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Cas Database

100-25-4

100-25-4

Identification

  • Product Name:1,4-DINITROBENZENE

  • CAS Number: 100-25-4

  • EINECS:202-833-7

  • Molecular Weight:168.109

  • Molecular Formula: C6H4 N2 O4

  • HS Code:29042090

  • Mol File:100-25-4.mol

Synonyms:Benzene,p-dinitro- (8CI); 1,4-Dinitrobenzene; NSC 3809; Para-dinitrobenzene;p-Dinitrobenzene

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Safety information and MSDS view more

  • Pictogram(s):A suspected carcinogen and poison by ingestion. TWA 0.15 ppm (skin). Mixture with nitric acid is a high explosive.

  • Hazard Codes:T+,N,T,F

  • Signal Word:Danger

  • Hazard Statement:H300 Fatal if swallowedH310 Fatal in contact with skin H330 Fatal if inhaled H410 Very toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Artificial respiration may be needed. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention . INHALATION OR INGESTION: Headache, vertigo, nausea, vomiting, diarrhea, fever, rapid weak pulse, decreased blood pressure, cyanosis, exhaustion, hepatomegaly, jaundice, albuminurea, hematuria, visual scotomata, amblyopia and nystagmus. EYES: Irritation. SKIN: Stains skin yellow; if skin contact is prolonged, can be absorbed into blood causing same symptoms as for inhalation. (USCG, 1999) Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/

  • Fire-fighting measures: Suitable extinguishing media For rescue purposes wear full protective clothing. Fight fire from an explosion-resistant location. In advanced or massive fires, area should be evacuated. If fire occurs in vicinity of this material water should be used to keep containers cool. /1,2-Dinitrobenzene/ Special Hazards of Combustion Products: When heated to decomposition toxic fumes of oxides of nitrogen released. Behavior in Fire: Decomposes explosively. Can be detonated by shock or heat under confinement that will permit high pressure buildup (USCG, 1999) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Consult an expert! Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: complete protective clothing including self-contained breathing apparatus. 1. Remove all ignition sources. 2. Ventilate area of spill. 3. For small quantities, sweep onto paper or other suitable material and burn in suitable combustion chamber which allows burning in unconfined condition and is equipped with appropriate effluent gas cleaning device. Large quantities may be reclaimed; however, if this is not practical, dissolve in fuel oil and atomize in suitable combustion chamber equipped with cleaning an appropriate effluent gas cleaning device.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants, strong bases, strong acids and food and feedstuffs. See Chemical Dangers.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 10 Hr Time-Weighted avg: 1 mg/cu m; skin.Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. 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. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,4-Dinitrobenzene >99.0%(GC)
  • Packaging:25g
  • Price:$ 167
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:1,4-Dinitrobenzene >99.0%(GC)
  • Packaging:5g
  • Price:$ 46
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dinitrobenzene 98%
  • Packaging:5g
  • Price:$ 58.6
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:1,4-Dinitrobenzene analytical standard
  • Packaging:442250
  • Price:$ 55.8
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:1,4-Dinitrobenzene, 98+%
  • Packaging:25g
  • Price:$ 155
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:1,4-Dinitrobenzene, 98+%
  • Packaging:100g
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  • Manufacture/Brand:Alfa Aesar
  • Product Description:1,4-Dinitrobenzene, 98+%
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  • Manufacture/Brand:AK Scientific
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  • Manufacture/Brand:AHH
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Relevant articles and documentsAll total 75 Articles be found

Highly efficient dinitration of aromatic compounds in fluorous media using ytterbium perfluorooctanesulfonate and perfluorooctanesulfonic acid as catalysts

Yi, Wen-Bin,Cai, Chun

, p. 2957 - 2961 (2006)

Ytterbium perfluorooctanesulfonate [Yb(OPf)3] and perfluorooctanesulfonic acid [PfOH] catalyze the highly efficient dinitration of toluene, benzene, benzyl chloride, and chlorobenzene in fluorous media. Notably the process produces almost no waste acid, as opposed to the traditional case. The fluorous phase-containing catalyst could be easily and efficiently recovered for reuse by simple phase separation. Copyright Taylor & Francis Group, LLC.

-

Hodgson,Ward

, p. 556,558 (1948)

-

-

Pounder,Masson

, p. 1357,1359 (1934)

-

-

Hetherington,Masson

, p. 105,113 (1933)

-

Ipso Nitration of Aryl Boronic Acids Using Fuming Nitric Acid

Baucom, Kyle D.,Brown, Derek B.,Caille, Seb,Murray, James I.,Quasdorf, Kyle,Silva Elipe, Maria V.

