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2,4,6-Trinitro-m-cresol

HCID 11772
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Basic information

CAS
602-99-3
Standard SMILES
Cc1c([N+](=O)[O-])cc([N+](=O)[O-])c(O)c1[N+](=O)[O-]
InChIKey
YYGJRRYSYLLCQH-UHFFFAOYSA-N
Molecular formula
C7H5N3O7
Average molar mass
243.13 g/mol
Monoisotopic mass
243.01274951

Overview

Trinitrometacresol appears as a detonating explosive in the form of yellow needles. Readily soluble in alcohol, ether, and acetone. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments. Under prolonged exposure to fire or heat the containers may explode violently.

Names & identifiers

Preferred name
2,4,6-Trinitro-m-cresol
IUPAC
3-methyl-2,4,6-trinitrophenol

Names & synonyms

2,4,6-Trinitro-m-cresolCresyliteTrinitro-m-cresolPhenol, 3-methyl-2,4,6-trinitro-602-99-3Trinitro-meta-cresol3-Methylpicric acidMethylpicric acid3-Methyl-2,4,6-trinitro-phenolEINECS 210-027-1AI3-15427DTXSID0075285
Show more names
HSDB 8403UN 0216RefChem:82160DTXCID2042773210-027-1YYGJRRYSYLLCQH-UHFFFAOYSA-N3-methyl-2,4,6-trinitrophenolPicric acid, methyl-

Database identifiers

CAS
602-99-3
PubChem CID
11772
DTXSID
DTXSID0075285
UNII
7BLY4MK2AN
EC Number
210-027-1
Nikkaji
J55.424C

Properties

Computed structural properties

XLogP
2
Topological polar surface area
158 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
7
Rotatable bonds
0
Heavy atoms
17
Formal charge
0
Complexity
343

Experimental & physicochemical properties

SpringerMaterials PropertiesBoiling point
LogP2.0
Density1.75 g/cu cm
Color/Form · 2 items

Yellow crystals

Yellow needles

Solubility · 2 items

In water, 2200 mg/L at 25 °C

Readily soluble in alcohol, ether and acetone

Boiling PointExplodes at 150 °C
DecompositionWhen heated to decomposition it emits highly toxic fumes of NOx and explodes.
Melting Point106 °C
Vapor Pressure1.3X10-6 mm Hg at 25 °C
Heat of CombustionEnthalpy of Combustion: -3217.7 kJ/mol
Physical Description · 1 item

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H201: (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P210, P230, P240, P250, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P370+P380, P372, P373, P401, and P501 (click each P-code to see the statement)

Danger

H201: (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P210, P230, P240, P250, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P370+P380, P372, P373, P401, and P501 (click each P-code to see the statement)

Hazard information

DOT LabelExplosive 1.1D
Fire HazardsExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Health HazardsExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Reactivity AlertsExplosive
Reactivity Profile · 1 item

TRINITROMETACRESOL is a nitroaryl derivative. It is sensitive to heat. Nitroaryls range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds 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.

Chemistry & industry

Uses & manufacturing

Uses · 2 items

Bursting charges and other high explosive uses.

Explosives

General Manufacturing InformationTrinitrocresol is not as powerful a high explosive as TNT or picric acid.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Trinitrometacresol appears as a detonating explosive in the form of yellow needles. Readily soluble in alcohol, ether, and acetone. Primary hazard is blast of an instantaneous explosion, not flying projectiles or fragments. Under prolonged exposure to fire or heat the containers may explode violently.

Other Experimental Properties · 2 items

Under prolonged exposure to fire or heat the containers may explode violently.

Can react vigorously with oxidizing materials

DOT Hazard Classification · 3 items

Trinitro-m-cresol

UN0216

Div 1.1 Explosives (with a mass explosion hazard) (49 eCFR § 173.50)

Air and Water ReactionsSlightly soluble in water.
Hazard Classes and Categories · 2 items

Explosive - division 1.1

Expl. 1.1

DHS Chemicals of Interest (COI) · 6 items

Trinitro-meta-cresol

A Commercial Grade

5000

A Commercial Grade

400

Explosive chemical that can be released at a facility.

