5-Bromopyrimidine (HCID 78344)

概要

a radiosensitizing agent

名称と識別子

優先名称: 5-Bromopyrimidine
IUPAC: 5-bromopyrimidine
現地名: 5-ブロモピリミジン
英語名: 5-Bromopyrimidine
分子式: C4H3BrN2
分子量: 158.98

名称と別名

5-Bromopyrimidine4595-59-9Pyrimidine, 5-bromo-5Z9X6MAT38DTXSID40635315-BrPy compoundRefChem:102211DTXCID6040458224-992-1MFCD000061175-bromo pyrimidine5-bromo-pyrimidine

名称をさらに表示

5-ブロモピリミジン5‐ブロモピリミジン5-ブロモピリミジン臭化物5-ブロモピリミジン, 98%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

データベース識別子

CAS: 4595-59-9
PubChem CID: 78344
DTXSID: DTXSID4063531
ChEMBL: CHEMBL3423442
UNII: 5Z9X6MAT38
EC Number: 224-992-1
Nikkaji: J236.494H

物性

構造計算による物性

XLogP: 0.7
極性表面積: 25.8 Å²
水素結合供与体数: 0
水素結合受容体数: 2
回転可能結合数: 0
重原子数: 7
形式電荷: 0
複雑度: 51.7

実験および物理化学的性質

Physical DescriptionDry Powder

物理化学的性質

融点: 67 · 67-73 °C (lit.)
沸点: 168 °C · 168°C(lit.)
比重(密度): 1.6448 · 1.6448 (rough estimate)
屈折率: 1.526 · 1.5260 (estimate)
貯蔵温度: Sealed in dry,Room Temperature
溶解性: クロロホルムに可溶。
外見: 結晶性粉末またはチャンク
酸解離定数(Pka): 1.4 · 1.40±0.10(Predicted)
色: 黄色からベージュブラウン
BRN: 107326 · 107326
InChI: InChI=1S/C4H3BrN2/c5-4-1-6-3-7-2-4/h1-3H
InChIKey: GYCPLYCTMDTEPU-UHFFFAOYSA-N
SMILES: C1=NC=C(Br)C=N1
CAS データベース: 4595 · 4595-59-9(CAS DataBase Reference)
NISTの化学物質情報: 5 · Pyrimidine, 5-bromo-(4595-59-9)
EPAの化学物質情報: 5 · Pyrimidine, 5-bromo- (4595-59-9)

化学的性質

化学的特性yellow solid crystalline, insoluble in water, soluble in organic solvents such as benzene and toluene.

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

Regulatory Information · 2 件

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 · 6 件

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

安全データ

wgk: 3
tsca: TSCA listed
hs_code: 29335990
risk_code: 36/37/38-36/38
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-36-37/39
hazard_class: IRRITANT, KEEP COLD
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
ストレージクラス: 11 - Combustible Solids

化学と産業

用途と製造

U.S. Production2023: 50,000 - <250,000 lb

Industry UsesIntermediate

General Manufacturing Information · 2 件

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

Pyrimidine, 5-bromo-: ACTIVE

応用分野 · 4 件

用途有機合成原料。

説明5-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.

使用5-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.

一般的な説明Rapid nucleophilic displacement reactions of 5-bromopyrimidine with nucleophiles under microwave irradiation has been studied. 5-Bromopyrimidine undergoes direct metallation with lithuium diisopropylamide to yield 4-lithio-5-bromopyrimidine.

調製方法

製造方法5-Bromopyrimidine is prepared by reacting dibromodifuranone with formamide in the presence of B2O2 catalyst at 180-185°C to obtain the product.