5-Bromocytidine

Base Information

• Chemical Name: 5-Bromocytidine
• CAS No.: 3066-86-2
• Molecular Formula: C₉H₁₂BrN₃O₅
• Molecular Weight: 322.115
• Hs Code.: 2934999090
• European Community (EC) Number: 878-375-2
• DSSTox Substance ID: DTXSID40430887
• Nikkaji Number: J258.983D
• Wikidata: Q82244622
• ChEMBL ID: CHEMBL217543
• Mol file: 3066-86-2.mol

Synonyms:5-bromocytidine;3066-86-2;4-AMINO-5-BROMO-1-[(2R,3R,4S,5R)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]PYRIMIDIN-2-ONE;4-amino-5-bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;Cytidine, 5-bromo-;C9H12BrN3O5;5-Bromo-D-cytidine;SCHEMBL114750;CHEMBL217543;DTXSID40430887;AMY41844;MFCD00057461;AKOS016009470;DS-5637;AC-32306;BP-58608;B4165;CS-0041014;A848615;J-700331;4-amino-5-bromo-1-((2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

Chemical Property of 5-Bromocytidine

Chemical Property:

• Melting Point: 183-185 °C
• Boiling Point: 555.408 °C at 760 mmHg
• PKA: 13.48±0.70(Predicted)
• Flash Point: 289.701 °C
• PSA: 130.83000
• Density: 2.284 g/cm³
• LogP: -1.21930
• Storage Temp.: 2-8°C
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 320.99603
• Heavy Atom Count: 18
• Complexity: 426

Purity/Quality:

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

5-Bromocytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=NC(=O)N1C2C(C(C(O2)CO)O)O)N)Br
• Isomeric SMILES: C1=C(C(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N)Br
• Description: 5-Bromocytidine is a pyrimidine nucleoside. 5-Bromocytidine is used in the synthesis of substituted cytidine analogs identification of potent inhibitor of viral rnadependent RNA polymerases and has been shown to inhibit the replication of influenza virus in cell culture.

Technology Process of 5-Bromocytidine

There total 3 articles about 5-Bromocytidine 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: 92.0%

CYTIDINE (65-46-3) → 5-bromocytidine (3066-86-2,17676-66-3)

Guidance literature:

With pyridine; bromine; In tetrachloromethane; at 20 ℃; Cooling with ice;

DOI:10.1039/c4ob00597j

Reference yield:

O2',O3',O5'-triacetyl-5-bromo-cytidine (58629-98-4) → 5-bromocytidine (3066-86-2,17676-66-3)

Guidance literature:

With ammonia;

DOI:10.1021/ja01614a010

Reference yield:

→ 5-bromocytidine (3066-86-2,17676-66-3)

Guidance literature:

Cytidin, Br2;

DOI:10.1021/jo00929a009

upstream raw materials:

O^2'_,O3'_,O5'-triacetyl-5-bromo-cytidine

CYTIDINE

Downstream raw materials:

5-[4'-methoxybenzylsulfanyl]-O^2',O^3',O^5',N⁴-tetrapivaloylcytidine

CYTIDINE

4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(4-methoxystyryl)pyrimidin-2(1H)-one

4-amino-1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(4-(trifluoromethyl)styryl)pyrimidin-2(1H)-one

Refernces

• 1、 Maity, Jyotirmoy,Stromberg, Roger. "An efficient and facile methodology for bromination of pyrimidine and purine nucleosides with sodium monobromoisocyanurate (SMBI)". . p. 12740 - 12750. Retrieved 2013/11/06.
• 2、 Kumar, Vineet,Yap, Jeremy,Muroyama, Andrew,Malhotra, Sanjay V.. "Highly efficient method for C-5 halogenation of pyrimidine-based nucleosides in ionic liquids". experimental part. p. 3957 - 3962. Retrieved 2010/03/26.