4-Chloro-3-nitrocinnamic acid

Base Information

• Chemical Name: 4-Chloro-3-nitrocinnamic acid
• CAS No.: 20797-48-2
• Molecular Formula: C9H6ClNO4
• Molecular Weight: 227.604
• Hs Code.: 29163990
• European Community (EC) Number: 672-278-7
• Nikkaji Number: J236.003I,J254.938G
• Wikidata: Q106902760
• Mol file: 20797-48-2.mol

Synonyms:4-Chloro-3-nitrocinnamic acid;20797-48-2;(e)-3-(4-chloro-3-nitrophenyl)acrylic acid;trans-4-Chloro-3-nitrocinnamic acid;199679-38-4;3-(4-Chloro-3-nitrophenyl)acrylic acid;(E)-3-(4-chloro-3-nitrophenyl)prop-2-enoic acid;(2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoic acid;3-(4-chloro-3-nitrophenyl)prop-2-enoic acid;SCHEMBL832790;SCHEMBL832791;QBDALTIMHOITIU-DUXPYHPUSA-;CK2238;MFCD00063311;STK053601;AKOS000288883;AC-26151;MS-10585;trans-4-Chloro-3-nitrocinnamic acid, 97%;(e)-3-(4-chloro-3-nitrophenyl)acrylicacid;AM20030319;CS-0356702;EN300-10634;(2E)-3-(4-chloro-3-nitrophenyl)acrylic acid;A21730;EN300-832980;J-013633;(2E)-3-(4-Chloro-3-nitrophenyl)-2-propenoic acid #;Z2311573955;Tert-4-Chloro-3-nitrocinnamic acid;Trans-4-Chloro-3-nitrocinnamic acid;InChI=1/C9H6ClNO4/c10-7-3-1-6(2-4-9(12)13)5-8(7)11(14)15/h1-5H,(H,12,13)/b4-2+

Chemical Property of 4-Chloro-3-nitrocinnamic acid

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 2.08E-07mmHg at 25°C
• Melting Point: 188-190 °C(lit.)
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 408.552 °C at 760 mmHg
• PKA: 4.03±0.10(Predicted)
• Flash Point: 200.885 °C
• PSA: 83.12000
• Density: 1.529 g/cm³
• LogP: 2.86920
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 226.9985354
• Heavy Atom Count: 15
• Complexity: 286

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-3-nitrocinnamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=CC(=O)O)[N+](=O)[O-])Cl
• Isomeric SMILES: C1=CC(=C(C=C1/C=C/C(=O)O)[N+](=O)[O-])Cl
• Uses: trans-4-Chloro-3-nitrocinnamic acid may be used in chemical synthesis.

Technology Process of 4-Chloro-3-nitrocinnamic acid

There total 7 articles about 4-Chloro-3-nitrocinnamic 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: 95.0%

cycl-isopropylidene malonate (2033-24-1) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 4-chloro-3-nitro-cinnamic acid (20797-48-2,199679-38-4)

Guidance literature:

With hydroxy sulfonylurea; In neat (no solvent); at 110 ℃; for 0.25h; Reagent/catalyst; Green chemistry;

DOI:10.1039/c5ra14001c

Reference yield: 35.0%

malonic acid (141-82-2) + 4-chloro-3-nitro-benzaldehyde (16588-34-4) → 3-amino-3-(4-chloro-3-nitro-phenyl)-propionic acid + 2-(4-chloro-3-nitro-benzylidene)-malonic acid + (E)-4-chloro-3-nitrocinnamic acid (20797-48-2,199679-38-4)

Guidance literature:

With ammonium acetate; In butan-1-ol; Heating;

DOI:10.1007/s11176-005-0377-9

Reference yield:

α,p-Dichlor-m-nitro-hydrozimtsaeure-methylester (30565-73-2) → 4-chloro-3-nitro-cinnamic acid (20797-48-2,199679-38-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 80 ℃;

upstream raw materials:

β-(4-Chlor-3-nitro-phenyl)-α-chlor-propionsaeure

α,p-Dichlor-m-nitro-hydrozimtsaeure-methylester

3-(4-chlorophenyl)prop-2-enoic acid

nitric acid

Downstream raw materials:

3-(4-chloro-3-nitrophenyl)propionic acid

(E)-ethyl 3-(4-chloro-3-nitrophenyl)acrylate

4-chloro-3,β-dinitro-styrene

Refernces

• 1、 Lebedev,Lebedeva,Sheludyakov,Kovaleva,Ustinova,Kozhevnikov. "Competitive formation of β-amino acids, propenoic, and ylidenemalonic acids by the Rodionov reaction from malonic acid, aldehydes, and ammonium acetate in alcoholic medium". . p. 1113 - 1124. Retrieved 2007/10/03.