249515-06-8

Basic information

• Product Name: 4-BENZYLOXY-3,5-DIBROMO-BENZALDEHYDE
• Synonyms: 4-BENZYLOXY-3,5-DIBROMO-BENZALDEHYDE;AKOS B029362;ASISCHEM R22384
• CAS NO: 249515-06-8
• Molecular Formula: C₁₄H₁₀Br₂O₂
• Molecular Weight: 370.04
• Mol File: 249515-06-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-BENZYLOXY-3,5-DIBROMO-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZYLOXY-3,5-DIBROMO-BENZALDEHYDE(249515-06-8)
• EPA Substance Registry System: 4-BENZYLOXY-3,5-DIBROMO-BENZALDEHYDE(249515-06-8)

Safety Data

• Hazardous Substances Data: 249515-06-8(Hazardous Substances Data)

Upstream product

• 2973-77-5 3,5-dibromo-4-hydroxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 100-39-0 benzyl bromide 

Downstream Products

• 210824-98-9 1-(4-Benzyloxy-3,5-dibromo-benzyl)-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-imino-1,6,7,9-tetrahydro-purin-8-one 
• 210824-99-0 N-(4-benzyloxy-3,5-dibromobenzyl)-8-oxoadenosine 
• 210825-00-6 N-(4-benzyloxy-3,5-dibromobenzyl)-2'-deoxy-8-oxoadenosine 
• 210825-04-0 1-(4-Benzyloxy-3,5-dibromo-benzyl)-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6-imino-1,6,7,9-tetrahydro-purin-8-one 
• 210825-01-7 N-(4-benzyloxy-3,5-dibromobenzyl)-8-oxoadenine 
• 1026812-13-4 4-benzyloxy-3,5-dibromobenzyl bromide 
• 249515-07-9 4-benzyloxy-3,5-dibromobenzyl alcohol 

Relevant articles and documents

Fluorescent analogs of the marine natural product psammaplin A: Synthesis and biological activity

The symmetrical disulfide psammaplin A from the marine sponge Pseudoceratina sp. was synthesized and structurally altered by replacement of one of the α-(hydroxyimino)acyl units by a fluorescent 4-coumarinacetyl moiety. Thus, the first fluorescent analogs of psammaplin A were obtained. Structural variation also covered the substitution pattern of the phenyl ring. Cytotoxicity of psammaplin A against the mouse fibroblast cell line L-929 (IC50 0.42 μg mL-1) was about two-fold higher than that of the fluorescent hybrid compounds, whereas the disulfide containing two 4-coumarinacetyl moieties was inactive. Fluorescence microscopy revealed uptake of the 4-coumarinacetyl-α-(hydroxyimino)acyl hybrids into the cytoplasm leading to fluorescence in close proximity of the nuclear envelope, most likely in the Golgi apparatus. We did not observe strong fluorescence inside the nucleus, where most of the target histone deacetylases are located. We conclude that reduction of the disulfide probably takes place outside the nucleus. The psammaplin-derived thiol exhibited potent activity against histone deacetylase in the low nanomolar range, but diminished cytotoxicity. Antimicrobial activity of the new derivatives was also determined.

Synthesis and structure of the marine ascidian 8-oxoadenine aplidiamine

Alkylation of 8-oxoadenosine (13) with 4-benzyloxy-3,5-dibromobenzyl bromide (20), followed by Dimroth rearrangement and acid hydrolysis, provided N-(3,5-dibromo-4-hydroxybenzyl)-8-oxoadenosine (15). The 2'- deoxy version of this reaction sequence accomplished the first synthesis of N-(3,5-dibromo-4- hydroxybenzyl)-8-oxoadenine (16), which is the correct expression for marine ascidian purine aplidiamine.