39931-77-6

Basic information

• Product Name: ETHYL 3-PYRIDYLACETATE
• Synonyms: 3-Pyridineacetic acid ethyl;3-Pyridylacetic acid ethyl;Pyridine-3-acetic acid ethyl;Pyridin-3-ylacetic acid ethyl ester;ethyl 2-(pyridin-3-yl)acetate;Ethyl 3-pyridylacetate, 99% 5GR;3-Pyridylacetic Acid Ethyl Ester Ethyl 3-Pyridineacetate 3-Pyridineacetic Acid Ethyl Ester;(Pyridin-3-yl)acetic acid ethyl ester, 3-(2-Ethoxy-2-oxoethyl)pyridine
• CAS NO: 39931-77-6
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.19
• EINECS: 254-707-6
• Product Categories: Building Blocks;C8 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Pyridines;OLED materials,pharm chemical,electronic;Heterocyclic Compounds
• Mol File: 39931-77-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 80 °C0.4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.086 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00542mmHg at 25°C
• Refractive Index: n20/D 1.500(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Chlorofrom (Slightly), Methanol (Slightly)
• PKA: 4.82±0.10(Predicted)
• BRN: 123827
• CAS DataBase Reference: ETHYL 3-PYRIDYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 3-PYRIDYLACETATE(39931-77-6)
• EPA Substance Registry System: ETHYL 3-PYRIDYLACETATE(39931-77-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UR8950000
• Hazardous Substances Data: 39931-77-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 3-Pyridylacetate is used as a reagent in the preparation of piperidinylalkanoic acid derivatives, which are potent α4β1 integrin antagonists. These antagonists have potential applications in the treatment of various diseases, such as autoimmune disorders, inflammatory conditions, and cancer, due to their ability to modulate cell adhesion and migration.

InChI:InChI=1/C9H11NO2/c1-2-12-9(11)6-8-4-3-5-10-7-8/h3-5,7H,2,6H2,1H3

Upstream product

• 626-60-8 3-Chloropyridine 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 
• 6443-85-2 3-pyridinylacetonitrile 
• 64-17-5 ethanol 
• 6959-48-4 3-chloromethylpyridinium chloride 
• 100-55-0 3-hydroxymethylpyridin 
• 1120-90-7 3-iodopyridine 
• 141-97-9 ethyl acetoacetate 
• 95-92-1 oxalic acid diethyl ester 
• 6419-36-9 3-pyridineacetic acid hydrochloride 
• 3423-47-0 3-(2-ethoxy-2-oxoethyl)pyridin-1-ium-1-olate 
• 626-55-1 3-Bromopyridine 
• 6148-64-7 ethyl potassium malonate 
• 350-03-8 methyl-3-pyridylketone 

Downstream Products

• 106271-65-2 N-methyl-2-pyridin-3-yl-acetamide 
• 73579-06-3 3-(2-hydroxyethyl)piperidine 
• 501-81-5 pyridyl-3-yl-acetic acid 
• 3724-16-1 2-(pyridin-3-yl)acetamide 
• 143619-67-4 1-(3-pyridyl)cyclohexanecarboxylic acid ethyl ester 
• 110933-18-1 α,α-bis(4-fluorophenyl)-3-pyridineethanol 
• 131603-00-4 2-(3-pyridyl)-3-oxo-3,4-dihydro-2H-1,4-benzothiazine 
• 137-07-5 2-amino-benzenethiol 
• 115816-06-3 ethyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-(3-pyridinyl)propenoate 
• 6293-56-7 3-pyridinylethanol 
• 129793-82-4 1-(2,4-Difluorophenyl)-2-(pyridin-3-yl)ethanone 
• 57050-62-1 Di-p-tolylimino-oxalsaeurediethylester 
• 120690-70-2 ethyl 2-methyl-2-(pyridin-3-yl)propionate 
• 143619-77-6 N-methyl-1-(3-pyridyl)cyclohexanecarboxamide 

Relevant articles and documents

Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands

The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.

