123036-51-1

Basic information

• Product Name: 3-Aminophenylacetic acid, N-BOC protected
• Synonyms: 3-Aminophenylacetic acid, N-BOC protected;N-BOC-3-AMINOPHENYLACETIC ACID;2-(3-((tert-Butoxycarbonyl)aMino)phenyl)acetic acid;3-(Boc-aMino)phenylacetic acid;tert-Butyl [3-(carboxymethyl)phenyl]carbamate, 3-(Carboxymethyl)aniline, N-BOC protected;Benzeneacetic acid,3-[[(1,1-diMethylethoxy)carbonyl]aMino]-;3-[[(1,1-dimethylethoxy)carbonyl]amino]Benzeneacetic acid
• CAS NO: 123036-51-1
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.28
• Mol File: 123036-51-1.mol

Chemical Properties

• Melting Point: 100-102
• Boiling Point: 355.6 °C at 760 mmHg
• Flash Point: 168.9 °C
• Appearance: /
• Density: 1.22 g/cm³
• Vapor Pressure: 1.13E-05mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Aminophenylacetic acid, N-BOC protected(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminophenylacetic acid, N-BOC protected(123036-51-1)
• EPA Substance Registry System: 3-Aminophenylacetic acid, N-BOC protected(123036-51-1)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 123036-51-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Aminophenylacetic acid, N-BOC protected is used as a building block for the synthesis of pharmaceutical compounds due to its ability to be selectively deprotected, allowing for the creation of a wide range of biologically active molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-Aminophenylacetic acid, N-BOC protected is employed as a versatile intermediate for the preparation of peptides and amino acids, which are essential components in the development of new drugs and therapeutic agents.
Used in the Preparation of Biologically Active Molecules:
3-Aminophenylacetic acid, N-BOC protected is also utilized in the synthesis of biologically active molecules, where the BOC protecting group plays a crucial role in ensuring the selective deprotection of the amine group, facilitating the formation of complex molecular structures with potential applications in medicine and biotechnology.

InChI:InChI=1/C13H17NO4/c1-13(2,3)18-12(17)14-10-6-4-5-9(7-10)8-11(15)16/h4-7H,8H2,1-3H3,(H,14,17)(H,15,16)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 14338-36-4 3-amino phenylacetic acid 
• 150529-73-0 methyl 2-(3-bromophenyl)acetatee 
• 1878-67-7 3-Bromophenylacetic acid 

Downstream Products

• 1227745-54-1 tert-butyl {3-[2-(2-hydroxy-6-oxocyclohex-1-en-1-yl)-3-oxoethyl]phenyl}carbamate 
• 396091-20-6 C₁₉H₁₄FN₃O₂ 

Relevant articles and documents

Fibril-forming model synthetic peptides containing 3-aminophenylacetic acid

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Pharmacomodulation of the antimalarial plasmodione: Synthesis of biaryl-and N-arylalkylamine analogues, antimalarial activities and physicochemical properties

With the aim of increasing the structural diversity on the early antimalarial drug plasmodione, an efficient and versatile procedure to prepare a series of biaryl- and N-arylalkylamines as plasmodione analogues is described. Using the naturally occurring and commercially available menadione as starting material, a 2-step sequence using a Kochi-Anderson reaction and subsequent Pd-catalyzed Suzuki-Miyaura coupling was developed to prepare three representative biphenyl derivatives in good yields for antimalarial evaluation. In addition, synthetic methodologies to afford 3-benzylmenadione derivatives bearing a terminal -N(Me)2 or -N(Et)2 in different positions (ortho, meta and para) on the aryl ring of the benzylic chain of plasmodione were investigated through reductive amination was used as the optimal route to prepare these protonable N-arylalkylamine privileged scaffolds. The antimalarial activities were evaluated and discussed in light of their physicochemical properties. Among the newly synthesized compounds, the para-position of the substituent remains the most favourable position on the benzyl chain and the carbamate -NHBoc was found active both in vitro (42 nM versus 29 nM for plasmodione) and in vivo in Plasmodium berghei-infected mice. The measured acido-basic features of these new molecules support the cytosol-food vacuole shuttling properties of non-protonable plasmodione derivatives essential for redox-cycling. These findings may be useful in antimalarial drug optimization.