1643-19-2

Basic information

• Product Name: Tetrabutylammonium bromide
• Synonyms: Tetrabu ylammonium bromide (TBAB);1-Butanaminium,N,N,N-tributyl-, bromide (1:1);Tetrabutylammonium b;TetrabutylaMMoniuM BroMide(Ipc-Tba-Br );TetrabutylaMMoniuM broMide, 99+% 100GR;TetrabutylaMMoniuM broMide, 99+% 25GR;TetrabutylaMMoniuM broMide, 99+% 500GR;Butyl AMoniuM BroMide
• CAS NO: 1643-19-2
• Molecular Formula: C₁₆H₃₆BrN
• Molecular Weight: 322.37
• EINECS: 216-699-2
• Product Categories: Other Products;organo amine halide;Pharmaceutical intermediates;quarternary ammonium salts;Ammonium Bromides (Quaternary);Analytical Chemistry;HPLC Ion-Pair Reagents for Acidic Samples;Ion-Pair Reagents for HPLC;Quaternary Ammonium Compounds;Ammonium, Phosphonium, Sulfonium Salts (Ionic Liquids);Ionic Liquids;Synthetic Organic Chemistry;Ammonium Salts;Greener Alternatives: Catalysis;Phase Transfer Catalysts;Ammonium SaltsEssential Chemicals;Reagent Plus;Routine Reagents;Ammonium SaltsAnalytical Reagents;Electrochemistry;Supporting Electrolytes for Electrochemistry;Ion Pair Reagents - Anionic Concentrate;AnionicHPLC;Chromatography/CE Reagents;Ion Pair;Ion Pair Reagents;Ion Pair Reagents - Anionic
• Mol File: 1643-19-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: 102-106 °C(lit.)
• Boiling Point: 102 °C
• Flash Point: 100℃
• Appearance: White to slightly cream/Crystalline Powder
• Density: 1.039 g/mL at 25 °C
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: n20/D 1.422
• Storage Temp.: Store at RT.
• Solubility: H2O: 0.1 g/mL, clear, colorless
• PKA: 0[at 20 ℃]
• Water Solubility: 600 g/L (20 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents. Protect from moisture.
• BRN: 3570983
• CAS DataBase Reference: Tetrabutylammonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetrabutylammonium bromide(1643-19-2)
• EPA Substance Registry System: Tetrabutylammonium bromide(1643-19-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 1643-19-2(Hazardous Substances Data)

Usage

Physical and Chemical Properties

Tetrabutylammonium bromide, also known as tetrabutylammonium bromide. White crystal, deliquescence. 118 ℃ melting point. Soluble in water, alcohol, ether and acetone, slightly soluble in benzene. Figure 1:? a structural formula of tetrabutylammonium bromide

Application

(1) Used as a reagent for the analysis of organic synthesis. (2) Tetrabutylammonium bromide is also an effective phase transfer catalyst. Phase transfer catalyst, referred to as PTC, is able to transfer the aqueous phase (or organic phase) to the organic phase (or aqueous phase) catalyst, which can make the reaction between the aqueous phase and the organic phase of the catalyst. PTC has the function of changing the degree of ion solvation, increasing the activity of ion reaction, speeding up the reaction rate and so on. Solve the problem of the past in the two phases of the reaction is difficult to react. Common quaternary ammonium salt phase transfer catalysts are: benzyl triethyl ammonium chloride, trioctyl methyl ammonium chloride, tetramethyl ammonium bromide, tetrapropylammonium chloride, tetrabutylammonium bromide , tetrabutyl ammonium iodide, benzyl triethyl ammonium bromide, triethyl hexyl bromide, octyl triethylammonium bromide. Phase transfer catalyst is widely applied in organic synthesis: R2C for preparing compounds (carbene type compound), further preparation of the corresponding nitrile, isonitrile, Halon, dichloromethane cyclopropane derivatives, hydroxy acids and diazomethane. For the alkylation reaction, compared with traditional methods, to avoid the harsh conditions of dry operation, and high yield, it can also be used in the redox reaction, ester hydrolysis, substitution reaction, condensation reaction, addition reaction, polymerization reaction, addition reaction of carbon and the elimination of reaction and so on. (3) For organic synthesis intermediates, phase transfer catalyst (4) Ion-pairing reagents for the synthesis of bacampicillin, sultamicillin like. (5) Ion pair chromatography reagents, phase transfer catalyst. Bacampicillin, sultamicillin like synthesis.

