866-97-7

Basic information

• Product Name: TETRAPENTYLAMMONIUM BROMIDE
• Synonyms: Tetraamylaminium·bromide;Tetrapentylaminium·bromide;Tetrapentylammonium bromide ,99% [HPLC grade];TetrapentylaMMoniuM broMide, 99+% 25GR;TetrapentylaMMoniuM broMide, 99+% 5GR;TetrapentylaMMoniuM broMide, for ion-pair chroMatography;TETRAAMYLAMMONIUM BROMIDE;TETRAPENTYLAMMONIUM BROMIDE
• CAS NO: 866-97-7
• Molecular Formula: Br*C₂₀H₄₄N
• Molecular Weight: 378.47
• EINECS: 212-756-0
• Product Categories: Ammonium Bromides (Quaternary);Quaternary Ammonium Compounds;AnionicHPLC;Chromatography/CE Reagents;Ion Pair;Ion Pair Reagents;Ion Pair Reagents - Anionic;AmmoniumGreener Alternatives: Catalysis;Chemical Synthesis;Ionic Liquids;Ammonium Salts;Greener Alternatives: Catalysis;Phase Transfer Catalysts;Ammonium Salts;Phase Transfer Catalysts;Specialty Synthesis;Ammonium;Chemical Synthesis;Ionic Liquids;Synthetic Reagents
• Mol File: 866-97-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 100-101 °C(lit.)
• Appearance: White/Shiny Flakes
• Density: 0.92333 g/cm3 (35.00℃)
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Soluble in water
• BRN: 3658171
• CAS DataBase Reference: TETRAPENTYLAMMONIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAPENTYLAMMONIUM BROMIDE(866-97-7)
• EPA Substance Registry System: TETRAPENTYLAMMONIUM BROMIDE(866-97-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 866-97-7(Hazardous Substances Data)

Usage

Uses

Tetrapentylammonium bromide can be used:As a versatile structure-directing agent for the synthesis of Zeolite-like heterobimetallic cyanide frameworks.As an alkylating agent for rhodium(I)-catalyzed alkylation reaction of benzylic amines and for N-alkylation of azaheterocycles.As a precursor to prepare a Cobalt-complex, {[(Pentyl)4N]3CoBr3}Cl2, which is used as a catalyst in the synthesis of multiwalled carbon nanotubes (MWCNTs).Electrochemical synthesis of stable graphite intercalation compounds (GICs) containing tetrapentylammonium cations has been reported.

General Description

Tetrapentylammonium bromide is a quaternary ammonium salt with pentyl chains and a bromide counterion, which is generally used as a phase transfer catalyst.

Purification Methods

Crystallise it from pet ether, *benzene or acetone/ether mixtures and dry in vacuum at 40-50o for 2 days. It is used in ion-paired chromatography (Sagara et al. J Chromatogr 328 289 1985). [Beilstein 4 IV 677.]

InChI:InChI=1S/C20H44N.BrH/c1-5-9-13-17-21(18-14-10-6-2,19-15-11-7-3)20-16-12-8-4;/h5-20H2,1-4H3;1H/q+1;/p-1

Synthetic route

1-Bromopentane (110-53-2) + tripentylamine (621-77-2) → tetrapentylammonium bromide (866-97-7)

Conditions	Yield
In ethanol
In butanone
In acetonitrile Heating;
In acetonitrile

tetrapentylammonium iodide (2498-20-6) → tetrapentylammonium bromide (866-97-7)

Conditions	Yield
With ammonium bromide In dichloromethane; water

iron(II) chloride hydrate + chromium(III) chloride * 3H2O + tetrapentylammonium bromide (866-97-7) + potassium 1,2-dithiooxalate (17148-97-9, 20267-56-5) → tetra-n-pentylammonium [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%

4-Cyanochlorobenzene (623-03-0) + tetrapentylammonium bromide (866-97-7) + acrylic acid methyl ester (292638-85-8) → (E)-pentyl 3-(4-cyanophenyl)acrylate

Conditions	Yield
With C32H27N4O2Pd(1+)*BF4(1-); sodium acetate at 140℃; for 12h; Inert atmosphere; Schlenk technique; Green chemistry;	100%

potassium thioacyanate (333-20-0) + tetrapentylammonium bromide (866-97-7) → tetra(n-pentyl)ammonium thiocyanate (3475-60-3)

