4168-73-4

Basic information

• Product Name: TRIHEXYLPHOSPHINE
• Synonyms: TRIHEXYLPHOSPHINE;TRI-N-HEXYLPHOSPHINE;trihexylphosphane;Trihexylphosphin;Tri-n-hexylphosphine, Min. 96%
• CAS NO: 4168-73-4
• Molecular Formula: C₁₈H₃₉P
• Molecular Weight: 286.48
• EINECS: 224-025-3
• Product Categories: Mitsunobu Reaction;Phosphine Ligands;Phosphines (Mitsunobu Reaction);Synthetic Organic Chemistry
• Mol File: 4168-73-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 20℃
• Boiling Point: 227 °C / 50mmHg
• Flash Point: 179.1 °C
• Appearance: colorless/liquid
• Density: 0,83 g/cm3
• Vapor Pressure: 5.32E-05mmHg at 25°C
• Refractive Index: 1.4640 to 1.4680
• Sensitive: air sensitive
• CAS DataBase Reference: TRIHEXYLPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIHEXYLPHOSPHINE(4168-73-4)
• EPA Substance Registry System: TRIHEXYLPHOSPHINE(4168-73-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 4168-73-4(Hazardous Substances Data)

Usage

General Description

Trihexylphosphine is an organophosphorus compound that consists of a phosphorus atom with three hexyl groups bonded to it. It is commonly used as a ligand in coordination chemistry and catalysis reactions. Trihexylphosphine is a colorless liquid that is insoluble in water but soluble in organic solvents. It is known for its strong coordinating ability and is often used in the synthesis of various metal complexes. It is also used in the production of organic chemicals and pharmaceuticals. Trihexylphosphine is considered to be toxic and should be handled with care.

InChI:InChI=1/C18H39P/c1-4-7-10-13-16-19(17-14-11-8-5-2)18-15-12-9-6-3/h4-18H2,1-3H3

Synthetic route

n-hexylmagnesium chloride (44767-62-6) → trihexylphosphine (4168-73-4)

Conditions	Yield
With trichlorophosphate at -5℃; for 4h; Temperature;	92.6%

1-Iodohexane (638-45-9) → trihexylphosphine (4168-73-4)

Conditions	Yield
With phosphorous; Ni(0)bipy In N,N-dimethyl-formamide Electrochemical reaction; Zn anode;	75%

n-hexylmagnesium bromide (3761-92-0) → trihexylphosphine (4168-73-4)

Conditions	Yield
With diethyl ether; phosphorus trichloride

tris(n-hexyl)phosphine oxide (3084-48-8) → trihexylphosphine (4168-73-4)

Conditions	Yield
With trichlorosilane; triethylamine

decyl chloride (1002-69-3) + trihexylphosphine (4168-73-4) → decyl-trihexyl-phosphonium; chloride (850134-86-0)

Conditions	Yield
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h;	99%

1,10-dichlorodecane (2162-98-3) + trihexylphosphine (4168-73-4) → 1,10-di(trihexylphosphonium chloride)decane

Conditions	Yield
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h; Inert atmosphere;	99%

trihexylphosphine (4168-73-4) + heptyl 2-bromoacetate (18991-99-6) → tri-n-hexyl(heptoxycarbonylmethyl)phosphonium bromide (1227200-47-6)

Conditions	Yield
at 50℃; for 2h; Inert atmosphere;	99%

trihexylphosphine (4168-73-4) + pentyl 2-bromoacetate (52034-03-4) → tri-n-hexyl(pentoxycarbonylmethyl)phosphonium bromide (1227200-46-5)

Conditions	Yield
at 50℃; for 2h; Inert atmosphere;	99%

trihexylphosphine (4168-73-4) + chloromethyl methyl ether (107-30-2) → tri-n-hexyl(methoxymethyl)phosphonium chloride (1227200-50-1)

Conditions	Yield
at 50℃; for 5h; Inert atmosphere;	99%

n-propyl bromoacetate (35223-80-4) + trihexylphosphine (4168-73-4) → tri-n-hexyl(propoxycarbonylmethyl)phosphonium bromide (1227200-45-4)

