14937-45-2

Usage

Uses

Used in the Construction Industry:
Cetyltributylphosphonium bromide is used as a surface modifier for palygorskite, a natural clay mineral, to improve its thermal properties. This enhancement in thermal properties can lead to better performance in construction materials, such as increased durability and resistance to temperature fluctuations.
Used in the Water Treatment Industry:
Cetyltributylphosphonium bromide is used as an additive in water to improve the resistance of epoxy-anhydride matrices. This application can be particularly useful in the water treatment industry, where epoxy-anhydride matrices are often used to protect and reinforce water infrastructure, such as pipes and storage tanks.
Used in the Chemical Industry:
Cetyltributylphosphonium bromide is used as a modifier of phenolic resin to improve its thermal degradation properties. This modification can lead to the development of phenolic resins with enhanced thermal stability, which can be beneficial in various chemical applications, such as in the production of plastics, coatings, and adhesives.

InChI:InChI=1/C28H60P.BrH/c1-5-9-13-14-15-16-17-18-19-20-21-22-23-24-28-29(25-10-6-2,26-11-7-3)27-12-8-4;/h5-28H2,1-4H3;1H/q+1;/p-1

Synthetic route

1-bromo-butane (109-65-9) + hexadecyltributylphosphonium thiocyanate (67047-78-3) → n-butylthiocyanate (628-83-1) + cetyltributylphosphonium bromide (14937-45-2)

Conditions	Yield
In benzene-d6 at 60℃; for 50h; Equilibrium constant; Substitution;

benzyl bromide (100-39-0) + hexadecyltributylphosphonium thiocyanate (67047-78-3) → benzyl thiocyanate (3012-37-1) + cetyltributylphosphonium bromide (14937-45-2)

Conditions	Yield
With water In benzene-d6 at 60℃; Kinetics; Equilibrium constant; Substitution;

Methyl methanesulfonate (66-27-3) + cetyltributylphosphonium bromide (14937-45-2) → Tributylhexadecylphosphonium-methansulfonat (86471-19-4)

Conditions	Yield
In diethyl ether 1) 32 h, r.t., 2) 9 h, heating;	100%

propyl methanesulfonate (1912-31-8) + cetyltributylphosphonium bromide (14937-45-2) → propyl bromide (106-94-5) + Tributylhexadecylphosphonium-methansulfonat (86471-19-4)

Conditions	Yield
In benzene at 80℃;	A n/a B 99%

cetyltributylphosphonium bromide (14937-45-2) → C28H60P(1+)*2FH*F(1-)

Conditions	Yield
With potassium hydrogen bifluoride In dichloromethane for 0.5h; Ambient temperature;	98%

3-methoxyphenylacetonitrile (19924-43-7) + cetyltributylphosphonium bromide (14937-45-2) + allyl bromide (106-95-6) → 2-Allyl-2-(3-methoxy-phenyl)-pent-4-enenitrile (144828-82-0)

Conditions	Yield
In sodium hydroxide	98%

cetyltributylphosphonium bromide (14937-45-2) → hexadecyltributylphosphonium azide (66997-37-3)

Conditions	Yield
With sodium azide In diethyl ether	94%
With sodium azide; anion exchange resin azide form In methanol Substitution;

cetyltributylphosphonium bromide (14937-45-2) + 2-Chloronitrobenzene (88-73-3) → ortho-nitrofluorobenzene (1493-27-2)

Conditions	Yield
With potassium fluoride	91.2%

cetyltributylphosphonium bromide (14937-45-2) + potassium phtalimide (1074-82-4) → phthalimide (136918-14-4)

Conditions	Yield
In water; N,N-dimethyl-formamide; toluene	90%

N-methyl-bis(chloro-ethyl)amine monohydrochloride + 3-chloro-benzeneacetonitrile (1529-41-5) + cetyltributylphosphonium bromide (14937-45-2) → 1-methyl-4-(3-chlorophenyl)-4-piperidinecarbonitrile (126555-97-3)

