3-(4-Chlorophenyl)propiolic acid

Base Information

• Chemical Name: 3-(4-Chlorophenyl)propiolic acid
• CAS No.: 3240-10-6
• Molecular Formula: C9H5ClO2
• Molecular Weight: 180.59
• Hs Code.: 2916399090
• European Community (EC) Number: 841-890-8
• NSC Number: 408176
• UNII: 4GM85LD7I6
• DSSTox Substance ID: DTXSID20186113
• Nikkaji Number: J1.237.317A
• Wikidata: Q83057318
• ChEMBL ID: CHEMBL3274820
• Mol file: 3240-10-6.mol

Synonyms:3-(4-CHLOROPHENYL)PROPIOLIC ACID;3240-10-6;3-(4-chlorophenyl)prop-2-ynoic acid;4-Chlorophenylpropiolic acid;Propiolic acid, (p-chlorophenyl)-;p-Chlorophenylpropiolic acid;4GM85LD7I6;2-(4-CHLOROPHENYL)-2-PROPYNOIC ACID;(4-Chloro-phenyl)-propynoic acid;MFCD00046550;3-(4-Chlorophenyl)-2-propynoic acid;NSC-408176;2-Propynoic acid, 2-(4-chlorophenyl)-;3-(4-Chlorophenyl)propiolicacid;UNII-4GM85LD7I6;4-Chlorobenzenepropiolic acid;SCHEMBL2636129;CHEMBL3274820;HSDB 2675;3-(4-Chlorophenyl)propalic acid;DTXSID20186113;p-ChlorphenylpropiolsA currencyure;(4-chlorophenyl)-propargylic acid;HXUUKDJAFBRYMD-UHFFFAOYSA-N;4-CHLOROPHENYLPROPYNOIC ACID;Propynoic acid, (4-chlorophenyl)-;NSC408176;3-[4-(Chloro)-phenyl]propiolic acid;AKOS012949869;CS-W006758;FS-3645;NSC 408176;(4-CHLOROPHENYL)-2-PROPYNOIC ACID;Propiolic acid, (p-chlorophenyl)- (8CI);C3314;EN300-743518;2-PROPYNOIC ACID, 3-(4-CHLOROPHENYL)-;A918176

Chemical Property of 3-(4-Chlorophenyl)propiolic acid

Chemical Property:

• Vapor Pressure: 6.77E-05mmHg at 25°C
• Melting Point: 192-193 °C
• Refractive Index: 1.619
• Boiling Point: 330.2 °C at 760 mmHg
• PKA: 2.46±0.10(Predicted)
• Flash Point: 153.5 °C
• PSA: 37.30000
• Density: 1.4 g/cm³
• LogP: 1.77610
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 179.9978071
• Heavy Atom Count: 12
• Complexity: 227

Purity/Quality:

99% ^*data from raw suppliers

3-(4-Chlorophenyl)propiolic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC(=CC=C1C#CC(=O)O)Cl

Technology Process of 3-(4-Chlorophenyl)propiolic acid

There total 34 articles about 3-(4-Chlorophenyl)propiolic 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: 99.1%

4-n-chlorophenylacetylene (873-73-4) + carbon dioxide (124-38-9,18923-20-1) → (4-chlorophenyl)propiolic acid (3240-10-6)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 15h; under 760.051 Torr; Reagent/catalyst; Schlenk technique; Glovebox; Green chemistry;

DOI:10.1021/acs.inorgchem.6b02855

Reference yield: 85.0%

α,β-dibromo-p-chlorohydrocinnamic acid (31357-32-1,24653-99-4) → (4-chlorophenyl)propiolic acid (3240-10-6)

Guidance literature:

With potassium hydroxide; In methanol; for 2h; Reflux;

DOI:10.1039/c000684j

Reference yield: 79.0%

bromochlorobenzene (106-39-8) + Propiolic acid (471-25-0) → (4-chlorophenyl)propiolic acid (3240-10-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 25 ℃; for 24h;

DOI:10.1002/ejoc.201201606

upstream raw materials:

ethyl (E)-3-(4-chlorophenyl)prop-2-enoate

2,2-Dichlor-3-<4-chlor-phenyl>-propionitril

methyl 3-(4-chlorophenyl)-3-oxo-2-(triphenylphosphoranylidene)propanoate

ethyl 3-(4-chlorophenyl)propiolate

Downstream raw materials:

4-chlorobenzaldehyde

3-(4-chlorophenyl)prop-2-yn-1-ol

6-chloro-2,3-naphthalenedicarboxylic anhydride

1-(4-chlorophenyl)-7-chloro-2,3-naphthalenedicarboxylic anhydride

Refernces

• 1、 Bu, Ran,Zhang, Lin,Gao, Lu-Lu,Sun, Weng-Jie,Yang, Shuai-Liang,Gao, En-Qing. "Copper(I)-modified covalent organic framework for CO2 insertion to terminal alkynes". . . Retrieved 2020/12/21.
• 2、 Shi, Jun-Bin,Bu, Qingqing,Liu, Bin-Yuan,Dai, Bin,Liu, Ning. "Organocatalytic Strategy for the Fixation of CO2via Carboxylation of Terminal Alkynes". . p. 1850 - 1860. Retrieved 2021/01/14.