(E)-3-(2-cyanophenyl)acrylic acid

Base Information

• Chemical Name: (E)-3-(2-cyanophenyl)acrylic acid
• CAS No.: 2886-29-5
• Molecular Formula: C10H7NO2
• Molecular Weight: 173.171
• Hs Code.: 2916110090
• Mol file: 2886-29-5.mol

Synonyms:o-cyanocinnamic acid;trans-o-Cyanocinnamic-acid;2-cyano-trans-cinnamic acid;2-Cyan-trans-zimtsaeure;o-Cyan-trans-zimtsaeure;

Chemical Property of (E)-3-(2-cyanophenyl)acrylic acid

Chemical Property:

• PSA: 61.09000
• LogP: 1.65608

Purity/Quality:

97% ^*data from raw suppliers

(E)-3-(2-Cyano-phenyl)acrylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (E)-3-(2-cyanophenyl)acrylic acid

There total 8 articles about (E)-3-(2-cyanophenyl)acrylic 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: 77.0%

O-(diethoxyphosphinyl)-1,2-naphthoquinone oxime → Diethyl phosphate (598-02-7) + trans-3-(2-cyanophenyl)propenoic acid (2886-29-5)

Guidance literature:

With hydrogenchloride; In acetone; -5 deg C, 1 h then 20 deg C, 2 h;

Reference yield: 70.0%

malonic acid (141-82-2) + o-formylbenzonitrile (7468-67-9) → trans-3-(2-cyanophenyl)propenoic acid (2886-29-5)

Guidance literature:

With piperidine; pyridine; for 2h; Reflux;

Reference yield: 58.0%

diethyl chlorophosphate (814-49-3) → Tetraethyl pyrophosphate (107-49-3) + trans-3-(2-cyanophenyl)propenoic acid (2886-29-5)

Guidance literature:

With 1,2-naphthoquinone 1-oxime; In benzene; Heating;

upstream raw materials:

malonic acid

o-formylbenzonitrile

(Z)-3-(2-cyanophenyl)prop-2-enoic acid

1,2-naphthoquinone 1-oxime

Downstream raw materials:

3-(2-cyanophenyl)propionic acid

o-formylbenzonitrile

(E)-3-(2-Cyanophenyl)-2-propenoyl chloride

alpha-cyanocinnamic acid ethyl ester

Refernces

Organocatalytic enantioselective domino synthesis of highly functionalized cyclohexanes with an all-carbon quaternary stereocenter

10.1016/j.tetlet.2009.02.209

This research describes an organocatalytic enantioselective domino Michael/aldol reaction for the synthesis of highly functionalized cyclohexanes featuring an all-carbon quaternary stereocenter and multiple chiral stereocenters. The purpose of the study was to develop a method that could efficiently construct complex molecular scaffolds with high yields and enantioselectivity (83–98% ee). The researchers used chiral amines as catalysts and investigated the reaction between glutaraldehyde and various 2-cyanocinnamic acid esters. The process involved the formation of multiple carbon-carbon bonds and stereocenters in a one-pot reaction, which aligns with green chemistry principles by minimizing waste and solvents. The conclusions of the study were that the developed method allowed for the construction of four stereocenters with very high stereocontrol, and the products could serve as valuable scaffolds for further synthetic manipulations. The reaction was accelerated by heating and could be performed under microwave irradiation.

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