104060-23-3

Basic information

• Product Name: N-Boc-2-(4-aminophenyl)ethanol
• Synonyms: N-Boc-2-(4-aminophenyl)ethanol;tert-Butyl (4-(2-hydroxyethyl)phenyl)carbamate;N-Boc-2-(4-Aminophenyl);tert-butyl N-[4-(2-hydroxyethyl)phenyl]carbamate
• CAS NO: 104060-23-3
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.297
• Mol File: 104060-23-3.mol

Chemical Properties

• Boiling Point: 321.8°C at 760 mmHg
• Flash Point: 148.4°C
• Appearance: /
• Density: 1.136g/cm³
• Vapor Pressure: 0.000121mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: N-Boc-2-(4-aminophenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-2-(4-aminophenyl)ethanol(104060-23-3)
• EPA Substance Registry System: N-Boc-2-(4-aminophenyl)ethanol(104060-23-3)

Safety Data

• Hazardous Substances Data: 104060-23-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
N-Boc-2-(4-aminophenyl)ethanol is used as a key intermediate for the synthesis of various pharmaceuticals, leveraging its protected amine group to facilitate selective reactions that are essential in drug development. The Boc group allows chemists to perform reactions on other functional groups without affecting the amine, which is crucial for the formation of specific medicinal compounds.
Used in Organic Synthesis:
In the realm of organic synthesis, N-Boc-2-(4-aminophenyl)ethanol serves as a valuable building block for creating complex organic molecules. Its functional groups and reactivity contribute to the construction of intricate molecular structures that are vital in various chemical and material applications.
Used in Medicinal Chemistry:
N-Boc-2-(4-aminophenyl)ethanol is utilized as a component in the preparation of potential drug candidates. Its presence in these candidates allows for the exploration of new therapeutic agents, with the Boc protecting group ensuring that the amine remains intact and unreactive until the desired point in the synthesis process.
Used in Chemical Production:
Across the chemical industry, N-Boc-2-(4-aminophenyl)ethanol is employed in the production of a wide range of chemical compounds. Its versatility and the protective nature of the Boc group make it an indispensable intermediate for achieving specific chemical outcomes in various applications.

InChI:InChI=1/C13H19NO3/c1-13(2,3)17-12(16)14-11-6-4-10(5-7-11)8-9-15/h4-7,15H,8-9H2,1-3H3,(H,14,16)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 104-10-9 2-(4'-aminophenyl)ethyl alcohol 
• 100-27-6 2-(4-nitrophenyl)ethanol 
• 112918-77-1 methyl 2-(4-((tert-butoxycarbonyl)amino)phenyl)acetate 
• 623-04-1 4-aminobenzenemethanol 
• 218139-11-8 tert-butyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate 
• 123-91-1 1,4-dioxane 
• 81196-09-0 2-(4-(tert-butoxycarbonylamino)phenyl)acetic acid 
• 92814-31-8 4-amino-phenethyl alcohol; hydrochloride 
• 404586-94-3 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline 

Downstream Products

• 457631-44-6 4-(2-aminoethyl)-N-(tert-butoxycarbonyl)phenylamine 
• 13472-00-9 p-Aminophenethylamine 
• 327985-14-8 4-(2-fluoroethyl)aniline 
• 1289627-61-7 tert-butyl N-[4-(2-iodoethyl)phenyl]carbamate 
• 917381-83-0 C₁₈H₁₉ClFN₅O₂ 
• 917381-81-8 C₁₈H₂₀ClN₅O₂ 

Relevant articles and documents

Improved synthesis of the bifunctional chelator p-SCN-Bn-HOPO

The bifunctional ligand p-SCN-Bn-HOPO, which has four 1,2-hydroxypyridinone groups on a spermine backbone with an isothiocyanate linker, has been shown to be an efficient and stable chelator for Zr(iv) and, more importantly, the radioisotope 89Zr for use in radiolabeling antibodies for positron emission tomography (PET) imaging. Previous studies of 89Zr-HOPO-trastuzumab in mice showed low background, good tumor to organ contrast, and very low bone uptake which show p-SCN-Bn-HOPO to be an important next-generation bifunctional chelator for radioimmunoPET imaging with 89Zr. However, the reported synthesis of p-SCN-Bn-HOPO involves nine steps and multiple HPLC purifications with an overall yield of about 1.4%. Herein we report an improved and efficient synthesis of p-SCN-Bn-HOPO in four steps with 14.3% overall yield which will improve its availability for further biological studies and wider application in PET imaging. The new synthetic route also allows variation in linker length and chemistries which may be helpful in modifying in vivo clearance behaviors of future agents.

