1140518-42-8

Basic information

• Product Name: C₁₀H₁₂ClNO₃
• Synonyms: C₁₀H₁₂ClNO₃
• CAS NO: 1140518-42-8
• Molecular Weight: 229.663
• Mol File: 1140518-42-8.mol

Chemical Properties

• CAS DataBase Reference: C₁₀H₁₂ClNO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₀H₁₂ClNO₃(1140518-42-8)
• EPA Substance Registry System: C₁₀H₁₂ClNO₃(1140518-42-8)

Safety Data

• Hazardous Substances Data: 1140518-42-8(Hazardous Substances Data)

Upstream product

• 1001058-66-7 (S)-3-(4-chlorophenyl)-4-nitrobutyraldehyde 
• 1075-77-0 (E)-4-chlorocinnamic aldehyde 
• 1489016-24-1 3-(4-chlorophenyl)-4-nitrobutanal 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 75-07-0 acetaldehyde 

Relevant articles and documents

Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut

The two-step flow asymmetric synthesis of chiral γ-nitrobutyric acids as key intermediates of the GABA analogues baclofen, phenibut, and fluorophenibut is reported on a multigram scale. The telescoped process comprises an enantioselective Michael-type add

Reactivity and Selectivity of Iminium Organocatalysis Improved by a Protein Host

There has been growing interest in performing organocatalysis within a supramolecular system as a means of controlling reaction reactivity and stereoselectivity. Here, a protein is used as a host for iminium catalysis. A pyrrolidine moiety is covalently linked to biotin and introduced to the protein host streptavidin for organocatalytic activity. Whereas in traditional systems stereoselectivity is largely controlled by the substituents added to the organocatalyst, enantiomeric enrichment by the reported supramolecular system is completely controlled by the host. Also, the yield of the model reaction increases over 10-fold when streptavidin is included. A 1.1 ? crystal structure of the protein–catalyst complex and molecular simulations of a key intermediate reveal the chiral scaffold surrounding the organocatalytic reaction site. This work illustrates that proteins can be an excellent supramolecular host for driving stereoselective secondary amine organocatalysis.

Paraldehyde as an acetaldehyde precursor in asymmetric michael reactions promoted by site-isolated incompatible catalysts

A song of ice and fire! The usually innocent paraldehyde can be used as an acetaldehyde precursor in an organocatalytic asymmetric Michael addition (see scheme) thanks to the proper combination of two immobilized catalysts. The site isolation induced by the polymeric supports has proven crucial to preclude deactivation of the otherwise incompatible catalysts.

Asymmetric michael reaction of acetaldehyde with nitroolefins catalyzed by highly water-compatible organocatalysts in aqueous media

A novel category of diarylprolinol silyl ether catalysts which contain different lengths of alkylamine tags, was designed and synthesized. These catalysts were used, along with benzoic acid as the co-catalyst, to catalyze the asymmetric Michael reaction of the highly reactive acetaldehyde with nitroolefins. For the reactions studied, this catalytic system exhibited high reactivity in brine without any organic solvents; good yields (30-61%) and high enantioselectivities (80-97% ee) for a wide variety of nitrostyrenes were obtained.

Asymmetric michael reaction of acetaldehyde with nitroolefins catalyzed by highly water-compatible organocatalysts in aqueous media

A novel category of diarylprolinol silyl ether catalysts which contain different lengths of alkylamine tags, was designed and synthesized. These catalysts were used, along with benzoic acid as the co-catalyst, to catalyze the asymmetric Michael reaction of the highly reactive acetaldehyde with nitroolefins. For the reactions studied, this catalytic system exhibited high reactivity in brine without any organic solvents; good yields (30-61%) and high enantioselectivities (80-97% ee) for a wide variety of nitrostyrenes were obtained.

Asymmetric Michael reaction of acetaldehyde catalyzed by diphenylprolinol silyl ether

(Chemical Equation Presented) An acetaldehyde breakthrough: The catalytic asymmetric Michael addition reaction of acetaldehyde and various nitroalkenes in the presence of a chiral diphenylprolinol silyl ether organocatalyst is described (see scheme; TMS =

Diphenylprolinol silyl ether as catalyst of an asymmetric, catalytic, and direct Michael reaction of nitroalkanes with α,β-unsaturated aldehydes

(Chemical Equation Presented) A catalytic enantioselective direct conjugate addition of nitroalkanes to α,β-unsaturated aldehydes using diphenylprolinol silyl ether as an organocatalyst has been developed. Using this methodology as a key step, short syntheses of therapeutically useful compounds have also been accomplished.