1,2-Bis(dichlorophosphino)benzene

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1,2-Bis(dichlorophosphino)benzene
C6H4(PCCl2)2.svg
Names
Preferred IUPAC name
(1,2-Phenylene)bis(phosphonous dichloride)
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C6H4Cl4P2/c7-11(8)5-3-1-2-4-6(5)12(9)10/h1-4H
    Key: IGYHSFVSIYJSML-UHFFFAOYSA-N
  • C1=CC=C(C(=C1)P(Cl)Cl)P(Cl)Cl
Properties
C6H4Cl4P2
Molar mass 279.85 g·mol−1
Appearance colorless liquid
Boiling point 97–99 °C (207–210 °F; 370–372 K) 0.001 torr
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,2-Bis(dichlorophosphino)benzene is an organophosphorus compound with the formula C6H4(PCl2)2. A viscous colorless liquid, it is a precursor to chelating diphosphines of the type C6H4(PR2)2.[1] It is prepared from 1,2-dibromobenzene by sequential lithiation followed by treatment with (Et2N)2PCl (Et = ethyl), which affords C6H4[P(NEt2)2]2. This species is finally cleaved with hydrogen chloride:[2]

C6H4[P(NEt2)2]2 + 8 HCl → C6H4(PCl2)2 + 4 Et2NH2Cl

Related compounds[edit]

References[edit]

  1. ^ Hatakeyama, Takuji; Hashimoto, Toru; Kondo, Yoshiyuki; Fujiwara, Yuichi; Seike, Hirofumi; Takaya, Hikaru; Tamada, Yoshinori; Ono, Teruo; Nakamura, Masaharu (2010). "Iron-Catalyzed Suzuki−Miyaura Coupling of Alkyl Halides". Journal of the American Chemical Society. 132 (31): 10674–10676. doi:10.1021/ja103973a. PMID 20681696.
  2. ^ Reetz, Manfred T.; Moulin, Dominique; Gosberg, Andreas (2001). "BINOL-Based Diphosphonites as Ligands in the Asymmetric Rh-Catalyzed Conjugate Addition of Arylboronic Acids". Organic Letters. 3 (25): 4083–4085. doi:10.1021/ol010219y. PMID 11735590.