5-Bromocytosine

Base Information

• Chemical Name: 5-Bromocytosine
• CAS No.: 2240-25-7
• Molecular Formula: C4H4BrN3O
• Molecular Weight: 189.999
• Hs Code.: 29335990
• European Community (EC) Number: 218-806-8
• UNII: 2737MSZ714
• DSSTox Substance ID: DTXSID60176932
• Nikkaji Number: J209.448G
• Wikidata: Q27254159
• ChEMBL ID: CHEMBL184965
• Mol file: 2240-25-7.mol

Synonyms:5-bromocytosine

Chemical Property of 5-Bromocytosine

Chemical Property:

• Appearance/Colour: slightly yellow
• Melting Point: 240-243 °C (dec.)(lit.)
• Refractive Index: 1.765
• PKA: 7.34±0.10(Predicted)
• PSA: 72.03000
• Density: 2.25 g/cm³
• LogP: 1.10810
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in formic acid (50 mg/ml).
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 188.95377
• Heavy Atom Count: 9
• Complexity: 208

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Bromocytosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• 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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=O)NC(=C1Br)N
• Uses: 4-Amino-5-bromo-2-hydroxypyrimidine can be used in the synthesis of cross-link products under anaerobic and aerobic conditions. 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.

Technology Process of 5-Bromocytosine

There total 12 articles about 5-Bromocytosine 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: 95.6%

Cytosine (71-30-7) → 5-bromocytosine (2240-25-7)

Guidance literature:

With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 15 ℃; for 1h; Reagent/catalyst; Solvent; Sonication;

Reference yield: 73.0%

5-bromocytosine hydrobromide → 5-bromocytosine (2240-25-7)

Guidance literature:

With sodium carbonate; In water;

DOI:10.1016/j.tet.2014.11.049

Reference yield: 56.0%

6-amino-2-hydroxypyrimidine (71-30-7,66460-21-7) → 6-amino-5-bromo-1H-pyrimidin-2-one (2240-25-7)

Guidance literature:

With bromine; In water; at 20 ℃; for 1h;

DOI:10.1016/j.ejmech.2007.07.015

upstream raw materials:

5-bromo-2-methoxypyrimidin-4-amine

Cytosine

cytosine

6-amino-2-hydroxypyrimidine

Downstream raw materials:

Cytosine

C₁₂H₇BrClN₃O

C₂₈H₂₈BrN₃O₅

6-amino-5-bromo-2,4(1H,3H)-pyrimidinedione

Refernces

• 1、 Itahara,Ide. "Myeloperoxidase catalyzed bromination of nucleic acid bases and related compounds". . p. 3750 - 3751. Retrieved 1989.
• 2、 Yang, Yifei,Chen, Pan,Zhao, Leilei,Zhang, Fangqing,Zhang, Bing,Xu, Changliang,Zhang, Huibin,Zhou, Jinpei. "Exploiting the 7-methylimidazo[1,5-a]pyrazin-8(7H)-one scaffold for the development of novel chemical inhibitors for Bromodomain and Extraterminal Domain (BET) family". . . Retrieved 2019.
• 3、 -. "CYTOSINE-BASED TET ENZYME INHIBITORS". Paragraph 0174; 0175. . Retrieved 2020/11/24.
• 4、 -. "PRC2 INHIBITORS". Paragraph 0145; 0148-0150. . Retrieved 2019/08/26.