2-Naphthaleneboronic acid

Base Information

• Chemical Name: 2-Naphthaleneboronic acid
• CAS No.: 32316-92-0
• Molecular Formula: C10H9BO2
• Molecular Weight: 171.991
• Hs Code.: 29319090
• European Community (EC) Number: 628-070-3
• UNII: QP24ZQS9BM
• DSSTox Substance ID: DTXSID50370265
• Nikkaji Number: J734.887H
• Wikidata: Q72493434
• ChEMBL ID: CHEMBL141079
• Mol file: 32316-92-0.mol

Synonyms:2-Naphthaleneboronic acid;32316-92-0;Naphthalen-2-ylboronic Acid;2-Naphthylboronic acid;Naphthalene-2-boronic acid;2-naphthalene boronic acid;2-naphthaleneylboronic acid;Boronic acid, 2-naphthalenyl-;beta-naphthylboronic acid;MFCD00236051;Naphthalen-2-boronic acid;QP24ZQS9BM;B-2-Naphthalenylboronic acid;(2-Naphthalenyl)boronic acid;(Naphthalene-2-yl)boronic acid;Boronic acid, B-2-naphthalenyl-;UNII-QP24ZQS9BM;(naphthalen-2-yl)boronic acid;CHEMBL141079;2-Naphtahaleneboronic acid;2-naphthyl boronic acid;Naphthalene-2-boronicacid;2-NAPHTHYLBORONIC CAID;2-naphtylboronic acid;NAPHTHALEN-2-YL-2-BORONIC ACID;2-naphthaleneboric acid;2-naphthyl-boronic acid;2-napthaleneboronic acid;naphth-2-yl boronic acid;2-naphthalenylboronic acid;D0C8ZY;2-naphthalenyl boronic acid;SCHEMBL23150;naphthalen-2-yl boronic acid;naphthalen-2-yl-boronic acid;2-NAPHTHYLBENZOIC ACID;2-NAPHTHALENE BORIC ACID;2-Phenylnaphthalene Boronic Acid;2 -phenylnaphthalene boronic acid;DTXSID50370265;KPTRDYONBVUWPD-UHFFFAOYSA-N;BCP22773;2-Naphthylboronic acid, >=95.0%;BDBM50067913;AKOS004116357;AB05352;AC-3261;AC-5787;AS-2618;BCP9000056;CS-W002570;OL10083;NCGC00249473-01;NCGC00249473-02;SY004747;A5801;AM20060205;N0649;EN300-76567;Q-102222;Z381540938;2-Naphthaleneboronic Acid (contains varying amounts of Anhydride);2-Naphthaleneboronic Acid, (contains varying amounts of Anhydride)

Chemical Property of 2-Naphthaleneboronic acid

Chemical Property:

• Appearance/Colour: yellow crystal powder
• Vapor Pressure: 1.63E-06mmHg at 25°C
• Melting Point: 269-275 °C(lit.)
• Refractive Index: 1.638
• Boiling Point: 381.9 °C at 760 mmHg
• PKA: 8.53±0.30(Predicted)
• Flash Point: 184.8 °C
• PSA: 40.46000
• Density: 1.21g/cm³
• LogP: 0.51960
• Storage Temp.: 0-6°C
• Water Solubility.: Slightly soluble in water
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 172.0695597
• Heavy Atom Count: 13
• Complexity: 172

Purity/Quality:

≥99.0% ^*data from raw suppliers

2-Naphthaleneboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC2=CC=CC=C2C=C1)(O)O
• description: 2-Naphthalene Boronic Acid is an organometallic iridium complex with applications in catalysis and Pharmaceutical manufacturing. It can be also used in the study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols.?
• Uses: 2-Naphthaleneboronic acid is a useful research chemical for organic synthesis and other chemical processes. suzuki reaction Used in a study of an enantioselective rhodium-catalyzed addition of aryl boronic acids to 2,2,2-trifluoroacetophenones leading to chiral, tertiary trifluoromethyl alcohols. Also employed in a study of a palladium-catalyzed addition of aryl boronic acids to nitriles providing aryl ketones and to aryloxy nitriles providing benzofurans.

Technology Process of 2-Naphthaleneboronic acid

There total 27 articles about 2-Naphthaleneboronic 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: 98.0%

hydrogenchloride (7647-01-0,15364-23-5) + Trimethyl borate (121-43-7,63156-11-6) + 2-bromonaphthalene (580-13-2) → naphthalene-2-boronic acid (32316-92-0)

Guidance literature:

With BuLi; In tetrahydrofuran; N2-atmosphere; addn. of BuLi (in hexanes) to bromonaphthalene (in THF) at -78°C, stirring at -78°C for 30 min, dropwise addn. of B(OMe)3 (in THF; below -60°C), warming to room temp. overnight, addn. of 10 M HCl, stirring for 1 h; partitioning between Et2O and water, drying of org. layer (MgSO4), evapn. (reduced pressure);

DOI:10.1016/0022-328X(94)05367-K

Reference yield: 94.0%

potassium 2-naphthyltrifluoroborate → naphthalene-2-boronic acid (32316-92-0)

Guidance literature:

With iron(III) chloride; water; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2011.09.140

Reference yield: 90.0%

triethyl borate (150-46-9) + 2-bromonaphthalene (580-13-2) → naphthalene-2-boronic acid (32316-92-0)

Guidance literature:

2-bromonaphthalene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

triethyl borate; In tetrahydrofuran; for 6h;

upstream raw materials:

triisobutyl borate

2-naphthalenylmagnesium bromide

di-β-naphthyl mercurium

2-iodonaphthalene

Downstream raw materials:

2-(2-naphthyl)-5-methoxyphenylacetone

4-(2-naphthyl)benzoic acid methyl ester

4-(naphthalene-2-yl)benzaldehyde

naphthalene

Refernces

• 1、 Guo, Zhiqiang,Jin, Shuo,Liu, Bo. "Synthesis and photophysical processes of 9-bromo-10-naphthalen-2-yl-anthracene". . p. 672 - 675. Retrieved 2007.
• 2、 Hernández-Ruiz, Raquel,Rubio-Presa, Rubén,Suárez-Pantiga, Samuel,Pedrosa, María R.,Fernández-Rodríguez, Manuel A.,Tapia, M. José,Sanz, Roberto. "Mo–Catalyzed One-Pot Synthesis of N-Polyheterocycles from Nitroarenes and Glycols with Recycling of the Waste Reduction Byproduct. Substituent-Tuned Photophysical Properties". supporting information. p. 13613 - 13623. Retrieved 2021/08/23.
• 3、 Han, Min Su,Lim, Taeho,Ryoo, Jeong Yup. "Transition-Metal-Free Borylation of Aryl Bromide Using a Simple Diboron Source". . p. 10966 - 10972. Retrieved 2020/09/23.