1,3,5-Trinitrobenzene

Last updated
1,3,5-Trinitrobenzene [1]
Trinitrobenzene.svg
Trinitrobenzene-3D-balls.png
Names
Preferred IUPAC name
1,3,5-Trinitrobenzene
Other names
sym-Trinitrobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.502 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
UN number 0388
  • C1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])[N+](=O)[O-]
Properties
C6H3N3O6
Molar mass 213.105 g·mol−1
Density 1.76 g/cm3
Melting point 123.2 °C (253.8 °F; 396.3 K)
Boiling point 315 °C (599 °F; 588 K)
330 mg/L
-74.55·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
2
3
4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,3,5-Trinitrobenzene is an organic compound with the formula C6H3(NO2)3. It is one of three trinitrated benzene-derivatives. A pale yellow solid, the compound is highly explosive. [2]

Contents

Synthesis and reactions

1,3,5-Trinitrobenzene is produced by decarboxylation of 2,4,6-trinitrobenzoic acid. [2] [3]

1,3,5-Trinitrobenzene forms charge-transfer complexes with electron-rich arenes.

Reduction of 1,3,5-trinitrobenzene gives 1,3,5-triaminobenzene, a precursor to phloroglucinol. [4]

Uses and applications

Trinitrobenzene is more explosive than TNT, but too expensive. [2] It is primarily used as a high explosive compound for commercial mining and military applications. It has also been used as a narrow-range pH indicator, an agent to vulcanize natural rubber, and a mediating agent to mediate the synthesis of other explosive compounds. [5]

Explosive properties

1,3,5-Trinitrobenzene is a high explosive. [6]

See also

Related Research Articles

Ketone Class of organic compounds having structure RCOR

In chemistry, a ketone is a functional group with the structure R2C=O, where R can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond). The simplest ketone is acetone (R = R' = methyl), with the formula CH3C(O)CH3. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone.

Imine Chemical compound

An imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

Acyl halide Chemical compound

An acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

Acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl functional group into a chemical compound. Such compounds are termed acetate esters or acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

Nitro compound Organic compounds that contain one or more nitro functional groups

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.

Benzoyl chloride Chemical compound

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

Raney nickel Chemical compound

Raney nickel, also called spongy nickel, is a fine-grained solid composed mostly of nickel derived from a nickel–aluminium alloy. Several grades are known, of which most are gray solids. Some are pyrophoric, but most are used as air-stable slurries. Raney nickel is used as a reagent and as a catalyst in organic chemistry. It was developed in 1926 by American engineer Murray Raney for the hydrogenation of vegetable oils. Raney is a registered trademark of W. R. Grace and Company.

Amidine Organic compounds

Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2.

Phosphorus triiodide Chemical compound

Phosphorus triiodide (PI3) is an inorganic compound with the formula PI3. A red solid, it is a common misconception that PI3 is too unstable to be stored; it is, in fact, commercially available. It is widely used in organic chemistry for converting alcohols to alkyl iodides. It is also a powerful reducing agent. Note that phosphorus also forms a lower iodide, P2I4, but the existence of PI5 is doubtful at room temperature.

Phloroglucinol Chemical compound

Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed "polyphenols" by the cosmetic and parapharmaceutical industries, which does not match the scientifically accepted definition.

1,4-Benzoquinone Chemical compound

1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.

Phenylhydroxylamine Chemical compound

Phenylhydroxylamine is the organic compound with the formula C6H5NHOH. It is an intermediate in the redox-related pair C6H5NH2 and C6H5NO. Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or O-phenylhydroxylamine.

Diphenylmethane Chemical compound

Diphenylmethane is an organic compound with the formula (C6H5)2CH2 (often abbreviated CH
2
Ph
2
). The compound consists of methane wherein two hydrogen atoms are replaced by two phenyl groups. It is a white solid.

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.

1-Phenylethylamine Chemical compound

1-Phenylethylamine is the organic compound with the formula C6H5CH(NH2)CH3. Classified as a monoamine, this colorless liquid is often used in chiral resolutions. Like benzylamine, it is highly basic and forms stable ammonium salts and imines.

Benzenediazonium tetrafluoroborate Organic compound containing an –N≡N+ function

Benzenediazonium tetrafluoroborate is an organic compound with the formula [C6H5N2]BF4. It is a salt of a diazonium cation and tetrafluoroborate. It exists as a colourless solid that is soluble in polar solvents. It is the parent member of the aryldiazonium compounds, which are widely used in organic chemistry.

Organoiodine compounds are organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare in nature. The thyroxine hormones are organoiodine compounds that are required for health and the reason for government-mandated iodization of salt.

Propargyl bromide Chemical compound

Propargyl bromide, also known as 3-bromo-prop-1-yne, is an organic compound with the chemical formula HC≡CCH2Br. A colorless liquid, it is a halogenated organic compound consisting of propyne with a bromine substituent on the methyl group. It has a lachrymatory effect, like related compounds. The compound is used as a reagent in organic synthesis.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

2,4,6-Trinitrobenzoic acid Impact-resistant high explosive

2,4,6-Trinitrobenzoic acid (TNBA) is an organic compound with the formula (O2N)3C6H2CO2H. It is a high explosive nitrated derivative of benzoic acid.

References

  1. Record of 1,3,5-Trinitrobenzene in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. 1 2 3 Booth, Gerald (2005). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
  3. Clarke, H. T.; Hartman, W. W. (1922). "1,3,5-Trinitrobenzene". Organic Syntheses. 2: 93. doi:10.15227/orgsyn.002.0093.
  4. Clarke, H. T.; Hartman, W. W. (1929). "Phloroglucinol". Organic Syntheses. 9: 74. doi:10.15227/orgsyn.009.0074.
  5. John Pike (1997-05-21). "Explosives – Nitroaromatics". Globalsecurity.org. Retrieved 2013-10-28.
  6. Sax, N. I. and Lewis, R. J. Sr. (1987) Hazardous chemicals desk reference. Van Nostrand Reinhold, New York. p. 664.