99-35-4 Usage
Chemical Properties
Trinitrobenzene is a yellow crystalline solid.
Uses
Different sources of media describe the Uses of 99-35-4 differently. You can refer to the following data:
1. Trinitrobenzene is used as an explosive. It is obtained by oxidation of trinitrotoluene.
2. Explosive. 1,3,5-Trinitrobenzene is a vulcanizing agent for natural rubber. Indicator for pH 12.0-14.0.
3. 1,3,5-Trinitrobenzene can be used for direct analysis in real time mass spectrometry for fast screening of explosives.
Definition
ChEBI: A trinitrobenzene in which each of the nitro groups is meta- to the other two.
Synthesis Reference(s)
The Journal of Organic Chemistry, 22, p. 1046, 1957 DOI: 10.1021/jo01360a012
General Description
A light yellow crystalline sludge or slurry. Burns but may require some effort to ignite. A high explosive when dry. Easily ignited and burns very vigorously when dry. Soluble in alcohol and ether; insoluble in water. Produces toxic oxides of nitrogen during combustion.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Aromatic nitro compounds, such as TRINITROBENZENE, 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.
Health Hazard
The toxic effects from ingestion of the solid or inhalation of its dusts include irritation of respiratory tract, headache, dyspnea, and cyanosis. Other effects noted in animals were degenerative changes in the brain. The oral LD50 values in rats and mice are 450 and 570 mg/kg, respectively.
Fire Hazard
Trinitrobenzene is a high explosive, similar to trinitrotoluene. However, it is less sensitive to impact than the latter. Its brisance and power are higher than those of TNT. It detonates when heated rapidly. The dry material is highly sensitive to shock and heat.Slow and careful heating of a small amount of material does not cause detonation. Trinitrobenzene is a flammable solid. It reacts vigorously with reducing substances. It emits highly toxic oxides of nitrogen on decomposition.
.
Safety Profile
Poison by ingestion and
intravenous routes. Mutation data reported.
A severe explosion hazard when shocked or
exposed to heat. Trinitrobenzene is
considered a powerful high explosive and
has more shattering power than TNT.
Although it is less sensitive to impact than
TNT, it is not used much because it is
difficult to produce. The complex with
potassium trimethyl stannate explodes at
room temperature. Forms heat-sensitive
explosive complexes with alkyl or aryl
metallates (e.g., lithium or potassium salts of
trimethyl-, triethyl-, or triphenyl-germanate,
-silanate, or -stamate). Can react vigorously
with reducing materials. When heated to
decomposition it emits highly toxic fumes of
NOx and explodes. See also NITRO
COMPOUNDS of AROMATIC
HYDROCARBONS.
Potential Exposure
Trinitrobenzene is explosive when dry.
Used as an explosive; as a vulcanizing agent for natural
rubber. Trinitrobenzene may be more powerful than TNT;
and is reported to be less sensitive to impact than TNT.
However it is difficult to produce, and is not used as widely
as TNT.
storage
Storage and shipping are similar to those used for TNT and other high explosives. Trinitrobenzene is stored in a permanent magazine well separatedfrom initiator explosive, combustible and oxidizing materials, and heat sources. It is shipped in metal containers enclosed in wooden boxes or strong siftproof cloth or paper bags in amounts not exceeding 60 lb net weight (NFPA 1997).
Shipping
UN0214 Trinitrobenzene, dry or wetted with
<30% water, by mass, Hazard Class: 1.1D; Labels:1.1DExplosives
(with a mass explosion hazard); D-Substances
or articles which may mass detonate (with blast and/or
fragment hazard) when exposed to fire. UN1354
Trinitrobenzene, wetted with not <30% water, by mass,
Hazard Class: 4.1; Labels: 4.1-Flammable solid.
Purification Methods
Crystallise it from glacial acetic acid, CHCl3, CCl4, EtOH aqueous EtOH or EtOH/*benzene, after (optionally) heating with dilute HNO3. Dry it in air. Fuse it and crystallise it under vacuum. [Beilstein 5 H 271, 5 I 140, 5 II 203, 5 III 643, 5 IV 754.]
Incompatibilities
Sensitive to shock and heat. Incompatible
with initiating explosives, combustible materials. Aromatic
nitro compounds, such as trinitrobenzene, range from slight to
strong oxidizing agents. Keep away from strong reducing
agents, including hydrides, alkali metals; aluminium and
other metal powder; phosphorus; sulfides and nitrides, alkaline
material, strong bases; contact may initiate vigorous reactions
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 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. Incompatible with
strong oxidizers (chlorates, nitrates, peroxides, permanganates,
perchlorates, chlorine, bromine, fluorine, etc.); contact
may cause fires or explosions.
