Basic information
- CAS
4595-59-9- Standard SMILES
Brc1cncnc1- InChIKey
GYCPLYCTMDTEPU-UHFFFAOYSA-N- Molecular formula
- C4H3BrN2
- Average molar mass
- 158.98 g/mol
- Monoisotopic mass
- 157.9479602
Overview
a radiosensitizing agent
Names & identifiers
- Preferred name
- 5-Bromopyrimidine
- IUPAC
- 5-bromopyrimidine
- English name
- 5-Bromopyrimidine
- Molecular formula
- C4H3BrN2
- Molecular weight
- 158.98
Names & synonyms
5-Bromopyrimidine4595-59-9Pyrimidine, 5-bromo-5Z9X6MAT38DTXSID40635315-BrPy compoundRefChem:102211DTXCID6040458224-992-1MFCD000061175-bromo pyrimidine5-bromo-pyrimidine
Show more names
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
Database identifiers
- CAS
4595-59-9- PubChem CID
- 78344
- DTXSID
DTXSID4063531- ChEMBL
CHEMBL3423442- UNII
- 5Z9X6MAT38
- EC Number
- 224-992-1
- Nikkaji
- J236.494H
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 51.7
Experimental & physicochemical properties
Physical DescriptionDry Powder
Physicochemical properties
- Melting point
- 67 · 67-73 °C (lit.)
- Boiling point
- 168 °C · 168°C(lit.)
- Density
- 1.6448 · 1.6448 (rough estimate)
- refractive index
- 1.526 · 1.5260 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Soluble in chloroform.
- form
- Crystalline Powder or Chunks
- pka
- 1.4 · 1.40±0.10(Predicted)
- color
- 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
- SMILES
- C1=NC=C(Br)C=N1
Safety & regulation
GHS classification
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.
Hazard information
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
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
Chemistry & industry
Uses & manufacturing
U.S. Production2023: 50,000 - <250,000 lb
Industry UsesIntermediate
General Manufacturing Information
Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing
Pyrimidine, 5-bromo-: ACTIVE
Applications
Description5-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.
Uses5-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.
Uses5-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 protocolIntermediate for the synthesis of plant growth regulator flurprimidol
General DescriptionRapid 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.
Preparation methods
Preparation5-Bromopyrimidine is prepared by reacting dibromodifuranone with formamide in the presence of B2O2 catalyst at 180-185°C to obtain the product.
Related reactions
610 records
Compound notes
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