22399-01-5

Basic information

• Product Name: Propanedioic acid, [(4-bromophenyl)methylene]-, diethyl ester
• CAS NO: 22399-01-5
• Molecular Formula: C14H15BrO4
• Molecular Weight: 327.175
• Mol File: 22399-01-5.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, [(4-bromophenyl)methylene]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, [(4-bromophenyl)methylene]-, diethyl ester(22399-01-5)
• EPA Substance Registry System: Propanedioic acid, [(4-bromophenyl)methylene]-, diethyl ester(22399-01-5)

Safety Data

• Hazardous Substances Data: 22399-01-5(Hazardous Substances Data)

Upstream product

• 70146-78-0 diethyl 2-(4-bromobenzyl)malonate 
• 1122-91-4 4-bromo-benzaldehyde 
• 95-76-1 m,p-dichloroaniline 
• 105-53-3 diethyl malonate 
• 108-59-8 malonic acid dimethyl ester 
• 685-87-0 Diethyl 2-bromomalonate 

Downstream Products

• 23270-30-6 <α-(O,O-Diethyl-phosphono)-4-brom-benzyl>-malonsaeure-diethylester 
• 70146-78-0 diethyl 2-(4-bromobenzyl)malonate 
• 1312929-57-9 (2R,3S)-1,1-diethyl 3-methyl 2-(4-bromophenyl)-3-(diphenylmethyleneamino)propane-1,1,3-tricarboxylate 
• 99990-29-1 ethyl 3-(4-bromophenyl)-3-cyanopropanoate 

Relevant articles and documents

Ball-Milling-Enabled Reactivity of Manganese Metal**

Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.

Programmed Sequential Additions to Halogenated Mucononitriles

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,1,3-benzothiadiazole and undergo conjugate addition/elimination reactions with both nitrogen (40-95% yield) and carbon nucleophiles (72-93% yield). Secondary amines undergo monosubstitutions, while carbon nucleophiles are added twice. The sequence of addition of the nucleophiles could be controlled to give mixed addition products. The multicomponent coupling products could then be converted to natural product like motifs using intramolecular cyclization reactions.

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.