Name | Diphenylphosphine |
Synonyms | DPP AURORA KA-1107 Diphenylphosphin DIPHENYLPHOSPHINE Diphenyl phospine Diphenylphosphine diphenylphosphane Diphenyl-phosphane PHOSPHINE, DIPHENYL |
CAS | 829-85-6 |
EINECS | 212-591-4 |
InChI | InChI=1/C12H11P/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10,13H |
InChIKey | GPAYUJZHTULNBE-UHFFFAOYSA-N |
Molecular Formula | C12H11P |
Molar Mass | 186.19 |
Density | 1.07g/mLat 25°C(lit.) |
Melting Point | -14.5 °C |
Boling Point | 280°C(lit.) |
Flash Point | -18°C (Hexane) |
Water Solubility | Miscible with ethanol, ether, benzene, concentrated hydrochloric acid. Immiscible with water. |
Solubility | Chloroform |
Vapor Presure | 2 mm Hg ( 110 °C) |
Appearance | liquid |
Specific Gravity | 0.68 |
Color | colorless |
BRN | 742504 |
pKa | diphenylphosphine is weakly basic. The pKa of the protonated derivative is 0.03. |
Storage Condition | 2-8°C |
Sensitive | Air & Moisture Sensitive |
Refractive Index | n20/D 1.625(lit.) |
Risk Codes | R17 - Spontaneously flammable in air R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
UN IDs | UN 2845 4.2/PG 1 |
WGK Germany | 3 |
FLUKA BRAND F CODES | 8-10-13-23 |
HS Code | 29319090 |
Hazard Class | 4.2 |
Packing Group | I |
NIST chemical information | information provided by: webbook.nist.gov (external link) |
Introduction | diphenylphosphine is an organophosphorus compound commonly used in the laboratory. It is a colorless liquid with unpleasant odor and irritating, in the air is easy to be oxidized and spontaneous combustion, sensitive to air and light, need to use nitrogen protection. It can be used as a precursor for the synthesis of various organic phosphine ligands. It can be converted to diphenylphosphonates by Deprotonation: Ph2PH nBuLi → Ph2PLi nBuH, such as 1, 2-bis (diphenylphosphine) ethane and 1, the synthesis of a phosphine ligand such as 3-bis (diphenylphosphine) propane, the Wittig-Horner reagent, and the quaternary phosphonium salt typically requires alkylation of the diphenylphosphine. |
Use | diphenylphosphine is used in the synthesis of aminophosphine and as a catalyst. It can also be used to prepare chiral palladacyces with N-Heterocyclic Carbene Ligands as catalysts. organic intermediates, catalysts |
preparation method | diphenylphosphine or diphenylphosphonates such as sodium diphenylphosphine and lithium diphenylphosphine can be added to carbon as nucleophiles heteroatom double bond. For example, under the condition of concentrated hydrochloric acid at 100°C, diphenylphosphine can be added to the aldehyde carbon atom of benzaldehyde: Ph2PH PhCHO → Ph2P(O)CH2Ph, compared with Tertiary phosphine, diphenylphosphine is less basic. The pKa of the conjugate acid of diphenylphosphine is 0.03:Ph2PH2 → Ph2PH H preparation method: diphenylphosphine can be prepared from inexpensive triphenylphosphine by lithiation to form lithium diphenylphosphine followed by quenching with water:(1) PPh3 2 Li → LiPPh2 LiPh (2) LiPPh2 H2O → Ph2PH LiOH. |