Uses

Different sources of media describe the Uses of 1643-19-2 differently. You can refer to the following data:
1. Tetrabutylammonium bromide (TBAB) is a quaternary ammonium compound. It is the most widely used phase transfer catalyst. Its interfacial properties have been studied in case of hydroxide initiated reactions. This may be applied in understanding the mechanism of phase transfer reactions. TBAB is reported to decrease retention time and remove peak tailing by acting as an ion pair reagent during the chromatographic analysis of quaternary ammonium compounds. In the molten state TBAB behaves like an ionic liquid which is a promising green alternative to organic solvents in organic synthesis. Its molar heat capacity, entropy and free energy function have been determined.Recently, molten tetrabutylammonium bromide (TBAB) was used as a low toxic and cost-effective IL in a number of constructive synthetic transformations.Tetrabutylammonium bromide (TBAB) may be used in the molten state in the following processes:Synthesis of (2S)-5-(3-phenyl-2-phthalimidylpropanoylamino)isophthalic acid.Synthesis of alkyl-substituted pyrroles in the absence of catalyst and organic solvent.Synthesis of dithioacetals from acetals by transthioacetalisation in a solvent free environment.Synthesis of polyamides (PAs) by the polymerization of terephthalic acid and diisocyanates.Catalyze the addition of thiols to conjugated alkenes.Dehydrochlorination of poly(vinyl chloride).
2. Tetrabutylammonium Bromide is used in the synthesis of polymer solar cells. Also used in the synthesis of single component green-light emitting electrochemical cells.

preparation

Preparative Methods: several methods are available to recover the quaternary ammonium ion efficiently.Prepared by reaction of tri-n-butylamine and n-butyl bromide.

Toxicity

The acute oral LD50 (mouse): 590mg/kg. Inhalation, ingestion and skin contact toxic to the skin, eyes and respiratory system irritation. More information from the lookchem Xiaonan editor (2015-09-16).

Chemical Properties

white crystals or powder

Definition

ChEBI: Tetrabutylammonium bromide is a tetrabutylammonium salt with bromide as the anionic counterpart. It is an organic bromide salt and a tetrabutylammonium salt.

General Description

Tetrabutylammonium bromide, a quaternary ammonium compound widely used as a phase transfer catalyst. TBAB decreases the retention time and removes peak tailing by acting as an ion pair reagent during the chromatographic analysis of quaternary ammonium compounds. In the molten state, TBAB behaves like an ionic liquid, which is a promising green alternative to organic solvents in polymer synthesis.

Flammability and Explosibility

Notclassified

Purification Methods

Crystallise the salt from *benzene (5mL/g) at 80o by adding hot n-hexane (three volumes) and allowing to cool. Dry it over P2O5 or Mg(ClO4)2, under vacuum. The salt is very hygroscopic. It can also be crystallised from ethyl acetate or dry acetone by adding diethyl ether and dried in vacuo at 60o for 2 days. It has been crystallised from acetone by addition of diethyl ether. It is so hygroscopic that all manipulations should be carried out in a dry-box. It has been purified by precipitation from a saturated solution in dry CCl4 on addition of cyclohexane or by recrystallisation from ethyl acetate, then heating in vacuum to 75o in the presence of P2O5. [Symons et al. J Chem Soc, Faraday Trans 1 76 2251 1908.] It also recrystallises from CH2Cl2/diethyl ether and is dried in a vacuum desiccator over P2O5. [Blau & Espenson J Am Chem Soc 108 1962 1986, Beilstein 4 IV 657.]

InChI:InChI=1/C16H36N.N3/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-3-2/h5-16H2,1-4H3;/q+1;-1

Synthetic route

1-bromo-butane (109-65-9) + tributyl-amine (102-82-9) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In acetonitrile at 82℃; for 33h; Solvent; Temperature; Menshutkin Reaction;	98.9%
In acetonitrile for 24h; Heating;	80%
With ethanol

tributyl-amine (102-82-9) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
With 1-bromo-butane In acetonitrile at 80℃; under 7500.75 Torr; for 2h; Temperature; Inert atmosphere;	91%

3-bromo-3-methyl-2-trimethylsiloxy-1-pentene (138174-05-7) + tetrabutylammonium tricarbonylnitrosylferrate → (CH2C(OSi(CH3)3)C(CH3)C2H5)Fe(CO)2NO + tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In dichloromethane byproducts: CO; Stirring of mixt. at room temp. for 2 h.; Evapn. in vac., chromy. (silica gel, pentane).;	A 72% B n/a

