174579-31-8

Basic information

• Product Name: TERT-BUTYL-4-AMINOPHENYLACETATE
• Synonyms: tert-Butyl 2-(4-aMinophenyl)acetate;2-(4-aMinophenyl)-3,3-diMethylbutanoate;4-Aminophenylacetic acid tert-butyl ester;4-AMino-benzeneacetic acid tert-butyl ester
• CAS NO: 174579-31-8
• Molecular Formula: C₁₂H₁₇NO₂
• Molecular Weight: 207.27
• Mol File: 174579-31-8.mol
• Article Data: 8

Chemical Properties

• Melting Point: 30-32°C
• Boiling Point: 310.6°Cat760mmHg
• Flash Point: 164.1°C
• Appearance: /
• Density: 1.067g/cm³
• Vapor Pressure: 0.000593mmHg at 25°C
• Refractive Index: 1.533
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: TERT-BUTYL-4-AMINOPHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL-4-AMINOPHENYLACETATE(174579-31-8)
• EPA Substance Registry System: TERT-BUTYL-4-AMINOPHENYLACETATE(174579-31-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 174579-31-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Manufacturing:
Tert-Butyl-4-aminophenylacetate is utilized as an intermediate in the synthesis of various pharmaceuticals for its stability and low reactivity, contributing to the development of new drugs and improving existing ones.
Used in Organic Synthesis:
In the field of organic synthesis, Tert-Butyl-4-aminophenylacetate is employed as a key building block for the creation of complex organic compounds, facilitating the synthesis of a diverse range of chemical products.
Used in Research and Development:
Tert-Butyl-4-aminophenylacetate is used as a research compound in academic and industrial laboratories to explore new chemical reactions and develop innovative synthetic pathways, furthering the understanding of organic chemistry and its applications.
Used in Drug Development:
In drug development, Tert-Butyl-4-aminophenylacetate is leveraged as a precursor in the synthesis of potential therapeutic agents, playing a critical role in the discovery and optimization of new medications.
Used in Chemical Production:
Tert-Butyl-4-aminophenylacetate is employed in the chemical production industry as a versatile component in the manufacturing process of various chemical products, enhancing the efficiency and effectiveness of production lines.

InChI:InChI=1/C12H17NO2/c1-12(2,3)15-11(14)8-9-4-6-10(13)7-5-9/h4-7H,8,13H2,1-3H3

Upstream product

• 104-03-0 4-nitrobenzeneacetic acid 
• 106-40-1 4-bromo-aniline 
• 51656-70-3 (2-tert-butoxy-2-oxoethyl)zinc(II) bromide 
• 29704-38-9 (4-nitrophenyl)acetic acid tert-butyl ester 

Downstream Products

• 174579-27-2 {4-[Bis-(2-hydroxy-ethyl)-amino]-phenyl}-acetic acid tert-butyl ester 
• 119054-10-3 {4-[Bis-(2-chloro-ethyl)-amino]-phenyl}-acetic acid tert-butyl ester 
• 10477-72-2 4-bis(2-chloroethyl)aminophenylacetic acid 
• 934464-17-2 C₅₂H₇₂N₄O₁₀ 
• 1034776-13-0 {4-[(1H-indole-6-carbonyl)-amino]-phenyl}-acetic acid tert-butyl ester 
• 1246636-77-0 tert-butyl 2-(4-((2,4-diaminopteridin-6-yl)methylamino)phenyl)acetate 
• 181519-06-2 tert-butyl 2-(4-isocyanatophenyl)acetate 
• 1314003-57-0 meptazinol 4-aminophenylacetic acid tert-butyl ester carbamate 
• 1314003-16-1 meptazinol para-aminophenylacetic acid carbamate hydrochloride 
• 90798-99-5 [4-(2-chloro-acetylamino)-phenyl]-acetic acid 
• 1469894-76-5 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 7-(2-(4-(2-tert-butoxy-2-oxoethyl)phenylamino)-2-oxoethylamino)-7-oxoheptanoate 
• 1469894-61-8 2-(4-(2-(7-(2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yloxy)-7-oxoheptanamido)acetamido)phenyl)acetic acid 
• 1469894-68-5 tert-butyl 2-(4-(2-aminoacetamido)phenyl)acetate 
• 1469894-72-1 7-(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4-oxo-4H-chromen-3-yl 7-(2-(4-(2-tert-butoxy-2-oxoethyl)phenylamino)-2-oxoethylamino)-7-oxoheptanoate 

Relevant articles and documents

PYRIDAZINE-3-FORMAMIDE COMPOUND, AND PREPARATION METHOD THEREFOR AND MEDICAL USE THEREOF

Disclosed in the present invention are a pyridazine-3-formamide compound suitable for inhibiting or regulating the Janus kinase (JAK), in particular tyrosine kinase 2 (TYK2), and a preparation method therefor and the medical use thereof. In particular, disclosed in the present invention are a compound as represented by general formula (I) and a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the compound or the pharmaceutically acceptable salt thereof, a method for treating and/or preventing Janus kinase-mediated related diseases, in particular autoimmune diseases, inflammatory diseases and cancers, by means of using the compound or the pharmaceutically acceptable salt thereof, and a method for preparing the compound or the pharmaceutically acceptable salt thereof. Each substituent of general formula (I) has the same definition as that in the description.

