2-Bromo-3-formylpyridine

Base Information

• Chemical Name: 2-Bromo-3-formylpyridine
• CAS No.: 128071-75-0
• Molecular Formula: C6H4BrNO
• Molecular Weight: 186.008
• Hs Code.: 29333990
• European Community (EC) Number: 629-308-9
• DSSTox Substance ID: DTXSID20405795
• Nikkaji Number: J1.560.711D
• Wikidata: Q72511896
• ChEMBL ID: CHEMBL4473237
• Mol file: 128071-75-0.mol

Synonyms:2-bromo-3-pyridinecarboxaldehyde

Chemical Property of 2-Bromo-3-formylpyridine

Chemical Property:

• Vapor Pressure: 0.00802mmHg at 25°C
• Melting Point: 73 °C
• Refractive Index: 1.619
• Boiling Point: 267.7 °C at 760 mmHg
• PKA: -1.01±0.10(Predicted)
• Flash Point: 115.7 °C
• PSA: 29.96000
• Density: 1.683 g/cm³
• LogP: 1.65660
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 184.94763
• Heavy Atom Count: 9
• Complexity: 107

Purity/Quality:

99.0%, High purity. ^*data from raw suppliers

2-Bromonicotinaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36-43
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(N=C1)Br)C=O

Technology Process of 2-Bromo-3-formylpyridine

There total 14 articles about 2-Bromo-3-formylpyridine 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: 85.0%

2-bromo-pyridine (109-04-6) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-bromopyridine-3-carboxaldehyde (128071-75-0)

Guidance literature:

2-bromo-pyridine; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 3h;

N,N-dimethyl-formamide; In tetrahydrofuran; at -78 ℃; for 1h; Further stages.;

DOI:10.1016/j.tetlet.2008.02.112

Reference yield: 83.0%

2-bromo-3-(dibromomethyl)-pyridine (865449-15-6) → 2-bromopyridine-3-carboxaldehyde (128071-75-0)

Guidance literature:

With calcium carbonate; In water; for 8h; Heating;

DOI:10.1016/j.tetlet.2005.07.016

Reference yield: 83.0%

(2-bromopyrid-3-yl)methanol (131747-54-1) → 2-bromopyridine-3-carboxaldehyde (128071-75-0)

Guidance literature:

With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; for 1.5h; Ambient temperature;

DOI:10.1248/cpb.38.2446

upstream raw materials:

2-bromo-pyridine

N,N-dimethyl-formamide

2,6-Dibromopyridine

2,4-dibromopyridine

Downstream raw materials:

2-{4-(2-methoxymethylphenyl)buta-1,3-diynyl}pyridine-3-carbaldehyde

8-(2-bromo-pyridin-3-ylmethyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one

1-phenyl-1H-pyrazolo[3,4-b]pyridine

1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester

Refernces

• 1、 Wang,Snieckus. "Synthetic strategies based on aromatic metalation - Cross coupling links. A concise formal synthesis of the azaphenanthrene alkaloid eupolauramine". . p. 4883 - 4884. Retrieved 1991.
• 2、 Melnyk,Gasche,Thal. "Improved synthesis of 2-bromonicotin-aldehyde and acid". . p. 2727 - 2730. Retrieved 1993.
• 3、 Boutin, Jean A.,Bouillaud, Frederic,Janda, Elzbieta,Gacsalyi, István,Guillaumet, Gérald,Hirsch, Etienne C.,Kane, Daniel A.,Nepveu, Fran?oise,Reybier, Karine,Dupuis, Philippe,Bertrand, Marc,Chhour, Monivan,Le Diguarher, Thierry,Antoine, Mathias,Brebner, Karen,Da Costa, Hervé,Ducrot, Pierre,Giganti, Adeline,Goswami, Vishalgiri,Guedouari, Hala,Michel, Patrick P.,Patel, Aakash,Paysant, Jér?me,Stojko, Johann,Viaud-Massuard, Marie-Claude,Ferry, Gilles. "S29434, a quinone reductase 2 inhibitor: Main biochemical and cellular characterization". supporting information. p. 269 - 285. Retrieved 2019/05/14.
• 4、 Castelló-Micó, Alicia,Knochel, Paul. "Zincation and Magnesiation of Functionalized Silylated Cyanohydrins Using TMP-Bases". . p. 155 - 169. Retrieved 2017/10/07.