Conditions	Yield
at 50℃; for 2h; Inert atmosphere;	98%

4-iodobutyl acetate (40596-44-9) + trihexylphosphine (4168-73-4) → tri-n-hexyl(acetoxybutyl)phosphonium iodide (1227200-48-7)

Conditions	Yield
at 50℃; for 4h; Inert atmosphere;	98%

trihexylphosphine (4168-73-4) + 2-bromoethanol (540-51-2) → tri-n-hexyl(2-hydroxyethyl)phosphonium bromide (1227200-51-2)

Conditions	Yield
at 50℃; for 5h; Inert atmosphere;	98%

trihexylphosphine (4168-73-4) + allyl bromide (106-95-6) → tri-n-hexylallylphosphonium bromide

Conditions	Yield
at 50℃; for 5h; Inert atmosphere;	96%
In diethyl ether Ambient temperature;

1,10-diiododecane (16355-92-3) + trihexylphosphine (4168-73-4) → 1,10-di(trihexylphosphonium iodide)decane

Conditions	Yield
for 3h; Inert atmosphere; Glovebox; Microwave irradiation; Heating;	96%

1,3-propanesultone (1120-71-4) + trihexylphosphine (4168-73-4) → C21H45O3PS

Conditions	Yield
In toluene at 90℃; for 72h; Inert atmosphere;	95%

trihexylphosphine (4168-73-4) + carbonic acid dimethyl ester (616-38-6) → tri-n-hexyl(methyl)phosphonium methyl carbonate (1258887-13-6)

Conditions	Yield
In methanol at 140℃; for 24h; Inert atmosphere; Autoclave;	94%

Cyclohexyl isocyanide (931-53-3) + trihexylphosphine (4168-73-4) + cobalt(II) perchlorate hexahydrate → tetrakis(cyclohexylisocyanide)bis(tri-n-hexylphosphine)cobalt(III) perchlorate + tris(cyclohexylisocyanide)bis(tri-n-hexylphosphine)cobalt(I) perchlorate (138978-07-1)

Conditions	Yield
In ethanol dropwise add. of C6H11NC (stirring), dropwise addn. of P(C6H13-n)3 (stirring), standing (room temp., 10 min); pptn. on dropwise addn. of ether and chilling (60 min), sepn. of Co(III)-complex: washing (ether), extn. (MeCN), pptn. on ether addn. (chilling); sepn. of Co(I)-complex: addn. of ether to filtrate and chilling (overnight), sepn., washing; elem. anal.;	A 93% B 69%

myristyl chloride (2425-54-9) + trihexylphosphine (4168-73-4) → trihexyl(tetradecyl)phosphonium chloride (258864-54-9)

Conditions	Yield
at 145℃; for 24h;	90%
at 145℃; Inert atmosphere;	90%
at 80℃; for 48h; Inert atmosphere;

5-bromopentanoic acid (2067-33-6) + trihexylphosphine (4168-73-4) → C23H48O2P(1+)*Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 48h;	90%

trihexylphosphine (4168-73-4) + 4-Vinylbenzyl chloride (1592-20-7) → tri(hexyl)-4-vinylbenzyl phosphonium chloride (226710-73-2)

Conditions	Yield
In acetonitrile at 60℃; Inert atmosphere;	88%

1 ,6-dibromohexane (629-03-8) + trihexylphosphine (4168-73-4) → trihexyl(6-bromohexyl)phosphonium bromide

Conditions	Yield
In dichloromethane Inert atmosphere; Reflux;	88%

sodium tetrahydroborate (16940-66-2) + trihexylphosphine (4168-73-4) → tri-n-hexylphosphine-borane

Conditions	Yield
With iodine In tetrahydrofuran byproducts: NaI; (C6H13)3P was dissolved in THF, stirred under N2, NaBH4 was added to soln., I2 dissolved in THF was added dropwise to the mixt., refluxed for 2h, the mixt. was cooled, filtered to remove NaI; product was washed with H2O and extd. with ether; elem. anal.;	87%

1 ,6-dibromohexane (629-03-8) + trihexylphosphine (4168-73-4) → 1,6-di(trihexylphosphonium bromide)hexane