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.

Macrocyclic BACE1 inhibitors with hydrophobic cross-linked structures: Optimization of ring size and ring structure

Based on the X-ray crystallography of recombinant BACE1 and a hydroxyethylamine-type peptidic inhibitor, we introduced a cross-linked structure between the P1 and P3 side chains of the inhibitor to enhance its inhibitory activity. The P1 and P3 fragments bearing terminal alkenes were synthesized, and a ring-closing metathesis of these alkenes was used to construct the cross-linked structure. Evaluation of ring size using P1 and P3 fragments with various side chain lengths revealed that 13-membered rings were optimal, although their activity was reduced compared to that of the parent compound. Furthermore, the optimal ring structure was found to be a macrocycle with a dimethyl branched substituent at the P3 β-position, which was approximately 100-fold more active than the non-substituted macrocycle. In addition, the introduction of a 4-carboxymethylphenyl group at the P1′ position further improved the activity.

Pyridazine-3-carboxamide compound and preparation method and application thereof in medicine

The invention relates to a pyridazine-3-carboxamide compound suitable for inhibiting or regulating Janus kinase (JAK), especially tyrosine kinase 2 (TYK2), a preparation method of the pyridazine-3-carboxamide compound and an application of the pyridazine-3-carboxamide compound in medicine. Specifically, the invention relates to a compound represented by a general formula (I) and pharmaceutically acceptable salts thereof, a pharmaceutical composition containing the compound or the pharmaceutically acceptable salts thereof, and a method for treating and/or preventing Janus kinase-mediated related diseases, especially autoimmune diseases, inflammatory diseases and cancer by applying the compound or the pharmaceutically acceptable salts thereof, and a preparation method of the compound or thepharmaceutically acceptable salts thereof. Each substituent of the general formula (I) has the same definition as in the specification.

Palladium-catalyzed α-arylation of zinc enolates of esters: Reaction conditions and substrate scope

The intermolecular α-arylation of esters by palladium-catalyzed coupling of aryl bromides with zinc enolates of esters is reported. Reactions of three different types of zinc enolates have been developed. α-Arylation of esters occurs in high yields with i

Substituted indolines which inhibit receptor tyrosine kinases

Indolinones of the formula having an inhibitory effect on receptor tyrosine kinases and cyclin/CDK complexes, as well as on the proliferation of endothelial cells and various tumor cells. Exemplary are: (a) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-ethoxycarbonyl-2-indolinone, (b) 3-Z-[(1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-carbamoyl-2-indolinone, and (c) 3-Z-[1-(4-(piperidin-1-yl-methyl)-anilino)-1-phenyl-methylene]-6-metboxycarbonyl-2-indolinone.

Palladium-catalyzed α-arylation of esters and amides under more neutral conditions

Two procedures for the ∞-arylation of carbonyl compounds under conditions that are more neutral than those of reactions of aryl halides with alkali metal enolates are reported. The first procedure rests upon the development of catalysts bearing the hindered pentaphenylferrocenyl di-tert-butylphosphine (Q-phos) and the highly reactive dimeric Pd(I) complex {P(t-Bu)3]PdBr}2. By this procedure, zinc enolates prepared from ∞-bromo esters and amides react with aryl halides to form ∞-aryl esters and amides in high yields under mild conditions with 1-2 mol % catalyst and with remarkable functional group tolerance. By the second procedure, silyl ketene and silyl ketimine acetals react with aryl bromides in the presence of substoichiometric zinc fluoride, 1 mol % Pd(dba)2, and 2 mol % P(t-Bu)3 in DMF solvent at 80 °C. Reactions of zinc tert-butyl acetate and propionate enolates and trimethylsilyl ketene acetals of tert-butyl propionate and methyl isobutyrate with aryl bromides bearing electron-donating and potentially reactive, base-sensitive electron-withdrawing groups and with pyridyl bromides are reported. In addition, the diastereoselective coupling of phenyl bromide with an imide enolate bearing the Evans auxiliary is reported, and this study shows that racemization of base-sensitive stereocenters does not occur during the coupling process under these more neutral conditions. Copyright

New mustard prodrugs for antibody-directed enzyme prodrug therapy: Alternatives to the amide link

Antibody-directed enzyme prodrug therapy (ADEPT) is a two-step approach for the treatment of cancer which seeks to generate a potent cytotoxic agent selectively at a tumor site. In this work described the cytotoxic agent is generated by the action of an enzyme CPG2 on a relatively nontoxic prodrug. The prodrug 1 currently on clinical trial is a benzamide and is cleaved by CPG2 to a benzoic acid mustard drug 1a. We have synthesized a series of new prodrugs 3-8 where the benzamide link has been replaced by, for example, carbamate or ureido. Some of these alternative links have been shown to be good substrates for CPG2 and therefore new candidates for ADEPT. The active drugs 3a and 4a derived from the best of these prodrugs are potent cytotoxic agents (1-2 μM) some 100 times more than 1a. The prodrugs 3 and 4 are some 100-200-fold less cytotoxic, in a proliferating cell assay, than their corresponding active drugs 3a and 4a.