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2,4-Dinitrobenzyl chloride (CAS 610-57-1)

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Alternate Names:
α-Chloro-2,4-dinitrotoluene
CAS Number:
610-57-1
Molecular Weight:
216.58
Molecular Formula:
C7H5ClN2O4
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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2,4-Dinitrobenzyl chloride (2,4-DNBC) is a versatile chemical compound widely employed in organic synthesis, pharmaceuticals, and biochemistry. With its broad range of uses, 2,4-Dinitrobenzyl chloride serves as a valuable reagent for the synthesis of compounds, including amines, amides, and nitro compounds. Furthermore, it plays a role in the preparation of pharmaceuticals and other bioactive compounds. In the realm of organic synthesis, pharmaceuticals, and biochemistry, 2,4-Dinitrobenzyl chloride stands out as an indispensable reagent. It finds utility in synthesizing diverse compounds, encompassing amines, amides, and nitro compounds. Additionally, it plays a vital role in the synthesis of peptides, peptidomimetics, and enzyme inhibitors. The versatility of 2,4-Dinitrobenzyl chloride facilitates its broad applicability across multiple fields. 2,4-Dinitrobenzyl chloride operates as an electrophilic reagent, engaging with electron-rich nucleophiles like amines and alcohols. The reaction typically follows an SN2 mechanism, resulting in the displacement of the chlorine atom by the nucleophile. Beyond its synthetic utility, 2,4-Dinitrobenzyl chloride exhibits a diverse array of biochemical and physiological effects. Notably, it has been discovered to inhibit the activity of enzymes like tyrosinase, which plays a role in melanin biosynthesis. Additionally, it impedes the activity of enzymes involved in DNA synthesis, such as DNA polymerase. Furthermore, 2,4-Dinitrobenzyl chloride has shown efficacy in inhibiting the growth of specific cancer cells and inducing apoptosis in certain cell types. These findings highlight its potential applications in diverse biological applications.


2,4-Dinitrobenzyl chloride (CAS 610-57-1) References

  1. Organic qualitative analysis. IV. Identification of carboxylic acids by S-(p-nitrobenzyl)- and S-(2,4-dinitrobenzyl)-thiuronium chloride.  |  MOMOSE, T. and TANAKA, H. 1954. Pharm Bull. 2: 152-4. PMID: 13215024
  2. Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives.  |  Klimesová, V., et al. 2004. Farmaco. 59: 279-88. PMID: 15081345
  3. Generation and reactions of anionic sigma-adducts of 1,3-dinitrobenzene and 1,3,5-trinitrobenzene with carbanions in a gas phase, using an electrospray ion source as the chemical reactor.  |  Danikiewicz, W., et al. 2004. J Am Soc Mass Spectrom. 15: 927-33. PMID: 15144984
  4. Cytotoxicity and radiosensitising activity of synthesized dinitrophenyl derivatives of 5-fluorouracil.  |  Abdi, K., et al. 2012. Daru. 20: 3. PMID: 23226112
  5. 1-Substituted-5-[(3,5-dinitrobenzyl)sulfanyl]-1H-tetrazoles and their isosteric analogs: A new class of selective antitubercular agents active against drug-susceptible and multidrug-resistant mycobacteria.  |  Karabanovich, G., et al. 2014. Eur J Med Chem. 82: 324-40. PMID: 24927053
  6. Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and Thiadiazoles as Selective Antitubercular Agents Active Against Replicating and Nonreplicating Mycobacterium tuberculosis.  |  Karabanovich, G., et al. 2016. J Med Chem. 59: 2362-80. PMID: 26948407
  7. Enantioselective Organocatalytic Cyclopropanation of Enals Using Benzyl Chlorides.  |  Meazza, M., et al. 2016. J Org Chem. 81: 3488-500. PMID: 27080435
  8. Enterohepatic circulation of 2,4-dinitrobenzaldehyde, a mutagenic metabolite of 2,4-dinitrotoluene, in male Wistar rat.  |  Sayama, M., et al. 1989. Xenobiotica. 19: 83-92. PMID: 2756720
  9. A Photochemical Organocatalytic Strategy for the α-Alkylation of Ketones by using Radicals.  |  Spinnato, D., et al. 2020. Angew Chem Int Ed Engl. 59: 9485-9490. PMID: 32053279
  10. Sulfoxonium Ylides in Aminocatalysis: An Enantioselective Entry to Cyclopropane-Fused Chromanol Structures.  |  Bisag, GD., et al. 2022. Org Lett. 24: 5468-5473. PMID: 35856291
  11. Asymmetric Radical Bicyclization for Stereoselective Construction of Tricyclic Chromanones and Chromanes with Fused Cyclopropanes.  |  Lee, WC., et al. 2023. J Am Chem Soc.. PMID: 37129381
  12. The effect of physical and chemical properties of the sensitizing substance on the induction and elicitation of delayed contact sensitivity.  |  Godfrey, HP. and Baer, H. 1971. J Immunol. 106: 431-41. PMID: 5545150
  13. Solution-phase synthesis of phosphorothioate oligodeoxynucleosides by the phosphotriester method.  |  Barber, I., et al. 1995. Antisense Res Dev. 5: 39-47. PMID: 7613072

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

2,4-Dinitrobenzyl chloride, 1 g

sc-230998
1 g
$60.00