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Tributylphosphane
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  • Name Tributylphosphane
  • EINECS213-651-2
  • CAS No. 998-40-3
  • Density0.81 g/mL at 25 °C(lit.)
  • PSA13.59000
  • LogP4.86860
  • SolubilityInsoluble in water. Miscible with ether, methanol, ethanol and benzene.
  • Melting Point-65 °C
  • FormulaC12H27P
  • Boiling Point244.8 °C at 760 mmHg
  • Molecular Weight202.32
  • Flash Point112.2 °C
  • Transport InformationUN 3254
  • Appearancecolourless liquid
  • Safety41-36/37/39-26-16-45-43-17-5
  • Risk Codes36/38-34-21/22-17-11-37
  • Molecular Structure
    Molecular Structure of 998-40-3 (Tributylphosphine)
  • Hazard SymbolsCorrosiveC; FlammableF; IrritantXi
  • SynonymsCorrosiveC; FlammableF; IrritantXi
  • Article Data94

Tributylphosphane Synthetic route

tri(n-butyl)phosphine borane

998-40-3

tributylphosphine

Conditions
ConditionsYield
With methanol; 4 A molecular sieve In 1,4-dioxane at 115℃; for 28h;100%
109-69-3

n-Butyl chloride

998-40-3

tributylphosphine

Conditions
ConditionsYield
Stage #1: n-Butyl chloride With magnesium; methyl iodide In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 40 - 50℃; for 2.7h; Inert atmosphere;
Stage #2: With phosphorus trichloride In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene at 5℃; for 4h; Temperature; Inert atmosphere;		90.3%
55425-72-4

(2,2'-bipyridyl)(1,5-cyclooctadiene)nickel

13165-72-5

chlorosulfite de methyle

A

121837-93-2

(bipy)Ni(Cl)(metallasulfinat-Me)

B

998-40-3

tributylphosphine

C

5259-72-3, 10060-40-9, 111-78-4

1,5-dicyclooctadiene

Conditions
ConditionsYield
In tetrahydrofuran inert atmosphere; cooling soln. of Ni-compd. (-78°C), addn. of org. compd., stirring (room temp.); filtn., washing (hexane), drying; elem. anal.;A 83%
B n/a
C n/a
72315-65-2

tributyl(methylthio)phosphonium trifluoromethanesulfonate

998-40-3

tributylphosphine

Conditions
ConditionsYield
With Hexamethylphosphorous triamide In dichloromethane80%
814-29-9

Tributylphosphine oxide

998-40-3

tributylphosphine

Conditions
ConditionsYield
With phenylsilane In benzene-d6 at 100℃; for 6h; Kinetics; Temperature; Time; Solvent; Inert atmosphere; Sealed tube;72%
Stage #1: Tributylphosphine oxide With [Fe(CO)(1,3-bis(diphenylphosphino)propane)H(NO)]; phenylsilane; N-ethyl-N,N-diisopropylamine In toluene at 100℃; for 18h; Schlenk technique;
Stage #2: With sodium hydroxide In methanol; water; toluene at 20℃; for 1h; Schlenk technique; chemoselective reaction;		55%
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 10h;
109-65-9

1-bromo-butane

A

998-40-3

tributylphosphine

B

814-29-9

Tributylphosphine oxide

Conditions
ConditionsYield
With phosphorous; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide at 50℃; Electrochemical reaction; Mg anode;A 11%
B 55%
With phosphorous In N,N-dimethyl-formamide Electrochemical reaction; Mg anode;A 11%
B 55%
With phosphorus; potassium hydroxide; hydrazine hydrate; N-benzyl-N,N,N-triethylammonium chloride In toluene at 80 - 85℃; for 5h;A 6%
B 31%
17343-82-7

tri-n-butyl(ethoxycarbonylmethylene)phosphorane

A

998-40-3

tributylphosphine

B

814-29-9

Tributylphosphine oxide

C

623-91-6

diethyl Fumarate

Conditions
ConditionsYield
With water; 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate In tetrahydrofuran -30 deg C, 30 min; -30 deg C to RT;A n/a
B n/a
C 48%
51266-28-5

(Bu3P)2Ni(cyclo-octa-1,5-diene)

13360-57-1

dimethylamino sulfonyl chloride

A

Ni(sulfinato-O,O'-NMe2)2

B

998-40-3

tributylphosphine

C

5259-72-3, 10060-40-9, 111-78-4

1,5-dicyclooctadiene

Conditions
ConditionsYield
In tetrahydrofuran inert atmosphere; cooling soln. of Ni-compd. (-78°C), addn. of sulfonyl chloride, stirring (room temp.); filtn., washing (THF), drying; elem. anal.;A 40%
B n/a
C n/a
51266-28-5

(Bu3P)2Ni(cyclo-octa-1,5-diene)

