1565829-30-2

Upstream product

• 34420-17-2 (2-phenylethyl)boronic acid 
• 13480-36-9 (N-methylimino)diacetic acid anhydride 
• 4408-64-4 N-methyliminodiacetic acid 
• 100-42-5 styrene 

Downstream Products

• 34403-05-9 1-methyl-2-phenethylbenzene 
• 1565829-46-0 2-methoxy-5-phenethylpyridine 
• 1565829-37-9 1-(3-nitro-4-phenethylphenyl)ethanone 
• 143425-74-5 1-(2',4',6'-trimethylphenyl)-2-phenylethane 
• 785-78-4 4-phenethylacetophenone 
• 10270-27-6 1-(4-cyanophenyl)-2-phenylethane 
• 14310-21-5 1-(4-methoxyphenyl)-2-phenylethane 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 

Relevant academic research and scientific papers

Synthesis, Structure and Reactivities of Pentacoordinated Phosphorus–Boron Bonded Compounds

The isolation and reactivities of two pentacoordinated phosphorus–tetracoordinated boron bonded compounds were explored. A highly Lewis acidic boron reagent and electron-withdrawing ligand system were required to form the pentacoordinated phosphorus state of the P–B bond. The first compound, a phosphoranyl-trihydroborate, gave a THF stabilised phosphoranyl-borane intermediate upon a single hydride abstraction in THF. This compound could undergo a unique rearrangement, which involved a two-fold ring expansion, to give a fused bicyclic compound or it could act as a mono-hydroboration reagent. The hydroboration reactivity of the intermediate was found to be higher towards alkynes vs. alkenes, with good to moderate regioselectivity towards the terminal carbon. The second compound, a phosphoranyl-triarylborate, was found to have different reactivity as it was highly stable towards acids and bases. This is thought to be due to the large bulk around the P–B bond as shown in the crystal structure.

A Mild Method for Making MIDA Boronates

We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.