3-bromo-3-methyl-2-trimethylsiloxy-1-butene (69278-36-0) + tetrabutylammonium tricarbonylnitrosylferrate → (CH2C(OSi(CH3)3)C(CH3)2)Fe(CO)2NO + tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In dichloromethane byproducts: CO; Stirring of mixt. at room temp. for 2 h.; Evapn. in vac., chromy. (silica gel, pentane).;	A 68% B n/a

tetrabutylammonium perchlorate (1923-70-2) + triethylamine hydrobromide (636-70-4) → tetrabutylammomium bromide (1643-19-2) + Triethylammonium perchlorate (14999-75-8)

Conditions	Yield
In chloroform at 25℃; Equilibrium constant;

tetrabuthylammonium tribromide (38932-80-8) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
With 4-hydroxy-TEMPO benzoate; sodium acetate In ethanol; dichloromethane for 0.5h; Ambient temperature;	657 mg

tetra(n-butyl)ammonium 2-hydroxy-5-nitrotoluene-α-sulphonyl bromide → 5-Nitrobenz<1,6-d>-3H-1,2-oxathiole S,S-dioxide (14618-10-1) + tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In nitrobenzene Equilibrium constant; other solvent;

C16H36N(1+)*Br5Mo2(1-) + triethylphosphine (554-70-1) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In acetone for 48h; Heating; formation of complexes, other uni- and polydentate phosphines;

C18H30N4OS2*C16H36N(1+)*Br(1-) → tetrabutylammomium bromide (1643-19-2) + 1-butyl-3-{3-[(3-butyl-thioureido)-methyl]-2-hydroxy-benzyl}-thiourea (321898-65-1)

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

C77H98N4O7*C16H36N(1+)*Br(1-)*4Cl(1-)*4H(1+) → tetrabutylammomium bromide (1643-19-2) + C77H98N4O7*4ClH

Conditions	Yield
In chloroform-d1; d(4)-methanol at 24.85℃; Equilibrium constant;

C77H98N4O7*C16H36N(1+)*Br(1-)*2Cl(1-)*2HO(1-)*4H(1+) → tetrabutylammomium bromide (1643-19-2) + C77H98N4O7*2ClH*2H2O

Conditions	Yield
In dimethylsulfoxide-d6 at 24.85℃; Equilibrium constant;

tetrabutylammonium diiodobromide (3419-99-6) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In chloroform Equilibrium constant;

tetra-(n-butyl)ammonium iodide (311-28-4) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium n-heptyl; petroleum ether / 25 °C 2: alcohol / 100 °C View Scheme

tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) + 5-bromomethyl-benzo[b]thiophene (10133-22-9) → tetrabutylammomium bromide (1643-19-2) + tetrabutylammonium benzo[b]thiophene-5-methanesulfonate

Conditions	Yield
With sodium hydroxide; sodium sulfite In dichloromethane; water

tetrabutyl-ammonium chloride (1112-67-0) + potassium bromide (7558-02-3) → potassium chloride + tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In toluene Kinetics; ion exchange between solid KBr and Bu4NCl in toluene (50-105°C);

2N(C4H9)4(1+)*Ag(1+)*2CH3CO2(1-)*ClO4(1-)={N(C4H9)4Ag(CH3CO2)2}{N(C4H9)4ClO4} → tetrabutylammomium bromide (1643-19-2) + silver perchlorate

Conditions	Yield
In 1,2-dimethoxyethane dissociation in soln., determination of equilibrium constant;;
In tetrahydrofuran dissociation in soln., determination of equilibrium constant;;

carbonato{2,2'-bipyridyl}{1,2-bis(diphenylphosphino)ethano}osmium(II) (116882-28-1) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
With hydrogen bromide In acetone	>99

ethyl 6-diethylamino-2-benzo[b]furancarboxylate → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
With sodium hydroxide In methanol; water for 0.416667h; Microwave irradiation;

Br(1-)*C16H36N(1+)*C72H72N4O9 (1186217-10-6) → C72H72N4O9 (1186216-97-6) + tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In dimethylsulfoxide-d6; [D3]acetonitrile at 24.84℃; Equilibrium constant;

tetrabutyl-ammonium chloride (1112-67-0) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: (Cy3P)2Pd(Ph)(OH); water / tetrahydrofuran / 20 °C / Inert atmosphere; Sealed vial 2: (Cy3P)2Pd(Ph)Br; water / tetrahydrofuran / 20 °C / Inert atmosphere; Sealed vial View Scheme

tetra(n-butyl)ammonium hydroxide (2052-49-5) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
With (Cy3P)2Pd(Ph)Br; water In tetrahydrofuran at 20℃; Equilibrium constant; Inert atmosphere; Sealed vial;

benzyl bromide (100-39-0) + tetra-n-butylammonium phenol-phenolate (65801-07-2, 65801-28-7) → (benzyloxy)benzene (946-80-5) + tetrabutylammomium bromide (1643-19-2) + phenol (108-95-2)

