67249-02-9

Basic information

• Product Name: (2E)-3-[4-(Acetylamino)phenyl]-2-propenoic acid
• Synonyms: (2E)-3-[4-(Acetylamino)phenyl]-2-propenoic acid
• CAS NO: 67249-02-9
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.21
• Mol File: 67249-02-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 470.9 °C at 760 mmHg
• Flash Point: 238.6 °C
• Appearance: /
• Density: 1.297
• CAS DataBase Reference: (2E)-3-[4-(Acetylamino)phenyl]-2-propenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-[4-(Acetylamino)phenyl]-2-propenoic acid(67249-02-9)
• EPA Substance Registry System: (2E)-3-[4-(Acetylamino)phenyl]-2-propenoic acid(67249-02-9)

Safety Data

• Hazardous Substances Data: 67249-02-9(Hazardous Substances Data)

Usage

General Description

(2E)-3-[4-(Acetylamino)phenyl]-2-propenoic acid, also known as 2-(4-Acetamidophenyl)acrylic acid, is a chemical compound with the molecular formula C11H11NO3. It is categorized as an organic compound and is derived from both acrylic acid and acetanilide. (2E)-3-[4-(Acetylamino)phenyl]-2-propenoic acid is often used in pharmaceutical and medical applications as a building block for the synthesis of various drugs and bioactive molecules. Its structure contains a phenyl ring with an acetylamino group attached, as well as a propenoic acid group, making it a valuable intermediate in the production of pharmaceuticals. This chemical has the potential for a broad range of applications in the pharmaceutical industry.

Upstream product

• 2393-18-2 p-aminocinnamic acid 
• 108-24-7 acetic anhydride 
• 141-82-2 malonic acid 
• 122-85-0 para-acetamidobenzaldehyde 
• 110-89-4 piperidine 
• 97190-59-5 O--L-β-phenyllactic acid 
• 215258-04-1 ethyl 3-(4-acetylaminophenyl)-2-propenoate 
• 5048-82-8 (E)-ethyl 3-(4-aminophenyl)acrylate 
• 17570-30-8 trans-p-aminocinnamic acid 

Downstream Products

• 101441-86-5 N-(4'-formyl-trans-stilben-4-yl)-acetamide 
• 101442-47-1 4'-acetylamino-trans-stilbene-4-carboxylic acid 
• 17570-30-8 trans-p-aminocinnamic acid 
• 6325-43-5 3-(4-acetamidophenyl)propanoic acid 
• 106873-46-5 4-Acetamido-3-nitrocinnamic acid 
• 57259-97-9 1-[3-(4-acetylamino-phenyl)-acryloyl]-4-(4-oxo-5-phenyl-4,5-dihydro-oxazol-2-yl)-piperazine 
• 67248-43-5 1-[4-(4-acetylamino-styryl)-phenyl]-ethanone 
• 204915-93-5 3-[(E)-4-(acetylamino)cinnamoyl]-5-(tert-butyloxycarbonylamino)-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indole 
• 97190-59-5 O--L-β-phenyllactic acid 
• 1089-35-6 4'-amino-trans-stilbene-4-sulfonic acid amide 
• 108475-17-8 4'-aminostilbene-4-carboxylic acid 
• 28097-02-1 methyl 4-[(E)-2-(4-aminophenyl)ethenyl]benzoate 
• 24249-61-4 3,4-diamino-cinnamic acid 
• 24364-02-1 4-amino-3-nitro-cinnamic acid 

Relevant articles and documents

Toward a Scalable Synthesis and Process for EMA401, Part II: Development and Scale-Up of a Pyridine- A nd Piperidine-Free Knoevenagel-Doebner Condensation

During route scouting for EMA401 (1), an angiotensin II type 2 antagonist, we identified the synthesis of key amino acid intermediate 2 via its cinnamic acid derivative 3 as a streamlined option. In general, cinnamic acids can be synthesized from the corresponding aldehydes by a Knoevenagel-Doebner condensation in pyridine with piperidine as an organocatalyst. We aimed to replace both of these reagents and found novel conditions involving toluene as the solvent and morpholine as the organocatalyst. Scale-up of the process allowed the production of 25 kg of cinnamic acid 3 that was of the quality required for process development of the subsequent phenylalanine ammonia lyase-catalyzed step. The modified conditions were found to be widely applicable to alternative aldehydes and thus are of relevance to practitioners of chemical scale-up.

POLYMER RAW MATERIAL AND POLYMER MATERIAL

To provide a polymer material having properties that allow the polymer material to replace a polyimide and a polyamide synthesized from a petroleum raw material, said polymer material being synthesized from a raw material derived from natural molecules. [

Molecular puzzle ring: Pseudo[1]rotaxane from a flexible cyclodextrin derivative

A pseudo[1]rotaxane formed by a flexible cyclodextrin (CD) derivative (1-R) with a bulky end group has been investigated on kinetic quantitation. 1-Rs have the cinnamamide moiety as a guest and a bulky end group (R) as a rate-determining moiety of the threading process. The R groups play an important role for the formation of pseudo[1]rotaxane, and kinetics of the self-inclusion process was found to be controlled by the size and shapes of the R groups. 1-Ad and 1-Me derivatives, which have an adamantyl and methyl end group, respectively, formed self-inclusion complexes by threading of the arm moiety with a conformational conversion of altrose from 1C4 form to 4C1 form. Flexibility of the altro-α-CD cavity resulted in an induced fit (from 1C4 to 4C 1) to the arm moiety, and introducing a bulky end group allowed the stability of this pseudo[1]rotaxane to be enhanced.