23906-97-0

Basic information

• Product Name: TETRA-N-OCTYLPHOSPHONIUM BROMIDE
• Synonyms: TetraoctylphosphoniuM broMide, Min. 95%;Cyphos 166;Cyphos IL 166;Tetra-n-octylphosphonium Bromide;TETRAOCTYLPHOSPHONIUM BROMIDE;TETRA-N-OCTYLPHOSPHONIUM BROMIDE
• CAS NO: 23906-97-0
• Molecular Formula: Br*C₃₂H₆₈P
• Molecular Weight: 563.76
• EINECS: 245-935-7
• Product Categories: Phosphonium Compounds;Greener Alternatives: Catalysis;Phase Transfer Catalysts;Phosphonium Salts
• Mol File: 23906-97-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 38-43 °C(lit.)
• Flash Point: >230 °F
• Appearance: white to yellow, waxy/solid
• Storage Temp.: Store below +30°C.
• Stability: hygroscopic
• CAS DataBase Reference: TETRA-N-OCTYLPHOSPHONIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRA-N-OCTYLPHOSPHONIUM BROMIDE(23906-97-0)
• EPA Substance Registry System: TETRA-N-OCTYLPHOSPHONIUM BROMIDE(23906-97-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 23906-97-0(Hazardous Substances Data)

Usage

Uses

Tetra-N-octylphosphonium bromide (CAS# 23906-97-0) is an organic salt used as a catalyst in the synthesis of α-alkylidene cyclic carbonates from CO2 and propargylic alcohols, and in the conversion of lactide to acrylic acid.

InChI:InChI=1/C32H68P.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

1-bromo-octane (111-83-1) → tetra-n-octylphosphonium bromide (23906-97-0)

Conditions	Yield
(i) /BRN= 1733136/, phosphorus, I2, (ii) Na, (iii) /BRN= 1733136/; Multistep reaction;
(i) /BRN= 1733136/, Mg, (ii) PCl3, (iii) /BRN= 1733136/; Multistep reaction;

1-bromo-octane (111-83-1) + TOP (4731-53-7) → tetra-n-octylphosphonium bromide (23906-97-0)

Conditions	Yield
at 108℃;
at 70℃; for 16h; Inert atmosphere;
at 160℃; for 20h; Inert atmosphere;

C42H42N28O14*C32H68P(1+)*Br(1-) → tetra-n-octylphosphonium bromide (23906-97-0) + cucurbituril (259886-50-5)

Conditions	Yield
In methanol; water Equilibrium constant;

tetra-n-octylphosphonium bromide (23906-97-0) + bis(trifluoromethane)sulfonimide lithium (90076-65-6) → tetra-n-octylphosphonium bis(triuoromethylsulfonyl)imide

Conditions	Yield
In dichloromethane; water	97%
In chloroform; water for 24h;
In dichloromethane; water at 20℃; for 12h;

tetra-n-octylphosphonium bromide (23906-97-0) + potassium nonaflate (29420-49-3) → tetraoctylphosphonium nonafluorobutane-1-sulfonate

Conditions	Yield
In dichloromethane; water	96%

sodium tetrafluoroborate (13755-29-8) + tetra-n-octylphosphonium bromide (23906-97-0) → tetraoctylphosphonium tetrafluoroborate

Conditions	Yield
In pentan-1-ol	94.2%

tetra-n-octylphosphonium bromide (23906-97-0) + disodium cis-1,2-dicyano-1,2-ethylenedithiolate (5466-54-6) → 2C32H68P(1+)*C4N2S2(2-)

Conditions	Yield
In ethanol

2,3,5-trichloropyridine (16063-70-0) + tetra-n-octylphosphonium bromide (23906-97-0) → 2-Fluoro-3,5-dichloropyridine (823-56-3) + 5-chloro-2,3-difluoropyridine (89402-43-7)

Conditions	Yield
With potassium fluoride; potassium carbonate; cesium fluoride In sulfolane

ammonium μ-nitridohexasulphatotriaquotri-iridate(III, IV, IV) + tetra-n-octylphosphonium bromide (23906-97-0) → tetraoctylphosphonium μ-nitridohexasulphatotriaquotri-iridate(III, IV, IV)