Conditions	Yield
In acetonitrile at 20℃;

C16H36N(1+)*Br(1-)*C4H10O2 → tert.-butylhydroperoxide (75-91-2) + tetrabutylammomium bromide (1643-19-2)

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

[CuII(TPEN')Br][Br] + tetrabutylammonium trifluoromethylsulfonate (35895-70-6) → [CuII(TPEN)][OTf]2 + tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In acetone Equilibrium constant; Solvent;

1-bromo-butane (109-65-9) + triethylamine (121-44-8) → tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In water at 90℃; for 12h; Autoclave; Green chemistry;

tetrabutylammonium trifluoromethylsulfonate (35895-70-6) + Dibenziodoliumbromid → [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate (189999-35-7) + tetrabutylammomium bromide (1643-19-2)

Conditions	Yield
In acetonitrile at 20℃; Equilibrium constant; Inert atmosphere;

tetrabutylammomium bromide (1643-19-2) → tetra-n-butyl-ammonium dihydrogentrifluoride (148305-65-1, 148305-68-4, 148305-70-8)

Conditions	Yield
With potassium hydrogen bifluoride In dichloromethane for 0.5h; Ambient temperature;	100%

tetrabutylammomium bromide (1643-19-2) → tetrabutylammonium bromite

Conditions	Yield
With potassium bromide In water at 40 - 50℃; for 0.433333h; electrolysis;	100%

tetrabutylammomium bromide (1643-19-2) + 5',N3-bis(tert-butoxycarbonyl)-2'-deoxy-3'-α-(isobutylmethylenesulfonate)uridine (459425-69-5) → 5',N3-bis(tert-butoxycarbonyl)-2'-deoxy-3'-α-(methylenesulfonate)uridine tetrabutylammonium salt

Conditions	Yield
In acetone at 50℃; for 18h;	100%

2-oxo-3-tert-butoxycarbonylamino-5-(3-methyl-2-butenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine + tetrabutylammomium bromide (1643-19-2) + 2-bromo-1-o-tolylethanone (51012-65-8) → 1-(2-toluoylmethyl)-2-oxo-3-tert-butoxycarbonylamino-5-(3-methyl-2-butenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (209222-51-5)

Conditions	Yield
With sodium hydroxide In toluene	100%

(tetramethylammonium)12(H4P4W30Nb6O123)*16H2O (114594-66-0) + tetrabutylammomium bromide (1643-19-2) → (tetrabutylammonium)12(H4P4W30Nb6O123) (114594-65-9)

Conditions	Yield
In water To an aq. soln. of (Me4N)12H4P4W30Nb6O123*16H2O (pH 4.6) is added an aq. soln. of tetrabutylammonium bromide.; The ppt. is collected and washed with water, drying at 60°C for 12 h, elem. anal.;	100%
In water dissolving of heteropoly-salt in H2O (90°C, pH = 4.6), colling to room temp., addn. of Bu4NBr in single portion (pptn.); collecting, washing (H2O), drying (60°C, overnight); elem. anal.;	47-56

tetrabutylammomium bromide (1643-19-2) + methyltrioxorhenium(VII) (70197-13-6) → {bis(tetra(n-butyl)ammonium)}{(dibromo)methyltrioxorhenate(VII)}

Conditions	Yield
In diethyl ether addn. of NBu4Br to a soln. of MeReO3 at room temp.; after 10 min solvent removed, washed the residue with ether, drying in vac.; elem. anal.;	100%

manganese(II) chloride hexahydrate + chromium(III) chloride * 3H2O + tetrabutylammomium bromide (1643-19-2) + potassium 1,2-dithiooxalate (17148-97-9, 20267-56-5) → tetra-n-butylammonium [CoCr(dithiooxalato)3]

Conditions	Yield
In water K-salt in water was added to CrCl3*6H2O in water, the soln. was heated for 30 min at 60°C, chloride was added, the soln. was heated at 80°C for 20 min, ammonium salt was added, the soln. was maintained at 80°C, cooled; filtered, washed with water, methanol, diethyl ether; elem. anal.;	100%

nickel(II) dichloride hydrate + chromium(III) chloride * 3H2O + tetrabutylammomium bromide (1643-19-2) + potassium 1,2-dithiooxalate (17148-97-9, 20267-56-5) → tetra-n-butylammonium [NiCr(dithiooxalato)3]

