6-Bromonicotinaldehyde

Base Information

• Chemical Name: 6-Bromonicotinaldehyde
• CAS No.: 149806-06-4
• Molecular Formula: C6H4BrNO
• Molecular Weight: 186.008
• Hs Code.: 29333990
• European Community (EC) Number: 629-088-4
• UNII: Y2CE2F6NUU
• ChEMBL ID: CHEMBL4463248
• DSSTox Substance ID: DTXSID70472119
• Nikkaji Number: J1.047.431K
• Wikidata: Q72511880
• Mol file: 149806-06-4.mol

Synonyms:6-Bromonicotinaldehyde;149806-06-4;2-Bromopyridine-5-carbaldehyde;6-bromopyridine-3-carbaldehyde;2-Bromo-5-formylpyridine;6-Bromo-3-pyridinecarboxaldehyde;2-bromopyridine-5-carboxaldehyde;6-bromopyridine-3-carboxaldehyde;3-pyridinecarboxaldehyde, 6-bromo-;6-bromo-pyridine-3-carbaldehyde;2-Bromo-5-pyridinecarboxaldehyde;MFCD04115419;6-Bromo-3-formylpyridine;2-Bromo-5-pyridinecarbaldehyde;6-bromo-nicotinaldehyde;3-formyl-6-bromopyridine;Y2CE2F6NUU;2-bromo-5-formyl-pyridine;SCHEMBL104184;6-bromo-3-pyridinecarbaldehyde;CHEMBL4463248;DTXSID70472119;6-bromo-pyridine-3-carboxaldehyde;PVUKGNBRJFTFNJ-UHFFFAOYSA-N;2-Bromo-pyridine-5-carboxaldehyde;6-Bromo-3-pyridine carboxaldehyde;BCP04709;CS-D0958;AKOS005255345;AC-2805;PB27654;PS-4860;6-Bromo-3-pyridinecarboxaldehyde, 95%;HY-32786;SY002969;AM20070058;B3491;FT-0630093;EN300-91110;W-201328

Chemical Property of 6-Bromonicotinaldehyde

Chemical Property:

• Appearance/Colour: light yellow cryst
• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 104-110 °C(lit.)
• Refractive Index: 1.619
• Boiling Point: 284.1 °C at 760 mmHg
• PKA: -1.01±0.10(Predicted)
• Flash Point: 125.6 °C
• PSA: 29.96000
• Density: 1.683 g/cm³
• LogP: 1.65660
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: Soluble in dichloromethane, ether, ethyl acetate and methanol.
• 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% ^*data from raw suppliers

6-Bromopyridine-3-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC=C1C=O)Br
• Uses: 2-Bromopyridine-5-carbaldehyde can be a useful synthetic intermediate A useful synthetic intermediate. 6-Bromonicotinaldehyde is used in wittig reaction. Hydrodehalogenation of 6-bromonicotinaldehyde to produce alcohol.

Technology Process of 6-Bromonicotinaldehyde

There total 18 articles about 6-Bromonicotinaldehyde 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%

2-bromo-5-(dibromomethyl) pyridine (154321-32-1) → 6-bromonicotinaldehyde (149806-06-4)

Guidance literature:

With calcium carbonate; In water; at 105 ℃; for 16h;

Reference yield: 86.62%

2,5-dibromopyridine (624-28-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 6-bromonicotinaldehyde (149806-06-4)

Guidance literature:

2,5-dibromopyridine; With isopropylmagnesium chloride; In tetrahydrofuran; at 10 ℃; for 11h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; for 1.5h; Temperature; Inert atmosphere;

Reference yield: 66.0%

2,5-dibromopyridine (624-28-2) + butyl magnesium bromide (693-04-9) → 6-bromonicotinaldehyde (149806-06-4)

Guidance literature:

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

upstream raw materials:

6-bromonicotinic acid

2-bromo-5-(dimorpholinomethyl)pyridine

2,5-dibromopyridine

N,N-dimethyl-formamide

Downstream raw materials:

(6-bromo-pyridin-3-yl)-(2-dimethoxymethyl-4,5-dimethoxy-phenyl)-methanol

2-bromo-5-[1,3]dioxolan-2-yl-pyridine

2-bromo-5-(hydroxymethyl)pyridine

3-(6-bromo-pyridin-3-yl)-acrylic acid methyl ester

Refernces

• 1、 Romero-Salguero, Francisco Jose,Lehn, Jean-Marie. "Synthesis of multitopic bidentate ligands based on alternating pyridine and pyridazine rings". . p. 859 - 862. Retrieved 1999.
• 2、 -. "Preparation method of 2-bromo-5-aldehyde pyridine". Paragraph 0025; 0031-0038. . Retrieved 2021/03/13.
• 3、 Jiang, Ying,Sun, Bing,Fang, Wan-Yin,Qin, Hua-Li. "A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2". supporting information. p. 3190 - 3194. Retrieved 2019/05/21.