2240-25-7

Basic information

• Product Name: 6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE
• Synonyms: TIMTEC-BB SBB000280;5-BROMOCYTOSINE;6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE;2(1H)-Pyrimidinone, 4-amino-5-bromo-;4-amino-5-bromo-2(1h)-pyrimidinon;4-Amino-5-bromo-2(1H)-pyrimidinone;4-Amino-5-bromo-2-hydroxypyrimidine;5-BROMOCYTOSINE CRYSTALLINE
• CAS NO: 2240-25-7
• Molecular Formula: C₄H₄BrN₃O
• Molecular Weight: 190
• EINECS: 218-806-8
• Mol File: 2240-25-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 240-243 °C (dec.)(lit.)
• Appearance: White to yellow/Solid
• Density: 1.7513 (rough estimate)
• Refractive Index: 1.6520 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in formic acid (50 mg/ml).
• PKA: 7.34±0.10(Predicted)
• BRN: 127286
• CAS DataBase Reference: 6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE(2240-25-7)
• EPA Substance Registry System: 6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE(2240-25-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41-43-48-20/21/22
• Safety Statements: 24/25-22-36/37/39-26-45-7/8
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 2240-25-7(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT YELLOW AMORPHOUS POWDER

Uses

Different sources of media describe the Uses of 2240-25-7 differently. You can refer to the following data:
1. 4-Amino-5-bromo-2-hydroxypyrimidine can be used in the synthesis of cross-link products under anaerobic and aerobic conditions.
2. 5-Bromocytosine was used in the synthesis of five cross-link products- C[5-N6]A, C[5-2]A, C[5-8]A, A[2-5]C, and A[8-5]C, under both aerobic and anaerobic conditions.

General Description

5-Bromocytosine derivative (β isomer) is a potent anti-HIV agent.

Purification Methods

5-Bromocytosine is recrystallised from H2O or 50% aqueous EtOH. Alternatively, dissolve ca 3g in conc HCl (10mL) and evaporate to dryness. Dissolve the residual hydrochloride in the minimum volume of warm H2O and make faintly alkaline with aqueous NH3. Collect the crystals and dry them in a vacuum at 100o. [Hilbdert & Jensen J Am Chem Soc 56 134 1934, Beilstein 25 III/IV 3689.]

InChI:InChI=1/C4H4BrN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)

Upstream product

• 71-30-7 6-amino-2-hydroxypyrimidine 
• 71-30-7 cytosine 
• 71-30-7 Cytosine 
• 148214-56-6 5-bromo-2-methoxypyrimidin-4-amine 

Downstream Products

• 71-30-7 Cytosine 
• 1432446-11-1 C₁₂H₇BrClN₃O 
• 1220533-01-6 C₂₈H₂₈BrN₃O₅ 
• 6312-73-8 6-amino-5-bromo-2,4(1H,3H)-pyrimidinedione 
• 255818-55-4 5-bromo-1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-L-threo-pentofuranosyl)cytosine 
• 199486-81-2 N-1-(p-toluenesulfonyl)cytosine 
• 197452-35-0 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-5-bromocytosine 
• 197452-36-1 1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-5-bromocytosine 

Relevant articles and documents

Synthesis of [2-14C,5-3H]cytosine and [2-14C,5-3H]uracil via bromination and catalytic bromine-tritium gas exchange

In micro-scale experiments, [2-14C,5-3H]cytosine and [2-14C,5-3H]uracil were synthesized via bromination and catalytic Br-3H exchange reaction with the use of [2-14C]cytosine and -uracil and tritium gas. The double labelling percentages of these products were 70 and 26, respectively. It was assumed that [2-14C,5-Br]uracil was subjected to reaction with hydrogen atom originally adsorbed on a palladium catalyst. This is to a lesser extent valid for [2-14C,5-Br]cytosine. The percentages of 3H labelling at 5 position of pyrimidine ring of cytosine and uracil were proved to be 96 and 73, respectively. For the analysis and purification of products, the HPLC eluting conditions using C18 reverse column and NaH2PO4 aqueous solution or H2O/methanol mixture as eluent were studied. Unreacted tritium gas was recovered with the use of adsorbents such as active charcoal and Zr-V-Fe getter.

Synthesis, structure and rearrangement of iodinated imidazo[1,2-c]pyrimidine-5(6H)-ones derived from cytosine

We describe mild and selective iodination of various 8-substituted imidazo[1,2-c]pyrimidine-5(6H)-ones (ethenocytosines). Starting ethenocytosines were obtained by cyclization of 5-halogenocytosines with chloroacetaldehyde or by subsequent Suzuki-Miyaura

IMIDAZO[1,2-C]PYRIMIDINE DERIVATIVES AS PRC2 INHIBITORS FOR TREATING CANCER

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