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Cas Database

446065-11-8

446065-11-8

Identification

  • Product Name:Borate(1-),cyclohexyltrifluoro-, potassium, (T-4)- (9CI)

  • CAS Number: 446065-11-8

  • EINECS:

  • Molecular Weight:190.058

  • Molecular Formula: C6H11 B F3 . K

  • HS Code:

  • Mol File:446065-11-8.mol

Synonyms:Potassium cyclohexyltrifluoroborate

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Safety information and MSDS view more

  • Pictogram(s):C

  • Hazard Codes:C

  • Signal Word:Danger

  • Hazard Statement:H314 Causes severe skin burns and eye damage

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Potassium cyclohexyltrifluoroborate
  • Packaging:50mg
  • Price:$ 60
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Relevant articles and documentsAll total 17 Articles be found

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Chen, Bo,Kuai, Chang-Sheng,Xu, Jian-Xing,Wu, Xiao-Feng

supporting information, p. 487 - 492 (2021/12/06)

Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Amos, Stephanie G. E.,Cavalli, Diana,Le Vaillant, Franck,Waser, Jerome

supporting information, p. 23827 - 23834 (2021/09/25)

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C?H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.

Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation

Xie, Shasha,Li, Defang,Huang, Hanchu,Zhang, Fuyuan,Chen, Yiyun

supporting information, p. 16237 - 16242 (2019/10/14)

The intermolecular radical addition to the carbonyl group is difficult due to the facile fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to ketones, a valuable approach to construct quaternary carbon centers, remains a formidable synthetic challenge. Here, we report the first visible-light-induced intermolecular alkyl boronic acid addition to α-ketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly formed C-C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids at room temperature merely under visible light irradiation, without any additional reagent. This boron activation approach can be extended to alkyl dihydropyridines as radical precursors with external boron reagents for primary, secondary, and tertiary alkyl radical additions. The pharmaceutically useful anticholinergic precursors are easily scaled up in multigrams under metal-free conditions in flow reactors.

Selective C?N Borylation of Alkyl Amines Promoted by Lewis Base

Hu, Jiefeng,Wang, Guoqiang,Li, Shuhua,Shi, Zhuangzhi

supporting information, p. 15227 - 15231 (2018/10/25)

An efficient method for the metal-free deaminative borylation of alkylamines, using bis(catecholato)diboron as the boron source, to directly synthesize various alkyl potassium trifluoroborate salts is introduced. The key to this high reactivity is the utilization of pyridinium salt activated alkylamines, with a catalytic amount of a bipyridine-type Lewis base as a promoter. This transformation shows good functional-group compatibility (e.g., it is unimpeded by the presence of a ketone, indole, internal alkene, or unactivated alkyl chloride) and can serve as a powerful synthetic tool for borylation of amine groups in complex compounds. Mechanistic experiments and computations suggest a mechanism in which the Lewis base activated B2cat2 unit intercepts an alkyl radical generated by single-electron transfer (SET) from a boron-based reductant.

Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis

Pan, Yue,Jia, Kunfang,Chen, Yali,Chen, Yiyun

supporting information, p. 1215 - 1221 (2018/06/13)

The alkynylbenziodoxole derivatives are recently developed alkynylation reagents in organic synthesis, which demonstrate excellent radical alkynylation reactivity in photoredox catalysis reactions. Herein we report the synthesis of alkynylbenziodoxole derivatives with difluoro, monofluoro, monomethoxy, and dimethoxy substitution on the benziodoxole moiety, and investigated their radical alkynylation reactivity for the first time. A series of mechanistic experiments were conducted to study the radical acceptor and oxidative quencher reactivity of alkynylbenziodoxoles, in which unsubstituted alkynylbenziodoxoles played balancing roles in both processes, while electron-rich benziodoxole derivatives demonstrate synthetic advantages in some cases.

Process route upstream and downstream products

Process route

cyclohexylmagnesium bromide
931-50-0

cyclohexylmagnesium bromide

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
cyclohexylmagnesium bromide; With Trimethyl borate; In tetrahydrofuran; at -30 - 20 ℃; Inert atmosphere;
With potassium hydrogenfluoride; In tetrahydrofuran; water; at -10 - 20 ℃; for 2h;
cyclohexene
110-83-8

cyclohexene

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
cyclohexene; With PyBH2I; In dichloromethane; at 20 ℃;
With potassium hydrogen bifluoride; In methanol; at 20 ℃;
82%
Multi-step reaction with 3 steps
1: triethylsilane / water; hexane / 0 - 20 °C / Inert atmosphere
2: tetrahydrofuran; water; hexane / 0.5 h / Inert atmosphere
3: water / 0.25 h / Inert atmosphere
With triethylsilane; In tetrahydrofuran; hexane; water;
cyclohexylmagnesiumchloride
931-51-1

cyclohexylmagnesiumchloride

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
cyclohexylmagnesiumchloride; With Trimethyl borate; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 2h;
With hydrogenchloride; water; In tetrahydrofuran; diethyl ether; for 0.5h;
With potassium hydrogen difluoride; In methanol; water; at 20 ℃; for 1h;
65%
[(4R,5R)-4,5-dicyclohexyl-1-cyclohexyl]-1,3,2-dioxaborolane

[(4R,5R)-4,5-dicyclohexyl-1-cyclohexyl]-1,3,2-dioxaborolane

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
With potassium hydrogen difluoride; In methanol; water; at 22 ℃;
90%
cyclohexylboronic acid
4441-56-9

cyclohexylboronic acid

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
With potassium hydrogen difluoride; In methanol; water; at 20 ℃; for 0.5h;
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

cyclohexylboronic acid
4441-56-9

cyclohexylboronic acid

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
In methanol; water; for 2h; Inert atmosphere;
79%
In methanol; water; at 20 ℃; for 2h; Inert atmosphere;
78%
potassium hydrogen difluoride

potassium hydrogen difluoride

cyclohexylboronic acid
4441-56-9

cyclohexylboronic acid

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
In methanol; water; at 20 ℃; for 0.5h; Inert atmosphere;
16%
With water; In methanol; at 0 - 20 ℃; for 1h; Inert atmosphere;
In methanol; at 0 ℃; for 0.5h; Inert atmosphere;
In methanol; water; at 0 ℃; Inert atmosphere;
potassium hydrogenfluoride
1279123-63-5

potassium hydrogenfluoride

borane pyridine
110-51-0

borane pyridine

cyclohexene
110-83-8

cyclohexene

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
With iodine; In methanol; dichloromethane; to soln. of CHCHC4H8 in CH2Cl2 added PyBH3 and I2; then soln. of KHF2 inMeOH added; MS, NMR;
82%
potassium hydrogen difluoride

potassium hydrogen difluoride

tetrahydroxydiboron
13675-18-8

tetrahydroxydiboron

1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate
126812-30-4

1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
tetrahydroxydiboron; 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate; With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; In N,N-dimethyl-formamide; for 12h; Inert atmosphere; Schlenk technique; Irradiation;
potassium hydrogen difluoride; In methanol; water; at 0 ℃; for 3h; Inert atmosphere; Schlenk technique;
74%
potassium hydrogen bifluoride

potassium hydrogen bifluoride

cyclohexyldiisopropoxyborane
97782-70-2

cyclohexyldiisopropoxyborane

cyclohexyltrifluoro-λ<sup>4</sup>-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

Conditions
Conditions Yield
In water; for 0.25h; Inert atmosphere;
3.269 g

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