3-(4-Nitrophenyl)propiolic acid

Base Information

• Chemical Name: 3-(4-Nitrophenyl)propiolic acid
• CAS No.: 2216-24-2
• Molecular Formula: C9H5 N O4
• Molecular Weight: 191.143
• Hs Code.: 2916399090
• NSC Number: 61874
• DSSTox Substance ID: DTXSID50289545
• Nikkaji Number: J95.078E
• Wikidata: Q82026884
• ChEMBL ID: CHEMBL1980662
• Mol file: 2216-24-2.mol

Synonyms:3-(4-Nitrophenyl)propiolic acid;2216-24-2;3-(4-nitrophenyl)prop-2-ynoic acid;(4-NITROPHENYL)PROPIOLIC ACID;NSC61874;NSC 61874;p-Nitrophenylpropiolsaure;p-nitrophenylpropiolic acid;Cambridge id 5192591;4-nitro-phenylpropiolic acid;Oprea1_581849;CBDivE_003916;SCHEMBL1982414;3-(4-Nitrophenyl)propiolicacid;CHEMBL1980662;DTXSID50289545;p-NitrophenylpropiolsA currencyure;NSC-61874;3-{4-nitrophenyl}-2-propynoic acid;AKOS006275257;3-(4-Nitrophenyl)-2-propynoic acid #;NCI60_005625;CS-0437273;FT-0672901;EN300-743498;A919886;AG-690/36545021

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

Chemical Property:

• Vapor Pressure: 3.28E-07mmHg at 25°C
• Melting Point: 178-185oC
• Boiling Point: 402.8°Cat760mmHg
• Flash Point: 182.1°C
• PSA: 83.12000
• Density: 1.47g/cm³
• LogP: 1.55410
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 191.02185764
• Heavy Atom Count: 14
• Complexity: 298

Purity/Quality:

98% ^*data from raw suppliers

(4-Nitrophenyl)propiolicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C#CC(=O)O)[N+](=O)[O-]
• Uses: (4-Nitrophenyl)propiolic Acid (cas# 2216-24-2) is a compound useful in organic synthesis.

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

There total 25 articles about 3-(4-Nitrophenyl)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: 98.0%

(4-Nitrophenyl)acetylene (937-31-5) + carbon dioxide (124-38-9,18923-20-1) → 3-(4-nitrophenyl)-2-propynoic acid (2216-24-2)

Guidance literature:

(4-Nitrophenyl)acetylene; carbon dioxide; With caesium carbonate; In dimethyl sulfoxide; at 60 ℃; for 24h; under 760.051 Torr; Schlenk technique;

With hydrogenchloride; In water; Schlenk technique;

DOI:10.1016/j.mcat.2020.111319

Reference yield: 83.0%

para-nitrophenyl bromide (586-78-7) + Propiolic acid (471-25-0) → 3-(4-nitrophenyl)-2-propynoic acid (2216-24-2)

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

Reference yield: 51.0%

carbon dioxide (124-38-9,18923-20-1) + 4-nitro-1-(trimethylsilylethynyl)benzene (75867-38-8) → 3-(4-nitrophenyl)-2-propynoic acid (2216-24-2)

Guidance literature:

carbon dioxide; 4-nitro-1-(trimethylsilylethynyl)benzene; With cesium fluoride; In dimethyl sulfoxide; at 20 ℃; for 3h; Schlenk technique;

With hydrogenchloride; In water; at 0 ℃; pH=> 1;

DOI:10.1039/c3ob40760h

upstream raw materials:

2,3-dibromo-3-(4-nitro-phenyl)-propionic acid

phenylpropyolic acid

ethyl 3-(4-nitrophenyl)prop-2-ynoate

Methyl (Z)-β-chloro-p-nitrocinnamate

Downstream raw materials:

4-Nitrophenylpropiolsaeurechlorid

(4-Nitrophenyl)-ethinyl-phenylethinyl-keton

1-Phenyl-2-anilino-3-oxo-5-<4-nitro-phenyl>-penten-1-in-4

C₁₁H₁₁N₃O₃

Refernces

• 1、 Yun, Yapei,Sheng, Hongting,Bao, Kang,Xu, Li,Zhang, Yu,Astruc, Didier,Zhu, Manzhou. "Design and Remarkable Efficiency of the Robust Sandwich Cluster Composite Nanocatalysts ZIF-8@Au25@ZIF-67". . p. 4126 - 4130. Retrieved 2020.
• 2、 Newman,Merrill. "-". . p. 5549. Retrieved 1955.
• 3、 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.
• 4、 Bu, Ran,Gao, En-Qing,Liu, Xiao-Yan,Mu, Peng-Fei,Zhang, Lin. "Schiff-base molecules and COFs as metal-free catalysts or silver supports for carboxylation of alkynes with CO2". supporting information. p. 7620 - 7629. Retrieved 2021/10/12.