Conditions	Yield
at 130℃; for 3h; Inert atmosphere; Glovebox; Microwave irradiation;	87%

trihexylphosphine (4168-73-4) + 1,10-dibromodecane (4101-68-2) → 1,10-di(trihexylphosphonium bromide)decane

Conditions	Yield
at 130℃; for 3h; Inert atmosphere; Glovebox; Microwave irradiation;	85%

3-Bromopropionic acid (590-92-1) + trihexylphosphine (4168-73-4) → C21H44O2P(1+)*Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 48h;	80%

7-bromoheptanoic acid (30515-28-7) + trihexylphosphine (4168-73-4) → C25H52O2P(1+)*Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 48h;	70%

trihexylphosphine (4168-73-4) + 4-Bromobenzoic acid (586-76-5) → C25H44O2P(1+)*Br(1-)

Conditions	Yield
With nickel dibromide at 170℃; for 13.5h; Inert atmosphere;	70%

trihexylphosphine (4168-73-4) + 1,10-dibromodecane (4101-68-2) → trihexyl(10-bromodecyl)phosphonium bromide

Conditions	Yield
In dichloromethane Inert atmosphere; Reflux;	70%

trihexylphosphine (4168-73-4) → hexyl-phosphonous dichloride (6460-28-2)

Conditions	Yield
With phosphorus trichloride at 275℃; for 1h;	64%

trihexylphosphine (4168-73-4) + trihexyl(10-bromodecyl)ammonium bromide → 1-((trihexylammonium) bromide)-10-((trihexylphosphonium) bromide)decane

Conditions	Yield
at 130℃; for 3h; Inert atmosphere; Glovebox; Microwave irradiation;	57%

trihexylphosphine (4168-73-4) + acrylic acid (79-10-7) → 1-carboxyethyl-tri-hexylphosphonium betaine (1128277-50-8)

Conditions	Yield
In chloroform at 20℃; for 24h; Inert atmosphere;	56%

n-hexylmagnesium chloride (44767-62-6) → trihexylphosphine (4168-73-4)

Conditions	Yield
With trichlorophosphate at -5℃; for 4h; Temperature;	92.6%

1-Iodohexane (638-45-9) → trihexylphosphine (4168-73-4)

Conditions	Yield
With phosphorous; Ni(0)bipy In N,N-dimethyl-formamide Electrochemical reaction; Zn anode;	75%

n-hexylmagnesium bromide (3761-92-0) → trihexylphosphine (4168-73-4)

Conditions	Yield
With diethyl ether; phosphorus trichloride

tris(n-hexyl)phosphine oxide (3084-48-8) → trihexylphosphine (4168-73-4)

Conditions	Yield
With trichlorosilane; triethylamine

decyl chloride (1002-69-3) + trihexylphosphine (4168-73-4) → decyl-trihexyl-phosphonium; chloride (850134-86-0)

Conditions	Yield
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h;	99%

1,10-dichlorodecane (2162-98-3) + trihexylphosphine (4168-73-4) → 1,10-di(trihexylphosphonium chloride)decane

Conditions	Yield
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h; Inert atmosphere;	99%
at 140℃; for 24h; Inert atmosphere;	99%

trihexylphosphine (4168-73-4) + heptyl 2-bromoacetate (18991-99-6) → tri-n-hexyl(heptoxycarbonylmethyl)phosphonium bromide (1227200-47-6)

Conditions	Yield
at 50℃; for 2h; Inert atmosphere;	99%

trihexylphosphine (4168-73-4) + pentyl 2-bromoacetate (52034-03-4) → tri-n-hexyl(pentoxycarbonylmethyl)phosphonium bromide (1227200-46-5)

Conditions	Yield
at 50℃; for 2h; Inert atmosphere;	99%

trihexylphosphine (4168-73-4) + chloromethyl methyl ether (107-30-2) → tri-n-hexyl(methoxymethyl)phosphonium chloride (1227200-50-1)

Conditions	Yield
at 50℃; for 5h; Inert atmosphere;	99%

n-propyl bromoacetate (35223-80-4) + trihexylphosphine (4168-73-4) → tri-n-hexyl(propoxycarbonylmethyl)phosphonium bromide (1227200-45-4)

