55034-12-3

Usage

Functional groups

Nitro group, Bromine atom, Methoxy groups

Structure

Benzene ring with a bromine atom at the 1st position, methoxy groups at the 2nd and 5th positions, and a nitro group at the 3rd position

Application

Intermediate in the synthesis of pharmaceuticals and agrochemicals

Use in research

Reagent for the introduction of functional groups onto aromatic rings

Hazardous nature

Potentially hazardous

Toxicity

Toxic if swallowed or inhaled

Skin and eye irritation

May cause skin and eye irritation upon contact

Handling precautions

Should be handled with care due to its hazardous nature and potential for toxicity and irritation

InChI:InChI=1/C8H8BrNO4/c1-13-5-3-6(9)8(14-2)7(4-5)10(11)12/h3-4H,1-2H3

Upstream product

• 89-39-4 1,4-dimethoxy-2-nitrobenzene 
• 115929-59-4 6-bromo-4-methoxy-2-nitrophenol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 150-76-5 4-methoxy-phenol 
• 1568-70-3 4-methoxy-2-nitrophenol 

Downstream Products

• 115929-62-9 3-bromo-2,5-dimethoxyaniline 
• 1198600-29-1 1-(2,5-dimethoxy-3-nitrophenyl)-2-methylpropan-1-ol 
• 1198600-30-4 1-(3,6-dimethoxy-2-nitrophenyl)-2-methylpropan-1-ol 
• 1270942-86-3 (3E,6S,7S,8R,9Z)-12-{2,5-dimethoxy-3-[(3R,4E)-3-methoxyhepta-4,6-dienamido]phe-nyl}-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl1-[(cyclohex-1-ene)amido]cyclopropane-1-carboxylate 
• 1270942-87-4 C₄₇H₆₀N₂O₉ 
• 1270942-89-6 2-(2,5-dimethoxy-3-nitrophenethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1270942-79-4 4-[(2R,3R,4Z)-7-(2,5-dimethoxy-3-nitrophenyl)-3-(4-methoxybenzyloxy)-4-methyl-hept-4-en-2-yl]-2,2-dimethyl-1,3-dioxolane 
• 1270942-80-7 (2R,3R,4Z)-7-(2,5-dimethoxy-3-nitrophenyl)-3-(4-methoxybenzyloxy)-2,4-dimethyl-hept-4-enal 
• 1270942-81-8 (3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-ol 
• 1270942-82-9 (3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl 1-azidocyclopropane-1-carboxylate 
• 1270942-83-0 (3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl 1-aminocyclopropane-1-carboxylate 
• 1270942-85-2 (3E,6R,7S,8R,9Z)-12-(2,5-dimethoxy-3-nitrophenyl)-8-(4-methoxybenzyloxy)-7,9-dimethyldodeca-1,3,9-trien-6-yl 1-[(cyclohex-1-ene)amido]cyclopropane-1-carboxylate 
• 1270942-93-2 2,5-dimethoxy-1-nitro-3-vinylbenzene 
• 70563-58-5 herbimycin A 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of exiguamine A analogues as IDO1 inhibitors

A series of exiguamine A analogues were designed and synthesized via 15 steps. Their inhibitory activities against IDO1 were tested and the structure-activity relationships were studied. Most compounds exhibited potent IDO1 inhibitory activities with IC50 values at the level of 10?7–10?8 M. Compound 21f was the most potent IDO1 inhibitor with an IC50 value of 65.3 nM, which was comparable with the positive control drug epacadostat (IC50 = 46 nM). Moreover, compound 21f showed higher selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO) and no cytotoxicity at its effective concentration, rending it justifiable for further optimization and evaluation.

A formal synthesis of lavendamycin methyl ester, nitramarine, and their analogues: A povarov approach

A convergent formal synthesis of lavendamycin methyl ester and synthesis of its analogues have been delineated through the Povarov approach. This protocol is also applied to the formal synthesis of nitramarine (3) in good yield.

Total synthesis of herbimycin A

(Chemical Equation Presented) Hsp90 has recently emerged as a promising biological target for treatment of cancer. Herbimycin A and other members of the benzoquinoid ansamycin class of natural products are known to inhibit Hsp90 activity. The total synthesis of herbimycin A was achieved from the commercially available Roche ester 1 by using allylmetals to control the stereogenic centers at C6, C7, C10, C11, and C12 and a ring-closing metathesis to control the (Z)-double bond of the (E,Z)-dienic moiety.