2-Chloroanthraquinone

Reported in EPA TSCA Inventory.

The 9,10-Anthracenedione,2-chloro-, with the CAS registry number 131-09-9, is also known as 2-Chloro-9,10-anthraquinone. It belongs to the product categories of Intermediates of Dyes and Pigments; Organics; Electronic Chemicals; Anthraquinones; Chloroanthraquine, etc.; C13 to C14; Carbonyl Compounds; Ketones. Its EINECS number is 205-010-0. This chemical's molecular formula is C₁₄H₇ClO₂ and molecular weight is 242.66. What's more, its systematic name is 2-chloroanthracene-9,10-dione. It is used in the dye industry. It should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from moisture and sun.

Physical properties of 9,10-Anthracenedione,2-chloro- are: (1)ACD/LogP: 4.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.11; (4)ACD/LogD (pH 7.4): 4.11; (5)ACD/BCF (pH 5.5): 777.22; (6)ACD/BCF (pH 7.4): 777.22; (7)ACD/KOC (pH 5.5): 4079.93; (8)ACD/KOC (pH 7.4): 4079.93; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 34.14 Å²; (13)Index of Refraction: 1.665; (14)Molar Refractivity: 63.56 cm³; (15)Molar Volume: 171 cm³; (16)Polarizability: 25.19×10^-24cm³; (17)Surface Tension: 58 dyne/cm; (18)Density: 1.418 g/cm³; (19)Flash Point: 179.7 °C; (20)Enthalpy of Vaporization: 68.04 kJ/mol; (21)Boiling Point: 425.7 °C at 760 mmHg; (22)Vapour Pressure: 1.87E-07 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-chloro-anthracene at the temperature of 70 °C. This reaction will need reagent t-butylhydroperoxide and solvent benzene with the reaction time of 11 hours. This reaction will also need catalyst PhCl(PPh₃)₃. The yield is about 91%.

Uses of 9,10-Anthracenedione,2-chloro-: it can be used to produce 2-methoxy-anthraquinone by heating. It will need reagent NaOMe with the reaction time of 72 hours. The yield is about 59%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. It may cause sensitisation by skin contact. When using it, you must avoid contact with eyes and need wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc3ccc2C(=O)c1c(cccc1)C(=O)c2c3
(2)Std. InChI: InChI=1S/C14H7ClO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7H
(3)Std. InChIKey: FPKCTSIVDAWGFA-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	oral	> 10gm/kg (10000mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(7), Pg. 93, 1990.
rat	LD	oral	> 10gm/kg (10000mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(7), Pg. 93, 1990.
rat	LD50	intraperitoneal	4310mg/kg (4310mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(4), Pg. 90, 1984.