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Dipicrylamine

Dipicrylamine structure

Dipicrylamine 

structure
  • CAS No:

    131-73-7

  • Formula:

    C12H5N7O12

  • Chemical Name:

    Dipicrylamine

  • Synonyms:

    Benzenamine,2,4,6-trinitro-N-(2,4,6-trinitrophenyl)-;Diphenylamine,2,2′,4,4′,6,6′-hexanitro-;2,4,6-Trinitro-N-(2,4,6-trinitrophenyl)benzenamine;Dipicrylamine;2,4,6,2′,4′,6′-Hexanitrodiphenylamine;Hexamine (potassium reagent);Hexyl;2,2′,4,4′,6,6′-Hexanitrodiphenylamine;Hexyl (reagent);Bis(2,4,6-trinitrophenyl)amine;Hexanitrodiphenylamine;Hexamine;NSC 1786;N,N-Bis(2,4,6-Trinitrophenyl)amine;35860-31-2

  • Categories:

    Active Pharmaceutical Ingredients  >  Antiallergic Drugs

Description

Yellow solid.decomposes violently at higher temperatures. Insoluble in water and alcohol; soluble in alkalies and warm acetic or nitric acid.


Dipicrylamine appears as a yellow solid. Decomposes violently at high temperatures. Insoluble in water and alcohol. Used as a booster explosive. May explode under prolonged exposure to heat or fire. Primary hazard is the blast effect of an instantaneous explosion and not flying projectiles and fragments.


Dipicrylamine appears as a yellow solid. Decomposes violently at high temperatures. Insoluble in water and alcohol. Used as a booster explosive. May explode under prolonged exposure to heat or fire. Primary hazard is the blast effect of an instantaneous explosion and not flying projectiles and fragments.

Dipicrylamine Basic Attributes

439.21

439.21

205-037-8

14STR4KG8T

1786

0079

DTXSID4059621

Pale yellow prisms from acetic acid|Yellow solid|Yellow prisms

2921499090

Characteristics

287

3.35 (est)

Dipicrylamine appears as a yellow solid. Decomposes violently at high temperatures. Insoluble in water and alcohol. Used as a booster explosive. May explode under prolonged exposure to heat or fire. Primary hazard is the blast effect of an instantaneous explosion and not flying projectiles and fragments.

1.6613 (rough estimate)

244 °C (decomp)

550.83°C (rough estimate)

275.9ºC

1.6400 (estimate)

In water, 60 mg/L at 17 deg C

6.34X10-14 mm Hg at 25 deg C (est)

Oral-Rat LD: >500 mg/kg

Combustion produces toxic nitrogen oxide fumes

Under prolonged exposure to heat or fire /it/ can explode.

Henry's Law constant = 2.33X10-17 atm cu m/mol at 25 °C (est)

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Explosive

DIPICRYLAMINE is an oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides may begin a vigorous reaction that culminates in a detonation. May explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

Safety Information

1.1D

0079

3

2-26/27/28-33-51/53

35-36-45-61

E,T+,N

Handle lightly; storeroom ventilated, away from open flames, high temperature, sunlight; stored separately from oxidants and flammables

High heat, vibration, impact, friction can be explosive

Extremely stable

P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P370+P380, P372, P373, P391, P401, P403+P233, P405, P501

H201

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: MAY EXPLODE AND THROW FRAGMENTS 1600 METERS (1 MILE) OR MORE IF FIRE REACHES CARGO. For information on "Compatibility Group" letters, refer to Glossary section. (ERG, 2016)|Flammable - 3rd degree, Reactive - 3rd degree

|Danger|H201: Explosive; mass explosion hazard [Danger Explosives]|P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P370+P380, P372, P373, P391, P401, P403+P233, P405, and P501|P210, P230, P240, P250, P280, P370+P380, P372, P373, P401, and P501

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: Isolate spill or leak area immediately for at least 500 meters (1/3 mile) in all directions. LARGE SPILL: Consider initial evacuation for 800 meters (1/2 mile) in all directions. FIRE: If rail car or trailer is involved in a fire, ISOLATE for 1600 meters (1 mile) in all directions; also, initiate evacuation including emergency responders for 1600 meters (1 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. DO NOT OPERATE RADIO TRANSMITTERS WITHIN 100 METERS (330 FEET) OF ELECTRIC DETONATORS. DO NOT CLEAN-UP OR DISPOSE OF, EXCEPT UNDER SUPERVISION OF A SPECIALIST. (ERG, 2016)

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Wear appropriate chemical protective gloves and goggles.

Flammable by spontaneous chemical reaction; practically all nitrates are powerful oxidizing agents. /Nitrates/

Explodes on shock or exposure to heat, dangerous.|A powerful and violent explosive used as a booster explosive.|Under prolonged exposure to heat or fire /it/ can explode.

If material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn.|Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.|Evacuation: If the material is on fire or involved in fire consider evacuation of one (1) mile radius.

The primary hazard is from blast effect where the entire load can explode instantaneously and not from flying projectiles and fragments.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material wet. Wet spilled material before picking it up. Do not attempt to sweep up dry material.|Personnel protection: Avoid breathing dusts, and fumes from burning material ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

D003; A waste containing 2,2',4,4',6,6'-hexanitrodiphenylamine may (or may not) be characterized a hazardous waste following testing for the reactivity characteristics as prescribed by the Resource Conservation and Recovery Act (RCRA) regulations.

