(2-methoxynaphthalen-1-yl)boronic Acid

Base Information

• Chemical Name: (2-methoxynaphthalen-1-yl)boronic Acid
• CAS No.: 104116-17-8
• Molecular Formula: C11H11BO3
• Molecular Weight: 202.018
• Hs Code.: 2931900090
• European Community (EC) Number: 687-037-1
• DSSTox Substance ID: DTXSID00400748
• Nikkaji Number: J1.043.427K
• Wikidata: Q82203765
• Mol file: 104116-17-8.mol

Synonyms:104116-17-8;(2-methoxynaphthalen-1-yl)boronic Acid;2-METHOXY-1-NAPHTHALENEBORONIC ACID;2-METHOXYNAPHTHALENE-1-BORONIC ACID;(2-Methoxy-1-naphthyl)boronic acid;Boronic acid, (2-methoxy-1-naphthalenyl)-;MFCD11044173;21MONBA;2-methoxynaphthylboronic acid;SCHEMBL1004416;2-methoxy-1-naphthylboronic acid;DTXSID00400748;NHVWTZOWDLOBBS-UHFFFAOYSA-N;2-Methoxy-1-naphthaleneboronicacid;2-methoxynaphth-1-yl-boronic acid;AMY29826;AKOS003585326;DS-14769;SY040531;CS-0061937;FT-0713509;W16723;EN300-3219440;A896282;Z733389678

Chemical Property of (2-methoxynaphthalen-1-yl)boronic Acid

Chemical Property:

• Melting Point: 125-130°C
• Boiling Point: 425.2±47.0 °C(Predicted)
• PKA: 8.53±0.30(Predicted)
• PSA: 49.69000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 0.52820
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 202.0801244
• Heavy Atom Count: 15
• Complexity: 210

Purity/Quality:

98%, ^*data from raw suppliers

(2-Methoxynaphthalen-1-yl)boronicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=C(C=CC2=CC=CC=C12)OC)(O)O
• Uses: Reactant for:Design of phosphorus C,P-ligands for environmentally benign cross-coupling reactionsSterically hindered Suzuki-Miyaura couplingPalladium-catalyzed cross-coupling reactionsDeboronation homocoupling reactionsCopper-catalyzed N-arylation of imidazolesStereoselective preparation of biaryl compounds via palladium-catalyzed asymmetric Suzuki-Miyaura coupling

Technology Process of (2-methoxynaphthalen-1-yl)boronic Acid

There total 11 articles about (2-methoxynaphthalen-1-yl)boronic 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: 86.0%

Triisopropyl borate (5419-55-6) + 1-bromo-2-methoxynaphthalene (3401-47-6) → 2-methoxynaphthalene-1-boronic acid (104116-17-8)

Guidance literature:

1-bromo-2-methoxynaphthalene; With magnesium; In tetrahydrofuran; at 20 ℃; for 1h; Heating;

Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 18h;

With water; In tetrahydrofuran; for 1h;

DOI:10.1016/j.tet.2018.07.048

Reference yield: 82.0%

Trimethyl borate (121-43-7,63156-11-6) + 1-bromo-2-methoxynaphthalene (3401-47-6) → 2-methoxynaphthalene-1-boronic acid (104116-17-8)

Guidance literature:

1-bromo-2-methoxynaphthalene; With n-butyllithium; In diethyl ether; hexane; at -78 - 20 ℃; Inert atmosphere;

Trimethyl borate; In diethyl ether; hexane; at -78 - 20 ℃; Inert atmosphere;

With hydrogenchloride; In diethyl ether; hexane; water; for 1h;

DOI:10.1016/j.tet.2018.07.048

Reference yield: 80.0%

1-bromo-2-methoxynaphthalene (3401-47-6) → 2-methoxynaphthalene-1-boronic acid (104116-17-8)

Guidance literature:

1-bromo-2-methoxynaphthalene; With magnesium; In tetrahydrofuran; at 20 - 50 ℃; for 3h;

With Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(02)00169-6

upstream raw materials:

1-bromo-2-methoxynaphthalene

1-bromo-2-naphthol

boric acid tributyl ester

Trimethyl borate

Downstream raw materials:

4-o-methoxynaphthalen-1′-yl-2-phenylquinazoline

2-benzyl-4-(2-methoxy-naphthalen-1-yl)-quinazoline

Refernces

• 1、 Flanagan, Susan P.,Goddard, Richard,Guiry, Patrick J.. "The preparation and resolution of 2-(2-pyridyl)- and 2-(2-pyrazinyl)- Quinazolinap and their application in palladium-catalysed allylic substitution". . p. 9808 - 9821. Retrieved 2005.
• 2、 Castanet, Anne-Sophie,Colobert, Francoise,Broutin, Pierre-Emmanuel,Obringer, Michel. "Asymmetric Suzuki cross-coupling reaction: Chirality reversal depending on the palladium-chiral phosphine ratio". . p. 659 - 665. Retrieved 2002.
• 3、 Lim, Chung Woo,Tissot, Olivier,Mattison, Andrew,Hooper, Mark W.,Brown, John M.,Cowley, Andrew R.,Hulmes, David I.,Blacker, A. John. "Practical preparation and resolution of 1-(2′-diphenylphosphino-1′-naphthyl)isoquinoline: A useful ligand for catalytic asymmetric synthesis". . p. 379 - 384. Retrieved 2003.
• 4、 -. "2 - Hydroxynaphthalene -1 - boric acid synthesis method (by machine translation)". . . Retrieved 2019/02/19.