928048-21-9

Basic information

• Product Name: Benzene, 1,3-dibromo-2-(dimethoxymethyl)-
• CAS NO: 928048-21-9
• Molecular Formula: C9H10Br2O2
• Molecular Weight: 309.985
• Mol File: 928048-21-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzene, 1,3-dibromo-2-(dimethoxymethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,3-dibromo-2-(dimethoxymethyl)-(928048-21-9)
• EPA Substance Registry System: Benzene, 1,3-dibromo-2-(dimethoxymethyl)-(928048-21-9)

Safety Data

• Hazardous Substances Data: 928048-21-9(Hazardous Substances Data)

Upstream product

• 108-36-1 1,3-dibromobenzene 
• 67713-23-9 2,6-dibromobenzaldehyde 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 1443497-71-9 C₁₆H₂₄OSi 
• 1443497-70-8 C₁₇H₁₆O 
• 1443497-72-0 C₁₃H₁₄O 
• 1443497-88-8 C₁₂H₁₅BrO₂ 
• 928048-16-2 2-formyl-3-(trimethylsilyl)phenylboronic acid 
• 928048-13-9 3-iodo-2-formylphenylboronic acid 
• 928048-18-4 1,3-dihydroxy-4-bromo-1-bora-2-oxaindan monohydrate 
• 944908-04-7 3-(dihydroxyboryl)-1,2-phthalaldehyde 
• 944908-03-6 1,2-bis(dimethoxymethyl)-3-bromobenzene 
• 928048-12-8 (3-bromo-2-formylphenyl)boronic acid 

Relevant articles and documents

Design, synthesis and structure of a frustrated benzoxaborole and its applications in the complexation of amines, amino acids, and protein modification

This study describes the design and synthesis of arylboronic acid 2, the first example of a permanently open "frustrated" benzoxaborole, along with an exploration of its application in bioconjugation. An efficient and high yielding seven-step synthesis was optimized. NMR experiments confirmed that compound 2 exists in the open ortho-hydroxyalkyl arylboronic acid structure 2-I, a form that is effectively prevented to undergo a dehydrative cyclization as a result of unfavorable geometry. Compound 2-I conjugates effectively with amines to form stable hemiaminal ether structures, including a highly effective reaction with lysozyme. Complexation with cysteine induces an open structure containing a free hydroxymethyl arm, with the amino and thiol groups reacting preferentially with the formyl group to form a N,S-acetal.

A tautomeric equilibrium between functionalized 2-formylphenylboronic acids and corresponding 1,3-dihydro-1,3-dihydroxybenzo[c][2,1]oxaboroles

Functionalized 2-formylphenylboronic acids undergo an unprecedented tautomeric rearrangement in solution to form corresponding 1,3-dihydro-1,3- dihydroxybenzo[c][2,1]oxaboroles. X-Ray analyses of selected examples revealed diverse solid-state molecular structures from a planar open form with a hydrogen-bonded carbonyl group (X = 3-F) through a twisted conformer showing a weak carbonyl-boron interaction (X = 3,5-Br2) to a cyclic oxaborole derivative (X = 3-Br). Variable-temperature 1H NMR spectroscopy was used to determine equilibrium constants as well as enthalpies and entropies of tautomerization in a mixed solvent [D6]acetone-D2O (95:5). A computational approach to the process by DFT (B3LYP) and MP2 methods has also been performed. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.