98-09-9

benzenesulfonyl chloride

A

Ni(sulfinato-O,O'-Ph)2

B

998-40-3

tributylphosphine

C

5259-72-3, 10060-40-9, 111-78-4

1,5-dicyclooctadiene

Conditions
ConditionsYield
In tetrahydrofuran inert atmosphere; cooling soln. of Ni-compd. (-78°C), addn. of sulfonyl chloride, stirring (room temp.); filtn., washing (THF), drying; elem. anal.;A 39%
B n/a
C n/a
51266-28-5

(Bu3P)2Ni(cyclo-octa-1,5-diene)

124-63-0

methanesulfonyl chloride

A

Ni(sulfinato-O,O'-Me)2

B

998-40-3

tributylphosphine

C

5259-72-3, 10060-40-9, 111-78-4

1,5-dicyclooctadiene

Conditions
ConditionsYield
In tetrahydrofuran inert atmosphere; cooling soln. of Ni-compd. (-78°C), addn. of sulfonyl chloride, stirring (room temp.); filtn., washing (THF), drying; elem. anal.;A 36%
B n/a
C n/a

Tributylphosphane Chemical Properties

Molecular Structure:

Molecular Formula: C12H27P
Molecular Weight: 202.316541 g/mol
Appearance: colorless pale yellow clear liquid
Melting Point: -65 °C
Boiling Point: 150 °C  at 50 mm Hg
Flash Point: 99 °F
Solubility: methanol, ether, ethanol, benzene
Insolubility: water
Density: 0.81 g/mL at 25 °C
Vapor density: 9
Refractive index:n: 20/D 1.462
Storage temp.: 2-8°C 
Sensitive: Moisture, Air
BRN: 1738261
EINECS: 213-651-2
IUPAC Name: tributylphosphane
Synonyms of Tributylphosphine (CAS NO.998-40-3): TRIBUTYLPHOSPHINE(998-40-3): Tri-n-butylphosphine ; 4-16-00-01699 (Beilstein Handbook Reference) ; AI3-28071 ; BRN 1738261 ; EINECS 213-651-2 ; NSC 91700 ; Tri-n-butylphosphine ; Tributylfosfin ; Tributylfosfin [Czech] ; Tributylphosphane ; Tributylphosphane [UN3254] [Spontaneously combustible] ; Tris(butyl)phosphine ; UN3254 ; Phosphine, tributyl-
Categories: Tertiary Phosphines;Ligand;Mitsunobu Reaction;Phosphine Ligands;Phosphines (Mitsunobu Reaction);Synthetic Organic Chemistry

Tributylphosphane Uses

 Tributylphosphine (CAS NO.998-40-3) is used as main ligand of homogeneous catalyst in the petrochemical. It is also used as reducing agent, olefin polymerization catalyst.

Tributylphosphane Production

 Tributylphosphine (CAS NO.998-40-3) is prepared industrially by the reaction of phosphine with butene.
PH3 + 3CH2=CHCH2CH3 → P(CH2CH2CH2CH3)3
It can be prepared in the laboratory by reaction of the appropriate Grignard reagent with phosphorus trichloride.
3BuMgCl + PCl3 → PBu3 + 3MgCl2

Tributylphosphane Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin 2gm/kg (2000mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 600, 1969.
rat LD50 oral 750mg/kg (750mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 600, 1969.

Tributylphosphane Consensus Reports

Reported in EPA TSCA Inventory.

Tributylphosphane Safety Profile

Safety Information of Tributylphosphine (CAS NO.998-40-3):
Hazard Codes:Xi  ,F  ,C
Risk Statements:36/38-34-21/22-17-11-37
36/38:Irritating to eyes and skin
11:Highly flammable
17:Spontaneously flammable in air
21/22:Harmful in contact with skin and if swallowed
34:Causes burns
Safety Statements:41-36/37/39-26-16-45-43-17-5
41:In case of fire and/or explosion do not breathe fumes
16:Keep away from sources of ignition - No smoking
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water)
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
17:Keep away from combustible material
5:Keep contents under ... (appropriate liquid to be specified by the manufacturer)
RIDADR:UN 3254 4.2/PG 1
WGK Germany:3
RTECS:SZ3270000
F:10-13-23
HazardClass:4.2
PackingGroup:I
Moderately toxic by ingestion. Slightly toxic by skin contact. When heated to decomposition it emits toxic vapors of POx.

Tributylphosphane Specification

First Aid Measures of Tributylphosphine (CAS NO.998-40-3):
Eyes:Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. 
Ingestion:Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Storage of Tributylphosphine (CAS NO.998-40-3):
Keep away from heat, sparks, and flame. Do not store near combustible materials. Store in a cool, dry place. Store in a tightly closed container. Flammables-area. Store under nitrogen.

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