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Trinitrobenzenesulfonic acid

Trinitrobenzenesulfonic acid structure

Trinitrobenzenesulfonic acid 

structure
  • CAS No:

    2508-19-2

  • Formula:

    C6H3N3O9S

  • Chemical Name:

    Trinitrobenzenesulfonic acid

  • Synonyms:

    Benzenesulfonic acid,2,4,6-trinitro-;2,4,6-Trinitrobenzenesulfonic acid;Picryl sulfonic acid;Trinitrobenzenesulfonic acid;2,4,6-Trinitrobenzene-1-sulfonic acid;2,4,6-Trinitrophenylsulfonic acid;NSC 127994;85600-65-3

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

ChEBI: The arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions.


Trinitrobenzene sulfonic acid appears as a detonating explosive substance derived from an organic sulfonic acid. 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.


Trinitrobenzene sulfonic acid appears as a detonating explosive substance derived from an organic sulfonic acid. 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.|2,4,6-trinitrobenzenesulfonic acid is the arenesulfonic acid that is benzenesulfonic acid with three nitro substituents in the 2-, 4- and 6-positions. It has a role as an epitope, an explosive and a reagent. It is a C-nitro compound and an arenesulfonic acid.|A reagent that is used to neutralize peptide terminal amino groups.

Trinitrobenzenesulfonic acid Basic Attributes

293.168

293.17

219-717-7

8T3HQG2ZC4

127994

0386

DTXSID0043715

2904909090

Characteristics

200.21000

0.51

Trinitrobenzene sulfonic acid appears as a detonating explosive substance derived from an organic sulfonic acid. 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.

2.0±0.1 g/cm3

58 °C

1.670

In water, 1.58X10+5 mg/L at 25 deg C (est)

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: -20 deg C.

5.2X10-12 mm Hg at 25 deg C (est)

pKa = 0.13

When heated to decomposition it emits toxic vapors of NOx and SOx

Soluble in water. Solution exhibits a strong acidic reaction.

Acids, Strong Oxidizing

Explosive

TRINITROBENZENE SULFONIC ACID is a nitroaryl oxidizing acid. 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.

Safety Information

1.1D

UN 3265 8/PG 3

1

R61

S53-S26-S36/37-S45-S36/37/39-S16

DA9138500

T,Xn,C,F

P280-P305 + P351 + P338-P310

H302-H314-H317

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|H317 (97.44%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H201 (100%): Explosive; mass explosion hazard [Danger Explosives]|P210, P230, P240, P250, P260, P261, P264, P270, P272, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P333+P313, P363, P370+P380, P372, P373, P401, P405, and P501|Aggregated GHS information provided by 76 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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)|Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Tightly fitting safety goggles. Faceshield (8-inch minimum). Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|For skin and body protection, complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

Fire-Fighting Measures. Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Special protective equipment for fire-fighters: Wear self contained breathing apparatus for fire fighting if necessary.

ACCIDENTAL RELEASE MEASURES. Personal precautions: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Wear protective gloves/ protective clothing/ eye protection/ face protection.|Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|If in eyes: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/ physician.|For more Preventive Measures (Complete) data for Picryl sulfonic acid (7 total), please visit the HSDB record page.