Conditions	Yield
In dichloromethane; water	98%

tetrapentylammonium bromide (866-97-7) + iron(III) chloride (7705-08-0) + sulfur (7704-34-9) + thiophenol (108-98-5) → 2((C5H11)4N)(1+)*[Fe2S2(S(C6H5))4](2-)=((C5H11)4N)2[Fe2S2(S(C6H5))4]

Conditions	Yield
With Triton X-100 In water; acetonitrile under anaerobic conditions, addn. of solid S to react. mixt. in aq. buffer/Triton/CH3CN; filtered after 2 d, washed with ether, water, and ether, dried in vac.,elem. anal.;	96%

ammonium tetrathiotungstate (13862-78-7) + tetrapentylammonium bromide (866-97-7) → tetrapentylammonium thiotungstate

Conditions	Yield
In water byproducts: NH4Br; stirred at 323 K for 10 min; crystd. overnight at room temp.;	95%
In water according to Alonso G., et al., Inorg. Chim. Acta, 1998, 274, 108; aq. soln. of (NH4)2WS4 was added to aq. soln. of bromide; stirred for 30 min; elem. anal.;	80%

ammonium tetrathiomolybdate + tetrapentylammonium bromide (866-97-7) → tetrapentylammonium thiomolybdate

Conditions	Yield
In water byproducts: NH4Br; stirred at 323 K for 10 min; crystd. overnight at room temp.;	95%
With sodium hydroxide In water (NH4)2MoS4 dissolved in water, stirred, ligand dissolved in soln. of NaOH in water, stirred, mixed, stirred for 30 min, kept over ice overnight; filtered, washed with cold water and EtOH;	90%
In water aq. soln. of (NH4)2MoS4 added to aq. soln. of tetrapentylammonium bromide; soln. stirred at room temp. for 10 min and then kept undisturbed overnight; pptn.;

sodium tetrafluoroborate (13755-29-8) + tetrapentylammonium bromide (866-97-7) → C20H44N(1+)*BF4(1-)

Conditions	Yield
In pentan-1-ol; water	94.5%

propyl methanesulfonate (1912-31-8) + tetrapentylammonium bromide (866-97-7) → propyl bromide (106-94-5) + Methanesulfonatetetrapentyl-ammonium; (113369-05-4)

Conditions	Yield
In benzene at 80℃;	A n/a B 92%

trimethyltin(IV)chloride (1066-45-1) + tetrapentylammonium bromide (866-97-7) + potassium hexacyanoferrate(III) → (C5H11)4N(1+)*2Sn(CH3)3(1+)*Fe(CN)6(3-)*0.5H2O=N(C5H11)4(Sn(CH3)3)2Fe(CN)6*0.5H2O

Conditions	Yield
In water soln. of Fe-complex in H2O was added under stirring to soln. of Sn-complex and ligand in H2O; filtered, washed with H2O, dried; elem. anal.;	90.9%

iron(III) chloride hexahydrate + tetrapentylammonium bromide (866-97-7) + sulfur (7704-34-9) + thiophenol (108-98-5) → 2((C5H11)4N)(1+)*[Fe2S2(S(C6H5))4](2-)=((C5H11)4N)2[Fe2S2(S(C6H5))4]

Conditions

Yield

In acetonitrile addn. of PhSH to FeCl3*6H2O in CH3CN; addn. of the soln. to Triton X-100; addn. of the soln. to a stirred mixt. of sodium N-(tris(hydroxymethyl)methyl)-3-aminopropanesulfonate, solid S, and (C5H11)4NBr at pH 9; stirring at room temp. for 8-9 h; Ar atm.;; pptn. on standing at room temp. for 2-10 days; the ppt. was filtered off, washed with ether and then H2O and finally with ether; dried under vac.; elem. anal.;;

87%

3(CH3)3Sn(1+)*Co(CN)6(3-)=((CH3)3Sn)3[Co(CN)6] + tetrapentylammonium bromide (866-97-7) → (C5H11)4N(1+)*2Sn(CH3)3(1+)*Co(CN)6(3-)*0.5H2O=N(C5H11)4(Sn(CH3)3)2Co(CN)6*0.5H2O

