Basic information
- Standard SMILES
CCCCP(CCCC)CCCC- InChIKey
TUQOTMZNTHZOKS-UHFFFAOYSA-N- Molecular formula
- C12H27P
- Average molar mass
- 202.32 g/mol
- Monoisotopic mass
- 202.18503749
Overview
Tributylphosphine is a colorless to yellowish liquid with a strong garlic-like odor. It is insoluble in water. It is liable to heat and ignite spontaneously in air. If involved in a fire phosphine gas, a highly flammable and toxic gas, will evolve. It is irritating to mucous membranes.
Names & identifiers
- Preferred name
- Tributylphosphine
- IUPAC
- tributylphosphane
- English name
- Tributylphosphine
- Molecular formula
- C12H27P
- Molecular weight
- 202.32
Names & synonyms
TributylphosphineTributylphosphaneTri-n-butylphosphine998-40-3Phosphine, tributyl-Tris(butyl)phosphineTributylfosfinDTXSID90469980O52FJR7WNUN3254NSC-91700DTXCID7026998
Show more names
TBUPP(n-Bu)3cytop 340TributylphosphorusNSC 91700(n-C4H9)3PCYTOP(R) 340
RefChem:190921213-651-2tributyl phosphineTri-n-butyl phosphinetributyl-phosphaneMFCD00009462Bu3PPBu3
Database identifiers
- CAS
998-40-3- PubChem CID
- 13831
- DTXSID
DTXSID9046998- ChEMBL
CHEMBL3185473- UNII
- 0O52FJR7WN
- EC Number
- 213-651-2
- Nikkaji
- J56.131B
Properties
Computed structural properties
- XLogP
- 3.7
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 9
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 72.1
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Phosphorus Compounds
Density0.812 @25 °C
Boiling Point240 °C @760 [mm Hg]
Vapor Pressure16 [mm Hg] @121 °C
Physical Description
Tributylphosphine is a colorless to yellowish liquid with a strong garlic-like odor. It is insoluble in water. It is liable to heat and ignite spontaneously in air. If involved in a fire phosphine gas, a highly flammable and toxic gas, will evolve. It is irritating to mucous membranes.
Liquid
Colorless to yellowish liquid with a strong odor like garlic; [CAMEO] Clear colorless liquid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- -65 °C · -65 °C
- Boiling point
- 150 °C50 · 150 °C50 mm Hg(lit.)
- Density
- 0.81 g/mL · 0.81 g/mL at 25 °C(lit.)
- vapor density
- 9 · 9 (vs air)
- vapor pressure
- 1.9 Pa · 1.9Pa at 20℃
- refractive index
- 20 · n20/D 1.462(lit.)
- Flash point
- 99 °F · 99 °F
- storage temp.
- 2 · 2-8°C
- form
- liquid
- color
- Clear colorless to pale yellow
- Specific Gravity
- 0.82 · 0.820 (20/4℃)
- Water Solubility
- insoluble
- Sensitive
- Moisture Sensitive/Air Sensitive
- BRN
- 1738261 · 1738261
- Stability
- Stable, but pyrophoric - spontaneously inflammable in air. Incompatible with oxidizing agents. Moisture sensitive.
- InChI
- 1S/C12H27P/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3
- InChIKey
- TUQOTMZNTHZOKS-UHFFFAOYSA-N
- SMILES
- CCCCP(CCCC)CCCC
- CAS DataBase Reference
- 998 · 998-40-3(CAS DataBase Reference)
- FDA UNII
- 0 O52FJR7WN · 0O52FJR7WN
- NIST Chemistry Reference
- Phosphine, tributyl-(998-40-3)
- EPA Substance Registry System
- Phosphine, tributyl- (998-40-3)
- UNSPSC Code
- 41105323 · 41105323
- NACRES
- 56 · NA.56
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS07,GHS09
- Signal word
- Danger
- Hazard statements
- 251 · H251-H302-H314-H411
- Precautionary statements
- 235 · P235-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xi,F,C,T
- Risk Statements
- 36 · 36/38-34-21/22-17-11-37-36/37/38-61
- Safety Statements
- 41 · 41-36/37/39-26-16-45-43-17-5-53
- RIDADR
- 3254 · UN 3254
- WGK Germany
- 3 · 3
- RTECS
- 3270000 · SZ3270000
- F
- 10 · 10-13-23
- Autoignition Temperature
- 392 °F · 392 °F
- TSCA
- TSCA listed
- HazardClass
- 4.2 · 4.2
- PackingGroup
- I
- HS Code
- 29319090 · 29319090
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 3 Eye · Aquatic Chronic 3Eye Dam. 1Repr. 1BSkin Corr. 1ASTOT SE 3
- REACH Registrations
- Active
- Excepted Quantities
- Forbidden
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (15.7%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P222, P231, P233, P235, P240, P241, P242, P243, P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P335+P334, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P370+P378, P391, P403+P235, P405, P407, P410, P413, P420, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 287 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Not Classified
Danger
Hazard information
Regulatory Information
Chemical: Phosphine, tributyl-
Phosphine, tributyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphine, tributyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 25-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/18531
Phosphine, tributyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
DOT LabelSpontaneously Combustible
Fire Hazards
Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
· Flammable/combustible material.