, (2021)

The ipso nitration of aryl boronic acid derivatives has been developed using fuming nitric acid as the nitrating agent. This facile procedure provides efficient and chemoselective access to a variety of aromatic nitro compounds. While several activating agents and nitro sources have been reported in the literature for this synthetically useful transformation, this report demonstrates that these processes likely generate a common active reagent, anhydrous HNO3. Kinetic and mechanistic studies have revealed that the reaction order in HNO3 is >2 and indicate that the ?NO2 radical is the active species.

-

White,Emmons

, p. 31,32,34 (1962)

-

Energy transfer, electron transfer, and addition reactions of triplet state of 1,3-dihydroimidazole-2-thiones investigated by laser flash photolysis

Alam, Maksudul M.,Ito, Osamu

, p. 339 - 345 (1999)

The transient absorption bands observed at ca. 400 and 550 nm for 1,3- dihydro-2H-imidazole-2-thione (IT), 1,3-dihydro-1-methyl-2H-imidazole-2- thione (MIT), and 1,3-dihydro-2H-benzimidazole-2-thione (BIT) have been assigned to their triplet states (3IT* 's) by the quenching and sensitizing experiments using laser flash photolysis technique. Short intrinsic triplet lifetimes and relatively high triplet energies have been evaluated as characteristics of 3IT* 's. For electron acceptors, photoinduced electron- transfer reaction occurs via 3IT* 's in the diffusion controlled limit. The nucleophilic character of 3IT* 's was confirmed by changing the substituents of alkenes on the addition reactions. MO calculations indicate that the lowest electronic configurations of both 3IT* and 3MIT* have 3(n,π*) character, while 3BIT* has 3(π,π*) character. The addition reactivity of 3BIT* is slightly higher than those of 3IT* and 3MIT*, which is opposite to the general tendency.

Danzig et al.

, p. 1071 (1960)

Nitration of deactivated aromatic compounds via mechanochemical reaction

Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin

supporting information, (2021/05/05)

A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Budinská, Alena,Katayev, Dmitry,Passera, Alessandro,Zhang, Kun

supporting information, (2020/03/30)

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

Process route upstream and downstream products

Process route

2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

p-Dinitrobenzol-Monoradikalanion
34505-33-4

p-Dinitrobenzol-Monoradikalanion

para-dinitrobenzene
100-25-4

para-dinitrobenzene

2,3-Dichlor-1,4-naphthosemichinon
59637-68-2,22062-59-5

2,3-Dichlor-1,4-naphthosemichinon

Conditions
Conditions Yield
In gas; at 150 ℃; Rate constant;
at 149.9 ℃; Thermodynamic data; Equilibrium constant;
3,5-dinitrobenzonitrile
4110-35-4

3,5-dinitrobenzonitrile

p-Dinitrobenzol-Monoradikalanion
34505-33-4

p-Dinitrobenzol-Monoradikalanion

para-dinitrobenzene
100-25-4

para-dinitrobenzene

3,5-Dinitrobenzonitril-Radikalanion

3,5-Dinitrobenzonitril-Radikalanion

Conditions
Conditions Yield
at 149.9 ℃; Thermodynamic data; Equilibrium constant;
2,6-dichloro-1,4-benzoquinone
697-91-6

2,6-dichloro-1,4-benzoquinone

p-Dinitrobenzol-Monoradikalanion
34505-33-4

p-Dinitrobenzol-Monoradikalanion

para-dinitrobenzene
100-25-4

para-dinitrobenzene

2,6-dichloro-p-benzoquinone anion radical
34537-54-7

2,6-dichloro-p-benzoquinone anion radical

Conditions
Conditions Yield
In gas; at 150 ℃; Rate constant;
4-methoxybenzenediazonium tetrafluoroborate
459-64-3

4-methoxybenzenediazonium tetrafluoroborate

p-dinitrobenzene anion-radical potassium salt

p-dinitrobenzene anion-radical potassium salt

para-dinitrobenzene
100-25-4

para-dinitrobenzene

4-methoxy-N-(4-nitrophenyl)aniline
730-11-0

4-methoxy-N-(4-nitrophenyl)aniline

methoxybenzene
100-66-3

methoxybenzene

Conditions
Conditions Yield
In tetrahydrofuran; at -30 ℃; for 0.166667h;
0.92 g
0.16 g
0.35 g
4-methoxybenzenediazonium tetrafluoroborate
459-64-3

