14866-33-2

Basic information

• Product Name: Tetraoctylammonium bromide
• Synonyms: TETRAOCTYLAMMONIUM BROMIDE;TETRA-N-OCTYLAMMONIUM BROMIDE;TETRAOCTYLAMMONIUM BROMIDE, FOR IPC;Tetra Octyl Amonium Bromide;1-Octanaminium, N,N,N-trioctyl-, bromide;Tetra-n-octylammonium bromide, 98+%;Tetraoctylammonium bromide ,98%;Tetraoctylaminium·bromide
• CAS NO: 14866-33-2
• Molecular Formula: Br*C₃₂H₆₈N
• Molecular Weight: 546.79
• EINECS: 238-936-9
• Product Categories: Ammonium Bromides (Quaternary);Quaternary Ammonium Compounds;Greener Alternatives: Catalysis;Analytical/Chromatography;Ion Sensor Materials;Ionophores Potentiometric for ISE;Ammonium Salts;AmmoniumGreener Alternatives: Catalysis;Chemical Synthesis;Ionic Liquids;Phase Transfer Catalysts;AnionicHPLC;Chromatography/CE Reagents;Ion Pair;Ion Pair Reagents;Ion Pair Reagents - Anionic
• Mol File: 14866-33-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 95-98 °C(lit.)
• Boiling Point: 209.3℃[at 101 325 Pa]
• Flash Point: Not expected to be a fire hazard
• Appearance: White to creamy-white/Powder or Flakes
• Density: 1.0041 (rough estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 600g/l
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• BRN: 4169176
• CAS DataBase Reference: Tetraoctylammonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraoctylammonium bromide(14866-33-2)
• EPA Substance Registry System: Tetraoctylammonium bromide(14866-33-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 14866-33-2(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 14866-33-2 differently. You can refer to the following data:
1. Tetraoctylammonium bromide (TOAB) has been used as a phase transfer agent to transfer gold tetrachloroaurate from aqueous phase to organic phase in a two-phase (organic-aqueous) method of alkanethiol stabilized gold nanoparticle synthesis. It is also used to prepare TOAB-capped gold nanoparticles, which shows well-defined plasmon absorption compared to thiol-capped nanoparticles.
2. TOAB has been used as recognition element in formulating potentiometric membrane to develop an electronic tongue system for monitoring nitrogen species level in water samples.

General Description

Tetraoctylammonium bromide is an organic surface coating agent commonly used to control the size and shape during nanoparticle synthesis.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C32H68N.BrH/c1-5-9-13-17-21-25-29-33(30-26-22-18-14-10-6-2,31-27-23-19-15-11-7-3)32-28-24-20-16-12-8-4;/h5-32H2,1-4H3;1H/q+1;/p-1

Synthetic route

methanol (67-56-1) + C32H68N(1+)*CH4O*Br(1-) → tetraoctyl ammonium bromide (14866-33-2)

Conditions	Yield
In dichloromethane at 26℃; Equilibrium constant; 9.1 - 10.6 M-1;

C6H5O(1-)*C6H6O*C32H68N(1+) (1392488-23-1) + benzyl bromide (100-39-0) → (benzyloxy)benzene (946-80-5) + tetraoctyl ammonium bromide (14866-33-2) + phenol (108-95-2)

Conditions	Yield
In acetonitrile at 20℃;

(η6-1-fluoro-3-methylbenzene)tricarbonylchromium(0) (33411-10-8) + tetraoctyl ammonium bromide (14866-33-2) + acetone oxime (127-06-0) → (CO)3CrC6H4(CH3)ONC(CH3)2 (97932-55-3)

Conditions	Yield
With potassium hydroxide In benzene (N2), stirred for 1 h; solvent removed under vac., residue dissolved in Et2O, filtered on Celite, evaporated, crystd. from di-isopropyl ether;	98%

propyl methanesulfonate (1912-31-8) + tetraoctyl ammonium bromide (14866-33-2) → propyl bromide (106-94-5) + tetraoctylammonium methanesulfonate (70098-05-4)

Conditions	Yield
In benzene at 80℃;	A n/a B 97%

potassium thioacyanate (333-20-0) + tetraoctyl ammonium bromide (14866-33-2) → tetra-n-octylammonium thiocyanate (66091-57-4)

Conditions	Yield
In dichloromethane; water	97%

tetraoctyl ammonium bromide (14866-33-2) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → tetraoctylammonium bis(trifluoromethanesulfonyl)imide

