2,4,6-Trimethylphenylboronic acid

Base Information

• Chemical Name: 2,4,6-Trimethylphenylboronic acid
• CAS No.: 5980-97-2
• Molecular Formula: C9H13BO2
• Molecular Weight: 164.012
• Hs Code.: 29209090
• European Community (EC) Number: 672-285-5
• NSC Number: 157832
• UNII: 7J3E8CV75Y
• DSSTox Substance ID: DTXSID70303313
• Nikkaji Number: J898.542A
• Wikidata: Q72514252
• Mol file: 5980-97-2.mol

Synonyms:2-Mesityleneboronicacid (6CI,8CI);Boronic acid, (2,4,6-trimethylphenyl)- (9CI);2,4,6-Trimethylbenzeneboronic acid;2,4,6-Trimethylphenylboronic acid;Mesitylboronic acid;Mesityleneboronic acid;NSC 157832;

Chemical Property of 2,4,6-Trimethylphenylboronic acid

Chemical Property:

• Appearance/Colour: Off-white cryst
• Vapor Pressure: 0.000282mmHg at 25°C
• Melting Point: 115-122 °C(lit.)
• Refractive Index: 1.519
• Boiling Point: 309.1 °C at 760 mmHg
• PKA: 9.00±0.58(Predicted)
• Flash Point: 140.7 °C
• PSA: 40.46000
• Density: 1.05 g/cm³
• LogP: 0.29160
• Storage Temp.: 0-6°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 164.1008598
• Heavy Atom Count: 12
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

Mesitylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,F
• Statements: 36/37/38-10
• Safety Statements: 37/39-26-33-29-16-3/7/9-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=C(C=C(C=C1C)C)C)(O)O
• Uses: suzuki reaction Reactant involved in:Cross-coupling with α-bromocarbonyl compounds or 2,6-disubstituted bromoarenesSuzuki-Miyaura coupling for synthesis of biphenyl arsine ligandsAddition reactions to naphthyridine N-oxides or β-aryloxyacrylates

Technology Process of 2,4,6-Trimethylphenylboronic acid

There total 15 articles about 2,4,6-Trimethylphenylboronic 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: 91.0%

2,4,6-trimethylphenyl bromide (576-83-0) → mesitylboronic acid (5980-97-2)

Guidance literature:

2,4,6-trimethylphenyl bromide; With diisobutylaluminium hydride; magnesium; lithium chloride; In tetrahydrofuran; toluene; at 20 ℃; for 15h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

With hydrogenchloride; water; In tetrahydrofuran; toluene; at 0 ℃; Inert atmosphere;

DOI:10.1021/ol2016252

Reference yield: 86.0%

triethyl borate (150-46-9) + mesityllithium (5806-59-7) → mesitylboronic acid (5980-97-2)

Guidance literature:

In tetrahydrofuran; addn. of B-compd. to org. compd. in THF, stirring (-78°C, 1.5 h); addn. of satd. soln. of aq. NH4Cl (-78°C), warming (room temp.),DDN: OF H2O, shaking with ether, washing of ether extracts (satd. aq. NaHCO3 and satd. brine), drying (Na2SO4), filtration, evapn. (vac.), crystn. (H2O);

Reference yield: 85.0%

Trimethyl borate (121-43-7,63156-11-6) + 2,4,6-trimethylphenyl bromide (576-83-0) → mesitylboronic acid (5980-97-2)

Guidance literature:

2,4,6-trimethylphenyl bromide; With magnesium; In tetrahydrofuran; for 3h; Reflux;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 12h;

DOI:10.1016/j.jorganchem.2017.04.031

upstream raw materials:

Trimethyl borate

2-mesitylmagnesium bromide

2,4,6-trimethylphenyl bromide

N,N-dimethyl-formamide

Downstream raw materials:

2-formyl-3-mesityl-1-tosylpyrrole

4’-bromo-2,4,6-trimethylbiphenyl

2,4,6-trimethylbenzeneboronic acid neopentyl glycol cyclic ester

4′-(2,4,6-trimethylphenyl)-2,2′:6′,2″-terpyridine

Refernces

• 1、 He, Junjie,Li, Song,Zeng, Heping. "The Photostability of Two Optical Materials Based on Perylene Diimide Substituted by Different Aromatic Groups at the Bay Area". . p. 2800 - 2807. Retrieved 2017/09/26.
• 2、 Usui, Kazuteru,Tanoue, Kensuke,Yamamoto, Kosuke,Shimizu, Takashi,Suemune, Hiroshi. "Synthesis of substituted azulenes via Pt(II)-Catalyzed ring-expanding cycloisomerization". . p. 4662 - 4665. Retrieved 2015/01/16.