89490-05-1

Basic information

• Product Name: 1-CYCLOHEXENYLBORONIC ACID
• Synonyms: CYCLOHEXEN-1-YLBORONIC ACID;1-CYCLOHEXEN-1-YL-BORONIC ACID;1-CYCLOHEXENE-1-BORONIC ACID;1-CYCLOHEXENYLBORONIC ACID;Cyclohexene-1-boronicacid;Cyclohex-1-ene-1-boronic acid;Cyclohexenylboronic acid;REF DUPL: Cyclohexene-1-boronic acid
• CAS NO: 89490-05-1
• Molecular Formula: C₆H₁₁BO₂
• Molecular Weight: 125.96
• Product Categories: blocks;BoronicAcids;API intermediates
• Mol File: 89490-05-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 165°C
• Boiling Point: 261.9 °C at 760 mmHg
• Flash Point: 112.2 °C
• Appearance: White to off-white/Powder
• Density: 1.05 g/cm³
• Vapor Pressure: 0.0016mmHg at 25°C
• Refractive Index: 1.48
• Storage Temp.: Keep Cold
• PKA: 9.43±0.20(Predicted)
• CAS DataBase Reference: 1-CYCLOHEXENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CYCLOHEXENYLBORONIC ACID(89490-05-1)
• EPA Substance Registry System: 1-CYCLOHEXENYLBORONIC ACID(89490-05-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-60-37
• Hazardous Substances Data: 89490-05-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

InChI:InChI=1/C6H11BO2/c8-7(9)6-4-2-1-3-5-6/h4,8-9H,1-3,5H2

Upstream product

• 18448-47-0 methyl cyclohex-1-ene-1-carboxylate 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 141091-37-4 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 212127-64-5 C₈H₁₅BO₂ 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 6562-41-0 chloro-bis(dimethylamino)borane 
• 930-66-5 1-chlorocyclohexene 

Downstream Products

• 954125-01-0 2-(3-cyclohex-1-enyl-4-nitro-phenyl)-malonic acid dimethyl ester 
• 915005-99-1 2-cyclohex-1-enyl-4-(1-oxy-pyridin-4-yl)-phenylamine 
• 915006-03-0 2-cyclohex-1-enyl-4-isopropyl-phenylamine 
• 915006-31-4 2-cyclohex-1-enyl-4-(morpholine-4-sulfonyl)-phenylamine 
• 1161846-52-1 (6-cyclohex-1-enylimidazo[1,2-b]pyridazin-8-yl)pyridin-2-ylamine 
• 1161846-83-8 1-(6-cyclohex-1-enylimidazo[1,2-a]pyridin-8-yl)-3-methylurea 
• 1055880-67-5 tert-butyl 9-(cyclohexa-1-en-1-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate 
• 1402704-60-2 C₁₅H₁₅NO₃ 
• 1402812-20-7 C₁₉H₁₇NO 
• 1402812-83-2 C₂₅H₂₅NO₃ 
• 1581695-40-0 2-(cyclohex-1-en-1-yl)pyrimidine 

Relevant articles and documents

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

Preparation of cyclopentyl (f) ene-1-boronic acid frequency that ester method

The invention discloses a method of preparing cyclopenten/cyclohexen-1-yl-boronic acid pinacol ester from methyl 1-cyclopentene/cyclohexene-1-carboxylate by three-step continuous operations. The method includes subjecting the raw material to alkaline hydrolysis to form the corresponding 1-alkylene carboxylic acid; performing addition with bromine; performing elimination and decarboxylation at the same time under the existence of DBU or DMAP to produce 1-bromo cyclopentene/cyclohexene; and allowing the 1-bromo cyclopentene/cyclohexene and methoxyboronic acid pinacol ester to form an ester under the existence of magnesium metal by a one-pot process to obtain the cyclopenten/cyclohexen-1-yl-boronic acid pinacol ester. The method is high in continuity, simple and convenient in operations, free of low-temperature reactions, and capable of obtaining the 1-bromo cyclopentene/cyclohexene intermediate with high purity and meeting market demands. The method adopts one-pot-process of Grignard reaction/esterification, so that the method is more convenient in operations and has less by-products, and the product is easier in rectification purification.

Novel synthesis of cyclic alkenylboronates via ring-closing metathesis [12]

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