4-(Pyrrolidin-1-yl)benzoic acid

Base Information

• Chemical Name: 4-(Pyrrolidin-1-yl)benzoic acid
• CAS No.: 22090-27-3
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.23
• Hs Code.: 29339900
• European Community (EC) Number: 625-792-0
• DSSTox Substance ID: DTXSID10383735
• Wikidata: Q82175524
• ChEMBL ID: CHEMBL3593490
• Mol file: 22090-27-3.mol

Synonyms:22090-27-3;4-(pyrrolidin-1-yl)benzoic acid;4-(1-PYRROLIDINYL)BENZOIC ACID;4-pyrrolidin-1-ylbenzoic acid;4-Pyrrolidin-1-yl-benzoic acid;4-(1-Pyrrolidinyl)benzenecarboxylic acid;MFCD01631241;Benzoic acid,4-(1-pyrrolidinyl)-;Oprea1_055593;SCHEMBL419882;F3099-6581;4-(pyrrolidin-1-yl)benzoicacid;CHEMBL3593490;DTXSID10383735;KPCBFFYRSJPCJH-UHFFFAOYSA-N;HMS1697K21;STK318150;AKOS000104827;AC-2825;BD-0212;CCG-316991;CS-W007278;4-(1-Pyrrolidinyl)benzoic acid, 97%;SY003056;BB 0217630;FT-0677754;EN300-92380;F11771;A878737;AF-399/15539058;W-206730

Chemical Property of 4-(Pyrrolidin-1-yl)benzoic acid

Chemical Property:

• Vapor Pressure: 2.37E-06mmHg at 25°C
• Melting Point: 262-296 °C (D)
• Refractive Index: 1.597
• Boiling Point: 376.9 °C at 760 mmHg
• PKA: 4.94±0.10(Predicted)
• Flash Point: 181.8 °C
• PSA: 40.54000
• Density: 1.221g/cm³
• LogP: 2.05000
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.094628657
• Heavy Atom Count: 14
• Complexity: 203

Purity/Quality:

97% ^*data from raw suppliers

4-(Pyrrolidin-1-yl)benzoicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C1)C2=CC=C(C=C2)C(=O)O

Technology Process of 4-(Pyrrolidin-1-yl)benzoic acid

There total 9 articles about 4-(Pyrrolidin-1-yl)benzoic 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: 90.0%

1-(4-bromo-phenyl)-pyrrolidine (22090-26-2) + carbon dioxide (124-38-9,18923-20-1) → 4-(pyrrolidine-1-yl)benzoic acid (22090-27-3)

Guidance literature:

1-(4-bromo-phenyl)-pyrrolidine; With n-butyllithium; In tetrahydrofuran; at -70 ℃; for 0.333333h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; at -70 ℃; for 2h;

Reference yield: 73.0%

4-(pyrrolidin-1-yl)benzaldehyde (51980-54-2) → 4-(pyrrolidine-1-yl)benzoic acid (22090-27-3)

Guidance literature:

With potassium hydroxide; sodium hydroxide; In neat (no solvent); Heating;

DOI:10.1080/00304948.2017.1260396

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-(pyrrolidine-1-yl)benzoic acid (22090-27-3)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / -10 - 20 °C

2: N-tert-butylaminoborane; potassium carbonate / 1,4-dioxane; water / 48 h / Reflux

3: water; sodium hydroxide / methanol / Reflux

With thionyl chloride; N-tert-butylaminoborane; water; potassium carbonate; sodium hydroxide; In 1,4-dioxane; methanol; water;

DOI:10.1021/jm301099x

upstream raw materials:

1-(4-bromo-phenyl)-pyrrolidine

4-(pyrrolidin-1-yl)benzoyl chloride

N-phenylpyrrolidine

4-amino-benzoic acid

Downstream raw materials:

4-(pyrrolidin-1-yl)benzoyl chloride

N-(4-hydroxymethylbenzyl)-4-pyrrolidin-1-ylbenzamide

N-(4-formyl-benzyl)-4-pyrrolidin-1-yl-benzamide

3-{4-[(4-pyrrolidin-1-ylbenzoylamino)methyl]phenyl}acrylic acid ethyl ester