Chlorodiisopropylphosphine Chemical Properties

Boiling point:

69 °C33 mm Hg(lit.)

Density 

0.959 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.475(lit.)

Flash point:

39 °F

storage temp. 

Refrigerator

form 

Liquid

color 

Clear light yellow

Sensitive 

air sensitive, moisture sensitive

InChI

InChI=1S/C6H14ClP/c1-5(2)8(7)6(3)4/h5-6H,1-4H3

InChIKey

JZPDBTOWHLZQFC-UHFFFAOYSA-N

SMILES

P(C(C)C)(C(C)C)Cl

CAS DataBase Reference

40244-90-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

F,C

Risk Statements 

11-34

Safety Statements 

16-26-27-36/37/39-45-1

RIDADR 

UN 2924 3/PG 2

WGK Germany 

3

HazardClass 

3.1

PackingGroup 

II

HS Code 

29310099

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Chlorodiisopropylphosphine Usage And Synthesis

Description

Chlorodiisopropylphosphine is an organophosphorus compound of particular interest in synthetic chemistry, where it is used as a reagent in the preparation of phosphine ligands for transition metal complexes. Its utility in synthesising these complexes is due to the reactivity of the chloro group, which other groups can substitute to create a diverse array of ligands. This reactivity is also exploited in the study of catalysis, as the resulting phosphine ligands can be used to modulate the activity and selectivity of metal catalysts. In addition, Chlorodiisopropylphosphine is investigated for its potential in forming new organophosphorus compounds with applications in materials science. Researchers are also interested in the compound′s role in synthesising flame retardants, where its phosphorus content could contribute to the material′s flame-retarding properties.

Chemical Properties

Colorless to light yellow liqui

Uses

Chlorodiisopropylphosphine can be used:

• To synthesize p-styryldiisopropylphosphine by reacting with 4-chlorostyrene via Grignard reaction.
• As a phosphination reagent in combination with [Cp2Zr(1-butene)(DMAP)] (Cp=cyclopentadienyl; DMAP= 4-(dimethylamino)pyridine)) for the zirconophosphination of alkynes to form zirconoalkenylphosphines.
• A luminescent mixed-donor platinum POCN pincer complex via cyclometalation process.

Application

Chlorodiisopropylphosphine is widely used for preparing organic phosphine pesticides, secondary phosphine, organic phosphine ligand and high-efficiency organic metal catalyst in thermoplastic elastomer synthesis, can also be used as an important component of a non-lethal weapon system, and is recently used for electrochemically synthesizing novel electrolyte salt fluoroalkyl lithium phosphonate of a lithium ion secondary battery as a green energy source due to the special structure of the organic phosphine catalyst.[1]

reaction suitability

reagent type: ligand
reaction type: Arylations

Synthesis

Chlorodiisopropylphosphine can be synthesized by using Mg, chloro iso-propane and phosphine trichloride as the main raw material. The optimum reacting condition for the synthesis includes, the material proportioning being PCl3 : i-C3H7C1 = 1 : 1.8 (mol ratio), the reaction temperature being -30 deg. C, dropping time being 1.25h. By employing THF for substituting ether as the solvent, the reaction can be accelerated and the yield can be increased.[1]

References

[1] The synthetic method of diisopropyl phosphine chloride. Patent CN1724548A.

Chlorodiisopropylphosphine(40244-90-4)Related Product Information

• Dicyclohexylchlorophosphine
• CHLORODIISOPROPYLPHOSPHINE
• DICYCLOHEXYLPHOSPHINYL CHLORIDE
• Di-tert-butylchlorophosphane
• DICHLORO(CHLORODI-T-BUTYLPHOSPHINE)PALLADIUM(II) DIMER
• DICHLOROBIS(CHLORODICYCLOHEXYLPHOSPHINE) PALLADIUM (II)
• DICHLORO(CHLORO-TERT-BUTYLCYCLOHEXYLPHOSPHINE) PALLADIUM (II) DIMER
• DICHLORO(CHLORODICYCLOHEXYLPHOSPHINE) PALLADIUM (II) DIMER
• DIBROMO(CHLORODI-TERT-BUTYLPHOSPHINE)PALLADIUM (II) DIMER
• DICHLOROBIS(CHLORODI-TERT-BUTYLPHOSPHINE) PALLADIUM (II)
• DI-1-ADAMANTYLPHOSPHINIC CHLORIDE
• DI-TERT-BUTYLCHLOROPHOSPHINE BORANE COMPLEX
• CHLORODICYCLOPENTYLPHOSPHINE
• DIBROMO(CHLORODI-T-BUTYLPHOSPHINE)PALLADIUM(II) DIMER
• DICHLOROBIS(CHLORO-T-BUTYLCYCLOHEXYLPHOSPHINE)PALLADIUM(II)
• AURORA KA-1182
• TERT-BUTYLCYCLOHEXYLCHLOROPHOSPHINE
• P-CYCLOHEXYL-P-(1,1-DIMETHYLETHYL)PHOSPHINOSELENOIC CHLORIDE