3958-60-9 | 2-Nitrobenzyl bromide

Packsize	Purity	Availability	Price	Discounted Price
5g	98%	in stock	$20.00	$14.00
25g	98%	in stock	$44.00	$31.00
100g	98%	in stock	$139.00	$97.00
500g	98%	in stock	$558.00	$391.00

Description

• Catalog Number: AB44192
• Chemical Name: 2-Nitrobenzyl bromide
• CAS Number: 3958-60-9
• Molecular Formula: C7H6BrNO2
• Molecular Weight: 216.032
• MDL Number: MFCD00007184
• SMILES: BrCc1ccccc1N(=O)=O
• NSC Number: 95415

Computed Properties

• Complexity: 146
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• XLogP3: 2.7

Upstream Synthesis Route

2-Nitrobenzyl bromide is a versatile compound commonly used in chemical synthesis for its unique reactivity and functionality. In organic chemistry, it serves as a key building block for the preparation of various important compounds. Due to the presence of the nitro group, 2-Nitrobenzyl bromide can participate in a range of nucleophilic substitution reactions, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and materials.One of the primary applications of 2-Nitrobenzyl bromide is in the synthesis of protected amines. By reacting with primary or secondary amines, the nitro group can be selectively substituted with the amino group, forming a stable amine protecting group. This allows for the selective manipulation of amine functionalities in complex molecules, crucial for the synthesis of peptides, natural products, and other bioactive compounds.Additionally, 2-Nitrobenzyl bromide can be utilized in the preparation of photolabile protecting groups. The photo-induced cleavage of the nitrobenzyl group enables the controlled release of functional groups under mild conditions, making it a valuable tool in drug delivery systems, polymer chemistry, and bioconjugation strategies.Overall, the unique reactivity and versatility of 2-Nitrobenzyl bromide make it an essential reagent in organic synthesis, playing a crucial role in the development of novel compounds and materials in the fields of medicinal chemistry, materials science, and chemical biology.

Literature

• 3-Carbamoyl-1-(2-nitrobenzyl)pyridin-ium bromide.

  Acta crystallographica. Section E, Structure reports online 20120501

• 1-(2-Nitro-benz-yl)-1H-pyrrole-2-carbaldehyde.

  Acta crystallographica. Section E, Structure reports online 20110601

• Photocaged variants of the MunI and PvuII restriction enzymes.

  Biochemistry 20110412

• 2-(Furan-2-yl)-5-(2-nitro-benz-yl)-2,3-dihydro-1,5-benzothia-zepin-4(5H)-one.

  Acta crystallographica. Section E, Structure reports online 20110101

• Distributed Drug Discovery, Part 2: global rehearsal of alkylating agents for the synthesis of resin-bound unnatural amino acids and virtual D(3) catalog construction.

  Journal of combinatorial chemistry 20090112

• Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers.

  European journal of medicinal chemistry 20060901