4-Isopropylpicolinic acid

Base Information

• Chemical Name: 4-Isopropylpicolinic acid
• CAS No.: 83282-36-4
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.192
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID20527986
• Wikidata: Q72486273
• Mol file: 83282-36-4.mol

Synonyms:4-isopropylpicolinic acid;83282-36-4;4-isopropyl-2-pyridinecarboxylic acid;4-propan-2-ylpyridine-2-carboxylic acid;4-isopropyl-pyridine-2-carboxylic acid;4-(Propan-2-yl)pyridine-2-carboxylic acid;4-ISOPROPYLPICOLINICACID;2-Pyridinecarboxylic acid, 4-(1-methylethyl)-;SCHEMBL101547;DTXSID20527986;GTEKHQRDHJAAAR-UHFFFAOYSA-N;GS2487;MFCD07437963;AKOS006285366;SB53654;TS-02217;CS-0456066

Chemical Property of 4-Isopropylpicolinic acid

Chemical Property:

• Vapor Pressure: 0.000218mmHg at 25°C
• Refractive Index: 1.538
• Boiling Point: 313 °C at 760 mmHg
• Flash Point: 143.1 °C
• PSA: 50.19000
• Density: 1.137 g/cm³
• LogP: 1.90320
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

98%min ^*data from raw suppliers

4-Isopropyl-2-pyridinecarboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CC(=NC=C1)C(=O)O
• Uses: 4-isopropylpicolinic acid was used in the synthetic preparation of selective N-type voltage activated calcium channel (VACC) blockers. 4-Isopropyl-2-pyridinecarboxylic acid was used in the synthetic preparation of selective N-type voltage activated calcium channel (VACC) blockers.

Technology Process of 4-Isopropylpicolinic acid

There total 4 articles about 4-Isopropylpicolinic 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: 75.0%

C9H10N2O → 4-isopropyl-pyridine-2-carboxylic acid (83282-36-4)

Guidance literature:

With hydrogenchloride; water; for 24h; Heating / reflux;

Reference yield:

4-s-propylpyridine (696-30-0) → 4-isopropyl-pyridine-2-carboxylic acid (83282-36-4)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂O₂; AcOH

2: (CH₃)2NCOCl / CH₂Cl₂

3: aq. HCl / Heating

With hydrogenchloride; dihydrogen peroxide; acetic acid; N,N-Dimethylcarbamoyl chloride; In dichloromethane; 1: Oxidation / 2: cyanidation / 3: Hydrolysis;

DOI:10.1016/S0957-4166(99)00473-5

Reference yield:

4-isopropylpyridine 1-oxide (22581-87-9) → 4-isopropyl-pyridine-2-carboxylic acid (83282-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1: (CH₃)2NCOCl / CH₂Cl₂

2: aq. HCl / Heating

With hydrogenchloride; N,N-Dimethylcarbamoyl chloride; In dichloromethane; 1: cyanidation / 2: Hydrolysis;

DOI:10.1016/S0957-4166(99)00473-5

upstream raw materials:

6-cyano-4-isopropylpyridine

4-s-propylpyridine

4-isopropylpyridine 1-oxide

Downstream raw materials:

(2R,4S)-cis-4-(2-propyl)-1,2-piperidinedicarboxylic acid 1-(phenylmethyl) ester

(2R,4S)-cis-4-(2-propyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

(2S,4S)-trans-4-(2-propyl)-1,2-piperidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

(2S,4S)-trans-4-(2-propyl)-2-piperidinecarboxylic acid methyl ester

Refernces

• 1、 Keenan, Terence P.,Yaeger, David,Holt, Dennis A.. "Synthesis of chiral nonracemic 4-trans-substituted pipecolic acid derivatives". . p. 4331 - 4341. Retrieved 2007/10/03.