Conditions	Yield
In water SnCo-complex was reacted with ligand in H2O, stirred for 12 h; filtered, washed with H2O, dried; elem. anal.;	86.6%

potassium hexacyanocobaltate(III) + trimethyltin(IV)chloride (1066-45-1) + tetrapentylammonium bromide (866-97-7) → (C5H11)4N(1+)*2Sn(CH3)3(1+)*Co(CN)6(3-)*0.5H2O=N(C5H11)4(Sn(CH3)3)2Co(CN)6*0.5H2O

Conditions	Yield
In water soln. of Co-complex in H2O was added under stirring to soln. of Sn-complex and ligand in H2O; filtered, washed with H2O, dried; elem. anal.;	86.2%

[(Me3Sn)3Fe(CN)6]n + tetrapentylammonium bromide (866-97-7) → (C5H11)4N(1+)*2Sn(CH3)3(1+)*Fe(CN)6(3-)*0.5H2O=N(C5H11)4(Sn(CH3)3)2Fe(CN)6*0.5H2O

Conditions	Yield
In water SnFe-complex was reacted with ligand in H2O, stirred for 12 h; filtered, washed with H2O, dried; elem. anal.;	83.3%

vanadyl(IV) phthalocyanine (13930-88-6) + tetrapentylammonium bromide (866-97-7) → C32H16N8OV(1-)*C20H44N(1+)

Conditions	Yield
With fluorenone radical anion sodium contact ion pair In 1,2-dichloro-benzene at 80℃; for 24h;	83%

oxotitanium(IV) phthalocyanine (26201-32-1) + tetrapentylammonium bromide (866-97-7) → C32H16N8OTi(1-)*C20H44N(1+)

Conditions	Yield
With fluorenone radical anion sodium contact ion pair In 1,2-dichloro-benzene at 80℃; for 24h;	74%

iron(II) chloride tetrahydrate + Li3(N(CH2-o-C6H4S)3) + carbon monoxide (201230-82-2) + tetrapentylammonium bromide (866-97-7) → [(n-C5H11)4N]Fe(N(CH2-o-C6H4S)3)CO

Conditions	Yield
In ethanol (under N2, Schlenk); EtOH soln. of FeCl2*4H2O and (C5H11)4NBr added to EtOH soln. of Li-salt, CO added into soln.; ppt. filtered, dried under CO atm.;	73%

vanadyl(IV) phthalocyanine (13930-88-6) + tetrapentylammonium bromide (866-97-7) + 1,2-dichloro-benzene (95-50-1) → C32H16N8OV(1-)*C28H60N(1+)*C6H4Cl2

Conditions	Yield
With fluorenone radical anion sodium contact ion pair In 1,2-dichloro-benzene at 80℃; for 24h;	72%

2-phenylpyridine (1008-89-5) + tetrapentylammonium bromide (866-97-7) → 2-(3-pentylphenyl)pyridine

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium 2,4,6-trimethylbenzoate; potassium hydroxide In toluene at 140℃; for 20h; Inert atmosphere; Glovebox;	71%

1-methyl-4-nitrobenzene (99-99-0) + tetrapentylammonium bromide (866-97-7) → 2-butyl-6-methyl-3-propylquinoline

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride; tin(ll) chloride In toluene at 180℃; for 20h;	62%

dimeric bis(tri-tert-butoxysilanethiolato)cadmium(II) + tetrapentylammonium bromide (866-97-7) + sodium diethyldithiocarbamate trihydrate (20624-25-3) → [Cd(SSi(OBu(t))3)2(S2CNEt2)][(C5H11)4N] (1105516-52-6)

Conditions	Yield
In water; toluene aq. soln. Et2NCS2Na and (C5H11)4NBr was added to soln. Cd complex in hottoluene and shaked for 4 h; org. layer was separated, washed with water and dried over MgSO4, soln. was evapd. to dryness, residue was recrystd. from toluene; elem. anal.;	62%

5-nitro-m-xylene (99-12-7) + tetrapentylammonium bromide (866-97-7) → 2-butyl-5,7-dimethyl-3-propylquinoline

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride; tin(ll) chloride In 1,4-dioxane at 180℃; for 20h;	61%

C6H5NCPd(P(C2H5)3)2CCPd(P(C2H5)3)2CNC6H5(2+)*2PF6(1-)=C40H70N2P4Pd2(2+)*2PF6(1-) + tetrapentylammonium bromide (866-97-7) → Br(P(C2H5)3)2PdCC(CNC6H5)2Pd(P(C2H5)3)2Br=C40H70Br2N2P4Pd2