Conditions	Yield
With sodium hydroxide In water	88%
With sodium hydroxide In water	88%

cetyltributylphosphonium bromide (14937-45-2) + 1-dodecylbromide (143-15-7) + ethyl 5-methyl-4-nitro-2-pyrrolcarboxylate potassium salt → ethyl 1-dodecyl-5-methyl-4-nitro-2-pyrrolcarboxylate (147871-47-4)

Conditions	Yield
In toluene	83%

1H-imidazole (288-32-4) + phosgene (75-44-5) + cetyltributylphosphonium bromide (14937-45-2) → Carbonyldiimidazole (64269-79-0)

Conditions	Yield
With sodium hydroxide In water; chlorobenzene	79.5%

3-(trimethylsilyl)-1-propanesulfonic acid,sodium salt (2039-96-5) + cetyltributylphosphonium bromide (14937-45-2) → C28H60P(1+)*C6H15O3SSi(1-)

Conditions	Yield
In water at 20℃;	77%
In water at 20℃;	77%

1-benzhydryl-3-azetidinyl methanesulfonate (33301-41-6) + cetyltributylphosphonium bromide (14937-45-2) + potassium phtalimide (1074-82-4) → 2-(1-benzhydrylazetidin-3-yl)isoindoline-1,3-dione (38353-74-1)

Conditions	Yield
In di-isopropyl ether; ethyl acetate; toluene	67.4%

9-(2-chloethyl)phenanthrene (119522-03-1) + cetyltributylphosphonium bromide (14937-45-2) + potassium phtalimide (1074-82-4) → 2-(9-Phenanthrenyl)ethylphthalimide

Conditions	Yield
In water	56.6%

methanolic hydrogen chloride + methyl 2-(3-methoxyphenoxy)-3-pyridinylacetate + cetyltributylphosphonium bromide (14937-45-2) + acetyl chloride (75-36-5) → methyl 2-(3-hydroxyphenoxy)-3-pyridinylacetate

Conditions	Yield
With potassium carbonate In methanol; 2-(3-methoxyphenoxy)-3-pyridinecarboxaldehyde; dichloromethane; water; hydrogen bromide	51%

3-phenoxybenzyl chloride (53874-66-1) + cetyltributylphosphonium bromide (14937-45-2) → m-phenoxy-benzyl fluoride (72223-90-6)

Conditions	Yield
With potassium fluoride In water	49%

Ethyl tiglate (5837-78-5) + Bromoform (75-25-2) + cetyltributylphosphonium bromide (14937-45-2) → ethyl 1,2-dimethyl-3,3-dibromo-1-cyclopropanecarboxylate (67074-39-9)

Conditions	Yield
With sodium hydroxide In dichloromethane; water	37%

n-butylthiocyanate (628-83-1) + cetyltributylphosphonium bromide (14937-45-2) → 1-bromo-butane (109-65-9) + hexadecyltributylphosphonium thiocyanate (67047-78-3)

Conditions	Yield
In benzene-d6 at 60℃; for 50h; Equilibrium constant; Substitution;

benzyl thiocyanate (3012-37-1) + cetyltributylphosphonium bromide (14937-45-2) → benzyl bromide (100-39-0) + hexadecyltributylphosphonium thiocyanate (67047-78-3)

Conditions	Yield
With water In benzene-d6 at 60℃; Kinetics; Equilibrium constant; Substitution;

cetyltributylphosphonium bromide (14937-45-2) + cobalt(II) chloride (7646-79-9) → bis[cetyltributylphosphonium]dibromo dichloro cobaltate

Conditions	Yield
In ethyl acetate for 2h; Heating / reflux;

6-(3-methoxyphenoxy)-1-(4-methylphenyl)-2-phenyl-1H-benzimidazole + cetyltributylphosphonium bromide (14937-45-2) → 3-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]phenol (1447672-93-6)

cetyltributylphosphonium bromide (14937-45-2) + 3-oxa-1,5-dichloropentane (111-44-4) + (3-iodophenyl)acetonitrile (130723-54-5) → 4-cyano-4-(3-iodophenyl)-3,4,5,6-tetrahydro-2H-pyran (179421-14-8)

