Di-tert-butylchlorophosphane Chemical Properties

Melting point:

2-3°C

Boiling point:

48 °C/3 mmHg (lit.)

Density 

0.951 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.482(lit.)

Flash point:

142 °F

solubility 

Miscible with terahydrofuran.

form 

Liquid

Specific Gravity

0.951

color 

Clear colorless

Sensitive 

Air & Moisture Sensitive

InChI

InChI=1S/C8H18ClP/c1-7(2,3)10(9)8(4,5)6/h1-6H3

InChIKey

MCRSZLVSRGTMIH-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

13716-10-4(CAS DataBase Reference)

NIST Chemistry Reference

Phosphinous chloride, bis(1,1-dimethylethyl)-(13716-10-4)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45-25

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

TSCA 

No

HazardClass 

8

PackingGroup 

II

HS Code 

29310099

MSDS

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

Di-tert-butylchlorophosphane Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

Di-tert-butylchlorophosphine is associated with palladium(II) acetate and used in Suzuki-Miyaura cross-couplings of arylboronic acids with aryl bromides and chlorides. It serves as a ligand and used in the preparation of mono- and bidentate phosphine ligands in metal complexes for catalytic chiral asymmetric hydrogenations. Further, it is used in asymmetric and transition metal coupling reactions. In addition to this, it plays an important role in the preparation of other phosphines in catalytic polymerization reactions.

Uses

Di-tert-butylchlorophosphine is used as a catalyst in organic synthesis.

Uses

Bulky ligand used with Pd(OAc)₂ in efficient Suzuki-Miyaura cross-couplings of arylboronic acids with aryl bromides and chlorides.

Application

Bulky ligand used with Pd(OAc)2 in efficient Suzuki-Miyaura cross-couplings of arylboronic acids with aryl bromides and chlorides.

reaction suitability

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Synthesis

General procedure for the synthesis of di-tert-butylphosphonium chloride from di-tert-butylphosphine: Di-tert-butylphosphine (13.5 g, 92 mmol) was added to a three-necked round-bottomed flask fitted with a thermometer, a charging funnel and a condenser under the protection of nitrogen and heated to 83-84 °C. The synthesis of di-tert-butylphosphonium chloride from di-tert-butylphosphine was carried out by the following procedure. Octyl trichloroacetate (25.4 g, 92 mmol) was slowly added dropwise over a period of 20 minutes. After the dropwise addition, the reaction mixture was continued to be stirred at 70 °C for 20 min, which showed 0.6% unreacted di-tert-butylphosphine by GC analysis. The addition funnel was removed and the short-circuit distillation head was adapted for distillation. Two fractions were collected and the former fraction (1.24 g) was discarded. The second fraction was collected to give 13 g (78.2% yield) of di-tert-butylphosphonium chloride as a clear, colorless liquid with a boiling point of 48-52 °C/3.2 mbar (literature value 48 °C/3 mm Hg). The purity of the product was 97% by GC-FID.

Precautions

Air and moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents and strong reducing agents.

References

[1] Patent: WO2009/147495, 2009, A2. Location in patent: Page/Page column 17
[2] J. Gen. Chem. USSR (Engl. Transl.), 1991, vol. 61, # 1.1, p. 114 - 118

Di-tert-butylchlorophosphane(13716-10-4)Related Product Information

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