Basic information
- CAS
829-85-6- Standard SMILES
c1ccc(Pc2ccccc2)cc1- InChIKey
GPAYUJZHTULNBE-UHFFFAOYSA-N- Molecular formula
- C12H11P
- Average molar mass
- 186.19 g/mol
- Monoisotopic mass
- 186.05983698
Names & identifiers
- Preferred name
- Diphenylphosphine
- IUPAC
- diphenylphosphane
- English name
- Diphenylphosphine
- Molecular formula
- C12H11P
- Molecular weight
- 186.19
Names & synonyms
Diphenylphosphine829-85-6Phosphine, diphenyl-F9B5T7O7ZYEINECS 212-591-4NSC-152123DIPHENYLPHOSPHINE [MI]DTXSID50232076NSC 152123RefChem:588939DTXCID50154567212-591-4
Show more names
Diphenylphosphin98% Ph2PHAURORA KA-1107Diphenyl phospinePHOSPHINE, DIPHENYLDPP/DIPHENYLPHOSPHIN
diphenylphosphaneHPPH2PH2PHMFCD00003040C12H11PUNII-F9B5T7O7ZYdiphenylphospinediphenyl-phosphane
Database identifiers
- CAS
829-85-6- PubChem CID
- 70017
- DTXSID
DTXSID50232076- UNII
- F9B5T7O7ZY
- EC Number
- 212-591-4
- Nikkaji
- J99.507J
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 116
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Phosphorus Compounds
SpringerMaterials Properties31P nuclear magnetic resonance spectrum
Physical DescriptionClear liquid with strong unpleasant odor; [Merck Index] Clear light yellow liquid; [Sigma-Aldrich MSDS]
Physicochemical properties
- Melting point
- -14.5 °C · -14.5 °C
- Boiling point
- 280 °C · 280 °C(lit.)
- Density
- 1.07 g/mL · 1.07 g/mL at 25 °C(lit.)
- vapor pressure
- 2 mm · 2 mm Hg ( 110 °C)
- refractive index
- 20 · n20/D 1.625(lit.)
- Flash point
- -18 °C · -18°C (Hexane)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform
- pka
- 0.03 · diphenylphosphine is weakly basic. The pKa of the protonated derivative is 0.03.
- form
- liquid
- color
- colorless
- Specific Gravity
- 0.68 · 0.68
- Water Solubility
- Miscible with ethanol, ether, benzene, concentrated hydrochloric acid. Immiscible with water.
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- Sensitive
- Air & Moisture Sensitive
- BRN
- 742504 · 742504
- InChIKey
- GPAYUJZHTULNBE-UHFFFAOYSA-N
- CAS DataBase Reference
- 829 · 829-85-6(CAS DataBase Reference)
- FDA UNII
- 9 B5T7O7ZY · F9B5T7O7ZY
- NIST Chemistry Reference
- Phosphine, diphenyl-(829-85-6)
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 250 · H250-H315-H319-H335
- Precautionary statements
- 210 · P210-P222-P231+P232-P302+P352-P305+P351+P338-P370+P378
- Hazard Codes
- F,Xi
- Risk Statements
- 17 · 17-36/37/38
- Safety Statements
- 26 · 26-36
- RIDADR
- 2845 · UN 2845 4.2/PG 1
- WGK Germany
- 3 · 3
- F
- 8 · 8-10-13-23
- HazardClass
- 4.2 · 4.2
- PackingGroup
- I
- HS Code
- 29319090 · 29319090
- REACH Registrations
- Active
- Limited Quantities
- 0.5 L · 0.5 L (0.1 gallon)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (300g or 300ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H250 (100%): Catches fire spontaneously if exposed to air [Danger Pyrophoric liquids]
P210, P222, P231, P233, P261, P264, P264+P265, P271, P280, P302+P335+P334, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 15-03-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/28173
Hazards SummaryPyrophoric and irritating; [Merck Index] Pyrophoric; Reacts violently with water; A skin and strong eye irritant; [Sigma-Aldrich MSDS] See Triphenylphosphine and Phenylphosphine.
Hazard Classes and CategoriesPyr. Liq. 1 (100%)
Safety data
- F
- 8-10-13-23
- wgk
- 3
- ridadr
- UN 2845 4.2/PG 1
- hs_code
- 29319090
- risk_code
- 17-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- safety_code
- 26-36
- hazard_class
- 4.2
- packing_group
- I
- Hazard statements
- H250-H315-H319-H335
- Limited Quantities
- 0.5 L (0.1 gallon)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (300g or 300ml)
- REACH Registrations
- Active
- Precautionary statements
- P210-P222-P231+P232-P302+P352-P305+P351+P338-P370+P378
Chemistry & industry
Uses & manufacturing
UsesUsed as a reagent in synthetic organic chemistry; [Merck Index]
Applications
UsesIt can be used the intermediates of organic, catalysts.
Usessuzuki reaction
UsesDiphenylphosphine is used in the synthesis of aminophosphines for application as catalysts. It is also used in the preparation of chiral palladacycles with N-heterocyclic carbene ligands as catalysts.
UsesDiphenylphosphine acts as an intermediate in the preparation of diphenylphosphide derivatives, phosphonium salts, phosphine ligands and Wittig-Horner reagents. The presence of hydrogen atom bonded to phosphorus undergoes Michael-like addition to activated alkenes. It is involved in the preparation of 1,2-bis(diphenylphosphino)ethane and (phenyl-(phenylmethyl)phosphoryl)benzene. Further, it is used in the synthesis of aminophosphines and chiral palladacycles with N-heterocyclic carbene ligands as catalysts.
Preparation methods
PreparationDiphenylphosphine can be prepared from triphenylphosphine by reduction to lithium diphenylphosphide, which can be protonated to give the title compound:PPh3 + 2 Li → LiPPh2 + LiPhLiPPh2 + H2O → Ph2PH + LiOH
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
257 records
Compound notes
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