[ CAS No. 165904-22-3 ] {[proInfo.proName]}

Name: 165904-22-3|Phenethylboronic Acid Pinacol Ester|98%
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SKU: A316032
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2D 3D

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COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 165904-22-3 ]

CAS No. :	165904-22-3	MDL No. :	MFCD03788721
Formula :	C₁₄H₂₁BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LVLQNRWCBBIVHR-UHFFFAOYSA-N
M.W :	232.13	Pubchem ID :	11333720
Synonyms :

Safety of [ 165904-22-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
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Application In Synthesis of [ 165904-22-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 165904-22-3 ]
Downstream synthetic route of [ 165904-22-3 ]

[ 165904-22-3 ] Synthesis Path-Upstream 1~1

1
[ 165904-22-3 ]
[ 34420-17-2 ]

Reference： [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 20, p. 4585 - 4589

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[ 165904-22-3 ]

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Yield	Reaction Conditions	Operation in experiment
96%	With chlorotris(triphenylphosphine)cobalt(I); sodium ethanolate; 1,3-dicyclohexylimidazol-2-ylidene In tert-butyl methyl ether at 50℃; for 16h; Inert atmosphere;
85%	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 18h;
81%	With copper(l) iodide; lithium methanolate; triphenylphosphine In N,N-dimethyl-formamide at 25℃; for 18h; Inert atmosphere;

81%	With catalyst: CuI/P(C₆H₅)3; LiOCH₃ In N,N-dimethyl-formamide under Ar; at 25°C for 18 h;
79%	With manganese(II) bromide; N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide In 1,2-dimethoxyethane; diethyl ether at 20℃; for 4h; Inert atmosphere;
75%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; P(t-Bu)2Me*HBF₄; sodium methylate In 1,4-dioxane at 25℃; for 24h; Inert atmosphere;
74%	With lithium tert-butoxide In N,N-dimethyl-formamide at 30℃; for 2h; Irradiation;	2.3. Photocatalytic reactions General procedure: Unless specified otherwise, the reactions were conducted underair with a pressure of 1 atm. A mixture of 1 mmol of alkyl halides,2 mmol of LiOtBu, 1.2 mmol of B2pin2 and 15 mg of Cu2.8Pd0.2/graphene catalyst was dissolved in DMF (10 mL) in a photocatalyticreactor equipped with a magnetic stirring bar. The reaction temperaturewas set at 30 C for alkyl bromides and 50 C for alkylchlorides, respectively, and controlled by a circulating water bath(RT4 circulator, ASONE). The mixture was stirred at 700 rpm during the reaction and exposed to a Xenon lamp (PLS-SXE300C/CUV, BeijingPerfect Light Scientific and Technical Co. Ltd). A low-pass opticalfilter was employed to block light with k < 400 nm. The lightintensity was maintained at 0.6 W/cm2. The effect of the wavelengthof light on catalytic performance was investigated usingvarious low pass optical filters to block light below specific cutoffwavelengths and using various light-emitting diode (LED) lampswith different wavelengths, respectively. For the former, employinga filter with a cut-off wavelength of 450 nm as an example,blocks light with wavelengths < 450 nm (the reaction mixturewas irradiated by light with wavelengths between 450 and800 nm). During this process, the light intensity without filteringfor the reaction remained unchanged.After reaction, the reaction mixture was diluted with dichloromethane(DCM, 10 mL), and filtered through a millipore filter (poresize: 0.22 lm), and n-dodecane (34 mg, 0.2 mmol) was added as aninternal standard. The product yields were determined by gaschromatography-mass spectrometry (GC-MS, BRUKER SCION SQ456 GC-MS) using n-dodecane as the internal calibration standard.The values given are the average of two experiments. The yieldswere calculated based on the amount of alkyl halide. The residuewas purified by column chromatography on silica gel (silica:200-300; eluant: hexane/ethyl acetate) to isolate the desiredproduct.
73%	With copper; lithium methanolate In N,N-dimethyl-formamide at 25℃; for 3h;
66%	With iron(III)-acetylacetonate; N,N,N,N,-tetramethylethylenediamine; ethylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 12h; Inert atmosphere;
65%	With fac-tris(2-phenylpyridinato-N,C₂')iridium(III); tributyl-amine; water In acetonitrile at 25℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; Irradiation;
35%	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In acetonitrile at 25℃; for 8h; Irradiation; Inert atmosphere;
96 %Chromat.	With potassium <i>tert</i>-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;
53 %Spectr.	Stage #1: bis(pinacol)diborane With potassium <i>tert</i>-butylate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene; zinc(II) chloride In tert-butyl methyl ether for 0.5h; Inert atmosphere; Schlenk technique; Glovebox; Stage #2: 1-phenyl-2-bromoethane In tert-butyl methyl ether at 20℃; for 2h; Inert atmosphere; Schlenk technique; Glovebox;
97 %Chromat.	With copper(I) oxide; lithium methanolate; pyrographite In ethanol for 12h; Inert atmosphere;
18 %Spectr.	With 1-(cyclopentadienyl)(4-benzyl-1-i-propyl-1,2,4-triazol-5-ylidene)nickel chloride; caesium carbonate In tetrahydrofuran at 70℃; for 20h; Schlenk technique; Inert atmosphere;
	With copper(l) iodide; lithium methanolate; triphenylphosphine In N,N-dimethyl-formamide at 35℃; for 18h; Schlenk technique; Inert atmosphere;
	With copper(l) iodide; lithium methanolate; triphenylphosphine In N,N-dimethyl-formamide at 37℃; for 24h; Schlenk technique; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
72%	With copper acetylacetonate; lithium hydroxide monohydrate; magnesium chloride In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 0.166667h;
54%	With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In water; N,N-dimethyl-formamide; acetonitrile for 16h; Inert atmosphere; Schlenk technique; Irradiation;

Yield	Reaction Conditions	Operation in experiment
83%	With chromium chloride; aluminium; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 15h; Schlenk technique; Inert atmosphere;
80%	Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(cyclopentadienyl)titanium dichloride; lithium methanolate In tert-butyl methyl ether for 0.5h; Stage #2: 1-phenyl-2-bromoethane In tert-butyl methyl ether at 60℃; for 24h; Inert atmosphere;	52 Example 52 bis(cyclopentadiene) titanium dichloride (denoted as Cp2TiCl2, 0.01 mmol, 2.5 mg), lithium methoxide (denoted as MeOLi, 0.2 mmol, 7.6 mg), methyl tert-butyl ether (1 mL) Hopinacol borane (denoted as HBpin, 0.4mmol,58μL) was added to the 38mL pressure tube in sequence, stirred for 30min, and then 1-bromophenylethane (denoted as 1m, 0.2mmol, 27.3μL) was added in nitrogen (1atm ) Stir at 60°C for 24h under an atmosphere, and purify by column chromatography with petroleum ether/ethyl acetate (40:1, v/v) as the eluent to obtain the structure compound represented by formula 2m (colorless transparent liquid, 2-(2) -Phenylethyl) borate pinacol ester). The isolated yield is 80%.
80%	Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With bis(cyclopentadienyl)titanium dichloride; lithium methanolate In tert-butyl methyl ether for 0.5h; Inert atmosphere; Glovebox; Stage #2: 1-phenyl-2-bromoethane In tert-butyl methyl ether at 60℃; for 24h; Sealed tube;

[ CAS No. 165904-22-3 ] {[proInfo.proName]}

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Application In Synthesis of [ 165904-22-3 ]

[ 165904-22-3 ] Synthesis Path-Upstream 1~1

[ 165904-22-3 ] Synthesis Path-Downstream 1~16