4-Cyclopropylpyridine

Base Information

• Chemical Name: 4-Cyclopropylpyridine
• CAS No.: 4904-21-6
• Molecular Formula: C8H9N
• Molecular Weight: 119.16400
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID30394267
• Wikidata: Q82193548
• Mol file: 4904-21-6.mol

Synonyms:4-cyclopropylpyridine;4904-21-6;4-CYCLOPROPYL-PYRIDINE;MFCD01099769;SCHEMBL1515255;DTXSID30394267;WLQVBFDHWAVUJN-UHFFFAOYSA-N;AKOS006272302;SB53412;AS-37540;SY275036;CS-0195741;EN300-88742;A871844

Chemical Property of 4-Cyclopropylpyridine

Chemical Property:

• PSA: 12.89000
• LogP: 1.95900
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 119.073499291
• Heavy Atom Count: 9
• Complexity: 90.7

Purity/Quality:

95% ^*data from raw suppliers

4-Cyclopropylpyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1C2=CC=NC=C2
• Uses: 4-Cyclopropylpyridine could be a useful compound for preparing COX-2 inhibitors with anti-pyretic and anti-inflammatory activity.

Technology Process of 4-Cyclopropylpyridine

There total 12 articles about 4-Cyclopropylpyridine 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%

4-bromopyridine hydrochloride (19524-06-2) + cyclopropylboronic acid (411235-57-9) → 4-cyclopropyl pyridine (4904-21-6)

Guidance literature:

With potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); cis,cis,cis-1,2,3,4-tetrakis (diphenylphosphinomethyl)cyclopentane; In xylene; at 130 ℃; for 20h;

DOI:10.1080/00397910500330833

Reference yield: 80.0%

4-pyridineboronic acid pinacol ester (181219-01-2) → 4-cyclopropyl pyridine (4904-21-6)

Guidance literature:

4-pyridineboronic acid pinacol ester; cyclopropylmagnesium halide; In tetrahydrofuran; at -78 - 20 ℃; for 2.25h; Inert atmosphere;

With trifluoroacetyl chloride; In tetrahydrofuran; at -78 - -40 ℃; for 18.5h; Further stages; Inert atmosphere;

DOI:10.1002/anie.201510027

Reference yield: 66.29%

2-chloro-4-methoxy-pyridine (17228-69-2) + cyclopropylboronic acid (411235-57-9) → 4-cyclopropyl pyridine (4904-21-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate; In 1,4-dioxane; water; at 80 ℃; for 16h; Inert atmosphere;

upstream raw materials:

3-(pyrid-4'-yl)-2-pyrazo-ine

4-(3-Hydroxypropyl)pyridine

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate

4-bromopyridine hydrochloride

Downstream raw materials:

4-cyclopropylpyridine-2-carbonitrile

1-amino-4-cyclopropylpyridin-1-ium 2,4,6-trimethylbenzenesulfonate

Refernces

• 1、 -. "METHODS OF USE FOR PYRIMIDINES AS FERROPORTIN INHIBITORS". Paragraph 618-621. . Retrieved 2021/11/06.
• 2、 -. "COMPOUNDS". Page/Page column 151. . Retrieved 2018/08/20.