129112-21-6

Basic information

• Product Name: 2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACID
• Synonyms: 2-[(DIETHYLAMINO)CARBONYL]BENZENEBORONIC ACID;2-(N,N-DIETHYLCARBAMOYL)PHENYLBORONIC ACID;2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACID;RARECHEM AH PB 0055;N,N-DIETHYL 4-BORONOBENZAMIDE;2-(Diethylcarbamoyl)benzeneboronic acid;2-(Diethylcarbamoyl)benzeneboronic acid 95%;N,N-Diethyl 2-boronobenzamide
• CAS NO: 129112-21-6
• Molecular Formula: C₁₁H₁₆BNO₃
• Molecular Weight: 221.06
• Product Categories: blocks;BoronicAcids;Boronate Ester;Boronic Acid;Potassium Trifluoroborate
• Mol File: 129112-21-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 64-70
• Boiling Point: 432 °C at 760 mmHg
• Flash Point: 215.1 °C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 3.13E-08mmHg at 25°C
• Refractive Index: 1.54
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACID(129112-21-6)
• EPA Substance Registry System: 2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACID(129112-21-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 129112-21-6(Hazardous Substances Data)

Usage

General Description

2-(N,N-Diethylaminocarbonyl)phenylboronic acid is a chemical compound with the molecular formula C14H20BNO3. It is commonly used as a reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. 2-(N,N-DIETHYLAMINOCARBONYL)PHENYLBORONIC ACID is a boronic acid derivative, which makes it a valuable tool in the synthesis of pharmaceuticals and other complex organic molecules. Its unique structure allows for the formation of stable complexes with certain organic molecules, making it an important component in the development of new drugs and materials. Additionally, 2-(N,N-Diethylaminocarbonyl)phenylboronic acid has also been studied for its potential applications in sensing and imaging technologies.

InChI:InChI=1/C11H16BNO3/c1-3-13(4-2)11(14)9-7-5-6-8-10(9)12(15)16/h5-8,15-16H,3-4H2,1-2H3

Upstream product

• 5419-55-6 Triisopropyl borate 
• 1696-17-9 N,N-diethylbenzamide 
• 121-43-7 Trimethyl borate 

Downstream Products

• 832-69-9 1-methylphenanthrene 
• 66552-94-1 9-isopropyl-1-methyl-phenanthrene 
• 84-11-7 9,10-phenanthrenequinone 
• 1258239-15-4 C₃₄H₃₂F₄N₂O₂ 
• 1195989-88-8 C₁₉H₂₂N₄O₂ 
• 1195989-87-7 C₁₈H₁₉ClN₄O 
• 1041642-83-4 C₂₅H₂₇F₃N₂O₃ 
• 120270-54-4 N,N-Diethyl-2-phenanthren-9-yl-benzamide 
• 120270-55-5 N,N-diethyl 10-(4'-nitrophenyl)phenanthren-9-yl-O-carbamate 
• 960-92-9 5-hydroxybenzanthracene 
• 24423-11-8 2-chlorophenanthrene 
• 484-17-3 9-Phenanthrol 
• 120270-45-3 N,N-diethyl 2-(3'-methylnaphth-2'-yl)benzamide 
• 129112-24-9 N,N-Diethyl-2-(2-methyl-cyclohex-1-enyl)-benzamide 

Relevant articles and documents

Atropisomerism in Tertiary Biaryl 2-Amides: A Study of Ar-CO and Ar-Ar′ Rotational Barriers

A rotational barrier study was performed on eight tertiary biaryl 2-amides using variable-temperature (VT) NMR and exchange (EXSY) spectroscopy experiments. Seven out of the eight 2-amido-2′-methylbiphenyls with additional 3- and 6-substitution patterns (1-7) were found to have approximately similar rotational barriers (ΔG?Tc = 56.5-67.5 kJ/mol). However, for both 3- and 6-substitution (8), the rotational barrier was found to be significantly higher (ΔG? = 102.6-103.8 kJ/mol). Computational studies performed on all eight compounds gave results in good agreement with the experimental rotational barriers. A transition state in which atropisomerism occurs by a cooperative rotation of the Ar-CO and Ar-Ar′ bonds depending on substituent location is proposed.

Regiospecific synthesis of alkylphenanthrenes using a combined directed ortho and remote metalation - Suzuki-Miyaura cross coupling strategy

Using a combined directed ortho metalation (DoM) - Suzuki-Miyaura cross coupling - directed remote metalation (DreM) approach, the alkylphenanthrenes (APs) 1-methyl- (5a), 1,7-dimethyl- (5b), 2,7-dimethyl- (Sc), 7-ethyl-1-methyl- (15), and 7-tert-butyl-1-methylphenanthrenes (27) have been synthesized in four to seven steps and 21%-36% overall yields. In contrast to classical protocols, this method, which may be scaled to gram quantities, provides single isomers of APs in high purity of value as analytical standards for environmental studies. Aminocarbonylation of triflates to N,N-diethylbenzamides (9 → 10) and anionic Fries rearrangement (23 → 24) provide other potential links to DoM chemistry.