2-Nitrocinnamaldehyde

Base Information

• Chemical Name: 2-Nitrocinnamaldehyde
• CAS No.: 1466-88-2
• Molecular Formula: C9H7NO3
• Molecular Weight: 177.159
• Hs Code.: 29130000
• European Community (EC) Number: 215-988-0,634-498-1
• NSC Number: 28458
• UNII: 72Y4RH8QTA
• Nikkaji Number: J130I,J388.270E
• Wikipedia: 2-Nitrocinnamaldehyde
• Wikidata: Q4596908
• ChEMBL ID: CHEMBL53723
• Mol file: 1466-88-2.mol

Synonyms:2-Nitrocinnamaldehyde;1466-88-2;trans-2-Nitrocinnamaldehyde;3-(2-nitrophenyl)acrylaldehyde;66894-06-2;o-Nitrocinnamaldehyde;(E)-3-(2-nitrophenyl)acrylaldehyde;3-(2-nitrophenyl)prop-2-enal;(E)-3-(2-nitrophenyl)prop-2-enal;(2E)-3-(2-nitrophenyl)prop-2-enal;2-Propenal, 3-(2-nitrophenyl)-;Cinnamaldehyde, o-nitro-;(E)-3-(2-nitrophenyl)-2-propenal;trans-o-Nitrocinnamaldehyde;(E)-2-Nitrocinnamaldehyde;(2E)-3-(2-Nitrophenyl)-2-propenal;2-Nitro-trans-cinnamaldehyde;72Y4RH8QTA;CCRIS 3775;EINECS 215-988-0;NSC-28458;2-Propenal, 3-(2-nitrophenyl)-, (E)-;2-Propenal, 3-(2-nitrophenyl)-, (2E)-;NSC 28458;NSC28458;MFCD00007188;2-Nitrobenzeneacrylaldehyde;UNII-72Y4RH8QTA;CHEMBL53723;SCHEMBL446484;3-(2-Nitrophenyl)-2-propenal;2-Propenal,3-(2-nitrophenyl)-;trans-2-Nitrocinnamaldehyde, 97%;BBL023054;STK062853;trans-3-(2-Nitrophenyl)-2-propenal;(2e)-3-(2-nitrophenyl)acrylaldehyde;(E)-3-(2-nitrophenyl)-acrylaldehyde;AKOS000119688;AM85593;NCGC00340914-01;(2E)-3-(2-Nitrophenyl)-2-propenal #;AS-47371;AS-60188;CS-0109978;CS-0356562;N0611;EN300-17903;F13471;AB01333489-02;EN300-7405166;A808539;J-500754;Q4596908;Z2311719610;InChI=1/C9H7NO3/c11-7-3-5-8-4-1-2-6-9(8)10(12)13/h1-7H/b5-3

Chemical Property of 2-Nitrocinnamaldehyde

Chemical Property:

• Appearance/Colour: light yellow to yellow-brown crystals or powder
• Vapor Pressure: 5.15E-05mmHg at 25°C
• Melting Point: 127-129 °C(lit.)
• Refractive Index: 1.617
• Boiling Point: 348.1 °C at 760 mmHg
• Flash Point: 178.1 °C
• PSA: 62.89000
• Density: 1.269g/cm³
• LogP: 2.33010
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in methanol. Insoluble in water.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 177.042593085
• Heavy Atom Count: 13
• Complexity: 219

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Nitrocinnamaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38-43
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C=CC=O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C(C(=C1)/C=C/C=O)[N+](=O)[O-]
• Uses: It finds its uses as a actinometer for the UV-A range of photostability testing of pharmaceuticals. 2-Nitrocinnamaldehyde can be oxidized to 2-nitrocinnamic acid which can be used in the Baeyer-Emmerling indole synthesis to produce indole and substituted indoles.

Technology Process of 2-Nitrocinnamaldehyde

There total 42 articles about 2-Nitrocinnamaldehyde 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: 94.0%

o-nitroiodobenzene (609-73-4) + acrolein (107-02-8,25068-14-8) → 2-nitrocinnamic aldehyde (1466-88-2,66894-06-2)

Guidance literature:

With 1,3-bis(5-ferrocenylisoxazoline-3-yl)benzene; tetrabutylammomium bromide; sodium acetate; palladium diacetate; In water; at 80 ℃; for 3h; diastereoselective reaction;

DOI:10.1002/aoc.3176

Reference yield: 88.0%

2-nitrophenyl bromide (577-19-5) + acrolein (107-02-8,25068-14-8) → 2-nitrocinnamic aldehyde (1466-88-2,66894-06-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 100 ℃; for 1h; Microwave irradiation;

DOI:10.1002/ejoc.202000066

Reference yield: 87.0%

acrolein (107-02-8,25068-14-8) + 2-nitrobenzenediazonium o-benzenedisulfonimide → 2-nitrocinnamic aldehyde (1466-88-2,66894-06-2)

Guidance literature:

With calcium carbonate; palladium diacetate; In tetrahydrofuran; at 40 ℃; for 5.5h;

DOI:10.1016/j.tet.2006.01.027

upstream raw materials:

acetic anhydride

acetaldehyde

2-nitro-benzaldehyde

3-phenyl-propenal

Downstream raw materials:

o-nitro-β-cinnamenyl-acrolein

5-(2-nitro-phenyl)-1-phenyl-penta-2,4-dien-1-one

1t,9t-bis-(2-nitro-phenyl)-nona-1,3t,6t,8-tetraen-5-one

(2-nitro-trans-cinnamylidene)-malonic acid diethyl ester

Refernces

• 1、 Singal, Kewal Krishan. "1,3-Dipolar cycloaddition reactions of C-(2-nitro)-styryl-N-phenyl nitrone leading to the regiospecific and stereospecific synthesis of new isoxazolidine derivatives". . p. 3571 - 3577. Retrieved 1996.
• 2、 Rodrigo, Eduardo,Baunis, Haralds,Suna, Edgars,Waldvogel, Siegfried R.. "Simple and scalable electrochemical synthesis of 2,1-benzisoxazoles and quinoline: N -oxides". . p. 12255 - 12258. Retrieved 2019.
• 3、 Hayashi, Yujiro,Koshino, Seitaro,Kwon, Eunsang,Monde, Kenji,Taniguchi, Tohru. "Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion". supporting information. p. 15786 - 15794. Retrieved 2021/10/14.