Phthaloyl chloride

Phthaloyl chloride
Names
	Other names o-Phthaloyl chloride
Identifiers
CAS Number	88-95-9;
3D model (JSmol)	Interactive image;
ChemSpider	13865683;
ECHA InfoCard	100.001.699
EC Number	201-869-0;
PubChem CID	6955;
UNII	8S64APH24W;
CompTox Dashboard (EPA)	DTXSID8038691 ;
	InChI InChI=1S/C8H4Cl2O2/c9-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H Key: FYXKZNLBZKRYSS-UHFFFAOYSA-N;
	SMILES C1=CC=C(C(=C1)C(=O)Cl)C(=O)Cl;
Properties
Chemical formula	C8H4Cl2O2
Molar mass	203.02 g·mol−1
Appearance	colorless oil
Melting point	15.5 °C (59.9 °F; 288.6 K)
Boiling point	135 °C (275 °F; 408 K) 15 torr
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H290, H312, H314, H317, H334, H335
Precautionary statements	P233, P234, P260, P264, P264+P265, P271, P272, P280, P284, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P333+P317, P342+P316, P362+P364, P363, P390, P403, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Phthaloyl chloride is an organic compound with the formula C₆H₄(COCl)₂. It is one of three isomers, the better known one being terephthaloyl chloride. The third isomer is isophthaloyl chloride. All three compounds are diacid chlorides, and hence they are susceptible to reactions with water (to give back the diacids), alcohols (to give diesters), and amines to give amides or imides.

Synthesis and reactions

Phthaloyl chloride can be prepared by treatment of phthalic anhydride with phosphorus pentachloride.^[1]

Upon heating with aluminium trichloride, phthaloyl chloride rearranges to an unsymmetrical ester.^[2]

Phthaloyl chloride reacts with arenes to make anthroquinones.

References

↑ Ott, E (1931). "Symmetrical and Unsymmetrical o-Phthalyl Chlorides". Organic Syntheses. 11: 88. doi:10.15227/orgsyn.011.0088.
↑ Sartori, Giovanni; Bigi, Franca; Tao, Xiaochun; Porta, Cecilia; Maggi, Raimondo; Predieri, Giovanni; Lanfranchi, Maurizio; Pellinghelli, Maria Angela (1995). "An Investigation of the Reaction Mechanism of the Bis-acylation of Aromatics with o-Phthaloyl Dichlorides: Regioselective Synthesis of Anthraquinones". The Journal of Organic Chemistry. 60 (20): 6588–6591. doi:10.1021/jo00125a054.

[1] Ott, E (1931). "Symmetrical and Unsymmetrical o-Phthalyl Chlorides". Organic Syntheses. 11: 88. doi:10.15227/orgsyn.011.0088.

[2] Sartori, Giovanni; Bigi, Franca; Tao, Xiaochun; Porta, Cecilia; Maggi, Raimondo; Predieri, Giovanni; Lanfranchi, Maurizio; Pellinghelli, Maria Angela (1995). "An Investigation of the Reaction Mechanism of the Bis-acylation of Aromatics with o-Phthaloyl Dichlorides: Regioselective Synthesis of Anthraquinones". The Journal of Organic Chemistry. 60 (20): 6588–6591. doi:10.1021/jo00125a054.

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