244160-46-1

Basic information

• Product Name: 1-bromo-4,5-dimethoxy-2-(propan-2-yloxy)benzene
• Synonyms: 1-bromo-4,5-dimethoxy-2-(propan-2-yloxy)benzene
• CAS NO: 244160-46-1
• Molecular Weight: 275.142
• Mol File: 244160-46-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-bromo-4,5-dimethoxy-2-(propan-2-yloxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromo-4,5-dimethoxy-2-(propan-2-yloxy)benzene(244160-46-1)
• EPA Substance Registry System: 1-bromo-4,5-dimethoxy-2-(propan-2-yloxy)benzene(244160-46-1)

Safety Data

• Hazardous Substances Data: 244160-46-1(Hazardous Substances Data)

Upstream product

• 93-07-2 Veratric acid 
• 2033-89-8 3,4-dimethoxyphenol 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 77106-50-4 1,2-dimethoxy-4-(propan-2-yloxy)benzene 

Downstream Products

• 181423-71-2 14-(3,4-dimethoxyphenyl)-2,3,11,12-tetramethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 897018-51-8 methyl 8-isopropoxy-2-(2-isopropoxy-4,5-dimethoxyphenyl)-1-(3-isopropoxyphenyl)-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate 

Relevant articles and documents

First total synthesis of medicinally important 3,4,7-trimethoxy-9,10-dihydrophenanthrene-1,5-diol

The first total synthesis was successfully achieved for biologically active 9,10-dihydrophenanthrene-1,5-diol. The key features of our synthetic approach are Perkin condensation, followed by bromination, palladium mediated intramolecular C-C bond coupling, and selective isopropyl ether cleavage. Synthesized compounds were purified and characterized by IR, 1HNMR, 13CNMR and HRMS/LC-MS.

Anomalous substituent effects in the Bischler-Napieralski reaction of 2-aryl aromatic formamides

Treatment of some 1-naphthylformamides (or formanilides) possessing a 2,4,5-trioxygenated phenyl substituent at the 2-position with POCl3 caused an unprecedented carbon insertion reaction into a benzene ring, producing 7-5 ring (azaazulene) systems as valence isomers of isoquinoline skeletons. Precise examination of this abnormal Bischler-Napieralski reaction (BNR) using various substrates led to the following scope and limitations: (i) the 7-5 ring systems were constructed when either 2-alkoxy-4,5-methylenedioxyphenyl- or 4,5-dialkoxy-2-hydroxyphenyl-substituted formamides were used as a starting substrate; (ii) in the former case the formyl carbon was inserted into the C1-C6 bond of the 2-phenyl group, and normal isoquinoline cyclization competed with an abnormal carbon insertion reaction; (iii) the presence of a hydroxy group at the 2′-position as in the latter cases caused exclusive carbon insertion, in which alternative C1-C2 insertion products were quantitatively formed; (iv) 3,6-dimethoxy-2-hydroxyphenyl-substituted formanilide electronically equivalent to 4,5-dialkoxy-2-hydroxy derivatives produced an indole-pyrone as an abnormal BNR product. Theoretical approaches using the PM-3 method indicated that these abnormal BNRs could be triggered by ipso attack at the 1′-position yielding spiro intermediates. Ring cleavege of the six-membered ring in the spiro intermediates to a ketene function followed by recyclization was proposed for the 2′-hydroxy-directed abnormal BNRs leading to the C1-C2 insertion product or the indole-pyrone derivative.