Name | diphenylphosphine oxide |
Synonyms | DPPO HPOPh2 AURORA KA-1314 Diphenylphosphinoxid Diphenylphosphinit TIMTEC-BB SBB005946 Diphenylphosphinoxid diphenylphosphane oxide diphenylphosphine oxide Diphenylphosphonousacid oxo(diphenyl)phosphonium Phosphine oxide,diphenyl- Diphenylphosphaneoxide Two phenylphosphate oxygen Diphenylphosphinigsαure Diphenylphosphinousacid |
CAS | 4559-70-0 |
EINECS | 625-671-2 |
InChI | InChI=1/C12H10OP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H/q+1 |
InChIKey | ASUOLLHGALPRFK-UHFFFAOYSA-N |
Molecular Formula | C12H11OP |
Molar Mass | 202.19 |
Melting Point | 56-57°C(lit.) |
Boling Point | 102-105°C 0,2mm |
Water Solubility | Slightly soluble in water. |
Appearance | Crystals |
Color | Yellow to light orange |
Storage Condition | Inert atmosphere,Room Temperature |
Sensitive | Moisture Sensitive |
Refractive Index | 1.608-1.61 |
Hazard Symbols | Xn - Harmful |
Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 2 |
HS Code | 29319090 |
Introduction | Diphenylphosphine oxide is an important organic synthesis intermediate, widely used in the synthesis of various pesticides and chiral phosphine ligands, and It can replace alkali metal cyanide as a coupling agent for the synthesis of heterocyclic compounds, such as the synthesis of the herbicide paraquat under mild conditions. |
use | diphenylphosphine oxide is mainly used as a chemical reagent commonly used in laboratories. |
Application | Diphenylphosphorous oxygen is often used to prepare triphenylphosphine oxide, alkenyldiphenylphosphine oxide, addition and Wittig-Horner reaction reagents with alkynes. Synthesis of diphenylphosphine derivatives Ph2P(O)H is coupled with aryl trifluoromethanesulfonate, and the phosphine oxide is reduced to diphenylarylphosphine, which is a commonly used chiral ligand. |
Synthesis method | There are three main synthesis methods for diphenylphosphine oxide. Method 1 uses POCl3 as raw material, after Friedel alkylation, and then reduces with lithium aluminum hydride to obtain the target substance; Method 2 uses diethyl phosphite as raw material and reacts with Grignard reagent to generate the product; Method 3 Miller et al. uses PCl3 as raw material, after Friedel alkylation, and then hydrolyzes the target substance appropriately, but the purification of its intermediate Ph2PCl is difficult, and the yield is low, only 37.0%. |