5-Bromopyrimidine

Base Information

• Chemical Name: 5-Bromopyrimidine
• CAS No.: 4595-59-9
• Molecular Formula: C4H3BrN2
• Molecular Weight: 158.985
• Hs Code.: 2933.59
• European Community (EC) Number: 224-992-1
• UNII: 5Z9X6MAT38
• DSSTox Substance ID: DTXSID4063531
• Nikkaji Number: J236.494H
• Wikidata: Q72512190
• ChEMBL ID: CHEMBL3423442
• Mol file: 4595-59-9.mol

Synonyms:5-bromopyrimidine;5-BrPy compound

Chemical Property of 5-Bromopyrimidine

Chemical Property:

• Appearance/Colour: Yellow solid
• Vapor Pressure: 0.437mmHg at 25°C
• Melting Point: 69 °C
• Refractive Index: 1.568
• Boiling Point: 201.431 °C at 760 mmHg
• PKA: 1.40±0.10(Predicted)
• Flash Point: 75.623 °C
• PSA: 25.78000
• Density: 1.727 g/cm³
• LogP: 1.23910
• Storage Temp.: Keep Cold
• Solubility.: Soluble in chloroform.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 157.94796
• Heavy Atom Count: 7
• Complexity: 51.7

Purity/Quality:

99% ^*data from raw suppliers

5-Bromopyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(C=NC=N1)Br
• Uses: 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. 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 protocolIntermediate for the synthesis of plant growth regulator flurprimidol

Technology Process of 5-Bromopyrimidine

There total 10 articles about 5-Bromopyrimidine 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: 48.0%

mucobromic acid (766-38-1) + formamide (77287-34-4,77287-35-5,60100-09-6) → 5-bromopyrimidine (4595-59-9)

Guidance literature:

With boron trioxide; In methanol; at 180 - 185 ℃; for 15h;

Reference yield: 40.0%

5-bromo-4-(1-ethyl-1H-indol-3-yl)-3,4-dihydropyrimidin-1-ium tetrafluoroborate → 5-bromopyrimidine (4595-59-9) + N-Ethylindole (10604-59-8) + 3-(5-Bromopyrimidin-4-yl)-1-ethyl-1H-indole (1433688-86-8)

Guidance literature:

With potassium hydroxide; potassium hexacyanoferrate(III); In water; at 20 ℃; for 2h;

DOI:10.1002/ejoc.201201035

Reference yield: 40.0%

5-bromo-4-(1H-indol-3-yl)-3,4-dihydropyrimidin-1-ium tetrafluoroborate → 5-bromopyrimidine (4595-59-9) + indole (120-72-9) + 3-(5-bromopyrimidin-4-yl)-1H-indole (1433688-83-5) + 3-(pyrimidin-4-yl)-1H-indole (57826-98-9)

Guidance literature:

With potassium hydroxide; potassium hexacyanoferrate(III); In water; at 20 ℃; for 2h;

DOI:10.1002/ejoc.201201035

upstream raw materials:

5-bromo-2-pyrimidinecarboxylic acid

pyrimidine hydrochloride

mucobromic acid

formamide

Downstream raw materials:

5-bromo-4-(thiophen-2-yl)pyrimidine

5-(pyridine-2-yl)pyrimidine

pyrimidine-5-carboxylic acid

5-Pent-1-ynyl-pyrimidine

Refernces

• 1、 Fukumoto, Hiroki,Fujiwara, Yoshiki,Yamamoto, Takakazu. "Preparation of head-to-tail φ-conjugated poly(thiophenepyridine) and polypyrimidine by organometallic polycondensation". scheme or table. p. 992 - 994. Retrieved 2011/12/05.
• 2、 Kress, Thomas J.,Szymanski, Edward. "Pyrimidines From Furfural. A Convenient Synthesis of 5-Bromo- and 5-Chloropyrimidine". . p. 1721 - 1722. Retrieved 2007/10/02.