Conditions	Yield
In water K-salt in water was added to CrCl3*6H2O in water, the soln. was heated for 30 min at 60°C, chloride was added, the soln. was heated at 80°C for 20 min, ammonium salt was added, the soln. was maintained at 80°C, cooled; filtered, washed with water, methanol, diethyl ether; elem. anal.;	100%

cobalt(II) chloride hydrate + chromium(III) chloride * 3H2O + tetrabutylammomium bromide (1643-19-2) + potassium 1,2-dithiooxalate (17148-97-9, 20267-56-5) → tetra-n-butylammonium [CoCr(dithiooxalato)3]

Conditions	Yield
In water K-salt in water was added to CrCl3*6H2O in water, the soln. was heated for 30 min at 60°C, chloride was added, the soln. was heated at 80°C for 20 min, ammonium salt was added, the soln. was maintained at 80°C, cooled; filtered, washed with water, methanol, diethyl ether; elem. anal.;	100%

iron(II) chloride hydrate + chromium(III) chloride * 3H2O + tetrabutylammomium bromide (1643-19-2) + potassium 1,2-dithiooxalate (17148-97-9, 20267-56-5) → tetra-n-butylammonium [FeCr(dithiooxalato)3]

Conditions	Yield
In water K-salt in water was added to CrCl3*6H2O in water, the soln. was heated for 30 min at 60°C, chloride was added, the soln. was heated at 80°C for 20 min, ammonium salt was added, the soln. was maintained at 80°C, cooled; filtered, washed with water, methanol, diethyl ether; elem. anal.;	100%

(tetrahydrofuran)(carbonyl)phthalocyaninato(2-)osmium(II) (71870-09-2) + tetrabutylammomium bromide (1643-19-2) → N(C4H9)4(1+)*[Os(CO)(Br)(C6H4C2N2)4](1-)=[N(C4H9)4][Os(CO)Br(C6H4C2N2)4] (186336-62-9)

Conditions	Yield
In tetrahydrofuran 1 h, 293+/-2 K; addn. of n-pentane, washing (H2O), drying (vac.); elem. anal.;	100%

di(aqua)phthalocyaninato(2-)chromium(III) iodide *3H2O + tetrabutylammomium bromide (1643-19-2) → N(C4H9)4(1+)*[CrBr2(C6H4N2C2)4](1-)*H2O=[N(C4H9)4][CrBr2(C6H4N2C2)4]*H2O

Conditions	Yield
In acetone refluxing (5 min), pptn.; centrifugation, washing (acetone/Et2O 1/3), drying (vac., over KOH); elem. anal.;	100%

dimethylsulfite (616-42-2) + tetrabutylammomium bromide (1643-19-2) → tetrabutylammonium methanesulfonate (65411-49-6)

Conditions	Yield
at 110 - 115℃; under 750.075 - 1125.11 Torr; for 96h; Product distribution / selectivity;	100%

tetrabutylammomium bromide (1643-19-2) + silver salt of 2,4-dinitrophenol (82816-20-4) → tetrabutylammonium 2,4-dinitrophenolate (3002-49-1)

Conditions	Yield
In ethanol at 20℃; Inert atmosphere; Darkness;	100%

bis(phthalocyaninato)terbium(III)tetrabutylammonium + tetrabutylammomium bromide (1643-19-2) → [Pc2Tb](-)[TBA](+)*9[TBA]Br

Conditions	Yield
In methanol; water at 20℃; for 0.166667h; Sonication;	100%

bis(phthalocyaninato)terbium(III)tetrabutylammonium + tetrabutylammomium bromide (1643-19-2) → [Pc2Tb](-)[TBA](+)*143[TBA]Br

Conditions	Yield
In methanol; water; acetonitrile at 20℃; for 0.166667h; Sonication;	100%

C36H16F24O4Si2(2-)*2Li(1+) + tetrabutylammomium bromide (1643-19-2) → 2C16H36N(1+)*C36H16F24O4Si2(2-)

Conditions	Yield
In water; acetone at 20℃;	100%

potassium dithizonate (1234510-08-7) + tetrabutylammomium bromide (1643-19-2) → C13H11N4S(1-)*C16H36N(1+)

Conditions	Yield
In acetone for 1h;	100%

sodium tetrakis(pentafluorophenyl)borate-dimethoxyethane complex + tetrabutylammomium bromide (1643-19-2) → tetra-n-butylammonium tetrakis(pentafluorophenyl)borate (136710-93-5)

Conditions	Yield
In water at 20℃;	100%
In water at 20 - 140℃; Inert atmosphere;	100%

hydrogenchloride (7647-01-0) + closo-Cs2[B8H8] + tetrabutylammomium bromide (1643-19-2) → closo-[tetrabutylammonium][B8H9] [N(C4H9)4][B8H9], tetragonal