Conditions	Yield
In acetone stirring at room temp. under nitrogen atm. for 24 h; evapd. to dryness in vac.; chromy. (alumina, benzene-dichloromethane), recrystn. from dichloromethane-hexane, elem. anal.;	60%

2,3,6,7,10,11-hexahydroxy-12d-methyltribenzotriquinacene + tetrapentylammonium bromide (866-97-7) → 4C23H18O6*3C20H44N(1+)*3Br(1-)

Conditions	Yield
In methanol for 48h; Inert atmosphere;	60%

tetrapentylammonium bromide (866-97-7) + 2-(N-benzylamino)-3-methylpyridine (70720-38-6) → 3-methyl-N-(1-phenylhexyl)pyridin-2-amine

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide In toluene at 140℃; for 16h; Inert atmosphere; Glovebox;	58%
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide In toluene at 140℃; for 16h; Inert atmosphere; Glovebox;	58%

3(CH3)3Sn(1+)*Ir(CN)6(3-)=((CH3)3Sn)3[Ir(CN)6] + tetrapentylammonium bromide (866-97-7) → (CH3)3Sn(H2O)(1+) (129732-09-8) + (C5H11)4N(1+)*((CH3)3Sn(H2O)NC)2Ir(CN)4(1-)=[(C5H11)4N][((CH3)3Sn(H2O)NC)2Ir(CN)4]

Conditions	Yield
In water (Me3Sn)3Ir(CN)6 suspended in soln. of (n-C5H11)4NBr in H2O; stirred; filtered; washed (cold H2O); dried; elem. anal.;	A n/a B 50%

tetrapentylammonium bromide (866-97-7) + nitrobenzene (98-95-3) → 2-n-butyl-3-n-propylquinoline (1531-51-7)

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride; tin(ll) chloride In 1,4-dioxane at 180℃; for 20h;	46%

triphenyltin(IV) trifluoroacetate + tetrapentylammonium bromide (866-97-7) → [(C5H11)4N](1+)*[(C6H5)3SnOCOCF3(Br)](1-) = [(C5H11)4N][(C6H5)3SnOCOCF3(Br)] (101214-73-7)

Conditions	Yield
In methanol (N2), mixture refluxed for 4 h; soln. concd., crystals washed with ether/pet. (40-60°C), dried in vacuo, elem. anal.;

Upstream product

• 2498-20-6 tetrapentylammonium iodide 
• 110-53-2 1-Bromopentane 
• 621-77-2 tripentylamine 

Downstream Products

• 106-94-5 propyl bromide 
• 113369-05-4 Methanesulfonatetetrapentyl-ammonium; 
• 4598-61-2 tetrapentylammonium hydroxide 
• 101214-73-7 [(C₅H₁₁)4N]⁽¹⁺⁾*[(C₆H₅)3SnOCOCF₃(Br)]^(1-) = [(C₅H₁₁)4N][(C₆H₅)3SnOCOCF₃(Br)] 
• 3475-60-3 tetra-n-pentylammonium thiocyanate 

Relevant articles and documents

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Anion and Cation Effects on Anion-Templated Assembly of Tetrahydroxytriptycene

A tetrahydroxytriptycene ligand 1 assembles through O-H···anion hydrogen bonds into a range of different structures. With tetrabutylammonium bromide, 1 forms a stable nanotube structure that is supported by O-H···anion hydrogen bonds, but its space is occupied by the large cation. In an effort to produce the nanotubes with different cations and anions, 1 was crystallized with different salts. The reaction of 1 with tetraethylammonium bromide gives a 2D net structure, while 1 and tetrapropylammonium bromide give a discrete 1:2 complex. Attempting to co-crystallize 1 and tetramethylammonium bromide gave crystals of an oxidized quinone form of the ligand. When 1 was crystallized with tetrabutylammonium terephthalate, two different one-dimensional anion coordination polymers were obtained, depending on the crystallization solvent: acetonitrile gave a zigzag polymer, while methanol gave a linear structure. In both cases, the tetrabutylammonium cations fill the gaps between the 1D polymers, giving a layered 2D morphology. The wide range of architectures prepared from a relatively simple ligand illustrates the potential utility of O-H···anion interactions for constructing solid-state materials.