4,5-Dimethoxy-2-nitrobenzyl bromide - ≥97% , CAS No.53413-67-5

CAS: 53413-67-5 Cat. No.: D170849 Molecular Weight: 276.08 EC Number: 627-578-2

GRADE & PURITY ≥97%

Storage

Room temperature

Shipped In

Normal

Overview

4,5-Dimethoxy-2-nitrobenzyl bromide (DMNBB, 1-(Bromomethyl)-4,5-dimethoxy-2-nitrobenzene) is a 4,5-dimethoxy-2-nitrobenzyl derivative. 4,5-Dimethoxy-2-nitrobenzyl (DMNB) group of DMNBB is used as a photolabile protecting group in caging technology to develop pro-drugs. 

Application：

4,5-Dimethoxy-2-nitrobenzyl bromide (DMNB bromide, 6-nitroveratryl bromide) is suitable reagent used in the synthesis of N-(4,5-dimethoxy-2-nitrobenzyl)vanillylamine which forms caged vanilloid.[3] It may be used in the synthesis of the following:
4-(4′,5′-dimethoxy-2-nitrobenzyloxy)benzaldehyde, a DMNB-caged aldehyde
N-[4-[(4,5-dimethoxy-2-nitrobenzyl)oxy]-3-methoxybenzyl]acetamide
caged derivative of pyridostatin ([C]-PDS)
photosensitive polyimide (PI-DMNB)
caged β-ecdysone
4-tert-butyldimethylsilyloxy-1-(2-deoxy-3,5-di-O-toluoyl-β-D-ribofuranosyl)-2-(6-nitroveratrylthio)-1H-benzimidazole, an intermediate in synthesis of phosphoramidite bearing 4-hydroxy-2-mercaptobenzimidazole (SBNV) nucleobase
alkylation of dihydrofluorescein[8]
4-(4′,5′-Dimethoxy-2′-nitrobenzyloxy)benzaldehyde

Specifications

Specifications & Purity

≥97%

Storage

Room temperature

Shipped In

Normal

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 488194167
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488194167
• Canonical Smiles: COC1=C(C=C(C(=C1)CBr)[N+](=O)[O-])OC
• IUPAC Name: 1-(bromomethyl)-4,5-dimethoxy-2-nitrobenzene
• InChIKey: UEKFEYNZISYRRH-UHFFFAOYSA-N
• INCHI: 1S/C9H10BrNO4/c1-14-8-3-6(5-10)7(11(12)13)4-9(8)15-2/h3-4H,5H2,1-2H3
• Isomeric SMILES: COC1=C(C=C(C(=C1)CBr)[N+](=O)[O-])OC
• WGK Germany: 3
• UN Number: 3261
• Packing Group: II
• Molecular Weight: 276.08
• Reaxy-Rn: 2529990
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2529990&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Nitrobenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Nitrobenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Nitrophenyl ethers
• Alternative Parents: Dimethoxybenzenes Methoxyanilines Phenoxy compounds Anisoles Benzyl bromides Nitroaromatic compounds Alkyl aryl ethers Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Organonitrogen compounds Hydrocarbon derivatives Organic oxides Organic salts Organobromides Alkyl bromides Organic cations
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Nitrophenyl ether - O-dimethoxybenzene - Dimethoxybenzene - Methoxyaniline - Phenoxy compound - Nitroaromatic compound - Anisole - Phenol ether - Methoxybenzene - Benzyl halide - Benzyl bromide - Alkyl aryl ether - C-nitro compound - Organic nitro compound - Ether - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organobromide - Alkyl bromide - Organohalogen compound - Organic oxide - Organic nitrogen compound - Alkyl halide - Organic oxygen compound - Organic salt - Organic cation - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Melt Point(°C): 131-133°C
• Molecular Weight: 276.080 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 274.979 Da
• Monoisotopic Mass: 274.979 Da
• Topological Polar Surface Area: 64.300 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 221.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1