Tetrazolylhydrazides as selective fragment-like inhibitors of the JumonjiC-domain-containing histone demethylase KDM4A

The JumonjiC-domain-containing histone demethylase 2A (JMJD2A, KDM4A) is a key player in the epigenetic regulation of gene expression. Previous publications have shown that both elevated and lowered enzyme levels are associated with certain types of cancer, and therefore the definite role of KDM4A in oncogenesis remains elusive. To identify a novel molecular starting point with favorable physicochemical properties for the investigation of the physiological role of KDM4A, we screened a number of molecules bearing an iron-chelating moiety by using two independent assays. In this way, we were able to identify 2-(1H-tetrazol-5-yl)acetohydrazide as a novel fragment-like lead structure with low relative molecular mass (Mr=142 Da), low complexity, and an IC50 value of 46.6 μm in a formaldehyde dehydrogenase (FDH)-coupled assay and 2.4 μm in an antibody-based assay. Despite its small size, relative selectivity against two other demethylases could be demonstrated for this compound. This is the first example of a tetrazole group as a warhead in JMJD demethylases. Anchor fragment: To develop non-promiscuous metalloenzyme inhibitors, a metal-complexing acetohydrazide group was integrated in a tetrazolyl fragment, which can be matured into a scaffold to promote further selectivity at the ligand backbone binding site of these emerging drug targets.

Alcohol assisted C-C bond breaking: Copper-catalyzed deacetylative α-arylation of β-keto esters and amides

A method of alcohol-assisted copper-catalyzed highly selective deacetylative α-arylation of β-keto esters and amides has been demonstrated, which illustrated an efficient example of achieving α-aryl esters and amides. From the synthetic point of view, this arylation protocol is general and practical, representing a simple way to produce α-arylated carbonyl compounds from basic starting materials at low cost.

Synthesis of arylacetates from benzylic alcohols and oxalate esters through decarboxylative coupling

Follow that dream: By combining a reversible transesterification between benzylic alcohols and dialkyl oxalates with catalytic decarboxylation of the resulting esters, a regiospecific C-C-bond-forming reaction to give α-arylacetates was achieved. In the overall process, CO2 and a volatile alcohol are the only byproducts. Various α-arylacetates were thus synthesized in high yields from easily accessible starting materials in the presence of catalytic amounts of Pd(OAc)2, dppp, and DABCO (see scheme). Copyright

Practical and scalable synthesis of ethyl (R)-piperidine-3-acetate

A practical and scalable synthesis of ethyl (R)-piperidine-3-acetate was achieved from commercially available 3-pyridylacetic acid in 76% overall yield. The practical synthesis was demonstrated on 100-g scale. One-pot reductive N-ethylation of the pyridinium salt with acetonitrile gave an N-ethyl piperidine derivative. Copyright Taylor & Francis Group, LLC.

Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero)aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model.

Pd-catalyzed decarboxylative cross-couplings of potassium malonate monoesters with aryl halides

An efficient catalytic protocol for Pd-catalyzed decarboxylative cross-coupling of potassium malonate monoesters and derivatives with aryl bromides and chlorides are described. Because of its broad applicability, this new catalytic system provides an alternative method for the preparation of diverse aryl acetic acids and derivatives.

Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates

Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright

Cu(I)Br-mediated preparation of 14C-labeled 3-pyridine-acetate derivatives and synthesis of a novel 14C-labeled PDE-IV inhibitor

An efficient protocol for the synthesis of 14C-labeled 3-pyridineacetate (1) and its N-oxide ([14C]2) is described. Oxidation of this pyridine ([14C]1) to its N-oxide ([ 14C]2) proceeded in high yield using H2O2 with MeReO3 as a catalyst. The reaction employs readily available diethyl [2-14C]malonate. This method has proven to be general in preparation of other pyridineacetate derivatives and their N-oxides which have been typically difficult to prepare by other means. Our development of the Cu(I)Br-coupling methodology as well as application to the synthesis of a 14C-labeled phosphodiesterase-IV (PDE-IV) inhibitor, [ 14C]3, are also reported. Copyright