Dissipative Catalysis with a Molecular Machine

We report on catalysis by a fuel-induced transient state of a synthetic molecular machine. A [2]rotaxane molecular shuttle containing secondary ammonium/amine and thiourea stations is converted between catalytically inactive and active states by pulses of a chemical fuel (trichloroacetic acid), which is itself decomposed by the machine and/or the presence of additional base. The ON-state of the rotaxane catalyzes the reduction of a nitrostyrene by transfer hydrogenation. By varying the amount of fuel added, the lifetime of the rotaxane ON-state can be regulated and temporal control of catalysis achieved. The system can be pulsed with chemical fuel several times in succession, with each pulse activating catalysis for a time period determined by the amount of fuel added. Dissipative catalysis by synthetic molecular machines has implications for the future design of networks that feature communication and signaling between the components.

1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline: A novel and chemoselective tert-butoxycarbonylation reagent

(formula presented) The use of 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) as tert-butoxycarbonylation reagent for aromatic and aliphatic amine hydrochlorides and phenols in the absence of a base has been demonstrated. The reactions proceed chemoselectively in high yield under mild conditions.

D2 Dopamine Receptor G Protein-Biased Partial Agonists Based on Cariprazine

Functionally selective G protein-coupled receptor ligands are valuable tools for deciphering the roles of downstream signaling pathways that potentially contribute to therapeutic effects versus side effects. Recently, we discovered both Gi/o-bi

Design of a True Bivalent Ligand with Picomolar Binding Affinity for a G Protein-Coupled Receptor Homodimer

Bivalent ligands have emerged as chemical tools to study G protein-coupled receptor dimers. Using a combination of computational, chemical, and biochemical tools, here we describe the design of bivalent ligand 13 with high affinity (KDB1 = 21 pM) for the dopamine D2 receptor (D2R) homodimer. Bivalent ligand 13 enhances the binding affinity relative to monovalent compound 15 by 37-fold, indicating simultaneous binding at both protomers. Using synthetic peptides with amino acid sequences of transmembrane (TM) domains of D2R, we provide evidence that TM6 forms the interface of the homodimer. Notably, the disturber peptide TAT-TM6 decreased the binding of bivalent ligand 13 by 52-fold and had no effect on monovalent compound 15, confirming the D2R homodimer through TM6 ex vivo. In conclusion, by using a versatile multivalent chemical platform, we have developed a precise strategy to generate a true bivalent ligand that simultaneously targets both orthosteric sites of the D2R homodimer.

A method of preparing P ethylamine

The invention discloses a preparation method of p-aminophenylethylamine, belonging to the technical field of organic synthesis. The technical scheme is as follows: the preparation method comprises the following steps: by using p-nitrophenylethanol as a raw material, carrying out catalytic hydrogenation to reduce the para-position nitro groups of the p-nitrophenylethanol into amino groups, carrying out Boc acid anhydride protection on the para-position nitro groups, carrying out substitution reaction on hydroxy groups with sulfonyl chloride compounds to obtain sulfonic acid compounds, aminating, and finally, removing Boc groups to obtain the p-aminophenylethylamine. The preparation process is simple and easy to implement, and has the advantages of cheap and accessible raw materials, higher reaction efficiency and favorable repetitiveness.

In situ deprotection and dynamic covalent assembly using a dual role catalyst

Utilization of constituent molecular precursors bearing covalently coreactive functional groups for self-assembly risks premature reaction, impeding synthetic and purification efforts. To prevent premature amine-aldehyde condensation for oligomers bearing both groups, we employ a dual-role Lewis acid catalyst for both in situ acetal deprotection and subsequent imine exchange, effecting oligomer assembly.

CONJUGATE OF MONOMETHYL AURISTATIN F AND TRASTUZUMAB AND ITS USE FOR THE TREATMENT OF CANCER

The present invention relates to an antibody-drug-conjugate or pharmaceutical composition comprising the same. From one aspect, the invention relates to an antibody-drug-conjugate (ADC) comprising an antibody consisting of the Trastuzumab or a biosimilar thereof, said antibody being conjugated to at least one drug consisting of a monomethyl auristatin F derivative. The invention also comprises method of treatment of cancer comprising administering to the subject an effective amount of said antibody-drug-conjugate or composition comprising the same.

COMPOSITION FOR THE TREATMENT OF IGF-1R EXPRESSING CANCER

The present invention relates to a method for the treatment of IGF-IR expressing cancers as well as to a compositions and a kit for said traitment. From one aspect, the invention reates to the combined use of a first antibody for the determination of the IGF-IR status of a cancer and a second antibody used as an ADC for the treatment of said cancer.

CONJUGATE OF MONOMETHYL AURISTATIN F AND TRASTUZUMAB AND ITS USE FOR THE TREATMENT OF CANCER

The present invention relates to an antibody-drug-conjugate. From one aspect, the invention relates to an antibody-drug-conjugate comprising an antibody consisting of the Trastuzumab, said antibody being conjugated to at least one drug consisting of a monomethyl auristatin F derivative. The invention also comprises method of treatment and the use of said antibody-drug-conjugate for the treatment of cancer.