5-Bromo-4-methylnicotinic acid

Base Information

• Chemical Name: 5-Bromo-4-methylnicotinic acid
• CAS No.: 677702-58-8
• Molecular Formula: C7H6BrNO2
• Molecular Weight: 216.03200
• Hs Code.: 2933399090
• European Community (EC) Number: 695-260-0
• DSSTox Substance ID: DTXSID50427647
• Nikkaji Number: J3.476.580D
• Wikidata: Q82240300
• Mol file: 677702-58-8.mol

Synonyms:5-BROMO-4-METHYLNICOTINIC ACID;677702-58-8;5-bromo-4-methylpyridine-3-carboxylic acid;MFCD07439973;5-bromo-4-methyl-pyridine-3-carboxylic Acid;SCHEMBL4518189;5-bromo-4-methyl-nicotinic acid;DTXSID50427647;RLENEIYXKWSGEX-UHFFFAOYSA-N;CCB70258;5-BROMO-4-METHYLNICOTINICACID;AKOS002666149;PB43264;AS-60296;SY162822;4-Methyl-5-bromopyridine-3-carboxylic acid;CS-0046901;EN300-187822;A849308;F1957-0022;Z1269195042

Chemical Property of 5-Bromo-4-methylnicotinic acid

Chemical Property:

• PSA: 50.19000
• LogP: 1.85070
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 214.95819
• Heavy Atom Count: 11
• Complexity: 163

Purity/Quality:

97% purity ^*data from raw suppliers

5-Bromo-4-methylnicotinicAcid ^*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)Br

Technology Process of 5-Bromo-4-methylnicotinic acid

There total 2 articles about 5-Bromo-4-methylnicotinic 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: 53.0%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + carbon dioxide (124-38-9,18923-20-1) → 5-bromo-4-methylpyridine-3-carboxylic acid (677702-58-8)

Guidance literature:

3,5-dibromo-4-methyl-pyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 1h;

Reference yield:

carbon dioxide (124-38-9,18923-20-1) → 5-bromo-4-methylpyridine-3-carboxylic acid (677702-58-8)

Guidance literature:

3,5-dibromo-4-methyl-pyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -100 ℃; for 0.25h;

carbon dioxide; In tetrahydrofuran; hexane; at -85 - 20 ℃; for 3.5h;

Reference yield:

5-bromo-4-methylpyridine-3-carboxylic acid (677702-58-8) → (rac)-4-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile (1469978-59-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

2.2: 1.75 h / Inert atmosphere

3.1: hydrogenchloride / water / 2.5 h / Inert atmosphere; Reflux

4.1: titanium(IV) isopropylate; ammonia / methanol / 5 h / 20 °C / Inert atmosphere

4.2: 2.17 h / 20 °C / Inert atmosphere

5.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; ethanol / 85 °C / Inert atmosphere

With titanium(IV) isopropylate; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ammonia; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; 5.1: |Suzuki Coupling;

upstream raw materials:

carbon dioxide

3,5-dibromo-4-methyl-pyridine

Downstream raw materials:

(rac)-4-(8-amino-5,6,7,8-tetrahydroisoquinolin-4-yl)benzonitrile

(rac)-N-(4-(4-cyanophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)ethanesulfonamide

(rac)-N-[4-(4-cyanophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl]-N'-propylsulfuric diamide

(rac)-1-(4-(4-cyanophenyl)-5,6,7,8-tetrahydroisoquinolin-8-yl)-3-ethylurea

Refernces

• 1、 -. "Indazolecarboxamide derivatives, preparation and use thereof as CDK1, CDK2 and CDK4 inhibitors". Page/Page column 20. . Retrieved 2008/06/13.