2435-53-2) + tetraethylammonium bromide (71-91-0) → N(C2H5)4(1+)*SnBr(O2C6Cl4)2(1-)={(C2H5)4N}{SnBr(O2C6Cl4)2}

Conditions	Yield
In toluene; acetonitrile under dry N2, finely divided metal and o-quinone refluxed in toluene (24 h), filtration, addn. of Et4NBr in minimum amount of CH3CN (light-brown solid deposit), stirred (2 h, room temp.), addn. of diethyl ether, pptn.; filtration, evapn.; elem. anal.;	99%

[Cs][Re(CO)3(η(5)-7,8-C2B9H11)] (58904-63-5) + tetraethylammonium bromide (71-91-0) → [NEt4][3,3,3-(CO)3-closo-3,1,2-ReC2B9H11]

Conditions	Yield
In dichloromethane	99%

2H3O(1+)*3Mn(2+)*2Re6Se8(CN)6(4-)*23.5H2O=(H3O)2((Mn(H2O)1.5)3(Re6Se8(CN)6)2)*19H2O + tetraethylammonium bromide (71-91-0) → 2(C2H5)4N(1+)*3Mn(2+)*2Re6Se8(CN)6(4-)*12.5H2O=((C2H5)4N)2((Mn(H2O)2)3(Re6Se8(CN)6)2)*6.5H2O

Conditions	Yield
In water (H3O)2((Mn(H2O)1.5)3(Re6Se8(CN)6)2)*19H2O was stirred in hot aq. soln. Et4NBr for 2 h; ppt. was filtered, washed with water and air-dried; elem. anal.;	99%

[HB(3,5-bis(trifluoromethyl)pyrazolyl)borate]Na(H2O) + tetraethylammonium bromide (71-91-0) → [Et4N][HB(3,5-bis(trifluoromethyl)pyrazolyl)borate]

Conditions	Yield
In dichloromethane byproducts: NaBr, water; N2-atmosphere; equimolar amts., room temp.; filtration, solvent removal from filtrate; can be recrystallized (CH2Cl2/hexane); elem. anal.;	99%

Cs[3,3,3-(CO)3-8-I-closo-3,1,2-ReC2B9H10] + tetraethylammonium bromide (71-91-0) → [NEt4][3,3,3-(CO)3-8-I-closo-3,1,2-ReC2B9H10]

Conditions	Yield
In dichloromethane react. mixt. was filtered through Celite, solvent was removed in vacuo;	99%

copper(II) choride dihydrate + 4Cs(1+)*Re6Te8(CN)6(4-)*3H2O=Cs4Re6Te8(CN)6*3H2O + tetraethylammonium bromide (71-91-0) + ammonia (7664-41-7) + ethylenediamine (107-15-3) → di(tetraethylammonium)[Cu(NH3) bis(ethylenediamine)]2[Cu bis(ethylenediamine)[Re6Te8(CN)6]2] (H2O)2

Conditions	Yield
In ammonia aq. NH3; Cu salt and ethylenediamine in aq.NH3 added to soln. of Re complex and Et4NBr in aq.NH3, kept in a closed vessel at room temp. for 2 weeks; filtered, dried, elem. anal.;	99%

nickel(II) chloride hexahydrate + 4,6-bis(4-methoxyphenyl)-thieno[3,4-d]-1,3-dithiol-2-one (1042436-03-2) + tetraethylammonium bromide (71-91-0) → N(CH2CH3)4(1+)*Ni(C4S3(C6H4OCH3)2)2(1-)=N(CH2CH3)4Ni(C4S3(C6H4OCH3)2)2

Conditions	Yield
With CH3CH2ONa In tetrahydrofuran (Ar); addn. of EtONa to a soln. of ligand in THF, stirring for 40 min, addn. of ammonium salt, then metal salt, react. for 24 h; filtration, washing with water; elem. anal.;	99%

tetraethylammonium bromide (71-91-0) + nickel(II) thiocyanate (13689-92-4) → (Et4N)4[Ni(NCS)6]

Conditions	Yield
With KNCS In water aq. soln. of Ni compd. and aq. soln. of bromide and K salt were combined; kept for 1 wk; elem. anal.;	99%