Conditions	Yield
In sulfuric acid; benzene aq. H2SO4; satn. of phosphonium salt (in benzene) by soln. of Ir-complex (in 0.01 MH2SO4); evapn. (vac., room temp.); elem. anal.;

potassium μ-oxohexasulphatotriaquotri-iridate(III, III, IV) + tetra-n-octylphosphonium bromide (23906-97-0) → tetraoctylphosphonium μ-oxohexasulphatotriaquotri-iridate(III, III, IV)

Conditions	Yield
In sulfuric acid; benzene aq. H2SO4; satn. of phosphonium salt (in benzene) by soln. of Ir-complex (in 0.01 MH2SO4); evapn. (vac., room temp.); elem. anal.;

tetra-n-octylphosphonium bromide (23906-97-0) → tetra-n-octylphosphonium formate (40333-00-4)

Conditions	Yield
With Amberlite IRN-78 In methanol; water
With Amberlite IRN 78 In methanol; water

(R)-Mecoprop (16484-77-8) + tetra-n-octylphosphonium bromide (23906-97-0) → tetraoctylphosphonium (+)-(R)-2-(4-chloro-2-methylphenoxy)-propionate (1314005-20-3)

Conditions	Yield
Stage #1: (R)-Mecoprop With sodium hydroxide In water at 59.84℃; Stage #2: tetra-n-octylphosphonium bromide In water

tetra-n-octylphosphonium bromide (23906-97-0) + silver nitrate → tetra-n-octylphosphonium nitrate (29578-61-8)

Conditions	Yield
In dichloromethane; water at 20℃; for 0.5h;

tetra-n-octylphosphonium bromide (23906-97-0) → tetra-n-octylphosphonium formate

Conditions	Yield
Multi-step reaction with 2 steps 1: pentan-1-ol 2: isopropyl alcohol / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium tetrafluoroborate / water; dichloromethane 2: isopropyl alcohol / 16 h View Scheme

tetra-n-octylphosphonium bromide (23906-97-0) → tetraoctylphosphonium tetrafluoroborate

Conditions	Yield
With sodium tetrafluoroborate In dichloromethane; water

tetra-n-octylphosphonium bromide (23906-97-0) + 4,6-dimethyl-2-meraptopyrimidine (22325-27-5) → C32H68P(1+)*C6H7N2S(1-)

Conditions	Yield
Stage #1: 4,6-dimethyl-2-meraptopyrimidine With potassium hydroxide In methanol at 60℃; for 0.666667h; Stage #2: tetra-n-octylphosphonium bromide for 30h;

tetra-n-octylphosphonium bromide (23906-97-0) → C32H68P(1+)*CH4O3P(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: Amberlite IRN 78 / methanol; water 2: methanol; water View Scheme

potassium perfluoro-n-octanesulfonate (2795-39-3) + tetra-n-octylphosphonium bromide (23906-97-0) → C8F17O3S(1-)*C32H68P(1+)

Conditions	Yield
In acetone at 20℃; for 24h;
In methanol at 20℃; for 24h;

C7H5N2O3S2(1-)*Ag(1+) + tetra-n-octylphosphonium bromide (23906-97-0) → C32H68P(1+)*C7H4N2O3S2(2-)*Ag(1+)

Conditions	Yield
In toluene for 0.05h;	80 mg

C3H7O3S2(1-)*Ag(1+) + tetra-n-octylphosphonium bromide (23906-97-0) → C3H6O3S2(2-)*Ag(1+)*C32H68P(1+)

Conditions	Yield
In toluene for 0.05h;	900 mg

tetra-n-octylphosphonium bromide (23906-97-0) + cucurbituril (259886-50-5) → C42H42N28O14*C32H68P(1+)*Br(1-)

Conditions	Yield
In methanol; water Equilibrium constant; Thermodynamic data;

Upstream product

• 111-83-1 1-bromo-octane 
• 4731-53-7 TOP 

Downstream Products

• 823-56-3 2-Fluoro-3,5-dichloropyridine 
• 89402-43-7 5-chloro-2,3-difluoropyridine 
• 40333-00-4 tetra-n-octylphosphonium formate 
• 1314005-20-3 tetraoctylphosphonium (+)-(R)-2-(4-chloro-2-methylphenoxy)-propionate 

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