Conditions	Yield
at 50℃; for 2h; Inert atmosphere;	98%

4-iodobutyl acetate (40596-44-9) + trihexylphosphine (4168-73-4) → tri-n-hexyl(acetoxybutyl)phosphonium iodide (1227200-48-7)

Conditions	Yield
at 50℃; for 4h; Inert atmosphere;	98%

trihexylphosphine (4168-73-4) + 2-bromoethanol (540-51-2) → tri-n-hexyl(2-hydroxyethyl)phosphonium bromide (1227200-51-2)

Conditions	Yield
at 50℃; for 5h; Inert atmosphere;	98%

trihexylphosphine (4168-73-4) + allyl bromide (106-95-6) → tri-n-hexylallylphosphonium bromide

Conditions	Yield
at 50℃; for 5h; Inert atmosphere;	96%
In diethyl ether Ambient temperature;

1,10-diiododecane (16355-92-3) + trihexylphosphine (4168-73-4) → 1,10-di(trihexylphosphonium iodide)decane

Conditions	Yield
for 3h; Inert atmosphere; Glovebox; Microwave irradiation; Heating;	96%

1,3-propanesultone (1120-71-4) + trihexylphosphine (4168-73-4) → C21H45O3PS

Conditions	Yield
In toluene at 90℃; for 72h; Inert atmosphere;	95%

trihexylphosphine (4168-73-4) + carbonic acid dimethyl ester (616-38-6) → tri-n-hexyl(methyl)phosphonium methyl carbonate (1258887-13-6)

Conditions	Yield
In methanol at 140℃; for 24h; Inert atmosphere; Autoclave;	94%

Cyclohexyl isocyanide (931-53-3) + trihexylphosphine (4168-73-4) + cobalt(II) perchlorate hexahydrate → tetrakis(cyclohexylisocyanide)bis(tri-n-hexylphosphine)cobalt(III) perchlorate + tris(cyclohexylisocyanide)bis(tri-n-hexylphosphine)cobalt(I) perchlorate (138978-07-1)

Conditions	Yield
In ethanol dropwise add. of C6H11NC (stirring), dropwise addn. of P(C6H13-n)3 (stirring), standing (room temp., 10 min); pptn. on dropwise addn. of ether and chilling (60 min), sepn. of Co(III)-complex: washing (ether), extn. (MeCN), pptn. on ether addn. (chilling); sepn. of Co(I)-complex: addn. of ether to filtrate and chilling (overnight), sepn., washing; elem. anal.;	A 93% B 69%

myristyl chloride (2425-54-9) + trihexylphosphine (4168-73-4) → trihexyl(tetradecyl)phosphonium chloride (258864-54-9)

Conditions	Yield
at 145℃; for 24h;	90%
at 145℃; Inert atmosphere;	90%
at 80℃; for 48h; Inert atmosphere;

5-bromopentanoic acid (2067-33-6) + trihexylphosphine (4168-73-4) → C23H48O2P(1+)*Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 48h;	90%

trihexylphosphine (4168-73-4) + 4-Vinylbenzyl chloride (1592-20-7) → tri(hexyl)-4-vinylbenzyl phosphonium chloride (226710-73-2)

Conditions	Yield
In acetonitrile at 60℃; Inert atmosphere;	88%

1 ,6-dibromohexane (629-03-8) + trihexylphosphine (4168-73-4) → trihexyl(6-bromohexyl)phosphonium bromide

Conditions	Yield
In dichloromethane Inert atmosphere; Reflux;	88%

sodium tetrahydroborate (16940-66-2) + trihexylphosphine (4168-73-4) → tri-n-hexylphosphine-borane

Conditions	Yield
With iodine In tetrahydrofuran byproducts: NaI; (C6H13)3P was dissolved in THF, stirred under N2, NaBH4 was added to soln., I2 dissolved in THF was added dropwise to the mixt., refluxed for 2h, the mixt. was cooled, filtered to remove NaI; product was washed with H2O and extd. with ether; elem. anal.;	87%

1 ,6-dibromohexane (629-03-8) + trihexylphosphine (4168-73-4) → 1,6-di(trihexylphosphonium bromide)hexane

