Allylboronic acid pinacol ester - ≥96%(GC) , CAS No.72824-04-5

CAS: 72824-04-5 Cat. No.: A136026 Peso molecular: 168.04 Número EC: 672-877-3

GRADE & PURITY ≥96%(GC)

Synonyms

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | Allylboronic acid pinacol ester | Allylboronic acid, pinacol cyclic ester | allyl boronic acid pinacol ester | 4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane | ALLYLBORONIC ACID PIRACOL ESTER

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Descripción general

Allylboronic acid pinacol ester is used as a nucleophile in the catalytic allylation of simple ketoimines.
Purpose
Reagent used for
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis
Intermolecular radical additions
Allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids
Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes
Nucleic acid-templated energy transfer leading to a photorelease reaction
Stereoselective indium-catalyzed Hosomi-Sakurai reactions
Reagent used in Preparation of
Cyclic sulfone hydroxyethylamines as BACE1 inhibitors for reduction of Amyloid β-Peptides
Transmetalation of carbene Ru iodide with Ag carboxylates to give C-H-activated Ru carbene complexes as catalysts for Z-selective olefin metathesis
Allylboronation reagent for the preparation of allylic alcohols[10], and homoallylic amines

Specifications

Sinónimos

2-Allyl-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane | Allylboronic acid pinacol ester | Allylboronic acid, pinacol cyclic ester | allyl boronic acid pinacol ester | 4, 4, 5, 5-tetramethyl-2-prop-2-enyl-1, 3, 2-dioxaborolane | ALLYLBORONIC ACID PIRACOL ESTER

Especificaciones y pureza

≥96%(GC)

Condiciones de almacenamiento de almacenamiento

Store at -20°C, Argon charged

Enviado en

Ice chest + Ice pads

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Pureza

≥96%(GC)

Nombres e identificadores

• Sonrisas canónicas: B1(OC(C(O1)(C)C)(C)C)CC=C
• IUPAC Name: 4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane
• InChIKey: YMHIEPNFCBNQQU-UHFFFAOYSA-N
• INCHI: 1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3
• Isómeros SMILES: B1(OC(C(O1)(C)C)(C)C)CC=C
• WGK Alemania: 3
• Número ONU: 1993
• Grupo de embalaje: III
• Peso molecular: 168.04
• Reaxy-Rn: 4244068
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4244068&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Clase Boronic acid derivatives
      • Subclass Boronic acid esters

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Clase: Boronic acid derivatives
• Subclass: Boronic acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Boronic acid esters
• Alternative Parents: Dioxaborolanes Oxacyclic compounds Organic metalloid salts Organooxygen compounds Monoalkylboranes Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: 1,3,2-dioxaborolane - Boronic acid ester - Oxacycle - Organic metalloid salt - Organoheterocyclic compound - Organic oxygen compound - Monoalkylborane - Alkylborane - Hydrocarbon derivative - Organic salt - Organooxygen compound - Organoboron compound - Aliphatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as boronic acid esters. These are compounds comprising the boronic acid ester functional group RN(X)OR' (R,R'=alkyl, aryl; X= any O, N, Hal residue).
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Solubilidad: Not miscible or difficult to mix in water.
• Sensibilidad: Heat & Moisture sensitive
• Índice de refracción: 1.43
• Punto de inflamación (°F): 114.8 °F
• Punto de inflamación (°C): 46°C
• Punto de ebullición (°C): 35°C/1mmHg
• Peso molecular: 168.040 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 168.132 Da
• Monoisotopic Mass: 168.132 Da
• Topological Polar Surface Area: 18.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 171.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

XLogP3

Referencias

1. Jiapei Gu, Xiangqian Li, Guofu Zhou, Wanqiang Liu, Jinwei Gao, Qianming Wang.  (2019)  A novel self-calibrating strategy for real time monitoring of formaldehyde both in solution and solid phase.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:31881494] [10.1016/j.jhazmat.2019.121883]

2. Cheng Chen, Jiali Guo, Chunlei Wu, Xianjian Duan, Lingzhi Zhang.  (2024)  Borate-Functionalized Disiloxane as Effective Electrolyte Additive for 4.5 V LiNi0.8Co0.1Mn0.1O2/Graphite Batteries.  ACS Applied Materials & Interfaces,      [PMID:38345337] [10.1021/acsami.3c16531]