2-Propenoic acid, 3-(4,5-dihydroxy-2-nitrophenyl)-, (2E)- (9CI)

Base Information

• Chemical Name: 2-Propenoic acid, 3-(4,5-dihydroxy-2-nitrophenyl)-, (2E)- (9CI)
• CAS No.: 402932-81-4
• Molecular Formula: C9H7NO6
• Molecular Weight: 225.15500
• Mol file: 402932-81-4.mol

Synonyms:6'-Nitro-1,3,3-trimethylindolinobenzopyrylspiran;nitrobenzospiropyran;1,3,3-Trimethylindolino-6'-nitrobenzopyrylospiran;6-nitrocaffeic acid;6-nitro-BIPS;1',3',3'-Trimethyl-6-nitroindolene-2-spiro-2-benzopyran;1,3,3-Trimethyl-6'-nitroindoline-2-spiro-2'-benzopyran;

Chemical Property of 2-Propenoic acid, 3-(4,5-dihydroxy-2-nitrophenyl)-, (2E)- (9CI)

Chemical Property:

• PSA: 123.58000
• LogP: 1.62700

Purity/Quality:

(2E)-3-(4,5-DIHYDROXY-2-NITROPHENYL)-2-PROPENOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Propenoic acid, 3-(4,5-dihydroxy-2-nitrophenyl)-, (2E)- (9CI)

There total 6 articles about 2-Propenoic acid, 3-(4,5-dihydroxy-2-nitrophenyl)-, (2E)- (9CI) 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: 85.0%

6-nitro-3,4-dimethoxycinnamic acid (20567-38-8) → (E)-3-(4,5-dihydroxy-2-nitrophenyl)propenoic acid (402932-81-4)

Guidance literature:

With boron tribromide; In dichloromethane; for 12h; Heating;

DOI:10.1016/0960-894X(96)00048-0

Reference yield: 65.0%

caffeic acid (331-39-5,501-16-6) → (E)-3-(4,5-dihydroxy-2-nitrophenyl)propenoic acid (402932-81-4)

Guidance literature:

With tetranitromethane; sodium carbonate; In methanol; ethyl acetate;

DOI:10.1021/jo015965v

Reference yield:

3,4-dimethoxy-6-nitrocinnamic acid (880074-30-6) → (E)-3-(4,5-dihydroxy-2-nitrophenyl)propenoic acid (402932-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: BBr₃ / CH₂Cl₂ / 20 °C

2: CH₂Cl₂; H₂O / 1 h / Heating

With boron tribromide; In dichloromethane; water; 1: Substitution / 2: Hydrolysis;

DOI:10.1002/1099-1395(200009)13:9<511::AID-POC283>3.0.CO;2-8

upstream raw materials:

6-nitro-3,4-dimethoxycinnamic acid

2-nitrochlorogenic acid

caffeic acid

chlorogenic acid

Refernces

• 1、 Cotelle, Philippe,Vezin, Hervé. "Reaction of caffeic acid derivatives with acidic nitrite". . p. 3303 - 3305. Retrieved 2001.
• 2、 Grenier,Cotelle,Catteau,Cotelle. "Synthesis and physico-chemical properties of nitrocaffeic acids". . p. 511 - 517. Retrieved 2007/10/03.