Conditions	Yield
at 130℃; for 3h; Inert atmosphere; Glovebox; Microwave irradiation;	87%

trihexylphosphine (4168-73-4) + 1,10-dibromodecane (4101-68-2) → 1,10-di(trihexylphosphonium bromide)decane

Conditions	Yield
at 130℃; for 3h; Inert atmosphere; Glovebox; Microwave irradiation;	85%

3-Bromopropionic acid (590-92-1) + trihexylphosphine (4168-73-4) → C21H44O2P(1+)*Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 48h;	80%

7-bromoheptanoic acid (30515-28-7) + trihexylphosphine (4168-73-4) → C25H52O2P(1+)*Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 48h;	70%

trihexylphosphine (4168-73-4) + 4-Bromobenzoic acid (586-76-5) → C25H44O2P(1+)*Br(1-)

Conditions	Yield
With nickel dibromide at 170℃; for 13.5h; Inert atmosphere;	70%

trihexylphosphine (4168-73-4) + 1,10-dibromodecane (4101-68-2) → trihexyl(10-bromodecyl)phosphonium bromide

Conditions	Yield
In dichloromethane Inert atmosphere; Reflux;	70%

Upstream product

• 44767-62-6 n-hexylmagnesium chloride 
• 638-45-9 1-Iodohexane 
• 3084-48-8 tris(n-hexyl)phosphine oxide 
• 3761-92-0 n-hexylmagnesium bromide 

Downstream Products

• 3084-48-8 tris(n-hexyl)phosphine oxide 
• 94698-36-9 Co(CNC₆H₃(C₂H₅)2)3(P(C₆H₁₃)3)2⁽¹⁺⁾*ClO₄^(1-) = Co(CNC₆H₃(C₂H₅)2)3(P(C₆H₁₃)3)2(ClO₄) 
• 94698-34-7 Co(CNC₆H₄CH₃)3(P(C₆H₁₃)3)2⁽¹⁺⁾*ClO₄^(1-) = Co(CNC₆H₄CH₃)3(P(C₆H₁₃)3)2(ClO₄) 
• 94698-32-5 Co(CNC₆H₅)3(P(C₆H₁₃)3)2⁽¹⁺⁾*ClO₄^(1-) = Co(CNC₆H₅)3(P(C₆H₁₃)3)2(ClO₄) 
• 258864-54-9 trihexyl(tetradecyl)phosphonium chloride 
• 654057-97-3 (trihexyl)(tetradecyl)phosphonium bromide 
• 226710-73-2 tri(hexyl)-4-vinylbenzyl phosphonium chloride 
• 1361417-78-8 (4-benzoylbenzyl)tri(n-hexyl)phosphonium bromide 

Relevant articles and documents

Synthesis method of trihexylphosphine

The invention discloses a synthesis method of trihexylphosphine, belonging to the field of compound preparation. The synthesis method comprises the following steps: firstly reacting chlorohexane and magnesium chips under the protection of nitrogen gas in a mixed solvent of toluene and tetrahydrofuran by taking iodine granules as an initiator so as to obtain hexyl magnesium chloride; and without purification, cooling the hexyl magnesium chloride, directly adding phosphorus trichloride to the hexyl magnesium chloride, stirring for reacting at low temperature, and after the reaction, directly carrying out reduced pressure distillation to obtain the trihexylphosphine product. The purity of the trihexylphosphine product is more than 99%, and the yield of the trihexylphosphine product is 92.6%; and the solvent used in the synthesis method is easy to recycle.

Method for manufacturing acryloxypropysilane

A method to manufacture acryloxypropylsilane to a high degree of purity is achieved by hydrosilation of (A) allyl acrylate or allyl methacrylate by (B) a hydrosilane compound, using (C) a platinum-containing compound as the catalyst and (D) an organic phosphorus compound as the promoter. The acryloxypropylsilane product is expressed by General Formula I where R1 represents a hydrogen or methyl group, R2 represents a hydrolyzable group, R3 represents an aryl, alkenyl or aryl group of carbon number 1-12, and n is 0, 1, 2, or 3.