7474-06-8

Basic information

• Product Name: 2-chloro-3-phenylpropanoic acid
• CAS NO: 7474-06-8
• Molecular Formula: C₉H₉ClO₂
• Molecular Weight: 184.6196
• Mol File: 7474-06-8.mol

Chemical Properties

• Boiling Point: 305.8°C at 760 mmHg
• Flash Point: 138.7°C
• Density: 1.271g/cm³
• Vapor Pressure: 0.000351mmHg at 25°C
• Refractive Index: 1.558
• CAS DataBase Reference: 2-chloro-3-phenylpropanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-3-phenylpropanoic acid(7474-06-8)
• EPA Substance Registry System: 2-chloro-3-phenylpropanoic acid(7474-06-8)

Safety Data

• Hazardous Substances Data: 7474-06-8(Hazardous Substances Data)

Upstream product

• 109-95-5 ethyl nitrite 
• 150-30-1 Phenylalanine 
• 17849-62-6 2-chloro-3-phenylpropionitrile 
• 81136-10-9 2-chloro-3-phenylpropanoic acid chloride 
• 63-91-2 L-phenylalanine 
• 76043-69-1 2,2-dichloro-3-phenylpropionaldehyde 
• 16503-53-0 2-bromo-3-phenylpropanoic acid 
• 7474-06-8 2-chloro-3-phenylpropionic acid 
• 20312-36-1 L-3-phenyllactic acid 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 123-91-1 1,4-dioxane 
• 100-39-0 benzyl bromide 
• 673-06-3 D-(R)-phenylalanine 
• 159213-09-9 (R)-2-Chloro-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-3-phenyl-propionamide 

Downstream Products

• 16503-53-0 2-bromo-3-phenylpropanoic acid 
• 150-30-1 Phenylalanine 
• 81136-10-9 2-chloro-3-phenylpropanoic acid chloride 
• 2566-35-0 N-methylphenylalanine 
• 18166-56-8 α-chloro-β-phenylpropionamide 
• 7497-19-0 (S)-2-chloro-3-phenyl-propionic acid ethyl ester 
• 1190832-61-1 C₁₅H₁₅ClN₂O 
• 7474-06-8 (S)-2-chloro-3-phenyl-propionic acid 
• 7474-06-8 (2R)-2-chloro-3-phenylpropionic acid 
• 59200-36-1 methyl (S)-2-chloro-3-phenylpropanoate 
• 90600-03-6 N-isopentyl-D-phenylalanine 
• 56564-52-4 N-methyl-D-phenylalanine 
• 408504-95-0 (2R,3S)-3-bromo-2-chloro-3-phenylpropanoic acid 
• 120680-91-3 N-(3-phenyl-1-(S)-chloropropionyl)-phenylalanine 

Relevant articles and documents

Substrate-Inspired Fragment Merging and Growing Affords Efficacious LasB Inhibitors

Extracellular virulence factors have emerged as attractive targets in the current antimicrobial resistance crisis. The Gram-negative pathogen Pseudomonas aeruginosa secretes the virulence factor elastase B (LasB), which plays an important role in the infection process. Here, we report a sub-micromolar, non-peptidic, fragment-like inhibitor of LasB discovered by careful visual inspection of structural data. Inspired by the natural LasB substrate, the original fragment was successfully merged and grown. The optimized inhibitor is accessible via simple chemistry and retained selectivity with a substantial improvement in activity, which can be rationalized by the crystal structure of LasB in complex with the inhibitor. We also demonstrate an improved in vivo efficacy of the optimized hit in Galleria mellonella larvae, highlighting the significance of this class of compounds as promising drug candidates.

A facile microwave assisted synthesis and structure elucidation of (3R)-3-alkyl-4,1-benzoxazepine-2,5-diones by crystallographic, spectroscopic and DFT studies

The use of microwave (MW) irradiation in organic synthesis has become increasingly popular within the pharmaceutical and academic arenas because it is a new enabling technology for drug discovery and development. It is a rapid way of synthesis, which involves faster reaction rates and high selectivity to conventional heating method of syntheses. The MW-assisted 7-exo-tet cyclization of N-acylanthranilic acids afforded (3R)-3-alkyl-4,1-benzoxazepines-2,5-diones in very short duration (20 min) with extraordinary high yields in comparison to conventional heating mode of synthesis. The method development, comparative yields of MW-assisted and thermal method of syntheses, crystallographic, spectroscopic and density functional theory (DFT) studies are reported herein. Four novel compounds with chemical formulas C10H9BrClNO3 5m, C19H19NO3 6e, C13H14ClNO3 6h and C12H11Br2NO3 6h were synthesized, validated by 1HNMR, 13CNMR, FT-IR, UVVis, EIMS spectroscopic techniques and confirmed by using single crystal X-ray diffraction (SC-XRD) study. The DFT and TDDFT calculations at B3LYP/6-311 + G(d,p) level of theory were performed for comparative analysis of spectroscopic data, optimized geometries, frontier molecular orbitals (FMOs), natural bond orbital (NBO) analysis and nonlinear optical (NLO) properties of 5m, 6e, 6h and 6o. Overall, experimental findings were supported nicely by corresponding DFT computed results. The NBO analysis confirmed that the presence of non-covalent interactions, hydrogen bonding and hyper- conjugative interactions are pivotal cause for the existence of 5m, 6e, 6h and 6o in the solid-state. NLO analysis showed that 5m, 6e, 6h and 6o have significant NLO properties as compared to prototype standard compound which disclosed their potential for technology related applications.