4-methoxybenzenediazonium tetrafluoroborate

potassium salt of the p-dinitrobenzene anion radical

potassium salt of the p-dinitrobenzene anion radical

para-dinitrobenzene
100-25-4

para-dinitrobenzene

4-methoxy-N-(4-nitrophenyl)aniline
730-11-0

4-methoxy-N-(4-nitrophenyl)aniline

methoxybenzene
100-66-3

methoxybenzene

Conditions
Conditions Yield
In tetrahydrofuran; at -30 ℃; for 0.166667h; Product distribution;
0.92 g
0.16 g
0.35 g
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

benzene-1,4-diamine hydrochloride
624-18-0,55972-71-9

benzene-1,4-diamine hydrochloride

para-dinitrobenzene
100-25-4

para-dinitrobenzene

Conditions
Conditions Yield
In water; acetone; for 23h; Ambient temperature;
82%
4-nitrophenyl azide
1516-60-5

4-nitrophenyl azide

para-dinitrobenzene
100-25-4

para-dinitrobenzene

4-nitrosonitrobenzene
4485-08-9

4-nitrosonitrobenzene

bis(4-nitrophenyl)diazene
3646-57-9,89103-79-7

bis(4-nitrophenyl)diazene

4,4'-dinitroazoxybenzene
614-25-5,21650-71-5,71297-95-5

4,4'-dinitroazoxybenzene

Conditions
Conditions Yield
With oxygen; In acetonitrile; for 0.1h; Product distribution; Irradiation; effect of the power of irradiation;
20 % Turnov.
12 % Turnov.
11 % Turnov.
28 % Turnov.
nitrobenzene
98-95-3,26969-40-4

nitrobenzene

meta-dinitrobenzene
99-65-0

meta-dinitrobenzene

para-dinitrobenzene
100-25-4

para-dinitrobenzene

1,2-Dinitrobenzene
528-29-0

1,2-Dinitrobenzene

Conditions
Conditions Yield
With Iron(III) nitrate nonahydrate; phosphorus pentoxide; In neat (no solvent); at 20 ℃; for 6h; Overall yield = 98 percent; Milling; Green chemistry;
86%
9%
3%
With nitronium hexafluorophosphate; In nitromethane; for 0.166667h; Product distribution; Ambient temperature; var. nitrating agents, var. solv., var. temp., rel. rate of the nitration;
11.1 % Chromat.
86.9 % Chromat.
1.9 % Chromat.
With methanesulfonic acid; Nitrogen dioxide; ozone; In dichloromethane; at -10 - 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With Nitrogen dioxide; ozone; methanesulfonic acid; In dichloromethane; at -10 - 0 ℃; for 9h;
91 % Chromat.
1 % Chromat.
8 % Chromat.
With nitric acid; Sulfate; zirconium(IV) oxide; In tetrachloromethane; at 20 ℃; for 5h; Yield given. Title compound not separated from byproducts;
With zeolite Hβ; nitric acid; trifluoroacetic anhydride; at -10 ℃; for 2h; Further Variations:; Reagents; Product distribution;
With dinitrogen pentoxide; H-faujasite zeolite F-720; In dichloromethane; at 0 ℃; Kinetics;
With dinitrogen pentoxide; H-faujasite zeolite F-720; In dichloromethane; at 0 ℃;
nitrobenzene
98-95-3,26969-40-4

nitrobenzene

meta-dinitrobenzene
99-65-0

meta-dinitrobenzene

para-dinitrobenzene
100-25-4

para-dinitrobenzene

3-Nitrochlorobenzene
121-73-3

3-Nitrochlorobenzene

1,2-Dinitrobenzene
528-29-0

1,2-Dinitrobenzene

Conditions
Conditions Yield
With hydrogenchloride; sulfuric acid; nitric acid; at 25 ℃; Product distribution;
1.2 % Chromat.
1.3 % Chromat.
96.4 % Chromat.
1.0 % Chromat.
3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

4-nitro-aniline
100-01-6,104810-17-5

4-nitro-aniline

para-dinitrobenzene
100-25-4

para-dinitrobenzene

Conditions
Conditions Yield
In acetone; at 22 ℃; for 0.5h;
98 % Chromat.

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