5-Bromo-2,2'-bipyridine

Base Information

• Chemical Name: 5-Bromo-2,2'-bipyridine
• CAS No.: 15862-19-8
• Molecular Formula: C10H7 Br N2
• Molecular Weight: 235.083
• Hs Code.: 2933399090
• European Community (EC) Number: 878-411-7
• DSSTox Substance ID: DTXSID50447305
• Nikkaji Number: J1.239.867K
• Mol file: 15862-19-8.mol

Synonyms:5-BROMO-2,2'-BIPYRIDINE;15862-19-8;5-Bromo-[2,2']bipyridinyl;2,2'-Bipyridine, 5-bromo-;5-bromo-2-pyridin-2-ylpyridine;5-Bromo-2,2/'-bipyridine;MFCD08234848;5-bromo-2,2'-bipyridyl;SCHEMBL40547;YSWG823;5-BROMO-2,2-BIPYRIDINE;AMY3434;DTXSID50447305;AWJPULCSDFBFDR-UHFFFAOYSA-N;5-bromo-2-(pyridin-2-yl)pyridine;AKOS015899554;CS-W004577;DS-6550;SB33961;SY096762;B6181;FT-0687521;F16786;10.14272/AWJPULCSDFBFDR-UHFFFAOYSA-N.1;5-Bromo-2,2 inverted exclamation mark -bipyridine;A853179;doi:10.14272/AWJPULCSDFBFDR-UHFFFAOYSA-N.1;J-400695

Chemical Property of 5-Bromo-2,2'-bipyridine

Chemical Property:

• Melting Point: 73 °C
• Boiling Point: 322.4±27.0 °C(Predicted)
• PKA: 3.55±0.22(Predicted)
• Flash Point: 148.8oC
• PSA: 25.78000
• Density: 1.493±0.06 g/cm3(Predicted)
• LogP: 2.90610
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 233.97926
• Heavy Atom Count: 13
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

5-Bromo-2,2'-bipyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=NC(=C1)C2=NC=C(C=C2)Br

Technology Process of 5-Bromo-2,2'-bipyridine

There total 20 articles about 5-Bromo-2,2'-bipyridine 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: 95.0%

2-iodo-5-bromopyridine (223463-13-6) + pyridin-2-ylzinc(II) bromide → 5-bromo-2,2'-bipyridyl (15862-19-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 75 ℃; for 18h;

DOI:10.1002/anie.201507295

Reference yield: 84.0%

2-bromo-pyridine (109-04-6) + 2,5-dibromopyridine (624-28-2) → 5-bromo-2,2'-bipyridyl (15862-19-8)

Guidance literature:

2-bromo-pyridine; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃;

With zinc(II) chloride; In tetrahydrofuran; at -78 - 20 ℃;

2,5-dibromopyridine; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 80 ℃;

DOI:10.1515/znb-2010-0316

Reference yield: 81.0%

2,5-dibromopyridine (624-28-2) + pyridin-2-ylzinc(II) bromide → 5-bromo-2,2'-bipyridyl (15862-19-8)

Guidance literature:

2,5-dibromopyridine; pyridin-2-ylzinc(II) bromide; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

With ethylenediaminetetraacetic acid; sodium carbonate; In tetrahydrofuran; water; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201605980

upstream raw materials:

tris(2-pyridyl)phosphine

tris(2-pyridyl)phosphine oxide

methanol

2,2'-bipyridine-5-carbonyl chloride

Downstream raw materials:

5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2’-bipyridine

5-(3',5'-di-pyridin-2-yl-biphenyl-4-yl)-[2,2']bipyridinyl

(2,2'-bipyridine)-5-carbonitrile

5-(4-bromophenyl)-2,2'-bipyridine

Refernces

• 1、 Chen, Guiting,Zhang, Fan,Liu, Meiyue,Song, Jun,Lian, Jiarong,Zeng, Pengju,Yip, Hin-Lap,Yang, Wei,Zhang, Bin,Cao, Yong. "Fabrication of high-performance and low-hysteresis lead halide perovskite solar cells by utilizing a versatile alcohol-soluble bispyridinium salt as an efficient cathode modifier". . p. 17943 - 17953. Retrieved 2017.
• 2、 Lehr, Marc,Paschelke, Tobias,Bendt, Victoria,Petersen, André,Pietsch, Lorenz,Harders, Patrick,McConnell, Anna J.. "Copper-Free One-Pot Sonogashira-Type Coupling for the Efficient Preparation of Symmetric Diarylalkyne Ligands for Metal-Organic Cages**". . p. 2728 - 2735. Retrieved 2021.
• 3、 Das, Nivedita,Bindra, Gurmeet Singh,Paul, Avishek,Vos, Johannes G.,Schulz, Martin,Pryce, Mary T.. "Enhancing Photocatalytic Hydrogen Generation: the Impact of the Peripheral Ligands in Ru/Pd and Ru/Pt Complexes". . p. 5330 - 5337. Retrieved 2017.
• 4、 Paul, Avishek,Das, Nivedita,Halpin, Yvonne,Vos, Johannes G.,Pryce, Mary T.. "Carboxy derivatised Ir(iii) complexes: synthesis, electrochemistry, photophysical properties and photocatalytic hydrogen generation". . p. 10423 - 10430. Retrieved 2015.
• 5、 Shi, Qi,Liu, Jiaxiang,Wang, Jia,Yang, Xiaohui,Zhang, Xingmei,Li, Shuna,Sun, Ping,Chen, Jin,Li, Beibei,Lü, Xingqiang. "Color-tunable white-light of binary tris-β-diketonate-(Dy3+, Gd3+ x) complexes’ blend under single wavelength excitation". . . Retrieved 2020.
• 6、 Uchida, Yuzuru,Oae, Shigeru. "Electrophilic substitutions on tris(pyridyl)phosphine". . p. 605 - 608. Retrieved 1996.
• 7、 Ma, Lihua,Guo, Song,Sun, Jifu,Zhang, Caishun,Zhao, Jianzhang,Guo, Huimin. "Green light-excitable naphthalenediimide acetylide-containing cyclometalated Ir(iii) complex with long-lived triplet excited states as triplet photosensitizers for triplet-triplet annihilation upconversion". . p. 6478 - 6488. Retrieved 2013.
• 8、 B?hm, Alexander,Bach, Thorsten. "Synthesis of Supramolecular Iridium Catalysts and Their Use in Enantioselective Visible-Light-Induced Reactions". . p. 1056 - 1060. Retrieved 2016.
• 9、 Das, Banibrata,Kandegedara, Ashoka,Xu, Liping,Antonio, Tamara,Stemmler, Timothy,Reith, Maarten E. A.,Dutta, Aloke K.. "A Novel Iron(II) Preferring Dopamine Agonist Chelator as Potential Symptomatic and Neuroprotective Therapeutic Agent for Parkinson's Disease". . p. 723 - 730. Retrieved 2017.
• 10、 Kirss, Rein,McCaskill, Emmett,Hua, Edward,Tongcharoensirikul, Pakamas,Olmsted, Sandra L.,Labaree, David,Hochberg, Richard B.. "Targeting the estrogen receptor with metal-carbonyl derivatives of estradiol Robert N. Hanson". . p. 1670 - 1673. Retrieved 2012.