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793434

Sigma-Aldrich

4-Tolyl-α-MIDA-boryl aldehyde

Synonym(s):

(6-Methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)(4-methylphenyl)acetaldehyde

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About This Item

Empirical Formula (Hill Notation):
C14H16BNO5
CAS Number:
1329422-56-1
Molecular Weight:
289.09
MDL number:
MFCD27665011
UNSPSC Code:
12352103
PubChem Substance ID:
329768076
NACRES:
NA.22

form

solid

mp

135-142 °C

functional group

aldehyde

storage temp.

2-8°C

SMILES string

O=C1OB(C(C2=CC=C(C)C=C2)C([H])=O)OC(CN(C)C1)=O

InChI

1S/C14H16BNO5/c1-10-3-5-11(6-4-10)12(9-17)15-20-13(18)7-16(2)8-14(19)21-15/h3-6,9,12H,7-8H2,1-2H3

InChI key

DCVSWHVQPHHNBM-UHFFFAOYSA-N

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General description

4-Tolyl-α-MIDA-boryl aldehyde is a-boryl aldehyde derivative. It can be synthesized from oxiranyl MIDA boronates, via rearrangement.

Application

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.

Other Notes

Amphoteric Alpha-Boryl Aldehydes

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Zhi He et al.
Journal of the American Chemical Society, 133(35), 13770-13773 (2011-08-04)
A new class of stable molecules, α-boryl aldehydes, has been prepared from oxiranyl N-methyliminodiacetyl boronates by a 1,2-boryl migration with concomitant epoxide scission. A range of boryl imines, alkenes, alcohols, acids, enol ethers, enamides, and other functionalized boronic acid derivatives

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