2,4,6-Trinitrobenzenesulfonic acid

Last updated
2,4,6-Trinitrobenzene Sulfonic Acid
Trinitrobenzenesulfonic acid.png
2,4,6-Trinitrobenzenesulfonic-acid-3D-balls.png
Names
Preferred IUPAC name
2,4,6-Trinitrobenzene-1-sulfonic acid
Other names
Picrylsulfonic acid; Trinitrobenzene sulfonate; TNBS
Identifiers
3D model (JSmol)
572358
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.017.925 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 219-717-7
1051138
PubChem CID
UNII
UN number 0386
  • InChI=1S/C6H3N3O9S/c10-7(11)3-1-4(8(12)13)6(19(16,17)18)5(2-3)9(14)15/h1-2H,(H,16,17,18) Yes check.svgY
    Key: NHJVRSWLHSJWIN-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H3N3O9S/c10-7(11)3-1-4(8(12)13)6(19(16,17)18)5(2-3)9(14)15/h1-2H,(H,16,17,18)
    Key: NHJVRSWLHSJWIN-UHFFFAOYAG
  • O=S(=O)(O)c1c(cc(cc1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
Properties
C6H3N3O9S
Molar mass 293.16 g·mol−1
Density 0.955 g/cm3
Hazards
GHS labelling:
GHS-pictogram-explos.svg GHS-pictogram-acid.svg GHS-pictogram-skull.svg
Danger
H317, H334
P261, P272, P280, P285, P302+P352, P304+P341, P321, P333+P313, P342+P311, P363, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazard OX: Oxidizer. E.g. potassium perchlorate
2
4
4
OX
Related compounds
Related compounds
Picric acid
Trinitroanisole
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Trinitrobenzenesulfonic acid (C6H3N3O9S) is a nitroaryl oxidizing acid. Due to its extreme oxidative properties, if mixed with reducing agents including hydrides, sulfides, and nitrides, it may begin a vigorous reaction that culminates in almost immediate 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 because of the explosive tendencies of aromatic nitro compounds which increase in the presence of multiple nitro groups. Not much is known about this compound, but it is used as a peptide terminal amino group neutralizer and is currently being investigated for its effects on the immune system. [1]

Contents

Uses

Its primary usage is primarily to neutralize peptide terminal amino groups in scientific research. [2] Occasionally it is used as a detonator for certain other explosive compounds.

It is also used to induce colitis in the colon of laboratory animals in order to model inflammatory bowel disease and post-infectious irritable bowel syndrome. [3]

Health concerns and safety precautions

The primary hazard of working with 2,4,6-trinitrobenzenesulfonic acid is the risk of instantaneous explosion. 2,4,6-Trinitrobenzenesulfonic acid is an extremely sensitive compound especially when mixed with other compounds, exposed to heat, or exposed to rapid temperature or pressure changes. The toxicological properties of this compound have not been investigated, so all health effects are unknown. To best prevent bodily harm or injury it is recommended that all direct contact be avoided and the compound be kept under extremely strict environmentally controlled conditions. In case of spillage it is recommended that a local fire department be called in advance prior to any attempt at cleaning. In case of fire it is recommended that the material be left to burn and the surrounding area be evacuated. If fire fighting is required it is recommended that a fully positive pressure self-contained breathing apparatus be used along with either foam or CO2 extinguishers. [4] [5]

Related Research Articles

<span class="mw-page-title-main">Nitroglycerin</span> Chemical compound

Nitroglycerin (NG), also known as trinitroglycerin (TNG), nitro, glyceryl trinitrate (GTN), or 1,2,3-trinitroxypropane, is a dense, colorless, oily, explosive liquid most commonly produced by nitrating glycerol with white fuming nitric acid under conditions appropriate to the formation of the nitric acid ester. Chemically, the substance is an organic nitrate compound rather than a nitro compound, but the traditional name is retained. Discovered in 1847 by Ascanio Sobrero, nitroglycerin has been used as an active ingredient in the manufacture of explosives, namely dynamite, and as such it is employed in the construction, demolition, and mining industries. It is combined with nitrocellulose to form double-based smokeless powder, which has been used as a propellant in artillery and firearms since the 1880s.