Conditions	Yield
In water; acetone at 20℃; for 12h;	96%
In water; acetone for 24h;	89%
In water at 20 - 70℃; for 73h;

sodium dodecyl-sulfate (151-21-3) + tetraoctyl ammonium bromide (14866-33-2) → tetraoctylammonium dodecyl sulfuric acid

Conditions	Yield
In water; acetone at 25℃; for 168h;	95%

potassium hexachloropalatinate(IV) + tetraoctyl ammonium bromide (14866-33-2) → bis(tetra-n-octylammonium)hexachloridoplatinum(IV) (16905-80-9)

Conditions	Yield
In dichloromethane; water soln. of the bromide in CH2Cl2 added to soln. of K2PtCl6 in H2O; resulting two-phase system stirred at room temp. until complete decoloration of the aq. layer (3-5 h); organic layer sepd. and dried over MgSO4; solvent distilled off; elem. anal.;	95%

[Pd(1-diphenylphosphino-2-di-tert-butylphosphinoethylferrocene)(P(o-tolyl)3)] (653569-66-5, 583872-36-0) + toluene-4-sulfonic acid phenyl ester (640-60-8) + tetraoctyl ammonium bromide (14866-33-2) → (C5H5)Fe(C5H3(P(C6H5)2)CH(CH3)P(C(CH3)3)2)Pd(C6H5)Br (583872-40-6, 654643-49-9)

Conditions	Yield
In benzene room temp., 9 h;	95%
In tetrahydrofuran Kinetics;

tetraoctyl ammonium bromide (14866-33-2) → Tetraoctylammonium tetrafluoroborate

Conditions	Yield
With potassium tetrafluoroborate In dichloromethane; water at 20℃; for 24h;	95%
With potassium tetrafluoroborate In dichloromethane; water at 20℃; for 24h;	95%

2-iodophenylamine (615-43-0) + tetraoctyl ammonium bromide (14866-33-2) → 2-heptyl-1H-benzothiazole (69938-51-8)

Conditions	Yield
With sulfur; potassium hydroxide In water at 140℃; for 14h; Green chemistry;	95%

tetraoctyl ammonium bromide (14866-33-2) + potassium tetrafluoroborate (14075-53-7) → Tetraoctylammonium tetrafluoroborate

Conditions	Yield
In dichloromethane; water at 20℃; for 24h;	95%

1,2,3-Benzotriazole (95-14-7) + tetraoctyl ammonium bromide (14866-33-2) → tetraoctylammonium benzotriazole

Conditions	Yield
With sodium hydroxide In water at 70℃; Heating;	95%

Au24Pt(SCH2CH2Ph)18 + tetraoctyl ammonium bromide (14866-33-2) → 18C8H9S(1-)*C32H68N(1+)*PtAu24(17+)

Conditions	Yield
Stage #1: Au24Pt(SCH2CH2Ph)18 With sodium tetrahydroborate In tetrahydrofuran; ethanol for 0.5h; Stage #2: tetraoctyl ammonium bromide In tetrahydrofuran; methanol; ethanol	95%

1,1,1-trifluoro-N-(pyridin-4(1H)-ylidene)methanesulfonamide + tetraoctyl ammonium bromide (14866-33-2) → tetraoctylammonium pyridin-4-yl((trifluoromethyl)sulfonyl)amide

Conditions	Yield
Stage #1: 1,1,1-trifluoro-N-(pyridin-4(1H)-ylidene)methanesulfonamide With methanol; sodium at 20℃; for 1h; Inert atmosphere; Stage #2: tetraoctyl ammonium bromide for 14h; Inert atmosphere;	95%

lithium aluminium tetrahydride (16853-85-3) + tetraoctyl ammonium bromide (14866-33-2) → C32H68N(1+)*AlH4(1-)

Conditions	Yield
at 50℃; for 4.66667h; Inert atmosphere; Reflux;	94.9%

tetraoctyl ammonium bromide (14866-33-2) + sodium dodecylbenzenesulfonate → tetraoctylammonium dodecylbenzenesulfonate

Conditions	Yield
Stage #1: tetraoctyl ammonium bromide; sodium dodecylbenzenesulfonate In water; acetone at 20℃; for 0.75h; Stage #2: In dichloromethane; water for 0.25h;	94.2%

