5-Brompyrimidin
5-Bromopyrimidine
Grundinformationen
- CAS
4595-59-9- Standard-SMILES
Brc1cncnc1- InChIKey
GYCPLYCTMDTEPU-UHFFFAOYSA-N- Summenformel
- C4H3BrN2
- Durchschnittliche Molmasse
- 158,98 g/mol
- Monoisotopische Masse
- 157,94796
Überblick
a radiosensitizing agent
Namen und Bezeichner
- Bevorzugter Name
- 5-Bromopyrimidine
- IUPAC
- 5-bromopyrimidine
- Lokaler Name
- 5-Brompyrimidin
- Englischer Name
- 5-Bromopyrimidine
- Summenformel
- C4H3BrN2
- Molmasse
- 158.98
Namen und Synonyme
5-Bromopyrimidine4595-59-9Pyrimidine, 5-bromo-5-BrPy compound5Z9X6MAT38DTXSID4063531RefChem:102211DTXCID6040458224-992-1MFCD000061175-bromo pyrimidine5-bromo-pyrimidine
Weitere Namen anzeigen
5-bromo-pyrimidin5-pyriMidine5-Brompyrimidin5-Bromo-1,3-diazinePYRIMIDINE, 2-BROMO-5-Bromopyrimidine,98%5-Bromopyrimidine >5-BROMOPYRIMIDINE 0.98
5-bromanylpyrimidineEINECS 224-992-1CHEMBL3423442STR00327HY-W008017PS-3029SY004103EN300-29556
Datenbank-Bezeichner
- CAS
4595-59-9- PubChem CID
- 78344
- DTXSID
DTXSID4063531- ChEMBL
CHEMBL3423442- UNII
- 5Z9X6MAT38
- EC Number
- 224-992-1
- Nikkaji
- J236.494H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,7
- Polarare Oberfläche (TPSA)
- 25,8 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 51,7
Experimentelle und physikochemische Eigenschaften
LogP0.66
Physical DescriptionDry Powder
Physikochemische Eigenschaften
- Schmelzpunkt
- 67 · 67-73 °C (lit.)
- Siedepunkt
- 168 °C · 168°C(lit.)
- Dichte
- 1.6448 · 1.6448 (rough estimate)
- Brechungsindex
- 1.526 · 1.5260 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- Soluble in chloroform.
- Aggregatzustand
- Crystalline Powder or Chunks
- pka
- 1.4 · 1.40±0.10(Predicted)
- Farbe
- Yellow to beige-brown
- BRN
- 107326 · 107326
- InChI
- InChI=1S/C4H3BrN2/c5-4-1-6-3-7-2-4/h1-3H
- InChIKey
- GYCPLYCTMDTEPU-UHFFFAOYSA-N
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H315 (57.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 91 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Pyrimidine, 5-bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Pyrimidine, 5-bromo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Pyrimidine, 5-bromo-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (57.1%)
CSL Reaction Information
CSL00135
ACETONE + 5-BROMOPYRIMIDINE + SULFURIC ACID + PERACETIC ACID
Upon drying the powder product was being scraped from a sintered glass funnel to complete the neutralization of the hemiacid salt when an explosion occurred. Subsequent testing determined that the peroxide dimer of acetone was the most likely cause of the explosion. This material is reported to be both shock and friction sensitive and known to sublime at room temperature.
Explosive
ACS Safety Letters
7/8/18
Sicherheitsdaten
- wgk
Chemie und Industrie
Verwendung und Herstellung
U.S. Production2023: 50,000 - <250,000 lb
Industry UsesIntermediate
General Manufacturing Information
Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing
Pyrimidine, 5-bromo-: ACTIVE
Anwendungen
Beschreibung5-Bromopyrimidine is an important structural unit in organic compounds, featuring a bromine functional group on its pyrimidine ring which serves as the active moiety enabling participation in diverse chemical reactions. Through acid-catalysed electrophilic alkylation of aromatic compounds with 5-bromopyrimidine, followed by oxidative rearrangement to form the dihydropyrimidine ring. Subsequent Sonogashira cross-coupling enables the preparation of 4-aryl-5-pyrimidylacetylene derivatives, which possess medicinal value.
Verwenden5-Bromopyrimidine was used in the synthesis of N-heteroaryl substituted 9-arylcarbazolyl derivatives via palladium-catalyzed aerobic and ligand-free Suzuki reaction, (5-(phenylethynyl)pyrimidine) via microwave assisted organic synthesis (MAOS) Sonogashira protocol.
Darstellung
synthetische5-Bromopyrimidine is prepared by reacting dibromodifuranone with formamide in the presence of B2O2 catalyst at 180-185°C to obtain the product.
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