1,4-Benzoquinone dioxime

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 29 , 1982,p. 185.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-179 ,1979. ; No Evidence: mouse NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-179 ,1979. . Reported in EPA TSCA Inventory.

The IUPAC name of 1,4-Benzoquinone dioxime is N-(4-nitrosophenyl)hydroxylamine. With the CAS registry number 105-11-3, it is also named as 1,4-Benzochinondioxim. The product's categories are Nitrogen Compounds; Organic Building Blocks; Oximes. Besides, it is pale yellow to brown crystals or powder, which should be stored in a closed, cool and ventilated place. It is stable, and incompatible with strong acids, strong oxidizing agents. In addition, its molecular formula is C₆H₆N₂O₂ and molecular weight is 138.12.

The other characteristics of this product can be summarized as: (1)EINECS: 203-271-5; (2)ACD/LogP: 1.17; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.17; (5)ACD/LogD (pH 7.4): 1.12; (6)ACD/BCF (pH 5.5): 4.56; (7)ACD/BCF (pH 7.4): 4.05; (8)ACD/KOC (pH 5.5): 103.08; (9)ACD/KOC (pH 7.4): 91.47; (10)#H bond acceptors: 4; (11)#H bond donors: 2; (12)#Freely Rotating Bonds: 3; (13)Index of Refraction: 1.594; (14)Molar Refractivity: 35.45 cm³; (15)Molar Volume: 104.4 cm³; (16)Surface Tension: 53.2 dyne/cm; (17)Density: 1.32 g/cm³; (18)Flash Point: 134.6 °C; (19)Melting Point: 243 °C; (20)Water solubility: <0.01 g/100 mL at 22.5 °C; (21)Enthalpy of Vaporization: 56.9 kJ/mol; (22)Boiling Point: 298.9 °C at 760 mmHg; (23)Vapour Pressure: 0.000552 mmHg at 25 °C.

Preparation of 1,4-Benzoquinone dioxime: this chemical can be prepared by the reaction as follows:

Uses of 1,4-Benzoquinone dioxime: this chemical is used as vulcanizer of butyl rubber, natural rubber, styrene butadiene rubber. It is also used for the determination of nickel. Additionally, it can react with 2-Carboxy-benzenediazonium; chloride to get 1-Hydroxy-1-(p-nitrosophenyl)-3-(o-carboxyphenyl)triazene.



This reaction needs aq. NaOH at temperature of 5 °C. The yield is 86 %.

When you are using this chemical, please be cautious about it as the following: it is harmful if swallowed. And limited evidence of a carcinogenic effect. You should wear suitable protective clothing and gloves. Moreover, in case of accident or if you feel unwell, please seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: C1=CC(=CC=C1NO)N=O
(2)InChI: InChI=1S/C6H6N2O2/c9-7-5-1-2-6(8-10)4-3-5/h1-4,7,9H
(3)InChIKey: DZCCLNYLUGNUKQ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	1420mg/kg (1420mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 29(10), Pg. 15, 1964.
rat	LD50	oral	464mg/kg (464mg/kg)		Progress Report for Contract No. NIH-NCI-E-C-72-3252, Submitted to the National Cancer Institute by Litton Bionetics, Inc. Vol. NCI-E-C-72-3252, Pg. 1973,