6-(Methylthio)pyridin-3-ylboronic acid

Base Information

• Chemical Name: 6-(Methylthio)pyridin-3-ylboronic acid
• CAS No.: 321438-86-2
• Molecular Formula: C6H8BNO2S
• Molecular Weight: 169.012
• Hs Code.: 2933399090
• European Community (EC) Number: 681-804-4
• DSSTox Substance ID: DTXSID60376379
• Wikidata: Q82165328
• ChEMBL ID: CHEMBL3236875
• Mol file: 321438-86-2.mol

Synonyms:321438-86-2;6-(Methylthio)pyridin-3-ylboronic acid;2-Methylthiopyridine-5-boronic acid;(6-methylsulfanylpyridin-3-yl)boronic Acid;6-(METHYLTHIO)PYRIDINE-3-BORONIC ACID;2-(Methylthio)-5-pyridinyl-boronic acid;(6-(methylthio)pyridin-3-yl)boronic acid;[6-(Methylsulfanyl)pyridin-3-yl]boronic acid;C6H8BNO2S;6-(Methylsulphanyl)pyridine-3-boronic acid;SCHEMBL212497;CHEMBL3236875;DTXSID60376379;UXWKVPJOPVIIRU-UHFFFAOYSA-N;6-methylthiopyridin-3-ylboronic acid;MFCD03788238;6-(Methylthio)pyridin-3-ylboronicacid;AKOS006344170;FD10014;PS-9636;6-methylsulfanyl-pyridine-3-boronic acid;CS-0063918;FT-0608853;2-Methylthiopyridine-5-boronic acid, AldrichCPR;J-501634;2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-(hexyl)oxyphenol

Chemical Property of 6-(Methylthio)pyridin-3-ylboronic acid

Chemical Property:

• Vapor Pressure: 4.58E-06mmHg at 25°C
• Melting Point: 151-154 °C
• Refractive Index: 1.586
• Boiling Point: 368 °C at 760 mmHg
• PKA: 6.86±0.10(Predicted)
• Flash Point: 176.4 °C
• PSA: 78.65000
• Density: 1.298 g/cm³
• LogP: -0.51670
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 169.0368798
• Heavy Atom Count: 11
• Complexity: 125

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Methylthiopyridine-5-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN=C(C=C1)SC)(O)O

Technology Process of 6-(Methylthio)pyridin-3-ylboronic acid

There total 1 articles about 6-(Methylthio)pyridin-3-ylboronic 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: 81.0%

5-bromo-2-(methylsulfanyl)pyridine (51933-78-9) → 6-(methylthio)pyridin-3-ylboronic acid (321438-86-2)

Guidance literature:

5-bromo-2-(methylsulfanyl)pyridine; With n-butyllithium; Triisopropyl borate; In tetrahydrofuran; hexanes; toluene; at -40 - 20 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; hexanes; water; toluene; at 20 ℃;

With sodium hydroxide; In tetrahydrofuran; hexanes; water; ethyl acetate; toluene; pH=7;

Reference yield: 88.7%

6-(methylthio)pyridin-3-ylboronic acid (321438-86-2) + 2-(4-(2-chloropyridin-4-yl)-3-(3-methoxy-5-methylphenyl)-1H-pyrazol-1-yl)acetonitrile (1192885-47-4) → 2-(3-(3-methoxy-5-methylphenyl)-4-(2-(6-(methylthio)pyridin-3-yl)pyridin-4-yl)-1H-pyrazole-1-yl)acetonitrile

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; water; at 70 ℃; for 12h; Inert atmosphere;

DOI:10.3390/molecules20011031

Reference yield: 62.0%

6-(methylthio)pyridin-3-ylboronic acid (321438-86-2) + 4-[(4-chloro-pyrimidin-2-ylamino)-methyl]-benzoic acid methyl ester (866000-39-7) → 4-{[4-(6-methylsulfanyl-pyridin-3-yl)-pyrimidin-2-ylamino]-methyl}-benzoic acid (866000-44-4)

Guidance literature:

6-(methylthio)pyridin-3-ylboronic acid; 4-[(4-chloro-pyrimidin-2-ylamino)-methyl]-benzoic acid methyl ester; With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In water; acetonitrile; at 90 - 100 ℃; for 24h;

With sodium hydroxide; water; In acetonitrile; at 90 - 100 ℃; for 2h;

With hydrogenchloride; In water; pH=5 - 6;

upstream raw materials:

5-bromo-2-(methylsulfanyl)pyridine

Downstream raw materials:

4-{[4-(6-methylsulfanyl-pyridin-3-yl)-pyrimidin-2-ylamino]-methyl}-benzoic acid

1-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methylsulfanyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

Refernces