Conditions	Yield
In water N(C4H9)4Br in H2O added to a soln. of Cs salt, concd. HCl added; sepd., washed (H2O), dried (vac.);	100%

cesium ethyl N-(trifluoroacetyl)-O-{4-[undecahydro-closo-dodecaboratooxy]butyl}-L-tyrosinate + tetrabutylammomium bromide (1643-19-2) → tetrabutylammonium 2-(4-[4-((S)-2-amino-2-carboxyethyl)phenoxy]butoxy)undecahydro-closo-dodecaborate

Conditions	Yield
Stage #1: cesium ethyl N-(trifluoroacetyl)-O-{4-[undecahydro-closo-dodecaboratooxy]butyl}-L-tyrosinate With hydrogenchloride In water for 16h; Reflux; Stage #2: tetrabutylammomium bromide In water	100%

hydrogenchloride (7647-01-0) + Cl14W6(2-)*3H2O*2H7O3(1+) + tetrabutylammomium bromide (1643-19-2) → (Bu4N)2W6Cl8(i)Cl6(a) (84648-02-2)

Conditions	Yield
In water-d2	100%

dichloromethane (75-09-2) + [Cu(1,3-bis-(3,5-dimethylpyrazol-1-ylmethyl)-2-phenyl-2,3-dihydro-1H-perimidine)]ClO4 (1200206-42-3) + tetrabutylammomium bromide (1643-19-2) → C29H30BrCuN6*CH2Cl2

Conditions	Yield
at 20℃; for 0.333333h; Inert atmosphere;	100%

bis(dithiobenzil)nickel + tetrabutylammomium bromide (1643-19-2) → C28H20NiS4(2-)*C16H36N(1+)

Conditions	Yield
Stage #1: bis(dithiobenzil)nickel With sodium tetrahydroborate In methanol; dichloromethane for 0.166667h; Stage #2: tetrabutylammomium bromide In methanol; dichloromethane for 0.166667h;	100%

[Ni{S2C2(Ph)(Ph-p-OCH3)}2] + tetrabutylammomium bromide (1643-19-2) → C30H24NiO2S4(2-)*C16H36N(1+)

Conditions	Yield
Stage #1: [Ni{S2C2(Ph)(Ph-p-OCH3)}2] With sodium tetrahydroborate In methanol; dichloromethane for 0.166667h; Stage #2: tetrabutylammomium bromide In methanol; dichloromethane for 0.166667h;	100%

Ni((CH3OC6H4)2C2S2)2 + tetrabutylammomium bromide (1643-19-2) → C32H28NiO4S4(2-)*C16H36N(1+)

Conditions	Yield
Stage #1: Ni((CH3OC6H4)2C2S2)2 With sodium tetrahydroborate In methanol; dichloromethane for 0.166667h; Stage #2: tetrabutylammomium bromide In methanol; dichloromethane for 0.166667h;	100%

tetrabutylammonium-[2-(2-ammonium-ethoxy)-ethoxy]-undecahydro-closo-dodecaborate + tetrabutylammomium bromide (1643-19-2) → 2- (2-aminoethoxy)ethoxyundecahydrocrossodedecaborate ditetrabutylammonium salt

Conditions	Yield
With potassium hydroxide In dichloromethane; water for 4h;	100%

2,5-dihydroxy-1,4-benzoquinone (615-94-1) + tetrabutylammomium bromide (1643-19-2) + nickel(II) acetate tetrahydrate (6018-89-9) → 1.5C6H2O4(2-)*Ni(2+)*C16H36N(1+)

Conditions	Yield
In water at 100℃; for 0.75h; Inert atmosphere;	100%

tetrabutylammomium bromide (1643-19-2) + C24H9N2O10S3(3-)*3Na(1+) → C24H9N2O10S3(3-)*3C16H36N(1+)

Conditions	Yield
In water at 20℃; for 5h;	100%

1H-imidazole (288-32-4) + tetrabutylammomium bromide (1643-19-2) → C16H36N(1+)*Br(1-)*C3H4N2

Conditions	Yield
at 100℃; for 0.5h;	100%

Upstream product

• 109-65-9 1-bromo-butane 
• 102-82-9 tributyl-amine 
• 311-28-4 tetra-(n-butyl)ammonium iodide 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 7558-02-3 potassium bromide 
• 116882-28-1 carbonato{2,2'-bipyridyl}{1,2-bis(diphenylphosphino)ethano}osmium(II) 
• 1186217-10-6 Br^(1-)*C₁₆H₃₆N⁽¹⁺⁾*C₇₂H₇₂N₄O₉ 
• 121-44-8 triethylamine 
• 35895-70-6 tetrabutylammonium trifluoromethylsulfonate 
• 100-39-0 benzyl bromide 
• 65801-07-2 tetra-n-butylammonium phenol-phenolate 
• 2052-49-5 tetra(n-butyl)ammonium hydroxide 
• 138174-05-7 3-bromo-3-methyl-2-trimethylsiloxy-1-pentene 
• 69278-36-0 3-bromo-3-methyl-2-trimethylsiloxy-1-butene 

