(4-METHYL-1-NAPHTHALENE)BORONIC ACID

Base Information

• Chemical Name: (4-METHYL-1-NAPHTHALENE)BORONIC ACID
• CAS No.: 103986-53-4
• Molecular Formula: C11H11BO2
• Molecular Weight: 186.018
• Hs Code.: 29319090
• European Community (EC) Number: 624-495-3
• DSSTox Substance ID: DTXSID60378510
• Nikkaji Number: J2.518.539K
• Wikidata: Q72493255
• Mol file: 103986-53-4.mol

Synonyms:1-Naphthaleneboronicacid, 4-methyl- (6CI);Boronic acid, (4-methyl-1-naphthalenyl)- (9CI);(4-Methylnaphthyl-1)boronic acid;4-Methyl-1-naphthaleneboronic acid;4-Methyl-1-naphthalenylboronic acid;

Chemical Property of (4-METHYL-1-NAPHTHALENE)BORONIC ACID

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 1.17E-06mmHg at 25°C
• Melting Point: 229-235 °C (dec.)(lit.)
• Refractive Index: 1.623
• Boiling Point: 386.302 °C at 760 mmHg
• PKA: 8.95±0.30(Predicted)
• Flash Point: 187.429 °C
• PSA: 40.46000
• Density: 1.183 g/cm³
• LogP: 0.82800
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 186.0852098
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

99% ^*data from raw suppliers

4-Methyl-1-naphthaleneboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C2=CC=CC=C12)C)(O)O
• Uses: Reactant for Suzuki-Miyaura coupling.

Technology Process of (4-METHYL-1-NAPHTHALENE)BORONIC ACID

There total 9 articles about (4-METHYL-1-NAPHTHALENE)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: 95.0%

Triisopropyl borate (5419-55-6) + 1-bromo-4-methylnaphthalene (6627-78-7) → 4-methyl-1-naphthylboronic acid (103986-53-4)

Guidance literature:

1-bromo-4-methylnaphthalene; With n-butyllithium; In diethyl ether; hexane; at -78 - 20 ℃;

Triisopropyl borate; In diethyl ether; hexane; at -78 - 20 ℃; for 15.5h;

With hydrogenchloride; In diethyl ether; hexane; water;

DOI:10.1016/j.tet.2012.09.033 DOI:10.1016/j.tet.2012.09.033

Reference yield:

triethyl borate (150-46-9) + 1-bromo-4-methylnaphthalene (6627-78-7) → 4-methyl-1-naphthylboronic acid (103986-53-4)

Guidance literature:

With n-butyllithium; N₂; In tetrahydrofuran; hexane;

Reference yield:

1-Bromonaphthalene (90-11-9) → 4-methyl-1-naphthylboronic acid (103986-53-4)

Guidance literature:

Multi-step reaction with 4 steps

1: Ni

2: NBS / acetonitrile

3: BuLi

4: H₂O

With N-Bromosuccinimide; n-butyllithium; water; nickel; In acetonitrile;

DOI:10.1002/chem.200600874

upstream raw materials:

boric acid tributyl ester

1-bromo-4-methylnaphthalene

1-Bromonaphthalene

1-Methylnaphthalene

Downstream raw materials:

4-nitro-1-methylnaphthalene

C₂₆H₂₃NO₄S

5-methyl-benzo{c}phenanthrene

Refernces

• 1、 Nagarajan, Samuthira,Barthes, Cecile,Girdhar, Navdeep K.,Dang, Tung T.,Gourdon, Andre. "Methylterrylene isomers". . p. 9371 - 9375,5. Retrieved 2012.
• 2、 -. "Composite taken as URAT 1 inhibitor". Paragraph 0028; 0030. . Retrieved 2018/05/16.
• 3、 -. "ROCK inhibitor comprising methylnaphthalene and propanediol thiophene amide structure". Paragraph 0041; 0042; 0045; 0046. . Retrieved 2018/07/06.