Toxicity

The aim of the present study is to investigate the treatment efficiency of intra-rectal (IR) and intra-peritoneal (IP) application of Origanum onites essential oil (OOEO), which is a well-known antioxidant, in the colitis model induced by 2,4,6-trinitrobenzenesulfonic acid (TNBS) and ethanol (E) in comparison with dexamethasone therapy through the morphologic damage score. Monoclonal antibodies against intercellular adhesion molecule-1 (ICAM-1, CD54), anti-rat granulocytes, and myeloperoxidase (MPO), were also investigated immunohistochemically. There was a significant difference in terms of ulceration, mucus cell depletion, inflammatory cell infiltration, vascular dilatation (p<0.001), crypt abscesses (p<0.01), and edema (p<0.05) between OOEO-1mg/kg-IR and control colitis groups. A significant difference was encountered in terms of mucus cell depletion, crypt abscesses, inflammatory cell infiltration, vascular dilatation (p<0.01), and ulceration (p<0.05) between the OOEO-0.1mg/kg-IR and control colitis groups. A significant difference was noticed in terms of ulceration, inflammatory cell infiltration, mucus cell depletion (p<0.001), vascular dilatation (p<0.01), and mucosal atrophy (p<0.05) between the OOEO-1mg/kg-IP and control colitis groups. There was a significant difference in terms of ulceration, mucus cell depletion, inflammatory cell infiltration (p<0.001), crypt abscesses, vascular dilatation (p<0.01), and mucosal atrophy (p<0.05) between the OOEO-0.1mg/kg-IP and control colitis groups. No significant difference was determined in terms of ulceration, inflammatory cyst, mucosal atrophy, edema, and vascular dilatation between the dexamethazone and control colitis groups (p>0.05) ...|A targeted delivery system for inflammatory bowel disease (IBD), Eudragit L100 (EuL)-coated chitosan (Ch)-succinyl-prednisolone (SP) conjugate microspheres (Ch-SP-MS/EuL), was designed and examined in vivo for efficacy and toxicity ... Experimental colitis was induced by instillation of 2,4,6-trinitrobenzenesulfonic acid (TNBS) into the colon in rats. Drugs were administered once or twice a day intragastrically for three consecutive days. Visible colitis severity, colon/body weight ratio and myeloperoxidase activity were measured as inflammatory indices. Toxicity was examined from the decrease in the thymus/body weight ratio. Efficacy was dose-dependent and the greatest in the order Ch-SP-MS/EuL>Ch-SP-MS>prednisolone (PD) alone, and Ch-SP-MS/EuL showed excellent recovery of colitis states. Toxicity was the greatest in the order PD>>Ch-SP-MS>Ch-SP-MS/EuL. Ch-SP-MS and Ch-SP-MS/EuL reduced significantly the thymic atrophy caused by PD. It was demonstrated that Ch-SP-MS/EuL enhanced effectiveness of PD and reduced toxic side effects of PD greatly ...|/The aim of the study was/ to evaluate the protective effects of ilomastat, an exogenous matrix metalloproteinase (MMP) inhibitor, on trinitrobenzenesulfonic acid (TNB)-induced ulcerative colitis (UC) in rats. Male SD rats were randomly divided into model group, protective groups A and B, and normal control group. Rats in the model group received only intra-colonic TNB. Rats in the protective groups A and B received intra-peritoneal ilomastat of 10 mg/kg and 20 mg/kg, respectively, beside TNB. Rats in the normal control group received only intra-colonic normal saline. After 3 wk, segments of colon were obtained. RT-PCR and immunohistochemistry were used to examine the expression of MMP-1 and TIMP-1. Hematoxylin-eosin (HE) staining was used for pathological study. The model of UC was successfully induced in rats. Inflammation of colonic mucosa greatly improved in protective groups A and B. Expression of MMP-1 and TIMP-1 in the model group, protective groups A and B was significantly higher than that in the normal control group (P < 0.0001) with MMP-1 expression increased more significantly than TIMP-1 expression. Expression of MMP-1 in protective groups A and B was significantly lower than that in the model group (P < 0.0001) . Expression of MMP-1 in protective group B was significantly lower than that in protective group A (P < 0.0001). Ilomastat /thus/ improves TNB-induced UC in rats by inhibiting the MMP-1 activity.|... The trinitrobenzenesulfonic acid model of colitis in the rat was used. Rats were treated orally with alendronate and its efficacy compared with that of oral sulfasalazine or vehicle, starting 2 h after colitis induction. The status of the animals was assessed 5 days later ... Alendronate treatment (25 or 75 mg/kg/day) resulted in a decrease in the colonic damage score and loss of body weight (at 25 mg/kg/day only). This was associated to a dramatic reduction in the mRNA levels of interleukin 1 beta (IL-1 beta), monocyte chemoattractant protein 1 (MCP-1) and interleukin 1 receptor antagonist (IL-1 ra). The magnitude of the beneficial effect was comparable to that of sulfasalazine (at a 6-20 fold higher dose) ...|For more Interactions (Complete) data for Picryl sulfonic acid (11 total), please visit the HSDB record page.

