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Atomfair 2-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane C14H25BO2 CAS 859217-67-7

2-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 859217-67-7) is a high-purity organoboron compound with the molecular formula C14H25BO2. This reagent is widely utilized in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The compound features a dioxaborolane ring and a 4,4-dimethylcyclohexenyl group, offering excellent stability and reactivity for aryl-aryl bond formation. Supplied as a crystalline solid or solution, it is rigorously tested for purity (typically ≥95-98%) via HPLC, GC, or NMR to ensure optimal performance in sensitive applications. Proper storage under inert atmosphere (argon/nitrogen) at 2-8°C is recommended to prevent degradation. Key Applications: Intermediate for pharmaceuticals, agrochemicals, and OLED materials; cross-coupling reactions;…

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Description

2-(4,4-Dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 859217-67-7) is a high-purity organoboron compound with the molecular formula C14H25BO2. This reagent is widely utilized in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. The compound features a dioxaborolane ring and a 4,4-dimethylcyclohexenyl group, offering excellent stability and reactivity for aryl-aryl bond formation. Supplied as a crystalline solid or solution, it is rigorously tested for purity (typically ≥95-98%) via HPLC, GC, or NMR to ensure optimal performance in sensitive applications. Proper storage under inert atmosphere (argon/nitrogen) at 2-8°C is recommended to prevent degradation.

Key Applications: Intermediate for pharmaceuticals, agrochemicals, and OLED materials; cross-coupling reactions; polymer synthesis.

Synonyms: 859217-67-7, DTXSID60630948, DTXCID20581700, 815-306-7

Properties

  • CAS Number: 859217-67-7
  • Complexity: 326
  • IUPAC Name: 2-(4,4-dimethylcyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  • InChI: InChI=1S/C14H25BO2/c1-12(2)9-7-11(8-10-12)15-16-13(3,4)14(5,6)17-15/h7H,8-10H2,1-6H3
  • InChI Key: JQEUELMRQYUNDS-UHFFFAOYSA-N
  • Exact Mass: 236.1947602
  • Molecular Formula: C14H25BO2
  • Molecular Weight: 236.16
  • SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CCC(CC2)(C)C
  • Topological: 18.5
  • Monoisotopic Mass: 236.1947602
  • Synonyms: 859217-67-7, 2-(4,4-dimethylcyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, DTXSID60630948, DTXCID20581700, 815-306-7, 2-(4,4-Dimethyl-1-cyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4,4-(Dimethylcyclohexen-1-yl)boronic acid pinacol ester, 2-(4,4-dimethylcyclohexen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4,4-Dimethylcyclohexen-1-ylboronic acid, pinacol ester, MFCD08690233, 4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID, PINACOL ESTER, 4,4-Dimethylcyclohexene-1-boronic Acid Pinacol Ester, 4,4-(Dimethylcyclohexene-1-yl)boronic acid pinacol ester, _x000D_44-Dimethylcyclohexene-1-boronic Acid Pinacol Ester, SCHEMBL1701389, (4,4-dimethylcyclohexene-1-yl)boronic acid, pinacol ester, JQEUELMRQYUNDS-UHFFFAOYSA-N, JJB21767, AKOS015960158, GS-6330, MB06490, SY025516, CS-0101262, EN300-114421, H10465, ?44-Dimethylcyclohexene-1-boronic Acid Pinacol Ester, Z1473566642, 4 pound not4-Dimethylcyclohexene-1-boronic Acid Pinacol Ester, _x005F_x000D_44-Dimethylcyclohexene-1-boronic Acid Pinacol Ester, 4,4-(DIMETHYLCYCLOHEXENE-1-YL)BORONIC ACID,PINACOL ESTER, (4,4-Dimethylcyclohexene-1-yl)boronic acid, pinacol ester, AldrichCPR, 4,4-dimethyl-cyclohex-1-enyl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, 2-(4,4-dimethyl-1-cyclohexenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, 2-(4,4-dimethyl-cyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, 2-(4,4-Dimethylcyclohex-1-enyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, 2-(4,4-DIMETHYLCYCLOHEX-1-ENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE

Application

This organoboron compound serves as a critical reagent in Suzuki-Miyaura cross-coupling reactions, enabling efficient carbon-carbon bond formation for pharmaceutical intermediates. Its stability makes it ideal for synthesizing complex biaryl structures used in drug discovery programs. The compound also finds use in material science for creating conjugated polymers in organic electronics.

Safety and Hazards

GHS Hazard Statements

  • H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
  • H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
  • H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

  • P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

  • Skin Irrit. 2 (100%)
  • Eye Irrit. 2A (100%)
  • STOT SE 3 (100%)

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Disclaimer

Intended Use & Restrictions

This product is sold exclusively for laboratory research, analytical testing, or non-commercial purposes.

  • Strictly prohibited: Resale, repackaging, or formulation into commercial products.
  • Not approved for human/animal use, diagnostics, or manufacturing (including pharmaceuticals, agrochemicals, or consumer goods).

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Certain molecules may be protected by active patents or regulatory restrictions.

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