1-Pyrenylboronic acid

Base Information

• Chemical Name: 1-Pyrenylboronic acid
• CAS No.: 164461-18-1
• Molecular Formula: C16H11BO2
• Molecular Weight: 246.073
• Hs Code.: 29319090
• European Community (EC) Number: 813-398-3
• DSSTox Substance ID: DTXSID60408164
• Nikkaji Number: J820.184F
• Wikidata: Q72503700
• Mol file: 164461-18-1.mol

Synonyms:1-Pyrenylboronic acid;Pyren-1-ylboronic Acid;164461-18-1;1-Pyreneboronic acid;Pyrene-1-boronic acid;Boronic acid, B-1-pyrenyl-;1-pyrenyl boronic acid;MFCD04974062;1-Pyreneboronic acid (contains varying amounts of Anhydride);Boronic acid, 1-pyrenyl-;(pyren-1-yl)boronic acid;C16H11BO2;pyreneboronic acid;pyren-1-boronic acid;pyren-1-ylboronicacid;SCHEMBL224652;YSSJ01086;DTXSID60408164;MWEKPLLMFXIZOC-UHFFFAOYSA-N;Pyrene-1-boronic acid, >=95.0%;AKOS015840457;AB21450;CS-W010239;FD14070;GS-6482;AM808106;SY022635;FT-0653019;P1625;pyren-1-ylboronic acid;1-Pyreneboronic Acid;A810568;J-010142;J-524083;1-Pyreneboronic Acid, (contains varying amounts of Anhydride)

Chemical Property of 1-Pyrenylboronic acid

Chemical Property:

• Vapor Pressure: 3.36E-11mmHg at 25°C
• Melting Point: 247-251 °C(lit.)
• Refractive Index: 1.804
• Boiling Point: 509.4 °C at 760 mmHg
• PKA: 8.53±0.30(Predicted)
• Flash Point: 261.9 °C
• PSA: 40.46000
• Density: 1.35 g/cm³
• LogP: 2.26380
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 246.0852098
• Heavy Atom Count: 19
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Pyren-1-ylboronicAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C2C=CC3=CC=CC4=C3C2=C(C=C1)C=C4)(O)O
• Uses: It is an important raw material and intermediate used in organic synthesis agrochemical, pharmaceutical and dyestuff field. Also used as a intermediate for organic light-emitting diode(OLED). suzuki reaction

Technology Process of 1-Pyrenylboronic acid

There total 13 articles about 1-Pyrenylboronic acid 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: 100.0%

1-bromopyrene (1714-29-0) → 1-pyrenylboronic acid (164461-18-1)

Guidance literature:

With n-butyllithium; Triisopropyl borate;

DOI:10.1021/tx0200111

Reference yield: 85.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1-bromopyrene (1714-29-0) → 1-pyrenylboronic acid (164461-18-1) + 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene (349666-24-6)

Guidance literature:

1-bromopyrene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With Triisopropyl borate; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.5h;

2,3-dimethyl-2,3-butane diol; In diethyl ether; hexane; at 40 ℃; for 0.75h;

DOI:10.1002/1099-0690(200110)2001:20<3819::AID-EJOC3819>3.0.CO;2-W

Reference yield: 85.0%

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene (349666-24-6) → 1-pyrenylboronic acid (164461-18-1)

Guidance literature:

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrene; With sodium periodate; In tetrahydrofuran; water; at 20 ℃;

With hydrogenchloride; In tetrahydrofuran; water; for 24h;

DOI:10.1039/c6cc03248f

upstream raw materials:

1-bromopyrene

2,3-dimethyl-2,3-butane diol

Trimethyl borate

oxonium

Downstream raw materials:

2-(1-Pyrenyl)benzaldehyde

1-(2-formyl-4-methoxyphenyl)pyrene

1-(3-bromophenyl)pyrene

1-(3,5-dibromophenyl)pyrene

Refernces

Tuning the spin-transition properties of pyrene-decorated 2,6-bispyrazolylpyridine based Fe(ii) complexes

10.1039/c1dt10420a

This research investigates the spin-transition properties of Fe(II) complexes functionalized with pyrene groups. The purpose of the study is to explore how the structure of these complexes, particularly the nature of the pyrene substitution and the flexibility of the linker, influences their spin-transition behavior, which is crucial for potential applications in molecular devices. The researchers synthesized three iron(II) complexes using two different 2,6-bispyrazolylpyridine ligands (L1 and L2) functionalized with pyrene. Pyreneboronic Acid is used in the Suzuki cross-coupling reaction to attach a pyrene group to 4'-iodo-2',6'-dipyrazolyl-pyridine, forming L1. Ligand L1 has a direct pyrene substitution via a C–C bond, while L2 includes a flexible benzyl ester group with a butanoic chain. The complex [Fe(L1)2](ClO4)2 (1) remains in a high-spin state due to strong intermolecular p–p stacking, which restricts structural changes. In contrast, [Fe(L2)2](ClO4)2 (2) and [Fe(L2)2](BF4)2·CH3CN·H2O (3) exhibit reversible spin transitions due to the flexibility of the pyrene linker in L2, which allows for structural rearrangements. The study concludes that the flexibility of the ligand is key to enabling spin transitions, and no correlation was found between the fluorescence of the pyrene group and the spin state of the complex core.