5-Bromodeoxycytidine

Base Information

• Chemical Name: 5-Bromodeoxycytidine
• CAS No.: 1022-79-3
• Molecular Formula: C9H12BrN3O4
• Molecular Weight: 306.116
• Hs Code.: 29389090
• NSC Number: 61765
• Mol file: 1022-79-3.mol

Synonyms:5-Bromo-2/'-deoxycytidine;Brcdr;4-amino-5-bromo-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;BCDR;NSC-61765;NCIOpen2_007914;SCHEMBL12731448;BCP30995;NSC61765;C.A.S. 1,793;FT-0633254;WLN: T6N CNJ DZ EE F- BT5OTJ EO1

Chemical Property of 5-Bromodeoxycytidine

Chemical Property:

• Boiling Point: 510.81 °C at 760 mmHg
• PKA: 14.03±0.60(Predicted)
• Flash Point: 262.728 °C
• PSA: 110.60000
• Density: 2.13 g/cm³
• LogP: -0.19010
• Storage Temp.: Store at 0°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 305.00112
• Heavy Atom Count: 17
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

5-Bromo-2’-deoxycytidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1N2C=C(C(=NC2=O)N)Br)CO)O

Technology Process of 5-Bromodeoxycytidine

There total 3 articles about 5-Bromodeoxycytidine 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: 90.0%

2'-Deoxycytidine (951-77-9) → 5-bromo-2'-deoxycytidine (1022-79-3)

Guidance literature:

With N-Bromosuccinimide; acetic acid; at 20 ℃; for 0.333333h;

DOI:10.1039/c1ob06411h

Reference yield:

2'-Deoxycytidine (951-77-9) → 5-bromo-2'-deoxycytidine (1022-79-3) + 5-Hydroxy-2'-deoxycytidine (52278-77-0)

Guidance literature:

With ammonium bromide; peroxynitrite; In phosphate buffer; at 37 ℃; for 5h; pH=7.4;

DOI:10.1016/j.bmc.2008.03.007

Reference yield:

2'-deoxycytidine monohydrochloride (3992-42-5) → 5-bromo-2'-deoxycytidine (1022-79-3)

Guidance literature:

With bromine; In water; Ambient temperature;

DOI:10.1016/S0040-4039(98)01932-7

upstream raw materials:

2'-Deoxycytidine

2'-deoxycytidine monohydrochloride

Downstream raw materials:

4-N-benzoyl-5-bromo-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine

4-N-benzoyl-5-bromo-5'-O-(4,4'-dimethoxytrityl)-deoxycytidine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)

4-N-benzoyl-5-bromodeoxycytidine

2'-Deoxycytidine

Refernces

• 1、 Suzuki, Toshinori,Ida, Kazuya,Uchibe, Shinya,Inukai, Michiyo. "Reaction of 2′-deoxycytidine with peroxynitrite in the presence of ammonium bromide". . p. 5164 - 5170. Retrieved 2008.
• 2、 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.
• 3、 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.