[Pd(1-dicyclohexylphosphino-2-di-tert-butylphosphinoethylferrocene)(P(o-tolyl)3)] (583872-37-1) + toluene-4-sulfonic acid phenyl ester (640-60-8) + tetraoctyl ammonium bromide (14866-33-2) → (C5H5)Fe(C5H3(P(C6H11)2)CH(CH3)P(C(CH3)3)2)Pd(C6H5)Br (583872-41-7)

Conditions	Yield
In benzene room temp., 5 min;	94%

ammonium hexachloropalladate(IV) + tetraoctyl ammonium bromide (14866-33-2) → (tetraoctylammonium)2PdCl6

Conditions	Yield
In propan-1-ol; water at 20℃;	91%

RhI(tetraphenylporphyrin) (69509-35-9) + tetraoctyl ammonium bromide (14866-33-2) → [Rh(5,10,15,20-tetraphenylporphyrinato)(n-octyl)] (1617001-65-6)

Conditions	Yield
With sodium hydroxide In water; benzene at 120℃; for 5h; Sealed tube;	91%

tricarbonyl(η(6)-4-fluorotoluene)chromium (12116-25-5) + tetraoctyl ammonium bromide (14866-33-2) + acetone oxime (127-06-0) → (CO)3CrC6H4(CH3)ONC(CH3)2 (97932-56-4)

Conditions	Yield
With potassium hydroxide In benzene (N2), stirred for 3.5 h; solvent removed under vac., residue dissolved in Et2O, filtered on Celite, evaporated, crystd. from di-isopropyl ether;	89%

1,1,2,2-tetrafluoro-2-(phenylsulfanyl)ethanesulfonyl fluoride (1000294-01-8) + tetraoctyl ammonium bromide (14866-33-2) → tetra-n-octylammonium 2-(phenylsulfanyl)-1,1,2,2-tetrafluoroethanesulfonate

Conditions	Yield
Stage #1: 1,1,2,2-tetrafluoro-2-(phenylsulfanyl)ethanesulfonyl fluoride With lithium hydroxide monohydrate In diethyl ether at 20℃; Stage #2: tetraoctyl ammonium bromide In acetone at 20℃; for 0.0833333h; Inert atmosphere;	89%

tetraoctyl ammonium bromide (14866-33-2) + 4-Fluoronitrobenzene (350-46-9) → 1-nitro-4-octyloxybenzene (49562-76-7)

Conditions	Yield
With water; copper(II) acetate monohydrate; caesium carbonate; Triphenylphosphine oxide at 145℃; Inert atmosphere;	86%

ammonium hexachloridoplatinate(IV) + tetraoctyl ammonium bromide (14866-33-2) → bis(tetra-n-octylammonium)hexachloridoplatinum(IV) (16905-80-9)

Conditions	Yield
In propan-1-ol; water at 20℃;	86%

(η6-fluorobenzene)tricarbonylchromium (12082-05-2) + tetraoctyl ammonium bromide (14866-33-2) + acetone oxime (127-06-0) → (CO)3CrC6H5ONC(CH3)2 (97932-53-1)

Conditions	Yield
With potassium hydroxide In benzene (N2), stirred for 0.5 h; solvent removed under vac., residue dissolved in Et2O, filtered on Celite, evaporated, crystd. from di-isopropyl ether;	85%

Au55(6+)*12Na(1+)*12P(C6H5)2(C6H4SO3)(1-)*6Cl(1-)=Au55(P(C6H5)2(C6H4SO3Na))12Cl6 + tetraoctyl ammonium bromide (14866-33-2) → Au55(P(C6H5)2C6H4SO3)12(tetraoctylammonium)12Cl6

Conditions	Yield
In dichloromethane; water byproducts: NaBr; addn. of CH2Cl2 soln. of ammonium compound to aq. soln. of Au compound with vigorous stirring, 3 h; separation of phases, washing of organic phase (H2O), removement of solvent (room temp., vacuum), dissolution (CH2Cl2), filtration, evapn. (vacuum), pptn. (pentane), drying (vacuum, overnight); elem. anal.;	85%

sodium molybdate dihydrate (7631-95-0) + ammonium vanadate(V) + tetraoctyl ammonium bromide (14866-33-2) → 3[(CH3(CH2)7)4N](1+)*[VMo12O40](3-) = [(CH3(CH2)7)4N]3[VMo12O40]

