1,2-Bis(dichlorophosphino)benzene

1,2-Bis(dichlorophosphino)benzene
Names
	Other names 1,2-phenylenebishosphonous dichloride
Identifiers
CAS Number	82495-67-8;
3D model (JSmol)	Interactive image;
ChemSpider	2564296;
PubChem CID	3316562;
CompTox Dashboard (EPA)	DTXSID10391390;
	InChI InChI=1S/C6H4Cl4P2/c7-11(8)5-3-1-2-4-6(5)12(9)10/h1-4H Key: IGYHSFVSIYJSML-UHFFFAOYSA-N;
	SMILES C1=CC=C(C(=C1)P(Cl)Cl)P(Cl)Cl;
Properties
Chemical formula	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 pictograms
GHS Signal word	Danger
GHS hazard statements	H314
GHS precautionary statements	P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, 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).
	Infobox references

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

1,2-Bis(dichlorophosphino)ethane

References

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.
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.

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[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.