5-Bromo-4,6-dimethylpyridine-3-carboxylic acid

Base Information

• Chemical Name: 5-Bromo-4,6-dimethylpyridine-3-carboxylic acid
• CAS No.: 93350-01-7
• Molecular Formula: C8H8BrNO2
• Molecular Weight: 230.05900
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID30427645
• Wikidata: Q72454987
• Mol file: 93350-01-7.mol

Synonyms:93350-01-7;5-Bromo-4,6-dimethyl-nicotinic acid;5-bromo-4,6-dimethylpyridine-3-carboxylic acid;5-BROMO-4,6-DIMETHYLNICOTINIC ACID;5-BROMO-4,6-DIMETHYLNICOTINICACID;SCHEMBL18299713;DTXSID30427645;AC9442;MFCD07366090;STL227801;AKOS000270435;SY261962;EN300-237970;F1957-0011

Chemical Property of 5-Bromo-4,6-dimethylpyridine-3-carboxylic acid

Chemical Property:

• Boiling Point: 346.0±42.0 °C(Predicted)
• PKA: 1.54±0.25(Predicted)
• PSA: 50.19000
• Density: 1.598±0.06 g/cm3(Predicted)
• LogP: 2.15910
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 228.97384
• Heavy Atom Count: 12
• Complexity: 186

Purity/Quality:

98%Min ^*data from raw suppliers

5-Bromo-4,6-dimethyl-nicotinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=NC=C1C(=O)O)C)Br

Technology Process of 5-Bromo-4,6-dimethylpyridine-3-carboxylic acid

There total 4 articles about 5-Bromo-4,6-dimethylpyridine-3-carboxylic 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: 79.0%

5-Bromo-3-cyano-4,6-dimethylpyridine (63644-86-0) → 5-bromo-4,6-dimethylpyridine-3-carboxylic acid (93350-01-7)

Guidance literature:

With water; potassium hydroxide; at 110 ℃; for 16h;

Reference yield:

5-bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (23819-87-6) → 5-bromo-4,6-dimethylpyridine-3-carboxylic acid (93350-01-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / POCl₃/PCl₅ / 8 h / Heating

2: 62 percent / 47percent aqueous HI/red phosphorus / 4 h / 140 °C

3: 4.5 g / KOH / H₂O / 72 h / Heating

With phosphorus; potassium hydroxide; phosphorus pentachloride; hydrogen iodide; trichlorophosphate; In water;

DOI:10.1021/jo00200a045

Reference yield:

3-Cyano-4,6-dimethyl-2(1H)-pyridon (769-28-8) → 5-bromo-4,6-dimethylpyridine-3-carboxylic acid (93350-01-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Bromine / acetic acid / 0.5 h

2: 86 percent / POCl₃/PCl₅ / 8 h / Heating

3: 62 percent / 47percent aqueous HI/red phosphorus / 4 h / 140 °C

4: 4.5 g / KOH / H₂O / 72 h / Heating

With phosphorus; potassium hydroxide; phosphorus pentachloride; hydrogen iodide; bromine; trichlorophosphate; In water; acetic acid;

DOI:10.1021/jo00200a045

upstream raw materials:

5-Bromo-3-cyano-4,6-dimethylpyridine

5-bromo-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

3-Cyano-4,6-dimethyl-2(1H)-pyridon

6-chloro-3-bromo-2,4-dimethylpyridine-5-carbonitrile

Downstream raw materials:

5-(4-butoxy-3-{[2-fluoro-4-(trifluoromethyl)phenylamido]methyl}phenyl)-4,6-dimethylpyridine-3-carboxylic acid

Methyl 4,6-Dimethyl-5-phenylnicotinate

Refernces

• 1、 Thompson, Wayne J.,Gaudino, John. "A General Synthesis of 5-Arylnicotinates". . p. 5237 - 5243. Retrieved 2007/10/02.