14937-45-2

Basic information

• Product Name: Cetyltributylphosphonium bromide
• Synonyms: (N-HEXADECYL)TRI-N-BUTYLPHOSPHONIUM BROMIDE;TRIBUTYLHEXADECYLPHOSPHONIUM BROMIDE;HEXADECYLTRIBUTYLPHOSPHONIUM BROMIDE;HEXADECYLTRI-N-BUTYLPHOSPHONIUM BROMIDE;CETYLTRIBUTYLPHOSPHONIUM BROMIDE;Cetyltri-n-butyl phosphonium bromide~Tri-n-butylhexadecylphosphonium bromide;Hexadecyltrinbutylphosphoniumbromidewhitextl;TBHDPB
• CAS NO: 14937-45-2
• Molecular Formula: Br*C₂₈H₆₀P
• Molecular Weight: 507.65
• EINECS: 239-014-9
• Product Categories: Phosphonium Salts;Aliphatics;Phosphonium Compounds;organophosphorus compound
• Mol File: 14937-45-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 56-58 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/crystal
• Density: g/cm³
• Storage Temp.: Store below +30°C.
• Solubility: methanol: 0.1 g/mL, clear
• Sensitive: Hygroscopic
• BRN: 4167404
• CAS DataBase Reference: Cetyltributylphosphonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Cetyltributylphosphonium bromide(14937-45-2)
• EPA Substance Registry System: Cetyltributylphosphonium bromide(14937-45-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 21
• TSCA: Yes
• Hazardous Substances Data: 14937-45-2(Hazardous Substances Data)

Usage

Uses

Tributylhexadecylphosphonium Bromide (CAS# 14937-45-2) is a dynamic compound used as a surface modifier for thermal properties of palygorskite, an additive in water to improve resistance of epoxy-anhydride matrices, and as a modifier of phenolic resin to improve thermal degradation.

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

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

Downstream Products

• 109-65-9 1-bromo-butane 
• 67047-78-3 hexadecyltributylphosphonium thiocyanate 
• 64269-79-0 Carbonyldiimidazole 
• 144828-82-0 2-Allyl-2-(3-methoxy-phenyl)-pent-4-enenitrile 
• 41272-12-2 tributylhexadecylphosphonium chloride 
• 1215220-54-4 4-(pentadec-2-yl)phenol 
• 38353-74-1 2-(1-benzhydrylazetidin-3-yl)isoindoline-1,3-dione 
• 13677-69-5 4-allyl-2,6-di-tert-butylphenol 
• 652-03-9 3,4,5,6-tetrafluorophthalic acid 
• 51043-72-2 bis(cyclopropyl)methylamine hydrochloride 
• 135903-78-5 1-(2-phenylethyl)-4-phenyl-4-piperidinecarbonitrile 
• 179421-14-8 4-cyano-4-(3-iodophenyl)-3,4,5,6-tetrahydro-2H-pyran 
• 1447672-93-6 3-[[1-(4-methylphenyl)-2-phenyl-1H-benzimidazol-6-yl]oxy]phenol 
• 126555-97-3 1-methyl-4-(3-chlorophenyl)-4-piperidinecarbonitrile