Waste Disposal
Consult with environmental
regulatory agencies for guidance on acceptable disposal
practices. Generators of waste containing this contaminant
(≥100 kg/mo) must conform with EPA regulations governing
storage, transportation, treatment, and waste disposal.
Dissolve in a combustible solvent and spray into an incinerator
equipped with afterburner and scrubber.
Check Digit Verification of cas no
The CAS Registry Mumber 99-35-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 99-35:
(4*9)+(3*9)+(2*3)+(1*5)=74
74 % 10 = 4
So 99-35-4 is a valid CAS Registry Number.
99-35-4Relevant articles and documents
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Jenkins
, p. 862,865 (1936)
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Synthesis of 1,3,5-trinitrosobenzene [2]
Klyuchnikov,Khairutdinov
, p. 1133 - 1134 (2004)
-
Evidence for a π dimer in the electrochemical reduction of 1,3,5-trinitrobenzene: A reversible N2-fixation system
Gallardo, Iluminada,Guirado, Gonzalo,Marquet, Jordi,Vila, Neus
, p. 1321 - 1325 (2007)
(Figure Presented) Electrochemical reduction of 1,3,5-trinitrobenzene (1) forms π dimer 2, which evolves to a more stable ω complex. The crystal structure of the NEt4+ salt of 2 shows π-stacked chains of radical anions. Solid 2 or dimeric 2 in solution reacts with N2 to give a dianion in which an azo group links two 1,3,5-trinitrobenzene units (see picture). The azo derivative is reversibly electrochemically oxidized to 1.
STERIC ACCELERATION OF REDUCTIVE DESULFONATION OF 1,8-NAPHTHALENEDISULFONATE BY AN NADH MODEL COMPOUND
Shinkai, Seiji,Kuroda, Hideo,Kusano, Yumiko,Manabe, Osamu
, p. 3201 - 3204 (1981)
1,8-Naphthalenedisulfonate was reductively desulfonated by N-benzyl-1,4-dihydronicotinamide, whereas no desulfonation was observed for the 1,6-isomer.The high reactivity of the 1,8-isomer is attributed to the steric-strain that enforces the shift of the initial state with the sp2-carbon close to the transition state with the sp3-carbon.
Preparation and vulcanizing properties of 1,3,5-trinitrosobenzene
Klyuchnikov,Khairutdinov,Klyuchnikov
, p. 1382 - 1385 (2004)
A procedure was developed for preparing a new trifunctional vulcanizing agent for unsaturated rubber composites, 1,3,5-trinitrosobenzene; its suitability as an additive to rubber-substrate adhesive formulations was examined.
Method for preparing 1, 3, 5-trinitrobenzene
-
Paragraph 0014; 0019-0023, (2021/07/24)
The invention relates to a method for preparing 1, 3, 5-trinitrobenzene, and belongs to the technical field of organic intermediates. The method comprises the following steps: respectively preparing a TNT alcoholic solution and a sodium chlorite aqueous solution, adjusting the pH value of the TNT alcoholic solution with hydrochloric acid, heating to a reaction temperature, dropwise adding the sodium chlorite aqueous solution into the TNT alcoholic solution, reacting at a constant temperature, and finally filtering, washing and recrystallizing to obtain the 1, 3, 5-trinitrobenzene. Sodium chlorite is adopted as an oxidizing agent, so that oxidation and decarboxylation reactions are completed in one step, the process is simplified, and the operation cost is reduced; the energy consumption required by the reaction is low, and the product purity is high; the reaction process is safer, and the reaction yield is higher.
Synthesis of thermally stable energetic 1,2,3-triazole derivatives
Kumar, A. Sudheer,Ghule, Vikas D.,Subrahmanyam,Sahoo, Akhila K.
, p. 509 - 518 (2013/02/23)
Various thermally stable energetic polynitro-aryl-1,2,3-triazoles have been synthesized through Cu-catalyzed [3+2] cycloaddition reactions between their corresponding azides and alkynes, followed by nitration. These compounds were characterized by analyti
The phthaloyl chloride-induced conversion reactions of trinitrobenzene into nitroaryl halides
Lee, Woong Hee,Park, Gyoo Soon,Kim, Seok Chan
scheme or table, p. 2820 - 2822 (2012/01/05)
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