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381020

Sigma-Aldrich

tert-Butyldichlorophosphine

98%

Synonym(s):

tert-Butylphosphine dichloride, tert-Butylphosphonous dichloride

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About This Item

Linear Formula:
(CH3)3CPCl2
CAS Number:
25979-07-1
Molecular Weight:
158.99
EC Number:
247-386-9
MDL number:
MFCD00013615
UNSPSC Code:
12352001
PubChem Substance ID:
24863784
NACRES:
NA.22

Assay

98%

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

mp

44-49 °C (lit.)

functional group

phosphine

SMILES string

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

InChI

1S/C4H9Cl2P/c1-4(2,3)7(5)6/h1-3H3

InChI key

NMJASRUOIRRDSX-UHFFFAOYSA-N

Application

tert-Butyldichlorophosphine can be used as a reactant for the synthesis of:
  • Dihydrobenzooxaphosphole core.
  • tert-Butyl functionalized 1,3-C6H4(CH2PR2)2 (PCP) pincer ligands.
  • Chloro-phosphinite reagent by reacting with sodium ethoxide.
  • 2-(tert-Butylhydrophosphoryl)-1-phenyl-1H-imidazole derivatives.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Solid-phase synthesis and catalytic screening of polystyrene supported diphosphines.
Samuels MC, et al.
Topics in Catalysis, 59(19-20), 1793-1799 (2016)
Imidazolio-substituted secondary phosphine oxides as potential carbene reagents.
Chang YC, et al.
Polyhedron, 100(19-20), 382-391 (2015)
Synthesis and coordination chemistry of new asymmetric donor/acceptor pincer ligands, 1, 3-C6H4 (CH2PtBu(Rf))2 (Rf= CF3, C2F5).
Debnath S, et al.
Dalton Transactions, 47(35), 12420-12430 (2018)
Synthesis of P-Chiral Dihydrobenzooxaphosphole Core for BI Ligands in Asymmetric Transformations.
Li G, et al.
The Journal of Organic Chemistry, 82(10), 5456-5460 (2017)

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