6-Phenoxynicotinic Acid

Base Information

• Chemical Name: 6-Phenoxynicotinic Acid
• CAS No.: 51362-38-0
• Molecular Formula: C12H9 N O3
• Molecular Weight: 215.208
• Hs Code.: 2933399090
• European Community (EC) Number: 639-286-2
• DSSTox Substance ID: DTXSID70380129
• Nikkaji Number: J1.921.728K
• Wikidata: Q82170200
• Mol file: 51362-38-0.mol

Synonyms:6-Phenoxynicotinic Acid;51362-38-0;6-phenoxypyridine-3-carboxylic acid;3-Pyridinecarboxylic acid, 6-phenoxy-;MFCD02682068;SDCCGMLS-0066018.P001;6-phenoxy-nicotinic acid;SCHEMBL1271501;DTXSID70380129;CHEBI:167789;GFEUNYLQJDQNAN-UHFFFAOYSA-N;BCA36238;2-Phenoxypyridine-5-carboxylic acid;6-phenoxynicotinic acid, AldrichCPR;BBL029751;STK638254;AKOS000150599;AC-7136;PS-7938;6-(phenyloxy)-3-pyridinecarboxylic acid;SY004187;CS-0108679;FT-0621300;EN300-43572;A871301;J-518980;Z240115494

Chemical Property of 6-Phenoxynicotinic Acid

Chemical Property:

• Vapor Pressure: 8.03E-07mmHg at 25°C
• Melting Point: 164oC
• Boiling Point: 391.2oC at 760 mmHg
• PKA: 3.55±0.10(Predicted)
• Flash Point: 190.4oC
• PSA: 59.42000
• Density: 1.298g/cm3
• LogP: 2.57210
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 215.058243149
• Heavy Atom Count: 16
• Complexity: 238

Purity/Quality:

98%min ^*data from raw suppliers

6-PhenoxynictinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=NC=C(C=C2)C(=O)O

Technology Process of 6-Phenoxynicotinic Acid

There total 5 articles about 6-Phenoxynicotinic 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: 99.0%

5-cyano-2-phenoxypyridine (99902-72-4) → 6-phenoxynicotinic acid (51362-38-0)

Guidance literature:

With sodium hydroxide; water; for 2h; Heating;

DOI:10.1016/S0022-328X(03)00347-4

Reference yield:

6-phenoxynicotinic acid methyl ester (595576-44-6) → 6-phenoxynicotinic acid (51362-38-0)

Guidance literature:

With lithium hydroxide; In methanol; water;

DOI:10.1021/jm400275h

Reference yield:

6-Chloro-3-pyridinecarboxylic acid (5326-23-8) → 6-phenoxynicotinic acid (51362-38-0)

Guidance literature:

Multi-step reaction with 3 steps

1: diazomethyl-trimethyl-silane / toluene / 0.5 h

2: caesium carbonate; potassium carbonate / acetonitrile; N,N-dimethyl-formamide / Reflux

3: lithium hydroxide / methanol; water

With potassium carbonate; caesium carbonate; lithium hydroxide; diazomethyl-trimethyl-silane; In methanol; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jm400275h

upstream raw materials:

5-cyano-2-phenoxypyridine

6-Chloronicotinic acid methyl ester

6-phenoxynicotinic acid methyl ester

6-Chloro-3-pyridinecarboxylic acid

Downstream raw materials:

N-{(1S)-1-[[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]-methyl]-2-methylpropyl}-5-phenoxypyridine-2-carboxamide

ethyl 2-butyl-3-[4-[2-(2-phenoxypyridine-5-carbonylamino)ethoxy]phenyl]propionate

N-cyclopentyl-6-phenoxynicotinamide

N,N-dimethyl-6-phenoxynicotinamide

Refernces

• 1、 Kormos, Chad M.,Jin, Chunyang,Cueva, Juan Pablo,Runyon, Scott P.,Thomas, James B.,Brieaddy, Lawrence E.,Mascarella, S. Wayne,Navarro, Hernán A.,Gilmour, Brian P.,Carroll, F. Ivy. "Discovery of N-{4-[(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl-2- methylpropyl}-4-phenoxybenzamide analogues as selective kappa opioid receptor antagonists". . p. 4551 - 4567. Retrieved 2013/07/19.
• 2、 Zhu, Yongbao,Cameron, Beth R.,Skerlj, Renato T.. "Cycloauration of substituted 2-phenoxypyridine derivatives and X-ray crystal structure of gold, dichloro[2-[[5-[(cyclopentylamino) carbonyl]-2-pyridinyl-κN]oxy]phenyl-κC]-, (SP-4-3)-". . p. 57 - 72. Retrieved 2007/10/03.