Conditions	Yield
In hydrogenchloride; water soln. of NH4VO3 (0.11 mmol) in 37% HCl added to aq. soln. of Na2MoO4*2H2O (1.2 mmol); stirred (30 min, room temp.); (CH3(CH2)7)4NBr (0.4 mmol) added; ppt. filtered; washed with H2O and EtOH; dried in air; dissolved in CH3CN; crystd. (4°C, 24 h); crystals collected; washed with H2O and EtOH; dried in air; elem. anal.;	85%

sodium mid-chain branched dodecyl sulfate + tetraoctyl ammonium bromide (14866-33-2) → tetraoctylammonium mid-chain branched dodecyl sulfate

Conditions	Yield
Stage #1: sodium mid-chain branched dodecyl sulfate; tetraoctyl ammonium bromide In water; acetone at 20℃; for 0.75h; Stage #2: In dichloromethane; water for 0.25h;	84.1%

tricarbonyl(p-methoxychlorobenzene)chromium (77490-88-1) + tetraoctyl ammonium bromide (14866-33-2) + acetone oxime (127-06-0) → (CO)3CrC6H4(OCH3)ONC(CH3)2

Conditions	Yield
With potassium hydroxide In benzene (N2), stirred for 1.75 h; solvent removed under vac., residue dissolved in Et2O, filtered on Celite, evaporated, crystd. from di-isopropyl ether;	84%

1-methyl-1H-imidazole (616-47-7) + tetraoctyl ammonium bromide (14866-33-2) → 1-octyl-3-methyl-imidazolium bromide

Conditions	Yield
In tetrahydrofuran for 72h; Reflux;	79.6%

gold(III) chloride hydrate (28587-97-5, 635727-68-3) + tetraoctyl ammonium bromide (14866-33-2) → chloroauric acid

Conditions	Yield
In propan-1-ol; water at 20℃;	77%

K8[α-SiW11O39]*13H2O + iron(III) chloride hexahydrate + tetraoctyl ammonium bromide (14866-33-2) → 5C32H68N(1+)*(SiW11O39Fe(H2O))(5-)

Conditions	Yield
Stage #1: K8[α-SiW11O39]*13H2O; iron(III) chloride hexahydrate In water at 55℃; for 1.5h; pH=5; Stage #2: tetraoctyl ammonium bromide In water; toluene at 20℃;	76%

Upstream product

• 67-56-1 methanol 
• 1392488-23-1 C₆H₅O^(1-)*C₆H₆O*C₃₂H₆₈N⁽¹⁺⁾ 
• 100-39-0 benzyl bromide 

Downstream Products

• 583872-40-6 (C₅H₅)Fe(C₅H₃(P(C₆H₅)2)CH(CH₃)P(C(CH₃)3)2)Pd(C₆H₅)Br 
• 49562-76-7 1-nitro-4-octyloxybenzene 
• 1392488-23-1 C₆H₅O^(1-)*C₆H₆O*C₃₂H₆₈N⁽¹⁺⁾ 
• 15243-48-8 cesium lead bromide 
• 862574-87-6 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarbonitrile 
• 1617001-65-6 [Rh(5,10,15,20-tetraphenylporphyrinato)(n-octyl)] 

Relevant articles and documents

Effects of charge separation, effective concentration, and aggregate formation on the phase transfer catalyzed alkylation of phenol

The factors that influence the rate of alkylation of phenol under phase transfer catalysis (PTC) have been investigated in detail. Six linear, symmetrical tetraalkylammonium cations, Me4N+, Et 4N+, (n-Pr)4N+, (n-Bu) 4N+, (n-Hex)4N+, and (n-Oct) 4N+, were examined to compare the effects of cationic radius and lipophilicity on the rate of alkylation. Tetraalkylammonium phenoxide·phenol salts were prepared, and their intrinsic reactivity was determined from initial alkylation rates with n-butyl bromide in homogeneous solution. The catalytic activity of the same tetraalkylammonium phenoxides was determined under PTC conditions (under an extraction mechanism) employing quaternary ammonium bromide catalysts. In homogeneous solution the range in reactivity was small (6.8-fold) for Me4N+ to (n-Oct) 4N+. In contrast, under PTC conditions a larger range in reactivity was observed (663-fold). The effective concentration of the tetraalkylammonium phenoxides in the organic phase was identified as the primary factor influencing catalyst activity. Additionally, titration of active phenoxide in the organic phase confirmed the presence of both phenol and potassium phenoxide aggregates with (n-Bu)4N+, (n-Hex)4N+, and (n-Oct)4N+, each with a unique aggregate stoichiometry. The aggregate stoichiometry did not affect the PTC initial alkylation rates.