Description

Potassium (cyclohex-1-en-1-yl)(trifluoro)borate(1-) (CAS: 1186667-20-8) is a highly specialized organoboron compound with the molecular formula C₆H₉BF₃K. This potassium trifluoroborate salt is a valuable reagent in synthetic organic chemistry, particularly in cross-coupling reactions such as Suzuki-Miyaura couplings, where it serves as a stable and air-tolerant boronate precursor. Its cyclohexenyl moiety offers unique reactivity for constructing complex cyclic frameworks. The compound is supplied as a white to off-white crystalline powder, with high purity (>95%) to ensure optimal performance in sensitive applications. Proper storage under inert conditions (argon or nitrogen atmosphere) at 2-8°C is recommended to maintain stability. Ideal for researchers in pharmaceuticals, agrochemicals, and materials science seeking to incorporate cyclohexenyl groups into target molecules.

Properties

• CAS Number: 1186667-20-8
• Complexity: 152
• IUPAC Name: potassium;cyclohexen-1-yl(trifluoro)boranuide
• InChI: InChI=1S/C6H9BF3.K/c8-7(9,10)6-4-2-1-3-5-6;/h4H,1-3,5H2;/q-1;+1
• InChI Key: HGMUFAMKMWVCQO-UHFFFAOYSA-N
• Exact Mass: 188.0386464
• Molecular Formula: C6H9BF3K
• Molecular Weight: 188.04
• SMILES: [B-](C1=CCCCC1)(F)(F)F.[K+]
• Monoisotopic Mass: 188.0386464
• Synonyms: 1186667-20-8, DTXSID00717202, Potassium (cyclohex-1-en-1-yl)(trifluoro)borate(1-), DTXCID30667948, Potassium cyclohex-1-en-1-yltrifluoroborate, Potassium cyclohexene-1-trifluoroborate, Potassium cyclohexenyltrifluoroborate, potassium;cyclohexen-1-yl(trifluoro)boranuide, potassium (cyclohex-1-en-1-yl)trifluoroboranuide, MFCD09992928, SCHEMBL664048, AKOS006314146, Potassiumcyclohex-1-en-1-yltrifluoroborate, DB-210142, C90164, EN300-2009708

Application

This potassium trifluoroborate salt is widely used as a coupling partner in palladium-catalyzed Suzuki-Miyaura reactions, enabling the formation of C-C bonds between aryl/vinyl halides and the cyclohexenyl group. It finds particular utility in medicinal chemistry for introducing saturated carbocycles into drug candidates. The compound’s stability makes it preferable to boronic acids in many applications. Researchers also employ it in the synthesis of functionalized cyclohexane derivatives for material science applications. Its trifluoroborate group offers improved handling characteristics compared to more sensitive boronic acid analogs.

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. 2 (100%)
• STOT SE 3 (100%)

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