3-CYANO-4-ISOPROPOXYBENZOIC ACID

Base Information

• Chemical Name: 3-CYANO-4-ISOPROPOXYBENZOIC ACID
• CAS No.: 258273-31-3
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• Hs Code.: 2926909090
• Mol file: 258273-31-3.mol

Synonyms:3-Cyano-4-[(1-methylethyl)oxy]benzoicacid;3-Cyano-4-isopropoxybenzoic acid;3-Cyano-4-isopropyloxybenzoic acid;

Chemical Property of 3-CYANO-4-ISOPROPOXYBENZOIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.551
• Boiling Point: 371.39 °C at 760 mmHg
• PKA: 4.09±0.10(Predicted)
• Flash Point: 178.41 °C
• PSA: 70.32000
• Density: 1.231 g/cm³
• LogP: 2.04368
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%, ^*data from raw suppliers

3-Cyano-4-isopropoxybenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 3-Cyano-4-isopropoxybenzoic Acid is a useful reagent in the preparation of cyanoaryloxadiazolyl-substituted nitrogen heterocycles as S1P3-sparing agonists of sphingosine phosphate receptors S1P1 and S1P5 for treatment of multiple sclerosis and their pharmacokinetics and side effect profiles. Preparayion and SAR of biaryl oxadiazoles as S1P1 receptor agonists.

Technology Process of 3-CYANO-4-ISOPROPOXYBENZOIC ACID

There total 13 articles about 3-CYANO-4-ISOPROPOXYBENZOIC 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: 92.0%

methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate (213598-11-9) → 3-cyano-4-isopropoxybenzoic acid (258273-31-3)

Guidance literature:

methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate; With ethanol; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 4h;

With hydrogenchloride; In tetrahydrofuran; water;

Reference yield:

1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate (1261173-10-7) → 3-cyano-4-isopropoxybenzoic acid (258273-31-3)

Guidance literature:

1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate; With water; lithium hydroxide; In 1,4-dioxane; at 30 ℃; for 1.5h;

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃;

Reference yield:

methyl 4-hydroxylbenzoate (99-76-3,156291-94-0) → 3-cyano-4-isopropoxybenzoic acid (258273-31-3)

Guidance literature:

Multi-step reaction with 4 steps

1: Iodine monochloride; acetic acid / 20 - 65 °C

2: sodium cyanide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere

3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere

4: sodium hydroxide / methanol / 16 h / 20 °C

With Iodine monochloride; potassium carbonate; acetic acid; sodium hydroxide; sodium cyanide; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

methyl 3-cyano-4-[(1-methylethyl)oxy]benzoate

3-bromo-4-hydroxy-benzoic acid

1-methylethyl 3-bromo-4-[(1-methylethyl)oxy]benzoate

1-methylethyl 3-cyano-4-[(1-methylethyl)oxy]benzoate

Downstream raw materials:

2-isopropoxy-5-[3-(2-methyl-4-vinyl-phenyl)-[1,2,4]oxadiazol-5-yl]-benzonitrile

tert-butyl 3-(5-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-6-methylpyridin-2-yl)propanoate

ethyl 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoate

ethyl 3-[4-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoate

Refernces

• 1、 -. "Method for preparing 3-cyano-4-isopropoxybenzoic acid". Paragraph 0022. . Retrieved 2017/08/29.
• 2、 -. "OXADIAZOLE SUBSTITUTED INDAZOLE DERIVATIVES FOR USE AS SPHINGOSINE 1-PHOSPHATE 1 (S1P1) RECEPTOR AGONISTS". Page/Page column 18. . Retrieved 2012/11/13.