C8H20N(1+)*C41H47B11N5O5(1-) + tetraethylammonium bromide (71-91-0) → C8H20N(1+)*C31H37B11N5(1-)

Conditions	Yield
Stage #1: C8H20N(1+)*C41H47B11N5O5(1-) With ammonium bromide In ethylenediamine at 80℃; for 22h; Microwave irradiation; Stage #2: tetraethylammonium bromide In water	99%

3,3,3',3'-tetrakis(trifluoromethyl)-1,1'(3H,3'H)-spirobi<2,1-benzoxasilole> (70091-69-9) + tetraethylammonium bromide (71-91-0) + trimethylsilylmethyllithium (1822-00-0) → C22H19F12O2Si2(1-)*C8H20N(1+)

Conditions	Yield
Stage #1: 3,3,3',3'-tetrakis(trifluoromethyl)-1,1'(3H,3'H)-spirobi<2,1-benzoxasilole>; trimethylsilylmethyllithium In diethyl ether at -78 - 20℃; for 3h; Stage #2: tetraethylammonium bromide In dichloromethane for 1h;	99%

2,3,5,6-tetramethylthiophenol (14786-84-6) + tetraethylammonium bromide (71-91-0) + iron(III) chloride (7705-08-0) → [Et4N][Fe(2,3,5,6-tetramethylbenzenethiolate)4]

Conditions	Yield
With Li In methanol N2-atmosphere; addn. of Li-wire to thiol, treatment with FeCl3 and Et4NBr;	98%
With Li In ethanol N2-atmosphere; addn. of Li-wire to thiol, treatment with FeCl3 and Et4NBr;	98%

dipotassium pentacarbonylchromate + tricarbonyl(η6-chlorobenzene)chromium (12082-03-0) + tetraethylammonium bromide (71-91-0) → (benzene)tricarbonylchromium (697302-50-4, 697302-51-5, 12082-08-5, 697302-53-7) + {Et4N}{η6-{(CO)5Cr}(C6H5)Cr(CO)3}

Conditions	Yield
In not given reaction of K2(Cr(CO)5) with (η6-ClC6H5)Cr(CO)3, aq. workup; 1H NMR, IR;	A 98% B 0%

dipotassium pentacarbonyltungstate(-II) + tricarbonyl(η6-chlorobenzene)chromium (12082-03-0) + tetraethylammonium bromide (71-91-0) → (benzene)tricarbonylchromium (697302-50-4, 697302-51-5, 12082-08-5, 697302-53-7) + {Et4N}{η6-{(CO)5W}(C6H5)Cr(CO)3} + (C2H5)4N(1+)*W2H(CO)10(1-)={(C2H5)4N}{W2H(CO)10}

Conditions	Yield
In not given reaction of K2(W(CO)5) with (η6-ClC6H5)Cr(CO)3, aq. workup; 1H NMR, IR;	A 98% B 0% C n/a

[closo-3-triphenylphosphine-3,3-nitrato-3,1,2-RhC2B9H11] (82807-97-4) + tetraethylammonium bromide (71-91-0) → [closo-3,3-(triphenylphosphine)2-3-bromide-3,1,2-RhC2B9H11] dichloromethane solvate

Conditions	Yield
With PPh3 In dichloromethane under Ar, Rh complex dissolved in CH2Cl2 at room temp., PPh3 added withstirring, after 5 min (C2H5)4NBr added, mixt. stirred for 45 min; chromd., treated with heptane, evapd., washed with petroleum ether, dried by suction;	98%

K3AsSe3 + tetraethylammonium bromide (71-91-0) + mercury dichloride → (C2H5)4N(1+)*HgAsSe3(1-)=(C2H5)4N[HgAsSe3]

Conditions	Yield
In water (N2), heating (sealed Pyrex tube, 110°C, 2 d); dissolving educts excess and KCl (water, methanol), washing (anhydrous eher); semiquantitative microprobe analysis;	98%

4-bromotetrahydro-2H-pyran (25637-16-5) + 3,3,3',3'-tetrakis(trifluoromethyl)-1,1'(3H,3'H)-spirobi<2,1-benzoxasilole> (70091-69-9) + tetraethylammonium bromide (71-91-0) → tetraethylammonium bis[α,α-bis(trifluoromethyl)benzenemethanolate(2-)-C2,O]-4-tetrahydropyranylsilicate

