101248-36-6

Basic information

• Product Name: Benzoic acid, 4-(2-propynylamino)-, ethyl ester (9CI)
• Synonyms: Benzoic acid, 4-(2-propynylamino)-, ethyl ester (9CI);4-(2-Propyn-1-ylamino)benzoic acid ethyl ester;NSC 202883;p-2-Propynylaminobenzoic acid ethyl ester;ethyl 4-(prop-2-ynylaMino)benzoate;Benzoic acid, 4-(2-propynylaMino)-, ethyl ester;4-(2-propynylamino)Benzoic acid ethyl ester
• CAS NO: 101248-36-6
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.23712
• Product Categories: AMINOACID
• Mol File: 101248-36-6.mol

Chemical Properties

• Melting Point: 78℃
• Boiling Point: 342.8±27.0 °C(Predicted)
• Appearance: /
• Density: 1.128
• PKA: 0.52±0.50(Predicted)
• CAS DataBase Reference: Benzoic acid, 4-(2-propynylamino)-, ethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-(2-propynylamino)-, ethyl ester (9CI)(101248-36-6)
• EPA Substance Registry System: Benzoic acid, 4-(2-propynylamino)-, ethyl ester (9CI)(101248-36-6)

Safety Data

• Hazardous Substances Data: 101248-36-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzoic acid, 4-(2-propynylamino)-, ethyl ester (9CI) is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs and medicinal compounds, contributing to the advancement of healthcare and treatment options.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, Benzoic acid, 4-(2-propynylamino)-, ethyl ester (9CI) serves as an intermediate in the synthesis of a wide range of organic compounds. Its versatile structure enables chemists to create diverse molecules with various applications, including materials science, agrochemicals, and specialty chemicals.

Upstream product

• 106-96-7 propargyl bromide 
• 94-09-7 p-aminoethylbenzoate 
• 107-19-7 propargyl alcohol 

Downstream Products

• 107174-54-9 4-prop-2-ynylamino-benzoic acid 
• 51857-99-9 4-[((E)-3,7-Dimethyl-octa-2,6-dienyl)-prop-2-ynyl-amino]-benzoic acid ethyl ester 
• 101248-37-7 ethyl 4-prop-2-ynylamino>benzoate 
• 101248-32-2 N¹⁰-propargyl-5,8-dideazapteroic acid 
• 873409-81-5 4-(2-oxopropyl)aminobenzoic acid 
• 73987-38-9 quinoline-6-carboxylic acid ethyl ester 
• 848738-27-2 ethyl 4-[(3-phenylprop-2-ynyl)amino]benzoate 

Relevant articles and documents

O -Phenylenediamine: A privileged pharmacophore of ferrostatins for radical-trapping reactivity in blocking ferroptosis

Ferroptosis is a non-apoptotic, iron dependent form of regulated cell death that is characterized by the accumulation of lipid hydroperoxides. It has drawn considerable attention owing to its putative involvement in diverse neurodegenerative diseases. Ferrostatins are the first identified inhibitors of ferroptosis and they inhibit ferroptosis by efficiently scavenging free radicals in lipid bilayers. However, their further medicinal application has been limited due to the deficient knowledge of the lipid peroxyl radical-trapping mechanism. In this study, experimental and theoretical methods were performed to illustrate the possible lipid hydroperoxide inhibition mechanism of ferrostatins. The results show that an ortho-amine (-NH) moiety from ferrostatins can simultaneously interact with lipid radicals, and then form a planar seven-membered ring in the transition state, and finally present greater reactivity. NBO analysis shows that the formed planar seven-membered ring forces ortho-amines into better alignment with the aromatic π-system. It significantly increases the magnitudes of amine conjugation and improves spin delocalization in the transition state. Additionally, a classical H-bond type interaction was discovered between a radical and an o-NH group as another transition state stabilizing effect. This type of radical-trapping mechanism is novel and has not been found in diphenylamine or traditional polyphenol antioxidants. It can be said that o-phenylenediamine is a privileged pharmacophore for the design and development of ferroptosis inhibitors.

Synthesis of 2-Indolyltetrahydroquinolines by Zinc(II)-Catalyzed Intramolecular Hydroarylation-Redox Cross-Dehydrogenative Coupling of N-Propargylanilines with Indoles

An intramolecular hydroarylation-redox cross-dehydrogenative coupling (CDC) of propargylic anilines with indoles proceeded in the presence of zinc(II) catalysts to give 2-indolyltetrahydroquinolines in good to high yields. Three C-H bonds (two sp2and one sp3) are activated in one shot and these hydrogen atoms are trapped by a propargylic triple bond in the molecule.

Analogues of 4-[(7-Bromo-2-methyl-4-oxo-3 H -quinazolin-6-yl)methylprop-2- ynylamino]- N -(3-pyridylmethyl)benzamide (CB-30865) as potent inhibitors of nicotinamide phosphoribosyltransferase (Nampt)

We have shown previously that the target of the potent cytotoxic agent 4-[(7-bromo-2-methyl-4-oxo-3H-quinazolin-6-yl)methyl-prop-2-ynylamino] -N-(3-pyridylmethyl)benzamide (CB38065, 1) is nicotinamide phosphoribosyltransferase (Nampt). With its cellular target known we sought to optimize the biochemical and cellular Nampt activity of 1 as well as its cytotoxicity. It was found that a 3-pyridylmethylamide substituent in the A region was critical to cellular Nampt activity and cytotoxicity, although other aromatic substitution did yield compounds with submicromolar enzymatic inhibition. Small unsaturated groups worked best in the D-region of the molecule, with 3,3-dimethylallyl providing optimal potency. The E region required a quinazolin-4-one or 1,2,3-benzotriazin-4-one group for activity, and many substituents were tolerated at C2 of the quinazolin-4-one. The best compounds showed subnanomolar inhibition of Nampt and low nanomolar cytotoxicity in cellular assays.

Folate Analogues. 26. Syntheses of Antifolate Activity of 10-Substituted Derivatives of 5,8-Dideazafolic Acid and of the Poly-γ-glutamyl Metabolites of N10-Propargyl-5,8-Dideazafolic Acid (PDDF)

The poly-γ-glutamyl derivatives of N10-propargyl-5,8-dideazafolic acid (PDDF) with a chain length of up to five glutamate residues were synthesized from N10-propargyl-5,8-dideazapteroic acid (7) by the solid-phase procedure.These com

Folate Analogues. 25. Synthesis and Biological Evaluation of N10-Propargylfolic Acid and Its Reduced Derivatives

N10-Propargylfolic acid (2), which is the closest pteridine analogue of the thymidylate synthase inhibitor N10-propargyl-5,8-dideazafolic acid (PDDF), was synthesized starting from diethyl -L-glutamate (5