2-Methoxypyrimidine-5-boronic acid

HCID 2736778CAS 628692-15-9

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Grundinformationen

Standard-SMILES: COc1ncc(B(O)O)cn1
InChIKey: YPWAJLGHACDYQS-UHFFFAOYSA-N
Summenformel: C5H7BN2O3
Durchschnittliche Molmasse: 153,93 g/mol
Monoisotopische Masse: 154,05497248

Namen und Bezeichner

Bevorzugter Name: 2-Methoxypyrimidine-5-boronic acid
IUPAC: (2-methoxypyrimidin-5-yl)boronic acid
Englischer Name: 2-Methoxypyrimidine-5-boronic acid
Summenformel: C5H7BN2O3
Molmasse: 153.93

Namen und Synonyme

2-Methoxypyrimidine-5-boronic acid628692-15-9DTXSID70371597RefChem:262814DTXCID80322631670-240-4(2-methoxypyrimidin-5-yl)boronic Acid2-Methoxy-5-pyrimidineboronic acid2-methoxypyrimidin-5-ylboronic acidMFCD03094664Boronic acid, (2-methoxy-5-pyrimidinyl)-2-Methoxy-5-pyrimidylboronic Acid

Weitere Namen anzeigen

2-METHOXYL-5-PYRIMIDYLBORIC ACID2-Methoxypyrimidine-5-boronicaci2-Methoxy PyriMidine boronic acid2-METHOXYL-5-PYRIMIDINEBORIC ACID2-MethoxypyriMidine-4-boronic acid

2-Methoxy-5-pyrimidinylboronic Acid(2-methoxypyrimidin-5-yl)boronicAcidHY-W0046982-METHOXYPYRIMIDIN-5-YL-5-BORONIC ACID2-Methoxy-pyrimidine-5-boronic acidMethoxypyrimidine-5-boronic acidA8682SCHEMBL9497

Datenbank-Bezeichner

CAS: 628692-15-9
PubChem CID: 2736778
DTXSID: DTXSID70371597
EC Number: 670-240-4
Nikkaji: J2.035.654E

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 75,5 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 5
Frei drehbare Bindungen: 2
Schwere Atome: 11
Formalladung: 0
Komplexität: 116

Physikochemische Eigenschaften

Schmelzpunkt: 161 °C · 161°C(lit.)
Siedepunkt: 378.3 · 378.3±52.0 °C(Predicted)
Dichte: 1.33 · 1.33±0.1 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit: soluble in Methanol
Aggregatzustand: powder to crystal
pka: 5.59 · 5.59±0.11(Predicted)
Farbe: White to Light yellow
InChI: InChI=1S/C5H7BN2O3/c1-11-5-7-2-4(3-8-5)6(9)10/h2-3,9-10H,1H3
InChIKey: YPWAJLGHACDYQS-UHFFFAOYSA-N
SMILES: B(C1=CN=C(OC)N=C1)(O)O
CAS Datenbank: 628692 · 628692-15-9(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (89.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (89.1%)

Sicherheitsdaten

wgk: WGK 3
hs_code: 29349990
risk_code: 36-41-36/37/38
hazard_code: Xi
safety_code: 26-39-36/37/39
hazard_class: IRRITANT
Speicherklasse: 11 - Combustible Solids
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2

Chemie und Industrie

Anwendungen · 1 Eintrag

Verwenden2-Methoxypyrimidine-5-boronic acid serves as a coupling partner in Suzuki–Miyaura reactions to synthesize diverse heterocyclic scaffolds. It reacts with intermediates such as compound 26 or 6-bromo-3-(4-hydroxyphenyl)-coumarin using potassium carbonate and palladium catalysts (e.g., Pd(OAc)₂ or 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride) in solvents including DMF or deep eutectic systems at 85 °C. The reagent also couples with 2-(4-((4-chloro-6-morpholino-1,3,5-triazin-2-yl)amino)phenyl)ethan-1-ol in DME/aqueous sodium carbonate under microwave heating[1][2][3]. The compound participates in Liebeskind–Srögl couplings with thioester or amide intermediates (such as series 18a–18c or 20a–20f) using tetrakis(triphenylphosphine)palladium(0) and copper(I) thiophene-2-carboxylate in THF at 100 °C, yielding target products in ranges of 22–55% or 29–50%[1].