Diphenylmethoxyphosphine

Diphenylmethoxyphosphine Property

Boiling point:

149 °C6 mm Hg(lit.)

Density 

1.078 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.604(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

form 

Liquid

Specific Gravity

1.078

color 

Clear colorless to very slightly yellow

Sensitive 

Air & Moisture Sensitive

BRN 

1640480

InChI

InChI=1S/C13H13OP/c1-14-15(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3

InChIKey

OAADXJFIBNEPLY-UHFFFAOYSA-N

SMILES

P(C1=CC=CC=C1)(C1=CC=CC=C1)OC

CAS DataBase Reference

4020-99-9(CAS DataBase Reference)

NIST Chemistry Reference

Methyl diphenylphosphinite(4020-99-9)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-36

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29310099

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Diphenylmethoxyphosphine Chemical Properties,Usage,Production

Chemical Properties

Colorless to light yellow liqui

Uses

Ased as:

• Catalyst for hydroformylative desymmetrization of bisalkenyl carbinols and bishomoallylic carbinols
• Ligand in rhodium-catalyzed hydroformylation of bishomoallylic alcohols
• Calatyst in preparation of γ-lactones via branched-regioselective hydroformylation reactions
• Ligand for nickel-catalyzed hydrocyanation reactions
• Catalyst in annulation reactions

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling

Synthesis

The general procedure for the synthesis of diphenylmethoxyphosphine from diphenylphosphonium chloride is as follows: 210 g (6.56 mol) of anhydrous methanol was cooled to -15°C under nitrogen protection. At this temperature, 200 g (0.907 mol) of diphenylphosphonium chloride was vigorously stirred and slowly added dropwise. Subsequently, 18 g (1.06 mol) of ammonia was passed. After cooling was withdrawn, stirring of the reaction mixture was continued for 10 h. Upon completion of the reaction, the product was separated by diafiltration. The filtrate was distilled under reduced pressure to remove methanol and excess ammonia. The residue was filtered by pumping through a glass sand core funnel to give 143 g of crude diphenylmethoxyphosphine in 73% yield of the theoretical value.

References

[1] Patent: US5705669, 1998, A