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Benzoquinone dioxime

Benzoquinone dioxime structure

Benzoquinone dioxime 

structure
  • CAS No:

    105-11-3

  • Formula:

    C6H6N2O2

  • Chemical Name:

    Benzoquinone dioxime

  • Synonyms:

    2,5-Cyclohexadiene-1,4-dione,1,4-dioxime;p-Benzoquinone,dioxime;2,5-Cyclohexadiene-1,4-dione,dioxime;Benzoquinone dioxime;p-Quinone dioxime;p-Quinone oxime;1,4-Benzoquinone dioxime;Actor Q;Vulnoc GM;Quinone dioxime;Vulnoc GM-P;GM-P;NSC 14433;NSC 4774;Vulnoc DM;Luxomaxx K-CDO

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

PHYSICAL DESCRIPTION: Pale yellow crystals or brown powder. (NTP, 1992)


P-quinone dioxime appears as pale yellow crystals or brown powder. (NTP, 1992)|DryPowder, WetSolid


P-quinone dioxime appears as pale yellow crystals or brown powder. (NTP, 1992)|Para-Benzoquinone dioxime is a quinone imine.

Benzoquinone dioxime Basic Attributes

138.12

138.12

2043234

203-271-5

MGE6YH92Q2

14433|4774

1325

DTXSID8021222

PALE YELLOW NEEDLES FROM WATER

2928000090

Characteristics

61.7

1.1

White Solid

1.3±0.1 g/cm3

243 °C (decomp)

315ºC

°C

1.594

H2O: <0.01 g/100 mL at 22.5 ºC;dioxane: soluble 0.1g/10 mL, clear

-20°C

0mmHg at 25°C

DECOMP @ 240 °C

Insoluble in water.

Alcohols and Polyols

P-QUINONE DIOXIME is incompatible with strong oxidizers and strong acids. (NTP, 1992)

Safety Information

NONH for all modes of transport

3

22-40

45-36/37-60

DK4900000

Xn

Stable. Incompatible with strong acids, strong oxidizing agents.

P260, P264, P270, P301+P312, P314, P330, P501

H302

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Bioassay of p-Quinone Dioxime for Possible Carcinogenicity (1979) Technical Rpt Series No. 179 DHEW Pub No. (NIH) 79-1735, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014.

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

|Danger|H228 (46.84%): Flammable solid [Danger Flammable solids]|P201, P202, P210, P240, P241, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 158 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P301+P312, P314, P330, and P501

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 133 [Flammable Solids]: As an immediate precautionary measure, isolate spill or leak area for at least 25 meters (75 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 100 meters (330 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Toxicity

LD50 Mouse oral 1542 mg/kg body weight|LD50 Rat oral 464 mg/kg body weight

A bioassay for the possible carcinogenicity of p-quinone dioxime was conducted using Fischer 344 rats and B6C3Fl mice. p-Quinone dioxime was administered in the feed, at either of two concentrations, to groups of 50 male and 50 female animals of each species. Twenty animals of each sex and species were placed on test as controls, with the exception of 18 in the control male mouse group. The high and low concentrations of p-quinone dioxime were 750 and 375 ppm for rats and 1,500 and 750 ppm for mice. The compound was administered to rats and mice for 104 weeks. The period of compound administration was followed by an observation period of 1 week for both species. There were no significant positive associations between the concentrations of p-quinone dioxime administered and mortality in rats or mice of either sex. Adequate numbers of animals in all groups survived sufficiently long to be at risk from late-developing tumors. Distinct dose-related mean body weight depression was observed among rats and slight mean body weight depression, relative to controls, was observed among mice, indicating that the dosages of p-quinone dioxime administered to the animals in this bioassay may have approximated the maximum tolerated concentrations. Tumors of the urinary bladder were observed only in dosed rats. For female rats, there was a significant positive association between concentration administered and the incidences of a combination of urinary bladder neoplasms. The high dose to control Fisher exact comparison was also significant for these tumors in female rats. No compound-related neoplasms were observed in male rats or mice of either sex. Under the conditions of this bioassay, dietary administration of p-quinone dioxime was carcinogenic to female Fischer 344 rats, causing neoplasms of the urinary bladder. The compound was not carcinogenic to male Fischer 344 rats or B6C3F1 mice of either sex.

Drug Information

Quinones (ie, 6,12-dione) have been shown to undergo oxidation-reduction cycles involving quinone, hydroquinone, and molecular oxygen, resulting in the formation of oxygen radicals and semiquinone radicals. /Quinones/

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the mucous membranes and upper respiratory tract. ACUTE/CHRONIC HAZARDS: This compound is harmful if swallowed, inhaled or absorbed through the skin. It is an irritant of the mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)

ACUTE EXPOSURE TO HIGH CONCN OF VAPOR.../CAUSED/ IRRITATION, PHOTOPHOBIA, LACRIMATION...CORNEAL ULCERATION... /HYDROQUINONE/

1,4-benzoquinone dioxime

Benzoquinone dioxime Use and Manufacturing

Methods of Manufacturing

Nitrosation of phenol generates p-nitrosophenol, which is transformed into p-quinone monooxime, and then reacted with hydroxylamine hydrochloride to obtain the product. Under stirring, slowly dissolve phenol in 30% sodium hydroxide solution, mix with sodium nitrite at 0°C, and add 30% sulfuric acid to keep the temperature at 7-8°C and stir for 1h. The crystals are filtered out and washed with water to remove the acidity to obtain p-nitrosophenol. After transposition, it is mixed with hydroxylamine hydrochloride aqueous solution and heated to 70°C for oximation reaction. After the reaction is completed, p-benzoquinone dioxime is obtained by filtration. Raw material consumption (kg/t) phenol 1500 hydroxylamine hydrochloride 1200 sodium nitrite (97%) 1600

Uses

Used as vulcanizing agent for butyl rubber, natural rubber, styrene butadiene rubber, etc.


Process regulators

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

TRADEMARK FOR PARA-QUINONEDIOXIME: "G-M-F".

Rubber product manufacturing|2,5-Cyclohexadiene-1,4-dione, 1,4-dioxime: ACTIVE

Computed Properties

Molecular Weight:138.12
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:138.042927438
Monoisotopic Mass:138.042927438
Topological Polar Surface Area:61.7
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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