Conditions	Yield
Stage #1: 4-bromotetrahydro-2H-pyran With iodine; magnesium In tetrahydrofuran at 60℃; Inert atmosphere; Stage #2: 3,3,3',3'-tetrakis(trifluoromethyl)-1,1'(3H,3'H)-spirobi<2,1-benzoxasilole> In tetrahydrofuran Inert atmosphere; Reflux; Stage #3: tetraethylammonium bromide In dichloromethane at 20℃; for 1h;	98%

tungsten hexacarbonyl (14040-11-0) + tetraethylammonium bromide (71-91-0) → tetraethylammonium bromopentacarbonyltungstate (14780-94-0)

Conditions	Yield
In 1,4-dioxane heating at reflux, 2 h; after cooling, addn. of petroleum ether, washing (petroleum ether), heated (60°C, under vac. for 2 h to remove unreacted W(CO)6), uptake in THF (under N2), mixture is filtered and stripped;	97%
In 1,4-dioxane for 2h; Reflux;	86%
In diethylene glycol Anhydrous Et4NBr was heated with an excess of M(CO)6 in dimethyldigol at 120°C under dry N2;; soln. was filtered hot under N2, light petroleum added and cooling at -5°C for ca. 8 h; crystals was washed and dried;;	90-95
In diethylene glycol byproducts: CO; NEt4Br (18 mmol) was heated with an excess of metal hexacarbonyl (23 mmol, purified by sublimation) in O(CH2CH2OMe)2 at ca. 120°C under dry N2;; filtration while hot under N2; addn. of equal amt. of light petroleum (b.p. 40-60°C) and cooling to -5°C for ca. 6 h; the solventwas decanted, the ppt. washed with light petroleum; heating at 60°C (0.001 mm Hg) for ca. 2 h;;	90-95
In 2-methoxy-ethanol byproducts: CO; N2 atmosphere; refluxing (2 h); cooling, solvent removal (vac.), recrystn. (CH2Cl2/hexane);

2N(CH2CH3)4(1+)*W3S7Br6(2-) =[N(CH2CH3)4]2[W3S7Br6] + tetraethylammonium bromide (71-91-0) + potassium thioacyanate (333-20-0) → 5(C2H5)4N(1+)*W3S4(4+)*9NCS(1-)=((C2H5)4N)5W3S4(NCS)9

Conditions	Yield
In acetonitrile (Et4N)2W3S7Br6 and KSCN boiled for 1 h in Ar, Et4NBr in water added; ppt. filtered, washed with water, ethanol, benzene and ether; elem. anal.;	97%

tungsten hexacarbonyl (14040-11-0) + potassium hydridotris(3,4,5-trimethyl-1H-pyrazol-1-yl)borate + tetraethylammonium bromide (71-91-0) → [NEt4][(hydridotris(3,4,5-trimethylpyrazolyl)borate)W(CO)3]

Conditions	Yield
Stage #1: tungsten hexacarbonyl; potassium hydridotris(3,4,5-trimethyl-1H-pyrazol-1-yl)borate In N,N-dimethyl-formamide at 130℃; for 2.5h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: tetraethylammonium bromide In water; N,N-dimethyl-formamide at 60℃; Inert atmosphere; Saturated gas; Glovebox;	97%

Upstream product

• 74-96-4 ethyl bromide 
• 121-44-8 triethylamine 
• 64-67-5 diethyl sulfate 
• 540-49-8 cis+trans-dibromoethylene 
• 108-88-3 toluene 
• 535-11-5 Ethyl 2-bromopropionate 
• 533-68-6 2-bromobutyric acid ethyl ester 
• 120782-58-3 Et₄N{Rh(1,5-cyclooctadiene)Br₂} 
• 1392488-19-5 C₆H₅O^(1-)*C₆H₆O*C₈H₂₀N⁽¹⁺⁾ 
• 100-39-0 benzyl bromide 
• 91-22-5 quinoline 
• 5437-45-6 Benzyl bromoacetate 
• 110-85-0 piperazine 
• 77-98-5 tetraethylammonium hydroxide 

