5123-13-7

Basic information

• Product Name: (5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZENE
• Synonyms: Phenylboronic acid neopentylglycol ester,(5,5-Dimethyl-2-phenyl-1,3,2-dioxaborinane, Phenyl boronic acid neopentylglycol ester;Phenylboronic acid neopentylglycol ester 97%;PHENYLBORONIC ACID, NEOPENTYL ESTER;5,5-DIMETHYL-2-PHENYL-1,3,2-DIOXABORINANE;(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZENE;Phenylboronic acid neopentylglycol ester, 97%;Phenylboronic Acid, neopentyl glycol cyclic ester;(5,5-Dimethyl-2-phenyl-1,3,2-dioxaborinane, Phenyl boronic acid neopentylglycol ester
• CAS NO: 5123-13-7
• Molecular Formula: C₁₁H₁₅BO₂
• Molecular Weight: 190.05
• Mol File: 5123-13-7.mol
• Article Data: 74

Chemical Properties

• Melting Point: 62-66 °C(lit.)
• Boiling Point: 287.761°C at 760 mmHg
• Flash Point: 127.834°C
• Appearance: /
• Density: 1.008g/cm³
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: 1.493
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• CAS DataBase Reference: (5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: (5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZENE(5123-13-7)
• EPA Substance Registry System: (5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZENE(5123-13-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 5123-13-7(Hazardous Substances Data)

Usage

General Description

(5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZENE is a chemical compound that consists of a benzene ring attached to a boron-containing five-membered ring. It is commonly used as a building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. (5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZENE is known for its ability to form strong covalent bonds with other molecules, making it useful in the creation of complex organic compounds. Additionally, it has been studied for its potential applications in materials science and catalysis. However, due to its boron-containing nature, (5,5-DIMETHYL-1,3,2-DIOXABORINAN-2-YL)BENZENE should be handled with care and proper safety measures to avoid any potential health or environmental risks.

InChI:InChI=1/C11H15BO2/c1-11(2)8-13-12(14-9-11)10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3

Upstream product

• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 1538-62-1 triphenylantimony(V) diacetate 
• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 57997-56-5 triphenylantimony bisbenzoate 
• 594-31-0 triphenylantimony dichloride 
• 20265-30-9 triphenylantimony dibromide 
• 2170-05-0 pentaphenylantimony 
• 603-36-1 triphenylantimony 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 603-33-8 triphenylbismuthane 
• 100-66-3 methoxybenzene 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 108-90-7 chlorobenzene 

Downstream Products

• 100-51-6 benzyl alcohol 
• 108478-28-0 methyl 6-methoxybiphenyl-3-carboxylate 
• 220616-20-6 1,4-diphenylpiperidine 
• 62787-21-7 3,5-di-tert-butylphenyl phenyl ether 
• 92-52-4 biphenyl 
• 14990-09-1 tert-butyl cinnamate 
• 591-50-4 iodobenzene 
• 70720-38-6 benzyl-(3-methyl-2-pyridinyl)amine 
• 59310-32-6 1-(3-phenylnaphthalen-2-yl)ethanone 

Relevant articles and documents

Photochemical and electrochemical C-N borylation of arylhydrazines

The C-N borylation of arylhydrazine hydrochlorides with bis(pinacolato)diboron was achieved under photochemical and electrochemical conditions, respectively. This novel and scalable transformation provides two efficient and mild transition-metal-free synt

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination

We disclose a nickel-catalyzed reaction, which enabled us to difunctionalize unactivated γ,δ-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction was made feasible by the use of 5-chloro-8-hydroxyquinoline as a ligand along with