392855

4,5-Dimethoxy-2-nitrobenzyl bromide

97%

• Synonym(s): 6-Nitroveratryl bromide
• Linear Formula: O₂NC₆H₂(OCH₃)₂CH₂Br
• CAS Number: 53413-67-5
• Molecular Weight: 276.08
• MDL number: MFCD00192064
• UNSPSC Code: 12352100
• PubChem Substance ID: 24864490
• NACRES: NA.22

Properties

• assay: 97%
• mp: 131-133 °C (lit.)
• functional group: bromo; nitro
• SMILES string: COc1cc(CBr)c(cc1OC)[N+]([O-])=O
• InChI: 1S/C9H10BrNO4/c1-14-8-3-6(5-10)7(11(12)13)4-9(8)15-2/h3-4H,5H2,1-2H3
• InChI key: UEKFEYNZISYRRH-UHFFFAOYSA-N

Description

General description

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.[1] Synthesis of 1-(bromomethyl)-4,5-dimethoxy-2-nitrobenzene by using 6-nitroveratraldehyde as starting reagent has been reported.[2]

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[4]
• N-[4-[(4,5-dimethoxy-2-nitrobenzyl)oxy]-3-methoxybenzyl]acetamide[4]
• caged derivative of pyridostatin ([C]-PDS)[1]
• photosensitive polyimide (PI-DMNB)[5]
• caged β-ecdysone[6]
• 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 (SB^NV) nucleobase[7]
• alkylation of dihydrofluorescein[8]
• 4-(4′,5′-Dimethoxy-2′-nitrobenzyloxy)benzaldehyde[1]

Safety Information

• pictograms: GHS05
• signalword: Danger
• hcodes: H314
• pcodes: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges