Basic information
- CAS
594-09-2- Standard SMILES
CP(C)C- InChIKey
YWWDBCBWQNCYNR-UHFFFAOYSA-N- Molecular formula
- C3H9P
- Average molar mass
- 76.08 g/mol
- Monoisotopic mass
- 76.04418692
Overview
Trimethylphosphine is a tertiary phosphine.
Names & identifiers
- Preferred name
- Trimethylphosphine
- IUPAC
- trimethylphosphane
- English name
- Trimethylphosphine
- Molecular formula
- C3H9P
- Molecular weight
- 76.08
Names & synonyms
Trimethylphosphine594-09-2Trimethyl phosphineTrimethylphosphorus5FL6SQK9H3CHEBI:35890DTXSID00208120RefChem:191804DTXCID20130611trimethylphosphane;trimethylphosphorus209-823-1trimethylphosphane
Show more names
Methyl phosphinerimethylphosphineTrimethyl-phosphanePHOSPHORUS TRIMETHYLTrimethylphosphine,99%TriMethylphosphine 97%
Phosphine, trimethyl-PMe3Me3P(CH3)3PMFCD00008510C3H9PtrimethylphospineEINECS 209-823-1
Database identifiers
- CAS
594-09-2- PubChem CID
- 68983
- DTXSID
DTXSID00208120- ChEBI
CHEBI:35890- UNII
- 5FL6SQK9H3
- EC Number
- 209-823-1
- Nikkaji
- J466I
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 4
- Formal charge
- 0
- Complexity
- 8
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Phosphorus Compounds
SpringerMaterials Properties31P nuclear magnetic resonance spectrum
Density0.735 @25 °C
Boiling Point37.5 °C @760 [mm Hg]
Physical DescriptionColorless liquid with a pungent odor; [Alfa Aesar MSDS]
Ionization Efficiency
Positive
0.29
5.53
Agilent XCT
Electrospray ionization
ammonium acetate (4nM)
Physicochemical properties
- Melting point
- -86 °C · -86 °C (lit.)
- Boiling point
- 38 · 38-40 °C (lit.)
- Density
- 0.738 g/mL · 0.738 g/mL at 20 °C (lit.)
- vapor pressure
- 7.24 psi · 7.24 psi ( 20 °C)
- refractive index
- 20 · n20/D 1.428(lit.)
- Flash point
- 4 °F · −4 °F
- storage temp.
- 2 · 2-8°C
- form
- liquid
- color
- colorless
- Specific Gravity
- 0.748 · 0.748
- Water Solubility
- Soluble in water.
- Sensitive
- Air & Moisture Sensitive
- BRN
- 969138 · 969138
- InChI
- 1S/C3H9P/c1-4(2)3/h1-3H3
- InChIKey
- YWWDBCBWQNCYNR-UHFFFAOYSA-N
- SMILES
- CP(C)C
- CAS DataBase Reference
- 594 · 594-09-2(CAS DataBase Reference)
- FDA UNII
- 5 FL6SQK9H3 · 5FL6SQK9H3
- NIST Chemistry Reference
- Phosphine, trimethyl-(594-09-2)
- UNSPSC Code
- 12352128 · 12352128
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H315-H319-H335
- Precautionary statements
- 210 · P210-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves
- Hazard Codes
- F,Xn,Xi
- Risk Statements
- 11 · 11-36/37/38-67-65-63-48/20-38-17-40-36/37-19
- Safety Statements
- 9 · 9-16-26-36/37/39-62-36/37-7/9-33
- RIDADR
- 1993 · UN 1993 3/PG 2
- WGK Germany
- 3 · 3
- F
- 10 · 10-13-23
- HazardClass
- 4.2 · 4.2
- PackingGroup
- I
- HS Code
- 29319090 · 29319090
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 Flam · Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2STOT SE 3
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryPyrophoric; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] See Tributylphosphine.
Hazard Classes and CategoriesFlam. Liq. 2 (100%)
Safety & protection
Protective Action Criteria (PAC)
12 [mg/m3]
130 [mg/m3]
790 [mg/m3]
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 10-13-23
- PPE
- Eyeshields, Faceshields, Gloves
- wgk
- 3
- ridadr
- UN 1993 3/PG 2
- hs_code
- 29319090
- risk_code
- 11-36/37/38-67-65-63-48/20-38-17-40-36/37-19
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xn,Xi
- safety_code
- 9-16-26-36/37/39-62-36/37-7/9-33
- hazard_class
- 4.2
- Storage Class
- 3 - Flammable liquids
- packing_group
- I
- target organs
- Respiratory system
- Hazard statements
- H225-H315-H319-H335
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P210-P302+P352-P305+P351+P338
Chemistry & industry
Applications
UsesTrimethylphosphine (PMe3) is an electron-rich phosphine ligand used as a reagent in Mitsunobu reaction.It can be used:In transformation of azides into carbamates; aziridines to azidoalcohols; and ketoximes to ketones with 2,2′-dipyridyl diselenide.In Aza-Wittig reaction;, C-H bond activation of imines; cross-coupling reactions.In the preparation of (cyanomethylene) trimethylphosphorane (CMMP) which is used as a reagent in Mitsunobu type reaction.As a reagent in the synthesis of ruthenium trimethylphosphine complexes, which in turn are used as catalysts for hydrogenation of CO2 to formic acid.
UsesTrimethylphosphine (PMe3) solution is the suitable reagent used in the synthesis of Fe/Te cluster type complex, Fe6Te8(PMe3)6. It may be employed as a probe to investigate the acid sites in Y-zeolite. It may be used for the synthesis of hexakis(trimethylphosphine)tris-μ-methylene-diruthenium(III).
UsesTrimethylphosphine is an electron-rich phosphine ligand used in the Mitsunobu reaction. It participates in the transformation of azides into carbamates, aziridines from azidoalcohols, iminophosphoranes and aza-Wittig reaction. This product is offered as a solution in 2-methyltetrahydrofuran for more convenient handling.
General DescriptionTrimethylphosphine is the reagent used in Mitsunobu reaction. It participates in the transformation of azides into carbamates, aziridines from azidoalcohols, iminophosphoranes and aza-Wittig reaction. Electron diffraction study of trimethylphosphine has been reported.
Upstream & downstream products
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Additional notes
DefinitionChEBI: Trimethylphosphine is a tertiary phosphine.
Related reactions
264 records
Compound notes
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