149648-14-6

Basic information

• Product Name: N'-(4-bromophenyl)-N-hydroxyoctanediamide
• Synonyms: N'-(4-bromophenyl)-N-hydroxyoctanediamide
• CAS NO: 149648-14-6
• Molecular Weight: 343.22
• Mol File: 149648-14-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N'-(4-bromophenyl)-N-hydroxyoctanediamide(CAS DataBase Reference)
• NIST Chemistry Reference: N'-(4-bromophenyl)-N-hydroxyoctanediamide(149648-14-6)
• EPA Substance Registry System: N'-(4-bromophenyl)-N-hydroxyoctanediamide(149648-14-6)

Safety Data

• Hazardous Substances Data: 149648-14-6(Hazardous Substances Data)

Upstream product

• 265980-86-7 monoethyl suberate 4-bromoanilide 
• 14113-02-1 ethyl 8-chloro-8-oxooctanoate 
• 14113-01-0 Ethyl hydrogen suberate 
• 3946-32-5 suberic acid monomethyl ester 
• 106-40-1 4-bromo-aniline 

Relevant articles and documents

Precursor-directed biosynthesis of aminofulvenes: New chalanilines from endophytic fungus chalara sp.

The plant endophyte Chalara sp. is able to biotransform the epigenetic modifier vorinostat to form unique, aniline-containing polyketides named chalanilines. Here, we sought to expand the chemical diversity of chalaniline A-type molecules by changing the aniline moiety in the precursor vorinostat. In total, twenty-three different vorinostat analogs were prepared via two-step synthesis, and nineteen were incorporated by the fungus into polyketides. The highest yielding substrates were selected for large-scale precursor-directed biosynthesis and five novel compounds, including two fluorinated chalanilines, were isolated, purified, and structurally characterized. Structure elucida-tion relied on 1D and 2D NMR techniques and was supported by low-and high-resolution mass spectrometry. All compounds were tested for their bioactivity but were not active in antimicrobial or cell viability assays. Aminofulvene-containing natural products are rare, and this high-yielding, precursor-directed process allows for the diversification of this class of compounds.

An efficient synthesis of N-hydroxy-N'-[4-3H]phenyloctanediamide ([4-3H]SAHA), a potent cytodifferentiating agent

We have developed an efficient synthesis of N-hydroxy-N'-[4-3H]phenyloctanediamide ([4-3H]SAHA) from the monoester of suberanilic acid. The starting material, a monoester of suberoyl chloride, was condensed with 4-bromoaniline in the presence of a base to give the 4-bromoanilide of monoethyl suberate in 92% yield. On further treatment with methanolic hydroxylamine hydrochloride and sodium methoxide, this compound gave 4-bromosuberanilohydroxamic acid in 94% yield. Catalytic tritium exchange of bromine using Pd/C in a tritium gas atmosphere resulted in [4-3H]SAHA with a specific activity of 2.49 Ci/mmol. From the key intermediate, 4-bromoanilide of monoethyl suberate by a non-catalytic tritium exchange reaction, we have also prepared [4-3H]SAHA with high specific activity of 27.5 Ci/mmol.