128376-65-8

Basic information

• Product Name: 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde
• Synonyms: AKOS BRN-0004;4-(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZALDEHYDE;4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde;4-FORMYLPHENYLBORONIC ACID, NEOPENTYL GLYCOL CYCLIC ESTER;4-FORMYLBENZENEBORONIC ACID 2,2-DIMETHYLPROPANEDIOL-1,3 CYCLIC ESTER;2-(4-FORMYLPHENYL)-5,5-DIMETHYL-1,3,2-DIOXABORANE;4-(5,5-Dimethyl-1,3,2-dioxaborin-2-yl)benzaldehyde;4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde, 5,5-Dimethyl-2-(4-formylphenyl)-1,3,2-dioxaborinane
• CAS NO: 128376-65-8
• Molecular Formula: C₁₂H₁₅BO₃
• Molecular Weight: 218.06
• Mol File: 128376-65-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 58-60 °C
• Boiling Point: 350.459 °C at 760 mmHg
• Flash Point: 165.752 °C
• Appearance: Light yellow powder
• Density: 1.082 g/cm³
• Vapor Pressure: 4.39E-05mmHg at 25°C
• Refractive Index: 1.504
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde(128376-65-8)
• EPA Substance Registry System: 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde(128376-65-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 128376-65-8(Hazardous Substances Data)

Usage

General Description

4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde is a chemical compound that belongs to the class of benzaldehydes. It is commonly used in organic synthesis and as a reagent in chemical reactions. The compound contains a benzene ring substituted with a formyl group and a boron-containing heterocycle. It is known for its use in cross-coupling reactions to form carbon-carbon bonds and in the preparation of various pharmaceuticals and agrochemicals. Additionally, it is used as a building block in the synthesis of various organic compounds and materials. Overall, 4-(5,5-Dimethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde has versatile applications in the field of organic chemistry and material science.

InChI:InChI=1/C12H15BO3/c1-12(2)8-15-13(16-9-12)11-5-3-10(7-14)4-6-11/h3-7H,8-9H2,1-2H3

Upstream product

• 328063-34-9 4-(OCH₂CH₂O-B)C₆H₄C(H)=O 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 87199-17-5 4-formylphenylboronic acid, 
• 1122-91-4 4-bromo-benzaldehyde 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 61568-51-2 2-(4-bromophenyl)-1,3-dioxane 
• 1006598-62-4 2-(4-dibromomethyl-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane 

Downstream Products

• 1571-08-0 methyl 4-formylbenzoate 
• 378785-71-8 tert-butyl N-{3-{{[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]methyl}amino}propyl}-N-{4-{[(tert-butyloxy)carbonyl]amino}butyl}carbamate 
• 378785-65-0 tert-butyl N-{4-{{[4-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)phenyl]methyl}amino}butyl}carbamate 
• 1415045-51-0 N,N-diethyl-2-(4-formylphenyl)furan-3-carboxamide 
• 1398508-34-3 1-(1,2,2-trifluoroethenyl)-4-(formyl)benzene 
• 1400888-14-3 2-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)-1H-anthra[1,2-d]imidazole-6,11-dione 
• 1400888-07-4 C₂₁H₁₃BN₂O₄ 
• 3748-17-2 4-(N,N-dibenzylamino)benzaldehyde 
• 1207323-50-9 3-ethyl-5-((1Z)-(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)methyl)-2,4-dimethyl-1H-pyrrole 

Relevant articles and documents

Borylated porphyrins: 5,10,15,20-tetrakis(5,5-dimethyl-1,3,2-dioxa-borinan- 2-yl)porphyrin nitrobenzene disolvate

The title compound, C64H66B4N4O8·2C6H5NO2, is a nitro-benzene solvate of a meso-tetra-phenyl-porphyrin species with unconventional peripheral boronic ester substituents. The porphyrin units reside in the crystal on centers of inversion and exhibit a chann

C-H activation by amide chelation control: Ruthenium-catalyzed direct synthesis of 2-Aryl-3-furanamides

A new, catalytic methodology for the synthesis of heterobiaryls by the ruthenium-catalyzed C-H activation/cross-coupling of heterocyclic amides with aryl boroneopentylates is surveyed. From this survey, the highly regioselective reaction of furan-3-carboxamide to give 2-aryl-3-furanamides is optimized and generalized in scope with respect to the aryl boroneopentylate coupling partners. Established thereby is a one-step synthetic method which may supercede the broadly applied two-step directed ortho metalation (DoM)-cross coupling reaction involving cryogenic and strong base conditions and which has potential for further ortho and remote metalation chemistry.

Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines

A tolerant coupling: The title reaction has been developed to deliver arylamines (see scheme; Bz=benzoyl, dppbz=1,2-bis(diphenylphosphino)benzene). The catalysis is based on electrophilic, umpolung amination and enables the use of secondary acyclic amines. Various functional groups are tolerated, thus opening up a new substrate class for the Chan-Lam-type coupling.