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97-00-7 - 1-Chloro-2,4-dinitrobenzene, 98% - 2,4-Dinitrochlorobenzene - A13774 - Alfa Aesar

A13774 1-Chloro-2,4-dinitrobenzene, 98%

CAS Number
97-00-7
Synonyms
2,4-Dinitrochlorobenzene

Size Price ($) Quantity Availability
100g 23.20
500g 72.10
2500g 230.58
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1-Chloro-2,4-dinitrobenzene, 98%

MDL
MFCD00007075
EINECS
202-551-4

Chemical Properties

Formula
C6H3ClN2O4
Formula Weight
202.55
Melting point
48-52°
Boiling Point
314-316°
Flash Point
186°(366°F)
Density
1.700
Solubility
Soluble in chloroform, ether, hot alcohol, and benzene. Insoluble in water.

Applications

1-Chloro-2,4-dinitrobenzene is used as a reagent for the detection and determination of pyridine compounds. It has been used as alkylating agent to evaluate the depletion of intracellular erythrocyte glutathione (GSH). It is an irreversible inhibitor of human thioredoxin reductase.

Notes

Incompatible with strong oxidizing agents, ammonia. Reacts with hydrazine hydrate.

Literature References

Elias S. J. Arner; Mikael Bjornstedt and Arne Holmgren. 1-Chloro-2,4-dinitrobenzene Is an Irreversible Inhibitor of Human Thioredoxin Reductase. Loss of thioredoxin disulfide reductase activity is accompanied by a large increase in nadph oxidase activity.Journal of Biological Chemistry.1995, 270 3479-3482.

YC Awasthi; HS Garg; DD Dao; CA Partridge and SK Srivastava. Enzymatic conjugation of erythrocyte glutathione with 1-chloro-2,4-dinitrobenzene: the fate of glutathione conjugate in erythrocytes and the effect of glutathione depletion on hemoglobin. bloodjournal.hematologylibrary.1981, 58 733-738.

The doubly-activated chloro-substituent is readily displaced by nucleophiles, e.g.:

Ammonia/ ammonium acetate to give 2,4-dinitroaniline: Org. Synth. Coll., 2, 221 (1943); or with ammonia gas in toluene in the presence of TBAB which improves the solubility of ammonia in the organic medium and accelerates the reaction: J. Chem. Soc., Chem. Commun., 1267 (1987). Benzyl mercaptan to give the thioether: Org. Synth. Coll., 5, 474 (1973). Iodide ion to give 2,4-dinitro-1-iodobenzene: Org. Synth. Coll., 5, 478 (1973). Nitrite in toluene (phase-transfer) to give 1,2,4-trinitrobenzene (caution!): J. Org. Chem., 56, 4967 (1991).

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H311-H331-H373-H400-H410

Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects.

Precautionary Statements: P260-P261-P273-P280-P301+P310-P361-P304+P340-P311-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Remove/Take off immediately all contaminated clothing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,2136
Beilstein
613161
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2904.90
TSCA
Yes
RTECS
CZ0525000

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