102244-86-0

Basic information

• Product Name: (Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate
• Synonyms: (Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate
• CAS NO: 102244-86-0
• Molecular Weight: 237.645
• Mol File: 102244-86-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate(102244-86-0)
• EPA Substance Registry System: (Z)-methyl 2-azido-3-(4-chlorophenyl)acrylate(102244-86-0)

Safety Data

• Hazardous Substances Data: 102244-86-0(Hazardous Substances Data)

Upstream product

• 1816-92-8 Methyl azidoacetate 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 372089-59-3 6-bromoindole 2-carboxylic acid methyl ester 
• 1584144-61-5 N-(4-(dimethylamino)phenethyl)-3-ethyl-6-chloro-1H-indole-2-carboxamide 
• 102245-06-7 4-Chlor-α-amino-zimtsaeuremethylester 
• 98081-81-3 methyl 2-(4-chlorophenyl)-2H-azirine-3-carboxylate 
• 98081-84-6 6-chloro-2-methoxycarbonylindole 
• 102245-02-3 methyl (Z)-2-acetylamino-3-(4-chlorophenyl)-2-propenoate 
• 102244-94-0 4-Chlor-α-(N,N-diacetylamino-)-zimtsaeuremethylester 

Relevant articles and documents

A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

Optimization of chemical functionalities of indole-2-carboxamides to improve allosteric parameters for the cannabinoid receptor 1 (CB1)

5-Chloro-3-ethyl-N-(4-(piperidin-1-yl)phenethyl)-1H-indole-2-carboxamide (1; ORG27569) is a prototypical allosteric modulator for the cannabinoid type 1 receptor (CB1). Here, we reveal key structural requirements of indole-2-carboxamides for allosteric modulation of CB1: a critical chain length at the C3-position, an electron withdrawing group at the C5-position, the length of the linker between the amide bond and the phenyl ring B, and the amino substituent on the phenyl ring B these significantly impact the binding affinity (KB) and the binding cooperativity (α). A potent CB1 allosteric modulator 5-chloro-N-(4-(dimethylamino)phenethyl)-3-propyl-1H-indole- 2-carboxamide (12d) was identified. It exhibited a KB of 259.3 nM with a strikingly high binding α of 24.5. We also identified 5-chloro-N-(4-(dimethylamino)phenethyl)-3-hexyl-1H-indole-2-carboxamide (12f) with a KB of 89.1 nM, which is among the lowest KB values obtained for any allosteric modulator of CB1 these positive allosteric modulators of orthosteric agonist binding nonetheless antagonized the agonist-induced G-protein coupling to the CB1 receptor, yet induced β-arrestin mediated ERK1/2 phosphorylation.

Intramolecular C-H amination reactions: Exploitation of the Rh 2(II)-catalyzed decomposition of azidoacrylates

Rhodium(II) perfluorobutyrate-mediated decomposition of vinyl azides provides a new, mild entry into Rh2(II) nitrenoid chemistry. This methodology allows rapid access to a variety of complex, functionalized N-heterocycles in two steps from commercially available starting materials. Copyright