Shipment Methods and Regulations · 3 items

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. Trinitr-m-cresol is included on the dangerous goods list.

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. Trinitro-m-cresol is included on the dangerous goods list.

Shipping Name/ Number DOT/UN/NA/IMO · 2 items

UN 0216; Trinitro-m-cresol

IMO 1.1D; Trinitro-m-cresol

Safety & protection

Fire FightingExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
First AidExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Fire Fighting Procedures · 2 items

Cargo fire: Do not fight fire when fire reaches cargo! Cargo may explode! Stop all traffic and clear the area for at least 1600 meters (1 mile) in all directions and let burn. Do not move cargo or vehicle if cargo has been exposed to heat. Tire or vehicle fire: Use plenty of water - flood it! If water is not available, use carbon dioxide, dry chemical or dirt. If possible, and without risk, use unmanned hose holders or monitor nozzles from maximum distance to prevent fire from spreading to cargo area. Pay special attention to tire fires as re-ignition may occur. Stand by, at a safe distance, with extinguisher ready for possible re-ignition.

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.

Cleanup MethodsIsolate 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.
Nonfire Spill ResponseExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Disposal Methods · 1 item

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Preventive Measures · 1 item

Non-fire response: 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.

Isolation and EvacuationExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Personal Protective Equipment (PPE)Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3760(SRC), determined from a structure estimation method(2), indicates that trinitro-meta-cresol is expected to have slight mobility in soil(SRC). The pKa of trinitro-meta-cresol is 2.53(3), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Trinitro-meta-cresol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.3X10-6 mm Hg at 25 °C(4). Screening studies using structurally similar compounds (2,4,6-trinitrophenol and trinitroresorcinol) suggest that trinitro-meta-cresol is resistant to biodegradation under aerobic conditions(5-7). Trinitro-meta-cresol contains chromophores that absorb at wavelengths >290 nm(8) and, therefore, may be susceptible to direct photolysis on surfaces exposed to sunlight(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3760(SRC), determined from a structure estimation method(2), indicates that trinitro-meta-cresol is expected to adsorb to suspended solids and sediment(SRC). A pKa of 2.53(3) indicates trinitro-meta-cresol will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(4), an estimated BCF of 11(SRC), from an estimated log Kow of 2.09(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Screening studies using structurally similar compounds (2,4,6-trinitrophenol and trinitroresorcinol) suggest that trinitro-meta-cresol is resistant to biodegradation under aerobic conditions(5-7). Trinitro-meta-cresol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(8). Trinitro-meta-cresol contains chromophores that absorb at wavelengths >290 nm(8) and, therefore, may be susceptible to direct photolysis on water surfaces exposed to sunlight(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trinitro-meta-cresol, which has a vapor pressure of 1.3X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase trinitro-meta-cresol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 58 days(SRC), calculated from its rate constant of 2.8X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase trinitro-meta-cresol may be removed from the air by wet and dry deposition(SRC). Trinitro-meta-cresol contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Toxicity SummaryIDENTIFICATION AND USE: Trinitro-meta-cresol is used in explosives. HUMAN STUDIES: There are no data available. ANIMAL STUDIES: It was found highly toxic when tested as a single ip dose in adult rats observed for seven days.
Effluent ConcentrationsTrinitro-meta-cresol was not detected (detection limit not reported) in leachate waters of a disposal site of a former ammunition plant in Stadtallendorf, Germany(1).
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc of trinitro-meta-cresol can be estimated to be 3760(SRC). According to a classification scheme(2), this estimated Koc value suggests that trinitro-meta-cresol is expected to have slight mobility in soil. The pKa of trinitro-meta-cresol is 2.53(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

Artificial Pollution SourcesTrinitro-meta-cresol's production and use in bursting charges and other high explosive uses(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 item

AEROBIC: Incubation studies using microorganisms from soil, water and mud suggested that 2,4,6-trinitroresorcinol (structurally similar to trinitro-meta-cresol) is recalcitrant to biodegradation(1). The structurally similar 2,4,6-trinitrophenol, present at 100 mg/L, reached 23% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test which classified the compound as not readily biodegradable(2). Other biodegradation screening studies have also found 2,4,6-trinitrophenol resistant to degradation under aerobic conditions(3,4).

