6-Bromopyridine-2-carbaldehyde

Base Information

• Chemical Name: 6-Bromopyridine-2-carbaldehyde
• CAS No.: 34160-40-2
• Molecular Formula: C6H4BrNO
• Molecular Weight: 186.008
• Hs Code.: 29333990
• DSSTox Substance ID: DTXSID10373691
• Nikkaji Number: J725.217J
• Wikidata: Q72511887
• ChEMBL ID: CHEMBL4560858
• Mol file: 34160-40-2.mol

Synonyms:6-bromopyridine-2-carbaldehyde;34160-40-2;6-Bromo-2-pyridinecarboxaldehyde;6-bromopicolinaldehyde;6-Bromopyridine-2-carboxaldehyde;6-Bromo-2-formylpyridine;6-bromo-pyridine-2-carbaldehyde;2-bromo-6-formylpyridine;2-Pyridinecarboxaldehyde, 6-bromo-;MFCD02683546;6-Bromo-2-Pyridine Carboxaldehyde;6-Bromopicoline aldehyde;2-formyl-6-bromopyridine;6-bromo-2-pyridinealdehyde;6-bromopyridine-2-aldehyde;6-Bromo-2-formyl-pyridine;6-bromo-2-pyridine aldehyde;SCHEMBL104173;2-bromopyridine-6-formaldehyde;6-bromo-2-pyridinecarbaldehyde;6-Bromo-pyridin-2-carbaldehyde;6-bromopyridine-2-caboxaldehyde;6-bromopyridine-2-carboaldehyde;6-bromo-2-pyridine carbaldehyde;CHEMBL4560858;(6-bromo-2-pyridyl)formaldehyde;2-bromo-6-pyridinecarboxaldehyde;DTXSID10373691;6-bromo pyridine-2-carboxaldehyde;6-bromo-2-pyridine-carboxaldehyde;6-bromo-pyridine-2-carboxaldehyde;QWFHFNGMCPMOCD-UHFFFAOYSA-N;(6-bromo-2-pyridyl)-formaldehyde;BCP14423;CS-D0741;BBL011062;GEO-00567;STK802241;AKOS005257664;AC-5124;AS-5650;PB27582;6-Bromo-2-pyridinecarboxaldehyde, 97%;SY005343;A6023;AM20051089;B3716;BB 0305529;FT-0621004;EN300-107792;W-200313

Chemical Property of 6-Bromopyridine-2-carbaldehyde

Chemical Property:

• Appearance/Colour: Light yellow flakes
• Vapor Pressure: 0.0246mmHg at 25°C
• Melting Point: 81-85 °C(lit.)
• Refractive Index: 1.619
• Boiling Point: 248.2 °C at 760 mmHg
• PKA: 1.00±0.10(Predicted)
• Flash Point: 103.9 °C
• PSA: 29.96000
• Density: 1.683 g/cm³
• LogP: 1.65660
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Sparingly), Dichloromethane, Ether, Ethyl Acetate, Methanol (Slightl
• Water Solubility.: Soluble in dichloromethane, ether, ethyl acetate and methanol. Insoluble in water.
• XLogP3: 1.7
• 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% ^*data from raw suppliers

6-Bromopyridine-2-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi, F
• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-20/21/22-10
• Safety Statements: 26-36-36/37/39-16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC(=C1)Br)C=O
• Uses: 6-Bromopyridine-2-carbaldehyde can be a useful synthetic intermediate. 6-Bromopyridine-2-carboxaldehyde is used in the study of a rhodium-catalyzed, reductive aldol coupling with divinyl ketones leading to syn ?-hydroxyenones. It is also used as a building block for Tris[(pyridyl)methyl]amine ligands.

Technology Process of 6-Bromopyridine-2-carbaldehyde

There total 19 articles about 6-Bromopyridine-2-carbaldehyde 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: 98.0%

2-bromo-6-(hydroxymethyl)pyridine (33674-96-3) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Guidance literature:

With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide; at 20 ℃; for 12h; chemoselective reaction;

DOI:10.1002/adsc.201900104

Reference yield: 97.0%

2,6-Dibromopyridine (626-05-1) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Guidance literature:

2,6-Dibromopyridine; With n-butyllithium; butyl magnesium bromide; In tetrahydrofuran; hexane; toluene; at -10 - -5 ℃; for 3.5h;

N,N-dimethyl-formamide; In tetrahydrofuran; hexane; toluene; at -10 - -5 ℃; for 0.5h; Further stages.;

DOI:10.1021/jo0157425

Reference yield: 95.0%

2,6-Dibromopyridine (626-05-1) + n-butyllithium (109-72-8,29786-93-4) + butyl magnesium bromide (693-04-9) → 6-bromo-2-pyridinecarbaldehyde (34160-40-2)

Guidance literature:

With acetic acid; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

2-bromo-6-(hydroxymethyl)pyridine

2,6-Dibromopyridine

N,N-dimethyl-formamide

2-(6-bromopyridinyl)lithium

Downstream raw materials:

6-bromo-2-(1,3-dioxolan-2-yl)pyridine

(+/-)-1-[2-(6-bromopyridyl)]ethanol

2-bromo-6-(hydroxymethyl)pyridine

6-phenylpyridine-2-carbaldehyde

Refernces

• 1、 Parks et al.. "-". . p. 2472,2473. Retrieved 1971.
• 2、 Haseloer, Alexander,Denkler, Luca Mareen,Jordan, Rose,Reimer, Max,Olthof, Selina,Schmidt, Ines,Meerholz, Klaus,H?rner, Gerald,Klein, Axel. "Ni, Pd, and Pt complexes of a tetradentate dianionic thiosemicarbazone-based O^N^N^S ligand". . p. 4311 - 4322. Retrieved 2021/04/06.
• 3、 Zha, Gao-Feng,Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li. "A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant". supporting information. p. 2262 - 2267. Retrieved 2019/04/17.