5-Bromonicotinic acid

Base Information

• Chemical Name: 5-Bromonicotinic acid
• CAS No.: 20826-04-4
• Molecular Formula: C6H4BrNO2
• Molecular Weight: 202.007
• Hs Code.: 2933.39
• European Community (EC) Number: 244-065-5
• NSC Number: 9461
• UNII: ZDB972TSH7
• DSSTox Substance ID: DTXSID70174944
• Nikkaji Number: J28.111E
• Wikipedia: 5-bromonicotinic acid
• Wikidata: Q63392865
• ChEMBL ID: CHEMBL247336
• Mol file: 20826-04-4.mol

Synonyms:5-bromo-3-pyridinecarboxylic acid;5-bromonicotinic acid

Chemical Property of 5-Bromonicotinic acid

Chemical Property:

• Appearance/Colour: Light yellow cryst.
• Vapor Pressure: 7.59E-05mmHg at 25°C
• Melting Point: 178-180 °C(lit.)
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 328.535 °C at 760 mmHg
• PKA: 3.08±0.10(Predicted)
• Flash Point: 152.5 °C
• PSA: 50.19000
• Density: 1.814 g/cm³
• LogP: 1.54230
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 200.94254
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

99% min ^*data from raw suppliers

5-Bromopyridine-3-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=NC=C1Br)C(=O)O
• Uses: 5-Bromopyridine-3-carboxylic acid (5-bromonicotinic acid) was used in the synthesis of 3-guanidinomethyl-5-iodopyridine.

Technology Process of 5-Bromonicotinic acid

There total 14 articles about 5-Bromonicotinic acid 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%

5-bromonicotinamide (28733-43-9) → 5-bromo-3-pyridinecarboxylic acid (20826-04-4)

Guidance literature:

With acetic acid; isopentyl nitrite; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.05.054

Reference yield: 94.0%

3-pyridinecarbonyl chloride (10400-19-8) → 5-bromo-3-pyridinecarboxylic acid (20826-04-4)

Guidance literature:

With bromine; at 0 - 155 ℃; for 10h;

Reference yield: 91.0%

5-bromo-3-pyridine carboxylic acid methyl ester (29681-44-5) → 5-bromo-3-pyridinecarboxylic acid (20826-04-4)

Guidance literature:

With potassium hydroxide; In methanol; water; for 12h; Ambient temperature;

DOI:10.1016/S0957-4166(00)82187-4

upstream raw materials:

3,5-dibromopyridine

nicotinic acid

3-bromoquinoline

5-Bromo-pyridine-2,3-dicarboxylic acid

Downstream raw materials:

3-bromo-5-(ethoxycarbonyl)aminopyridine

(5-bromopyridin-3-yl)methanol

5-(3-fluorophenyl)pyridine-3-carboxylic acid

nicotinic acid

Refernces

• 1、 Gabor,Hamilton,Pittner. "Drug-protein conjugates: Haptenation of 1-methyl-10α- methoxydihydrolysergol and 5-bromonicotinic acid to albumin for the production of epitope-specific monoclonal antibodies against nicergoline". . p. 1120 - 1125. Retrieved 1995.
• 2、 Potter, Garrett T.,Jayson, Gordon C.,Miller, Gavin J.,Gardiner, John M.. "Amyl nitrite-mediated conversion of aromatic and heteroaromatic primary amides to carboxylic acids". supporting information. p. 5153 - 5156. Retrieved 2015/08/19.
• 3、 Meier, Peter,Legraverant, Stephanie,Mueller, Sascha,Schaub, Josette. "Synthesis of formylphenylpyridinecarboxylic acids using Suzuki-Miyaura coupling reactions". . p. 551 - 554. Retrieved 2007/10/03.