1329422-26-5

Basic information

• Product Name: N-methyliminodiacetyl (2-oxo-1-phenylethyl)boronate
• Synonyms: N-methyliminodiacetyl (2-oxo-1-phenylethyl)boronate
• CAS NO: 1329422-26-5
• Molecular Weight: 275.069
• Mol File: 1329422-26-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 144-149°C
• CAS DataBase Reference: N-methyliminodiacetyl (2-oxo-1-phenylethyl)boronate(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyliminodiacetyl (2-oxo-1-phenylethyl)boronate(1329422-26-5)
• EPA Substance Registry System: N-methyliminodiacetyl (2-oxo-1-phenylethyl)boronate(1329422-26-5)

Safety Data

• Hazardous Substances Data: 1329422-26-5(Hazardous Substances Data)

Usage

Uses

This boronic acid derivative is in a series of the first known stable α-boryl aldehyde species. Through the employment of the MIDA-protected boronic ester, this building block has been shown as a precursor to the synthesis of unnatural amino acids.

Upstream product

• 1152427-93-4 C₁₃H₁₄BNO₄ 
• 1329422-25-4 C₁₃H₁₄BNO₅ 
• 1329422-31-2 N-methyliminodiacetyl (2-phenyloxiran-2-yl)boronate 
• 4648-54-8 trimethylsilylazide 

Downstream Products

• 1329422-35-6 N-methyliminodiacetyl (1-bromo-2-oxo-1-phenylethyl)boronate 
• 1329422-36-7 2-(N-methyliminodiacetylboryl)-2-phenylacetic acid 
• 1329422-45-8 (Z)-1-(2-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)pyrrolidin-2-one 
• 1329422-47-0 (E)-2-(dibenzylamino)-4-(2-oxopyrrolidin-1-yl)-3-phenylbut-3-enoic acid 
• 1329422-71-0 (E)-2-morpholino-4-(2-oxopyrrolidin-1-yl)-3-phenylbut-3-enoic acid 
• 1329422-39-0 (E)-N-methyliminodiacetyl (3,3-dibromo-1-phenylallyl)boronate 

Relevant articles and documents

Pd-Catalyzed coupling of benzyl bromides with BMIDA-substituted: N -tosylhydrazones: synthesis of trans -alkenyl MIDA boronates

A palladium-catalyzed stereoselective synthesis of alkenyl boronates from N-methyliminodiacetyl boronate (BMIDA)-substituted N-tosylhydrazone and benzyl bromides is developed. A range of trans-alkenyl MIDA boronates as single stereoisomers were obtained in moderate yields with good functional group compatibility. The resultant boronate products may be transformed to other boron-containing compounds and may also be directly used in cross-coupling reactions.

Access to Cyclic Amino Boronates via Rhodium-Catalyzed Functionalization of Alkyl MIDA Boronates

Herein, we describe the rhodium-catalyzed C-H amination reaction of 1,2-boryl sulfamate esters derived from amphoteric α-boryl aldehydes. Depending on the substitution pattern of the boryl sulfamate ester, a diverse range of five- or six-membered ring heterocycles are accessible using this transformation. The highly chemoselective nature of the C-H functionalization reaction preserves the alkyl boronate functional group, which enables the synthesis of B-C-N and B-C-C-N motifs that are present in a number of hydrolase inhibitors.

Pinene-derived iminodiacetic acid (PIDA): A powerful ligand for stereoselective synthesis and iterative cross-coupling of C(sp3) boronate building blocks

Efficient access to chiral C(sp3) boronates in stereochemically pure form is critical for realizing the substantial potential of such building blocks in complex-molecule synthesis. We herein report that a pinene-derived iminodiacetic acid (PIDA) ligand enables the highly diastereoselective synthesis of a wide range of oxiranyl C(sp3) boronates from the corresponding olefins. These oxiranyl PIDA boronates, in turn, can be readily transformed into unprecedented stable α-boryl aldehydes via a novel 1,2-migration of the boronate group that proceeds with complete maintenance of stereochemical purity. B-Protected haloboronic acids containing dual sp3-hybridized C centers are readily accessible via this platform, and the herein demonstrated capacity for stereocontrolled iterative C(sp3) cross-coupling with this novel type of bifunctional reagent to access a medicinally important chiral small-molecule target in highly enantioenriched form represents a substantial advance for the building-block-based approach to synthesis.