<span class="mw-page-title-main">TNT</span> Impact-resistant high explosive

Trinitrotoluene, more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagent in chemical synthesis, but it is best known as an explosive material with convenient handling properties. The explosive yield of TNT is considered to be the standard comparative convention of bombs and asteroid impacts. In chemistry, TNT is used to generate charge transfer salts.

<span class="mw-page-title-main">Nitration</span> Chemical reaction which adds a nitro (–NO₂) group onto a molecule

In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and nitric acid. The difference between the resulting molecular structures of nitro compounds and nitrates is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom, whereas in nitrate esters, the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups. The nitro group is one of the most common explosophores used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.

The regulatory T cells (Tregs or Treg cells), formerly known as suppressor T cells, are a subpopulation of T cells that modulate the immune system, maintain tolerance to self-antigens, and prevent autoimmune disease. Treg cells are immunosuppressive and generally suppress or downregulate induction and proliferation of effector T cells. Treg cells express the biomarkers CD4, FOXP3, and CD25 and are thought to be derived from the same lineage as naïve CD4+ cells. Because effector T cells also express CD4 and CD25, Treg cells are very difficult to effectively discern from effector CD4+, making them difficult to study. Research has found that the cytokine transforming growth factor beta (TGF-β) is essential for Treg cells to differentiate from naïve CD4+ cells and is important in maintaining Treg cell homeostasis.

<span class="mw-page-title-main">Peptide synthesis</span> Production of peptides

In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus). Protein biosynthesis in living organisms occurs in the opposite direction.

<span class="mw-page-title-main">Transforming growth factor beta</span> Cytokine

Transforming growth factor beta (TGF-β) is a multifunctional cytokine belonging to the transforming growth factor superfamily that includes three different mammalian isoforms and many other signaling proteins. TGFB proteins are produced by all white blood cell lineages.

Pyrylium is a cation with formula C5H5O+, consisting of a six-membered ring of five carbon atoms, each with one hydrogen atom, and one positively charged oxygen atom. The bonds in the ring are conjugated as in benzene, giving it an aromatic character. In particular, because of the positive charge, the oxygen atom is trivalent. Pyrilium is a mono-cyclic and heterocyclic compound, one of the oxonium ions.

Immune tolerance, or immunological tolerance, or immunotolerance, is a state of unresponsiveness of the immune system to substances or tissues that would otherwise have the capacity to elicit an immune response in a given organism. It is induced by prior exposure to that specific antigen and contrasts with conventional immune-mediated elimination of foreign antigens. Tolerance is classified into central tolerance or peripheral tolerance depending on where the state is originally induced—in the thymus and bone marrow (central) or in other tissues and lymph nodes (peripheral). The mechanisms by which these forms of tolerance are established are distinct, but the resulting effect is similar.

<span class="mw-page-title-main">Carboxypeptidase</span>

A carboxypeptidase is a protease enzyme that hydrolyzes (cleaves) a peptide bond at the carboxy-terminal (C-terminal) end of a protein or peptide. This is in contrast to an aminopeptidases, which cleave peptide bonds at the N-terminus of proteins. Humans, animals, bacteria and plants contain several types of carboxypeptidases that have diverse functions ranging from catabolism to protein maturation. At least two mechanisms have been discussed.

Nitrophenols are compounds of the formula HOC6H5−x(NO2)x. The conjugate bases are called nitrophenolates. Nitrophenols are more acidic than phenol itself.

<span class="mw-page-title-main">TGF beta 1</span> Protein-coding gene in the species Homo sapiens

Transforming growth factor beta 1 or TGF-β1 is a polypeptide member of the transforming growth factor beta superfamily of cytokines. It is a secreted protein that performs many cellular functions, including the control of cell growth, cell proliferation, cell differentiation, and apoptosis. In humans, TGF-β1 is encoded by the TGFB1 gene.