D003; A solid waste containing 2,2',4,4',6,6'-hexanitrodiphenylamine may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.

SOIL: 2,2',4,4',6,6'-Hexanitrodiphenylamine was not detected in soil samples from the former munitions plant Nieder-Neuendorf (Brandeburg, Germany)(1).

Toxicity

moderately toxic

/AQUATIC SPECIES/ Aqueous samples containing various explosives, their reduced metabolites, as well as related compounds were subjected to the luminescent bacterium Vibrio fischeri NRRLB-11177 to determine their ecotoxicological potential. As the most important parameter, the EC50 values of 24 test compounds were calculated. ... HEXYL must be classified in the category "very toxic to aquatic organisms"...

2,2',4,4'6,6'-Hexanitrodiphenylamine's production and former use as a booster explosive(1) may have resulted in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.1X10+6(SRC), determined from a structure estimation method(2), indicates that 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to be immobile in soil(SRC). Volatilization of 2,2',4,4',6,6'-hexanitrodiphenylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-17 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2,2',4,4',6,6'-Hexanitrodiphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-14 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2010).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.1X10+6(SRC), determined from a structure estimation method(2), indicates that 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.3X10-17 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 76(SRC), from an estimated log Kow of 3.4(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC). Biodegradation data in water were not available(SRC, 2010).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2',4,4',6,6'-hexanitrodiphenylamine, which has an estimated vapor pressure of 6.3X10-14 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 2,2',4,4',6,6'-hexanitrodiphenylamine may be removed from the air by wet or dry deposition(SRC). 2,2',4,4',6,6'-Hexanitrodiphenylamine does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

2,2',4,4',6,6'-Hexanitrodiphenylamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). 2,2',4,4',6,6'-Hexanitrodiphenylamine does not contain chromophores that absorb at wavelengths >290 nm(1) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 76 was calculated in fish for 2,2',4,4',6,6'-hexanitrodiphenylamine(SRC), using an estimated log Kow of 3.4(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,2',4,4',6,6'-hexanitrodiphenylamine can be estimated to be 1.1X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to be immobile in soil.

The Henry's Law constant for 2,2',4,4',6,6'-hexanitrodiphenylamine is estimated as 2.3X10-17 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to be essentially nonvolatile from water and moist soil surfaces(2). 2,2',4,4',6,6'-Hexanitrodiphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-14 mm Hg(SRC), determined from a fragment constant method(3).

GROUNDWATER: Water samples in the surroundings of a former munitions plant at Elsnig, Germany were found to contain 2,2',4,4',6,6'-hexanitrodiphenylamine at a concentration range of 13 to 215 ug/L(1). The compound was detected, not quantified in the upper 4.6-6.9 m, but not the lower 16-18 m levels in the groundwater at this site(2).

Occupational exposure to 2,2',4,4',6,6'-hexanitrodiphenylamine may occur through dermal contact with this compound at workplaces where 2,2',4,4',6,6'-hexanitrodiphenylamine is produced or used(SRC). Limited monitoring data indicate that the general populated may have been exposed to 2,2',4,4',6,6'-hexanitrodiphenylamine via ingestion of drinking water. Occupational exposure and general population exposure should be low or non-existent since 2,2',4,4',6,6'-hexanitrodiphenylamine is no longer produced or used as an explosive in the US(1).

Drug Information

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: Fire may produce irritating, corrosive and/or toxic gases. (ERG, 2016)

Excerpt from ERG Guide 112 [Explosives* - Division 1.1, 1.2, 1.3 or 1.5]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. (ERG, 2016)

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic bases/Amines and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If patient is unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic bases/Amines and related compounds/|/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Nitrates, nitrites, and related compounds/|For more Antidote and Emergency Treatment (Complete) data for 2,2',4,4',6,6'-Hexanitrodiphenylamine (6 total), please visit the HSDB record page.

2,4,6,2',4',6'-hexanitrodiphenylamine

Dipicrylamine Use and Manufacturing

Methods of Manufacturing

Nitration of diphenylamine, also from dinitrochlorobenzene.

Uses

Reagent for gravimetric determination of potassium.

Production

(1972) NOT PRODUCED COMMERCIALLY IN US|(1975) NOT PRODUCED COMMERCIALLY IN US

Benzenamine, 2,4,6-trinitro-N-(2,4,6-trinitrophenyl)-: ACTIVE|A powerful and violent explosive used as a booster explosive; its use is superior to TNT. It is not as good for this purpose as tetryl, but is extremely stable and much safer to handle.|No longer used as an explosive.

Explosives and their biodegradation products were determined in contaminated soil and water samples from former ammunition facilities by a new method of automated multiple development high performance thin layer chromatography. A gradient for the mobile phases was found which allowed for the separation of the explosives hexyl (131737), picric-acid (88891), RDX (121824), HMX (2691410), tetryl (479458), 2,4-dinitrotoluene (121142) and 2,6-dinitrotoluene (606202), and 2,4,6-trinitrotoluene (118967). Byproducts could also be identified. The method was applied to the analysis of groundwater and soil samples taken from former ammunition production sites in Germany...

Fire Hazards -> Flammable - 3rd degree, Reactive - 3rd degree

Computed Properties

Molecular Weight:439.21
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:2
Exact Mass:438.99961862
Monoisotopic Mass:438.99961862
Topological Polar Surface Area:287
Heavy Atom Count:31
Complexity:662
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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