Picryl sulfonic acid's production and use as a laboratory reagent(1) and detonator(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that picryl sulfonic acid is expected to have high mobility in soil(SRC). The pKa of picryl sulfonic acid is estimated as 0.31(3), indicating that this compound will exist 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). Volatilization of picryl sulfonic acid from moist soil surfaces is not expected to be an important fate process(SRC) given its estimated pKa(3). Picryl sulfonic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.2X10-12 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2010).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 120(SRC), determined from a structure estimation method(2), indicates that picryl sulfonic acid is not expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 0.31(3) indicates picryl sulfonic acid will exist 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 3(SRC), from an estimated log Kow of -1.71(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Picryl sulfonic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(7). Biodegradation data were not available(SRC, 2010).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), picryl sulfonic acid, which has an estimated vapor pressure of 5.2X10-12 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 picryl sulfonic acid may be removed from the air by wet or dry deposition(SRC). Picryl sulfonic acid contains chromophores that absorb at wavelengths >290 nm(3) and may be susceptible to direct photolysis by sunlight(SRC).

Picryl sulfonic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). Picryl sulfonic acid contains chromophores that absorb at wavelengths >290 nm(1) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for picryl sulfonic acid(SRC), using an estimated log Kow of -1.71(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of picryl sulfonic acid can be estimated to be 120(SRC). According to a classification scheme(2), this estimated Koc value suggests that picryl sulfonic acid is expected to have high mobility in soil. The pKa of picryl sulfonic acid is estimated as 0.31(3), indicating that this compound will exist 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).

An estimated pKa of 0.31(1) indicates picryl sulfonic acid will exist entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces and moist soil is not expected to be an important fate process(SRC). Picryl sulfonic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.2X10-12 mm Hg(SRC), determined from a fragment constant method(2).

Occupational exposure to picryl sulfonic acid may occur through dermal contact with this compound at workplaces where picryl sulfonic acid is produced or used. (SRC)

Drug Information

Peroxynitrite, derived from the reaction of nitric oxide (NO) with superoxide (O(2)), is a potent nitrating and oxidizing agent that can induce apoptosis in a variety of different cell types. /This/ study ... investigated the possible role of peroxynitrite as a mediator of colon epithelial cell death in rat colitis. Rat colon inflammation was induced by intracolonic administration of 2,4,6-trinitrobenzenesulfonic acid (TNBS) and rats were sacrificed 24 hr after TNBS administration. Expression of inducible nitric-oxide synthase (iNOS) was detected by reverse transcription-polymerase chain reaction and immunohistochemistry. The enzymatic activities of Ca(2+)-independent iNOS and Ca(2+)-dependent constitutive nitric oxide synthase were determined biochemically. Evidence of peroxynitrite-mediated cell injury was detected by immunostaining of nitrotyrosine. Apoptosis was examined by in situ terminal deoxynucleotidyl transferase dUTP nick-end labeling (TUNEL) assay and DNA gel electrophoresis. To evaluate the specific contribution of peroxynitrite to the observed cell injury, a selective iNOS inhibitor, L-N(G)-[1-iminoethyl]lysine (L-NIL), was administered after TNBS induction. Morphological examination and analysis of TUNEL/cytokeratin double immunofluorescence revealed significant apoptosis in mucosal epithelial cells. Nitrotyrosine was colocalized with TUNEL, strongly demonstrating the association of peroxynitrite with the apoptotic death of colon epithelial cells. The administration of L-NIL reduced iNOS activity in 24 hr lesions by 92% and also significantly attenuated both nitrotyrosine staining and apoptotic cell counts in the colon epithelium. These results strongly suggest that local elevated level of peroxynitrite produced from increased iNOS expression and activity is a major contributor to colon epithelial apoptosis during colon inflammation.

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 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. /Inorganic acids 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 respirations if needed. 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 ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. Activated charcoal is not effective. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Inorganic acids 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. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . 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. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Inorganic acids and related compounds/

/SIGNS AND SYMPTOMS/ Skin sensitiser, Toxic by ingestion, Corrosive|/SIGNS AND SYMPTOMS/ May be harmful if inhaled. Material is extremely destructive to the tissue of the mucous membranes and upper respiratory tract. May be harmful if absorbed through skin. Causes skin burns. Causes eye burns.

2,4,6-Trinitrobenzene Sulfonate

Trinitrobenzenesulfonic acid Use and Manufacturing

Uses

Bioreagent ... determination of primary amines|Detonator

Benzenesulfonic acid, 2,4,6-trinitro-: ACTIVE

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

Computed Properties

Molecular Weight:293.17
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:1
Exact Mass:292.95899986
Monoisotopic Mass:292.95899986
Topological Polar Surface Area:200
Heavy Atom Count:19
Complexity:470
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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