<span class="mw-page-title-main">2,4,6-Trinitroaniline</span> Chemical compound

2,4,6-Trinitroaniline, C6H4N4O6, abbreviated as TNA and also known as picramide, a nitrated amine. Materials in this group 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. The appearance of trinitroaniline varies from yellow to orange to red depending on its purity and concentration.

The reduction of nitro compounds are chemical reactions of wide interest in organic chemistry. The conversion can be effected by many reagents. The nitro group was one of the first functional groups to be reduced. Alkyl and aryl nitro compounds behave differently. Most useful is the reduction of aryl nitro compounds.

Bioconjugation is a chemical strategy to form a stable covalent link between two molecules, at least one of which is a biomolecule.

The Bergmann degradation is a series of chemical reactions designed to remove a single amino acid from the carboxylic acid (C-terminal) end of a peptide. First demonstrated by Max Bergmann in 1934, it is a rarely used method for sequencing peptides. The later developed Edman degradation is an improvement upon the Bergmann degradation, instead cleaving the N-terminal amino acid of peptides to produce a hydantoin containing the desired amino acid.

<span class="mw-page-title-main">Formyl peptide receptor 2</span> Protein-coding gene in the species Homo sapiens

N-formyl peptide receptor 2 (FPR2) is a G-protein coupled receptor (GPCR) located on the surface of many cell types of various animal species. The human receptor protein is encoded by the FPR2 gene and is activated to regulate cell function by binding any one of a wide variety of ligands including not only certain N-Formylmethionine-containing oligopeptides such as N-Formylmethionine-leucyl-phenylalanine (FMLP) but also the polyunsaturated fatty acid metabolite of arachidonic acid, lipoxin A4 (LXA4). Because of its interaction with lipoxin A4, FPR2 is also commonly named the ALX/FPR2 or just ALX receptor.

T helper 3 cells (Th3) are a subset of T lymphocytes with immunoregulary and immunosuppressive functions, that can be induced by administration of foreign oral antigen. Th3 cells act mainly through the secretion of anti-inflammatory cytokine transforming growth factor beta (TGF-β). Th3 have been described both in mice and human as CD4+FOXP3 regulatory T cells. Th3 cells were first described in research focusing on oral tolerance in the experimental autoimmune encephalitis (EAE) mouse model and later described as CD4+CD25FOXP3LAP+ cells, that can be induced in the gut by oral antigen through T cell receptor (TCR) signalling.

<span class="mw-page-title-main">Chrysophanol</span> Chemical compound

Chrysophanol, also known as chrysophanic acid, is a fungal isolate and a natural anthraquinone. It is a C-3 methyl substituted chrysazin of the trihydroxyanthraquinone family.

2,4-Dinitroaniline is a chemical compound with a formula of C6H5N3O4. It is used as an explosive and as a reagent to detect and characterize aldehydes and ketones.

References

  1. Atsushi Kitani; Ivan J. Fuss; Kazuhiko Nakamura; Owen M. Schwartz; Takashi Usui; Warren Strober (2000). "Treatment of Experimental (Trinitrobenzene Sulfonic Acid) Colitis by Intranasal Administration of Transforming Growth Factor (Tgf)-β1 Plasmid: TGF-β1–Mediated Suppression of T Helper Cell Type 1 Response Occurs by Interleukin (Il)-10 Induction and IL-12 Receptor β2 Chain Downregulation". The Journal of Experimental Medicine. 192 (1): 41–52. doi:10.1084/jem.192.1.41. PMC   1887715 . PMID   10880525.
  2. Trinitrobenzenesulfonic Acid, Comparative Toxicogenomics Database.
  3. Antoniou, Efstathios; Margonis, Georgios Antonios; Angelou, Anastasios; Pikouli, Anastasia; Argiri, Paraskevi; Karavokyros, Ioannis; Papalois, Apostolos; Pikoulis, Emmanouil (2016-08-19). "The TNBS-induced colitis animal model: An overview". Annals of Medicine and Surgery. 11: 9–15. doi:10.1016/j.amsu.2016.07.019. ISSN   2049-0801. PMC   5021709 . PMID   27656280.
  4. MSDS, chemcas.com.
  5. savety, cameochemicals.