Downstream Products

• 311-28-4 tetra-(n-butyl)ammonium iodide 
• 106-98-9 1-butylene 
• 102-82-9 tributyl-amine 
• 106-97-8 n-butane 
• 61829-43-4 N-butyl-4-methoxyaniline 
• 82749-62-0 N,N-dibutyl-4-methoxylaniline 
• 496862-82-9 [Bu₄N][HB(C₆F₅)3] 
• 376642-59-0 2-(4-benzyloxyphenyl)-5-methyl-1-[3-(4-pentylcyclohexylmethoxy)propyl]-1H-pyrrole 
• 178979-06-1 [1-allyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazol-2-yl]methanol 
• 178980-78-4 4-[2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-1-ylmethyl]pyridine 
• 6314-28-9 benzo[b]thiophene-2-carboxylic acid 
• 224187-16-0 2-(4-Chloro-2-methyl-phenoxy)-5-(N-methylamino)pyridine 
• 90604-02-7 1-(diphenylmethyl)-3-azetidinol hydrochloride 
• 57356-28-2 5-nitro-2,3-dihydro-1,4-benzodioxin 

Related news

Thermal conductivity measurements of semiclathrate hydrates and aqueous solutions of Tetrabutylammonium bromide (cas 1643-19-2) (TBAB) and tetrabutylammonium chloride (TBAC) by the transient hot-wire using parylene-coated probe08/09/2019

The thermal conductivity of semiclathrate hydrates and aqueous solutions of tetrabutylammonium bromide (TBAB) and tetrabutylammonium chloride (TBAC) was measured for the first time in the temperature range from 223 to 303 K under atmospheric pressure. A transient hot-wire apparatus using a paryl...detailed

Phase equilibrium of ionic semiclathrate hydrates formed with Tetrabutylammonium bromide (cas 1643-19-2) and tetrabutylammonium chloride08/07/2019

This paper reports the accurate phase equilibrium measurements of two ionic semiclathrate hydrates with tetrabutylammonium bromide (TBAB) and tetrabutylammonium chloride (TBAC). These ionic semiclathrate hydrates are suggested as cool energy storage media for air-conditioning system since their ...detailed

Influence of butynediol and Tetrabutylammonium bromide (cas 1643-19-2) on the morphology and structure of electrodeposited cobalt in the presence of saccharin08/06/2019

To develop cobalt coating for use in diamond tools, cobalt electrodeposition was conducted in Watts-type baths. The effects of tetrabutylammonium bromide and 2-butyne-1,4-diol on the surface morphology, crystallographic structure, surface roughness and microhardness of thick cobalt deposits were...detailed

Relevant articles and documents

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Atom transfer radical addition (ATRA) catalyzed by copper complexes with N,N,N′,N′-tetrakis(2-pyridylmethyl)ethylenediamine (TPEN) ligand

Synthesis, characterization, electrochemical studies and ATRA activity of copper complexes with N,N,N′,N′-tetrakis(2-pyridylmethyl)ethylenediamine (TPEN) ligand in the presence of ascorbic acid as a reducing agent were reported. [CuII(TPEN′)Br][Br] (TPEN′ denotes tetracoordinated ligand) catalyst showed a very low activity in ATRA of CBr4 to 1-octene, methyl methacrylate, methyl acrylate and styrene in methanol, which is a typical solvent used for ATRA reactions employing ascorbic acid. On the contrary, the yields and stereoselectivity towards monoadduct formation were dramatically increased in slightly polar but aprotic acetone. Based on molecular structures of isolated [CuII(TPEN)][BPh4] and [CuII(TPEN′)Br][Br] complexes, as well as UV-Vis and cyclic voltammetry studies, an equilibrium was proposed involving inactive [CuII(TPEN)]2+ and ATRP active [CuII(TPEN′)Br]+ cations The halidophilicity of the bromide-based deactivating complex ([CuII(TPEN′)Br][Br]) decreased approximately 750 times upon changing the solvent from acetone (KBr = 3000 ± 230) to methanol (KBr = 4.1 ± 0.1), explaining poor catalytic activity in methanol. In acetone, [CuII(TPEN′)Br][Br] complex was nearly as active in ATRA reactions employing ascorbic acid as previously reported [CuII(TPMA)Br][Br].