Downstream Products

• 703-56-0 N-phenyl-2-oxazolidinone 
• 65368-15-2 C₂₁H₁₈BCl₂^(1-)*C₈H₂₀N⁽¹⁺⁾ 
• 1185-59-7 tetraethylammonium acetate 
• 97878-07-4 tetraethylammonium bis<α,α-bis(trifluoromethyl)benzenemethanolato (2-)-C²,O><3-(trifluoromethyl)phenyl>silicate(1-) 
• 97878-01-8 tetraethylammonium bis<α,α-bis(trifluoromethyl)benzenemethanolato(2-)-C²,O>(pentafluorophenyl)silicate(1-) 
• 128096-91-3 C₈H₂₀N⁽¹⁺⁾*C₈H₅BrN₂P^(1-) 
• 32580-88-4 tetraethylammonium 2,4-dinitrophenolate 
• 3774-76-3 Tentraethylammonium 4-nitrophenoxide 
• 108-86-1 bromobenzene 
• 120-92-3 cyclopentanone 
• 62-53-3 aniline 
• 103-84-4 Acetanilid 
• 121-44-8 triethylamine 
• 74-84-0 ethane 

Relevant articles and documents

Versatile Method for the Simultaneous Synthesis of Two Ionic Liquids, Otherwise Difficult to Obtain, with High Atom Economy

A new synthetic approach and full spectral (NMR, IR, MS) and ion chromatographic characterization (IC) of nitrogen-based ionic liquids bearing allyl- or ethyl- substituent and triflate, tosylate, methyl sulfate or methanesulfonate anion has been presented. On a sample of 16 new ionic liquids, the versatility of the anion exchange method has been proven. In the metathesis reactions that have been carried out, the halide anion was exchanged in ionic liquid with an alkyl sulfonate based anion using alkylating agents. The results obtained using ion chromatographic analysis on the newly synthesized compounds have been discussed. Also, the utilization of a gaseous methyl halide by-product, obtained in the metathesis reaction and otherwise difficult to synthesize, has been presented. This approach ensured high atom economy of the overall process, which makes the proposed methodology sustainable and eco-friendly.

Method of producing oxyborate Tetracyanobicyclo (by machine translation)

PROBLEM TO BE SOLVED: To provide a method for efficiently producing a tetracyanoborate compound (VI). SOLUTION: A boron compound (for example, boron trichloride) and an ammonium derivative having a halogenide ion as a counter anion are mixed in xylol; then, a trialkylsilyl cyanide is added and reacted; the reaction system is subjected to a treatment with hydrogen peroxide, and an extraction treatment with butyl acetate; and butyl acetate is distilled out to obtain a tetracyanoborate compound represented by formula (VI) wherein [Kt]m+ is an ammonium cation; and m=1. In the formula, [Kt]m+ denotes an organic cation or an inorganic cation; and m denotes an integer of 1 to 3. COPYRIGHT: (C)2012,JPO&INPIT

Physicochemical characterization of MFm--based ammonium ionic liquids

A series of ammonium-based ionic liquids (ILs), which share a homologous series of cations (CH3CH2)3N+(C nH2n+1) with n = 2, 4, 6, 8 and the anions with either BF4-, PF6-, or SbF6 -, was synthesized. Their structures were confirmed by 1H and 13C NMR, ESI-MS, and elemental analysis. Meanwhile, the content of impurity (e.g., water and bromide ions) was also determined using Karl Fischer titrator and ion chromatography. The thermal properties of the ILs were determined by TGA and DSC. Five of the investigated ILs have been shown to have a low melting point (2222]BF4, N,N,N,N-tetraethylammonium hexafluorophosphate, [N2222]PF6, N,N,N- triethylhexylammonium tetrafluoroborate, [N2226]BF4, N,N,N-triethyloctylammonium hexafluorophosphate, [N2228]PF 6 and N,N,N-triethyloctylammonium hexafluoroantimonate, [N 2228]SbF6. Densities, refractive indices, and miscibility of these 12 ILs were well studied systematically. Moreover, from the analysis of the structure-property relationship, the role of the alkyl chain length of the cation on these physical properties of the ILs has been assessed, and the influence of the nature of the anions on these experimental data of the ILs has been discussed. The studies may provide valuable contributions for the design and study of ILs.