Health Hazards
Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
· Fire will produce irritating, corrosive and/or toxic gases.
Hazards Summary
Pyrophoric; May ignite on contact with water or moisture; [CAMEO] Causes burns; [EPA OHM/TADS] Pyrophoric; Reacts violently with water; Causes burns and lachrymation; Inhalation may cause corrosive injuries to upper respiratory tract; Harmful by ingestion and skin absorption; [Sigma-Aldrich MSDS] See Triphenylphosphine and tert-Butylphosphine.
DOT ID and Guide3254 135
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity AlertsHighly Flammable
Reactivity ProfileOrganophosphines, such as TRIBUTYLPHOSPHANE, are susceptible to partial oxidation by oxidizing agents, resulting in the release of phosphine oxides.
DOT Hazard Classification
Tributylphosphane
UN3254
Div 4.2 Spontaneously combustible material (49 eCFR § 173.124)
PG I: the degree of danger presented by the material is great
Air and Water ReactionsHighly flammable. May ignite on contact with air or moist air. Insoluble in water.
Hazard Classes and Categories
Flam. Liq. 3 (15.7%)
Pyrophoric liquids - Category 1
Safety & protection
Fire FightingExcerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
General First Aid:
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Nonfire Spill ResponseExcerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
Isolation and Evacuation
Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
Immediate precautionary measure
Protective Action Criteria (PAC)
2.3 [mg/m3]
25 [mg/m3]
150 [mg/m3]
Personal Protective Equipment (PPE)Excerpt from ERG Guide 135 [Substances - Spontaneously Combustible]:
Emergency Response Planning Guidelines· DO NOT USE WATER, CO2 OR FOAM ON MATERIAL ITSELF.
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 10-13-23
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SZ3270000
- ridadr
- UN 3254
- hs_code
- 29319090
- risk_code
- 36/38-34-21/22-17-11-37-36/37/38-61
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS07,GHS09
- hazard_code
- Xi,F,C,T
- safety_code
- 41-36/37/39-26-16-45-43-17-5-53
- hazard_class
- 4.2
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- I
- target organs
- Respiratory system
- Hazard statements
- H251-H302-H314-H411
- Excepted Quantities
- Forbidden
- REACH Registrations
- Active
- Hazard Classifications
- Aquatic Chronic 3Eye Dam. 1Repr. 1BSkin Corr. 1ASTOT SE 3
- Autoignition Temperature
- 392 °F
- Precautionary statements
- P235-P273-P280-P301+P312-P303+P361+P353-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Uses
Used as a polymerization cross-linking catalyst, organic intermediate, and as a catalyst component for hydrogenation in the petroleum industry; [EPA OHM/TADS]
Petroleum Production and Refining [Category: Industry]
U.S. Production2023: 50,000 - <250,000 lb
Industry UsesIntermediate
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Phosphine, tributyl-: ACTIVE
Applications
Uses1,4-addition catalyst; used with disulfides for the thioetherification of alcohols; acylation catalyst; used to prepare active esters.
Usessuzuki reaction
UsesTributylphosphine is usually used as catalyst for Domino reactions of activated conjugated dienes with β,γ-unsaturated-α-ketoesters, [3+2]-Cycloadditions,Umpolung addition reactions,Reductive carbonylation, Allylation reactions.
General DescriptionTributylphosphane is a colorless to yellowish liquid with a strong garlic-like odor. Tributylphosphane is insoluble in water. Tributylphosphane is liable to heat and ignite spontaneously in air. If involved in a fire phosphine gas, a highly flammable and toxic gas, will evolve. Tributylphosphane is irritating to mucous membranes.
Upstream & downstream products
Upstream raw materials
Downstream products
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