A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids

The homologation of carbon dioxide with stable, (enantiopure) magnesium carbenoids constitutes a valuable method for preparing α-halo acid derivatives. The tactic features a high level of chemocontrol, thus enabling the synthesis of variously functionalized analogues. The flexibility to generate magnesium carbenoids through sulfoxide-, halogen- or proton- Mg exchange accounts for the wide scope of the reaction. (Figure presented.).

Di(1-naphthyl) methanol ester of carboxylic acids for absolute stereochemical determination

The absolute stereochemistry of chiral carboxylic acids is determined as a di(1-naphthyl)methanol ester derivative. Computational scoring of conformations favoring either P or M helicity of the naphthyl groups, capable of exciton-coupled circular dichroic coupling, leads to a predicted stereochemistry for the derivatized carboxylic acids.

Preparation method of alpha-chloro carboxylic acid

The invention discloses a preparation method of alpha-chloro carboxylic acid. According to the preparation method, amino acids are dissolved into hydrochloric acid to form a homogeneous solution; thenobtained homogeneous solution and a sodium nitrite water solution are simultaneously pumped into a mixing valve through an injection pump A and an injection pump B of a micro-channel reaction apparatus; after the solutions are fully mixed, the mixed solution is pumped into a micro reactor of the micro-channel reaction apparatus to carry out reactions at a constant flowing speed, and the flow-outliquid namely alpha-chloro carboxylic acid is collected. The provided method realizes the continuous production of alpha-chloro carboxylic acid; furthermore, the product quality is good, the operationis simple, the using amount of raw materials is little, the process is safe, the method is green and environmentally friendly, energy is saved, the efficiency is high, and thus the method is suitablefor industrial production.

Synthesis and anti-parasitic activity of C-benzylated (N-arylcarbamoyl)alkylphosphonate esters

Unexpected substituent-dependent regioselectivty challenges in the synthesis of C-benzylated (N-arylcarbamoyl)phosphonate esters have been resolved. The C-benzylated N-furfurylcarbamoyl derivative showed low micromolar PfLDH inhibition, while one of the C-benzylated N-arylcarbamoyl analogues was active against Nagana Trypanosoma brucei parasites which are responsible for African trypanosomiasis in cattle.

Enantioselective organocatalytic synthesis of 2-oxopiperazines from aldehydes: Identification of the elusive epoxy lactone intermediate

An organocatalytic linchpin catalysis approach was envisaged to convert simple aldehydes into enantioenriched 2-oxopiperazines. A four-step reaction sequence (chlorination, oxidation, substitution, and cyclization) was developed and led to different substitution patterns in high yields and selectivities. The reaction mechanism was studied, and the previously elusive epoxy lactone intermediate was identified by HRMS.

Chiral Pool-Based Synthesis of Naphtho-Fused Isocoumarins

A variety of chiral derivatives of benzo[d]naphtho[1,2-b]pyran-6-one were prepared in a single step by Et3N-mediated condensation of homophthalic anhydride with different derivatives of (S)-amino acid chlorides at -5 °C by employing a chiral pool methodology. Chirality 27:951-957, 2015.

Chiron based synthesis of isocoumarins: Reactivity of α-substituted carboxylic acids

The asymmetric synthesis of a novel (S)-isocoumarin has been attempted in a single step by the coupling of homophthalic acid with (S)-N-protected amino acids and α-chloroacids at high temperature by exploiting a chiral pool methodology. The coupling of homophthalic acid with N-protected (S)-amino acids gave exclusion of the carboxyl/alkyl group. However, coupling of homophthalic acid with α-chloroacids afforded asymmetric isocoumarins in high yield.

Visible light photoredox-catalysed intermolecular radical addition of α-halo amides to olefins

We present α-chloro amides as a new class of α-acetyl radical precursors, which undergo a tin-free, photoredox-catalysed intermolecular α-alkylation with various olefins exclusively in an anti-Markovnikov fashion. The reaction represents a reductive atom