Conditions	Yield
With sodium hydroxide	2.38 g (76%)

4-toluenesulfonyl azide (941-55-9) + cetyltributylphosphonium bromide (14937-45-2) + (tert-butyl)[(5-chloro(2-thienyl))sulfonyl]amine (155731-14-9) → 3-amino-N-(tert-butyl)-5-chlorothiophene-2-sulfonamide (194086-62-9)

Conditions	Yield
With n-butyllithium; sodium borohydrid In tetrahydrofuran; hexane; water; ethyl acetate

(-)-2-[(1,4,5,6-tetrahydropyrimidin-2-yl)thio]methyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methyl-1,4-dihydropyridine (689211-91-4) + 2-bromoethylamine hydrobromide (2576-47-8) + cetyltributylphosphonium bromide (14937-45-2) + (2E)-but-2-enedioic acid (110-17-8) → (-)-2-(aminoethylthio)methyl-3-carboethoxy-5-carbomethoxy-4-(3-nitrophenyl)-6-methyl-1,4-dihydropyridine fumarate

Conditions	Yield
With sodium hydroxide In ethyl acetate; benzene

sodium sulfide nonahydrate + 2-bromo-1,1,1-trifluoroethane (421-06-7) + cetyltributylphosphonium bromide (14937-45-2) → bis-(2,2,2-trifluoromethyl) disulphide + bis(2,2,2-trifluoroethyl) disulfide (674-63-5)

Conditions	Yield
With hydrogen sulfide In water

2-aminobenzothiazole-6-carboxylic acid (93-85-6) + hexane (110-54-3) + cetyltributylphosphonium bromide (14937-45-2) + ethylene dibromide (106-93-4) → 2(R,S)-methoxycarbonyl-3,4-dihydro-2H-1,4-benzothiazine (96988-53-3)

Conditions	Yield
With potassium hydroxide In methanol; chloroform; water; ethyl acetate

Upstream product

• 109-65-9 1-bromo-butane 
• 67047-78-3 hexadecyltributylphosphonium thiocyanate 
• 100-39-0 benzyl bromide 

Downstream Products

• 106-94-5 propyl bromide 
• 86471-19-4 Tributylhexadecylphosphonium-methansulfonat 
• 109-65-9 1-bromo-butane 
• 67047-78-3 hexadecyltributylphosphonium thiocyanate 
• 100-39-0 benzyl bromide 
• 126555-97-3 1-methyl-4-(3-chlorophenyl)-4-piperidinecarbonitrile 
• 1447672-93-6 3-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]phenol 
• 64269-79-0 Carbonyldiimidazole 
• 144828-82-0 2-Allyl-2-(3-methoxy-phenyl)-pent-4-enenitrile 
• 179421-14-8 4-cyano-4-(3-iodophenyl)-3,4,5,6-tetrahydro-2H-pyran 
• 135903-78-5 1-(2-phenylethyl)-4-phenyl-4-piperidinecarbonitrile 
• 51043-72-2 bis(cyclopropyl)methylamine hydrochloride 
• 652-03-9 3,4,5,6-tetrafluorophthalic acid 
• 13677-69-5 4-allyl-2,6-di-tert-butylphenol 

Relevant academic research and scientific papers

Thiocyanation of alkyl halides with alkyl thiocyanates in the presence of quaternary phosphonium halides

Alkyl thiocyanates undergo simple SN2 reactions with the counter ions of quaternary phosphonium salts in nonpolar solvents and thiocyanate ions are liberated as the leaving ion. Depending on the nucleophile, the reaction proceeded irreversibly or reversibly. The reaction of benzyl thiocyanate with azide ions afforded a quantitative yield of benzyl azide. The reactions of alkyl thiocyanates with halide ions gave an equilibrium mixture where the reverse reaction of the alkyl halides produced with the liberated thiocyanate ions took place simultaneously. Thus, thiocyanate-halide exchange reactions between an alkyl thiocyanate and an alkyl halide were possible in the presence of a catalytic amount of a quaternary salt.