4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid

Base Information

• Chemical Name: 4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid
• CAS No.: 179055-26-6
• Molecular Formula: C9H12BNO4
• Molecular Weight: 209.01
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID40394910
• Wikidata: Q82194607
• Mol file: 179055-26-6.mol

Synonyms:179055-26-6;4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid;4-(methoxy(methyl)carbamoyl)phenylboronic acid;(4-(METHOXY(METHYL)CARBAMOYL)PHENYL)BORONIC ACID;[4-[methoxy(methyl)carbamoyl]phenyl]boronic acid;{4-[methoxy(methyl)carbamoyl]phenyl}boronic acid;4-[Methoxy(methyl)carbamoyl]benzeneboronic acid;4-(N,O-DIMETHYLHYDROXYAMINOCARBONYL)PHENYLBORONIC ACID;4-(N,O-DIMETHYLHYDROXYLAMINOCARBONYL)PHENYLBORONICACID;SCHEMBL130927;DTXSID40394910;PISDDPDFGJLSQA-UHFFFAOYSA-N;MFCD04115671;AKOS015893851;AB20365;AM88190;FT-0707029;I12615;(4-{[methoxy(methyl)amino]carbonyl}phenyl)boronic acid;4-(N,O-Dimethyl hydroxylaminocarbonyl)phenylboronic acid

Chemical Property of 4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid

Chemical Property:

• Vapor Pressure: 1.87E-08mmHg at 25°C
• Melting Point: 118-124 °C
• Refractive Index: 1.549
• Boiling Point: 438.2 °C at 760 mmHg
• Flash Point: 218.8 °C
• PSA: 70.00000
• Density: 1.25 g/cm³
• LogP: -1.00020
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 209.0859380
• Heavy Atom Count: 15
• Complexity: 216

Purity/Quality:

98%min ^*data from raw suppliers

4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(C=C1)C(=O)N(C)OC)(O)O

Technology Process of 4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid

There total 1 articles about 4-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic 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: 56.0%

4-carboxyphenylboronic acid (14047-29-1) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (4-{[methoxy(methyl)amino]carbonyl}phenyl)boronic acid (179055-26-6)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1016/S0968-0896(97)10009-8

Reference yield: 73.0%

2-bromo-5-fluoropyridine (41404-58-4) + (4-{[methoxy(methyl)amino]carbonyl}phenyl)boronic acid (179055-26-6) → 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide (1022154-74-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In methanol; toluene; at 90 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/ml100196d

Reference yield:

(4-{[methoxy(methyl)amino]carbonyl}phenyl)boronic acid (179055-26-6) → 1-cycloheptyl-1-(4'-dimethylamino-biphenyl-4-ylmethyl)-3-(2,4,6-trimethyl-phenyl)-urea

Guidance literature:

Multi-step reaction with 5 steps

1: 44 percent / aq. Na₂CO₃ / Pd(Ph₃P)4 / 1,2-dimethoxy-ethane / 16 h / Heating

2: 33 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / 5 - 20 °C

3: Heating

4: NaBH₄ / ethanol / 20 °C

5: 85 percent / CH₂Cl₂ / 20 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; 1: Suzuki cross-coupling / 2: Reduction / 3: Condensation / 4: Reduction / 5: Addition;

DOI:10.1016/S0968-0896(97)10009-8

upstream raw materials:

4-carboxyphenylboronic acid

N,O-dimethylhydroxylamine*hydrochloride

Downstream raw materials:

4’-(dimethylamino)-[1,1’-biphenyl]-4-carbaldehyde

4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide

1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

1-[4-(2,2-dimethylpropyl)-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl) phenyl]propan-2-ol

Refernces