2,4,6-Trinitrobenzenesulfonic acid

2,4,6-Trinitrobenzene Sulfonic Acid

Names
IUPAC name 2,4,6-Trinitrobenzenesulfonic acid
Other names Picrylsulfonic acid; Trinitrobenzene sulfonate; TNBS
Identifiers
CAS Number	2508-19-2
3D model (Jmol)	Interactive image
ChEBI	CHEBI:53063
ChemSpider	10577
ECHA InfoCard	100.017.925
UN number	0386
InChI 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) Key: NHJVRSWLHSJWIN-UHFFFAOYSA-N 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
SMILES O=S(=O)(O)c1c(cc(cc1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O
Properties
Chemical formula	C6H3N3O9S
Molar mass	293.16 g·mol^−1
Density	0.955 g/cm^3
Hazards
R-phrases	R11 R36/38
S-phrases	S16 S26 S33 S37/39
NFPA 704	4 2 4 OX
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Trinitrobenzenesulfonic acid (C₆H₃N₃O₉S) is an 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]

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 ulcerative colitis in the large intestine and colon of laboratory animals in order to model inflammatory bowel disease.^[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 has not been investigated, so all health effects are unknown. To best prevent bodily harm or injury its recommended that all direct contact be avoided and the compound be kept under extremely strict environmentally controlled conditions. In case of spillage its recommended that a local fire department be called in advance prior to any attempt at cleaning. In case of fire its recommended that the material is left to burn and the surrounding area is evacuated. If fire fighting is required its recommended that a fully positive pressure self-contained breathing apparatus is used along with either foam or CO₂ extinguishers.^[4][5]

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. Scheiffele, F; Fuss, IJ (2002). "Induction of TNBS colitis in mice". Current Protocols in Immunology. Chapter 15: Unit 15.19. doi:10.1002/0471142735.im1519s49. ISBN 0471142735. PMID 18432874.
4. MSDS, chemcas.com.
5. savety, cameochemicals.