Structure and Stability of Quaternary Ammonium Interhalides: Experimental and Quantum-Chemical Study

The electronic structure of a series of ammonium interhalides [R 1R2R3R4N]XI2, where R1 = CH3, C2H5, C3H 7, F, H; R2 = R3 = R4 = CH 3, H; X = Cl, Br, I, was studied by ab initio calculations (RHF/3-21G, RHF/HW, MP2/HW). The thermodynamic stability of these compounds correlates with the strength of the hydrogen bond N-H...X and three-center interhalide bond X-I-I. Calculations confirmed that, in polar solvents, these compounds preferably decompose to [R1R2R3R 4N]+ and XI2- (with subsequent decomposition of the anion), and in nonpolar solvents, to the neutral species [R1R2R3R4N]X and I2. The calculation results were compared to the experimental data obtained by single crystal X-ray diffraction, 1H NMR spectroscopy, and spectrophotometry.

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Synthesis method of tetrabutylammonium bromide

The invention discloses a synthesis method of tetrabutylammonium bromide, which comprises the steps of reflux reaction, crystallization, centrifugation, mother liquor application, centrifugal machine washing and the like, the desolvation operation of dichloroethane is omitted, the evaporation loss of dichloroethane in the desolvation process is avoided, the raw materials are saved, and after the front-section centrifugal mother liquor is supplemented to the formula amount, infinite times of return use can be basically realized, bromobutane and a small amount of tetrabutylammonium bromide contained in the front-section centrifugal mother liquor can be completely put into the production of the next batch, the yield of the product is improved, impurities in the product can be washed away by washing a centrifugal machine with ethyl acetate, the chromaticity of the product is improved, and meanwhile, the post-stage centrifugal mother liquor obtained after centrifugation can be repeatedly used under the condition that the post-stage centrifugal mother liquor is inspected to be qualified, so that raw materials are saved.

Lewis Acidity Scale of Diaryliodonium Ions toward Oxygen, Nitrogen, and Halogen Lewis Bases

Equilibrium constants for the associations of 17 diaryliodonium salts Ar2I+X- with 11 different Lewis bases (halide ions, carboxylates, p-nitrophenolate, amines, and tris(p-anisyl)phosphine) have been investigated by titrations followed by photometric or conductometric methods as well as by isothermal titration calorimetry (ITC) in acetonitrile at 20 °C. The resulting set of equilibrium constants KI covers 6 orders of magnitude and can be expressed by the linear free-energy relationship lg KI = sI LAI + LBI, which characterizes iodonium ions by the Lewis acidity parameter LAI, as well as the iodonium-specific affinities of Lewis bases by the Lewis basicity parameter LBI and the susceptibility sI. Least squares minimization with the definition LAI = 0 for Ph2I+ and sI = 1.00 for the benzoate ion provides Lewis acidities LAI for 17 iodonium ions and Lewis basicities LBI and sI for 10 Lewis bases. The lack of a general correlation between the Lewis basicities LBI (with respect to Ar2I+) and LB (with respect to Ar2CH+) indicates that different factors control the thermodynamics of Lewis adduct formation for iodonium ions and carbenium ions. Analysis of temperature-dependent equilibrium measurements as well as ITC experiments reveal a large entropic contribution to the observed Gibbs reaction energies for the Lewis adduct formations from iodonium ions and Lewis bases originating from solvation effects. The kinetics of the benzoate transfer from the bis(4-dimethylamino)-substituted benzhydryl benzoate Ar2CH-OBz to the phenyl(perfluorophenyl)iodonium ion was found to follow a first-order rate law. The first-order rate constant kobs was not affected by the concentration of Ph(C6F5)I+ indicating that the benzoate release from Ar2CH-OBz proceeds via an unassisted SN1-type mechanism followed by interception of the released benzoate ions by Ph(C6F5)I+ ions.

Method of manufacturing tetrabuthyl ammonium acetate (by machine translation)

PROBLEM TO BE SOLVED: use raw material, and the solvent through the proper selection of a simple and easy process suitable for the manufacture of solubility of cellulose tet love chill ammonium acetate. SOLUTION: and a starting material by tributylamine, tributylamine in polar aprotic organic solvent and by the reaction of halogenated butyl tetrabuthyl ammonium halide and a process for obtaining, in tetrabuthyl ammonium halide vopo and [...] by the reaction of an alkali metal hydroxide and a process for obtaining, in [...] vopo tetrabuthyl ammonium acetate and acetic acid tetrabuthyl by reaction of the process and to obtain. Selected drawing: fig. 1 (by machine translation)