4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane
• CAS No.: 159087-45-3
• Molecular Formula: C14H17 B O2
• Molecular Weight: 228.099
• Hs Code.: 2934999090
• European Community (EC) Number: 804-792-6
• DSSTox Substance ID: DTXSID60471378
• Nikkaji Number: J618.795A
• Wikidata: Q82299876
• Mol file: 159087-45-3.mol

Synonyms:159087-45-3;4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane;2-Phenyl-1-ethynylboronic acid pinacol ester;4,4,5,5-tetramethyl-2-(2-phenylethynyl)-1,3,2-dioxaborolane;MFCD09842761;SCHEMBL2122785;DTXSID60471378;VEIORNIWTVJLCN-UHFFFAOYSA-N;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(2-phenylethynyl)-;ZB0242;AKOS016000999;AS-1005;MB07880;SY277232;FT-0703838;EN300-212623;F10510;(PHENYLETHYNYL)BORONIC ACID PINACOL ESTER;2-Phenyl-1-ethynylboronic acid pinacol ester, 90%;J-009560;Z2044738588

Chemical Property of 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 49-68 °C
• Boiling Point: 265.4±23.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.03±0.1 g/cm3(Predicted)
• LogP: 2.66950
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 228.1321599
• Heavy Atom Count: 17
• Complexity: 326

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C#CC2=CC=CC=C2

Technology Process of 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane

There total 8 articles about 4,4,5,5-Tetramethyl-2-(phenylethynyl)-1,3,2-dioxaborolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

phenylacetylene (536-74-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane (159087-45-3)

Guidance literature:

With Cu⁽¹⁺⁾*CF₃O₃S^(1-)*C₂₂H₃₅N; triethylamine; In benzene; at 20 ℃; for 2h;

DOI:10.1039/c6sc02668k

Reference yield: 98.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + phenylacetylene (536-74-3) → 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane (159087-45-3)

Guidance literature:

phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Schlenk technique; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Schlenk technique; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; diethyl ether; hexane; at -78 - 20 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1021/ol502285s

Reference yield: 80.0%

phenylacetylene (536-74-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane (159087-45-3) + 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane (78782-27-1)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; iron(II) triflate; In toluene; at 100 ℃; for 72h; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/adsc.201800588

upstream raw materials:

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

phenylacetylene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Phenylacetylene-d1

Downstream raw materials:

3,6-bis(3,5-dimethylpyrazol-1-yl)-4-phenyl-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)pyridazine

(Z)-4,4,5,5-tetramethyl-2-(2-phenyl-1-buten-1-yl)-1,3,2-dioxaborolane

(C₅H₅)Co(C₁₀H₁₀(C₆H₅)2((CH₃)4C₂O₂B)2)

(C₅H₅)Co(C₆H₃((CH₃)4C₂O₂B)2(C₆H₅)3)

Refernces

• 1、 Liu, Xiaocui,Ming, Wenbo,Friedrich, Alexandra,Kerner, Florian,Marder, Todd B.. "Copper-Catalyzed Triboration of Terminal Alkynes Using B2pin2: Efficient Synthesis of 1,1,2-Triborylalkenes". . p. 304 - 309. Retrieved 2020.
• 2、 -. "Method for removing hydroboration of aluminum chloride catalytic terminal group alkyne". Paragraph 0016-0018. . Retrieved 2021/10/16.