Environmental Bioconcentration · 1 item

An estimated BCF of 1 was calculated in fish for trinitro-meta-cresol(SRC), using an estimated log Kow of 2.09(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). BCF values of <0.24 to <2.2 were measured in carp (Cyprinus carpio) exposed to the structurally similar 2,4,6-trinitrophenol over a 6 week exposure period(3).

Volatilization from Water/Soil · 1 item

A pKa of 2.53(1) indicates trinitro-meta-cresol will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces or moist soil is not expected to be an important fate process(SRC). Trinitro-meta-cresol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.3X10-6 mm Hg(2).

Non-Human Toxicity Excerpts · 1 item

/LABORATORY ANIMALS: Acute Exposure/ Numerous chemical compounds were experimentally screened for toxicity as a routine procedure for estimating a chronic dose for the Sarcoma 180 assay. Adult mice were given intraperitoneal, single doses of solutions or suspensions of each compound. Weight response was determined, and animals were observed for seven days. Compounds found highly toxic included 3,4-difluorobenzenearsonic-acid; 2,4,6-trinitro-m-cresol; 4-ethyl-2,6-dinitrophenol; 4-isopropyl-2,6-dinitrophenol; 2-(1-methylbutyl)-4,6-dinitrophenol; and 2-acetamido-4,5-bis-(acetoxymercuri)-thiazole. Seventy-nine compounds were tested.

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of trinitro-meta-cresol with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 58 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Trinitro-meta-cresol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Trinitro-meta-cresol contains chromophores that absorb at wavelengths >290 nm(2) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Under simulated solar radiation, the structurally similar 2,4,6-trinitrophenol concentration in seawater decreased from 3,510.55 umoles/L to 3,206.05 umoles/L after 47 days exposure(3).

Probable Routes of Human ExposureOccupational exposure to trinitro-meta-cresol may occur through inhalation and dermal contact with this compound at workplaces where trinitro-meta-cresol is produced or used. (SRC)
Environmental Fate/Exposure Summary · 1 item

Trinitro-meta-cresol's production and use in bursting charges and other high explosive uses may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 1.3X10-6 mm Hg at 25 °C indicates trinitro-meta-cresol will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase trinitro-meta-cresol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 58 days. Particulate-phase trinitro-meta-cresol will be removed from the atmosphere by wet and dry deposition. Trinitro-meta-cresol contains chromophores that absorb at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, trinitro-meta-cresol is expected to have slight mobility based upon an estimated Koc of 3760. The pKa of trinitro-meta-cresol is 2.53, indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil is not expected because the compound exists as an anion and anions do not volatilize. Trinitro-meta-cresol is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Screening studies using structurally similar compounds (2,4,6-trinitrophenol and trinitroresorcinol) suggest that trinitro-meta-cresol is resistant to biodegradation under aerobic conditions. If released into water, trinitro-meta-cresol is expected to adsorb to suspended solids and sediment based upon the estimated Koc. A pKa of 2.53 indicates trinitro-meta-cresol will exist almost entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process. An estimated BCF of 11 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to trinitro-meta-cresol may occur through inhalation and dermal contact with this compound at workplaces where trinitro-meta-cresol is produced or used. (SRC)

Regulatory information

DHS Chemicals of Interest (COI) · 6 items

Trinitro-meta-cresol

A Commercial Grade

5000

A Commercial Grade

400

Explosive chemical that can be released at a facility.