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| CAS No.: | 998-40-3 |
|---|---|
| Name: | Tributylphosphine |
| Article Data: | 94 |
| Molecular Structure: | |
|
|
|
| Formula: | C12H27P |
| Molecular Weight: | 202.32 |
| Synonyms: | Phosphine, tributyl-;Tributylfosfin;Tri-n-butylphosphine; |
| EINECS: | 213-651-2 |
| Density: | 0.81 g/mL at 25 °C(lit.) |
| Melting Point: | -65 °C |
| Boiling Point: | 244.8 °C at 760 mmHg |
| Flash Point: | 112.2 °C |
| Solubility: | Insoluble in water. Miscible with ether, methanol, ethanol and benzene. |
| Appearance: | colourless liquid |
| Hazard Symbols: |
 C;  F;  Xi
|
| Risk Codes: | 36/38-34-21/22-17-11-37 |
| Safety: | 41-36/37/39-26-16-45-43-17-5 |
| Transport Information: | UN 3254 |
| PSA: | 13.59000 |
| LogP: | 4.86860 |
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- 998-40-3
tributylphosphine
| Conditions | Yield |
|---|---|
| With methanol; 4 A molecular sieve In 1,4-dioxane at 115℃; for 28h; | 100% |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With Hexamethylphosphorous triamide In dichloromethane | 80% |
| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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
B
- 998-40-3
tributylphosphine
C
- 5259-72-3, 10060-40-9, 111-78-4
1,5-dicyclooctadiene
| Conditions | Yield |
|---|---|
| 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
B
- 998-40-3
tributylphosphine
C
- 5259-72-3, 10060-40-9, 111-78-4
1,5-dicyclooctadiene
| Conditions | Yield |
|---|---|
| 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
B
- 998-40-3
tributylphosphine
C
- 5259-72-3, 10060-40-9, 111-78-4
1,5-dicyclooctadiene
| Conditions | Yield |
|---|---|
| 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 |
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Chemistry
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
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.
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
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. |
Consensus Reports
Reported in EPA TSCA Inventory.
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.
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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