62129-44-6

Basic information

• Product Name: BOC-4-IODO-L-PHENYLALANINE
• Synonyms: N-ALPHA-T-BUTYLOXYCARBONYL-L-4-IODOPHENYLALANINE;N-alpha-t-Butyloxycarbonyl-4-iodo-L-phenylalanine;Boc-4-lodo-Phe-OH;N-(tert-butoxycarbonyl)-p-iodo-L-phenylalanine;Boc-L-4-Iodo-phe-OH;(2S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-iodophenyl)propanoic acid;N-(Tert-Butoxycarbonyl)-4-iodo-(L)-phenylalanine;N-Boc-4-Iodo-L-phenylalanine (Boc-Phe(4-I)-OH) ,99% (HPLC)
• CAS NO: 62129-44-6
• Molecular Formula: C₁₄H₁₈INO₄
• Molecular Weight: 391.2
• Product Categories: Phenylalanine [Phe, F];Unusual Amino Acids;Boc-Amino acid series;Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids
• Mol File: 62129-44-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: ~150 °C (dec.)
• Boiling Point: 475.3 °C at 760 mmHg
• Flash Point: 241.3 °C
• Appearance: White powder
• Density: 1.56 g/cm³
• Storage Temp.: Store at 0°C
• PKA: 3.84±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• Sensitive: Light Sensitive
• BRN: 4503851
• CAS DataBase Reference: BOC-4-IODO-L-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-4-IODO-L-PHENYLALANINE(62129-44-6)
• EPA Substance Registry System: BOC-4-IODO-L-PHENYLALANINE(62129-44-6)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• F: 8
• HazardClass: IRRITANT
• Hazardous Substances Data: 62129-44-6(Hazardous Substances Data)

Usage

Description

Boc-4-Iodo-L-phenylalanine, also known as N-Boc-4-iodo-L-phenylalanine, is a chemical compound derived from the amino acid L-phenylalanine. It is characterized by the presence of an iodo group at the para position of the phenyl ring and an N-Boc (tert-butyloxycarbonyl) protecting group. This white powder is a valuable building block in the synthesis of various pharmaceuticals and bioactive molecules.

Uses

Used in Pharmaceutical Industry:
Boc-4-Iodo-L-phenylalanine is used as a pharmaceutical intermediate for the synthesis of various drugs and bioactive compounds. Its N-Boc protection group ensures the stability of the molecule during the synthesis process, preventing unwanted side reactions and facilitating the selective introduction of functional groups.
Additionally, Boc-4-Iodo-L-phenylalanine serves as a p-iodo phenyl alanine derivative, which is an important component in the development of novel therapeutic agents. The presence of the iodo group at the para position of the phenyl ring allows for further functionalization and modification, making it a versatile building block in the pharmaceutical industry.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1991-81-7 4-iodo-L-phenylalanine 
• 16004-15-2 1-bromomethyl-4-iodobenzene 
• 102831-44-7 diethyl tert-butoxycarbonylaminomalonate 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 63-91-2 L-phenylalanine 

Downstream Products

• 137452-47-2 N-Boc-4-formyl-L-phenylalanine 
• 79385-56-1 methyl {(S)-2-[(tert-butoxycarbonyl)amino]-3-(4-iodophenyl)propanoyl}-L-phenylalaninate 
• 1026064-05-0 3-hydroxy-O-methyl-N-<4-iodo-N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanyl>-L-tyrosine methyl ester 
• 113850-81-0 (S)-2-tert-Butoxycarbonylamino-3-{4-[4-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-phenylsulfanyl]-phenyl}-propionic acid 
• 108826-83-1 Boc-Phe(I)-Gaba-OTmse 
• 108827-30-1 Bpoc-Phe(I)-D-Trp-Lys(Boc)-Thr(t-Bu)-Phe-Pro-OTmse 
• 138571-42-3 N-BOC-N-methyl-4-iodo-L-phenylalanine 
• 82565-70-6 Boc-Phe(4-I)-Gly-Leu-Met-NH₂ 
• 167316-03-2 3-acetoxy-N,O-dimethyl-N-<<(tert-butyloxy)carbonyl>-L-4'-iodophenylalanyl>-L-tyrosine methyl ester 
• 178896-43-0 5-[(S)-2-tert-Butoxycarbonylamino-3-(4-iodo-phenyl)-propionylamino]-isophthalic acid dibenzyl ester 
• 113850-76-3 N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester 
• 129150-58-9 benzyl Boc-4-iodophenylalanine 
• 262604-01-3 (4S)-3-t-butyloxycarbonyl-4-(4-iodobenzyl)-5-oxazolidinone 
• 130640-17-4 (S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-iodo-phenyl)-propionylamino]-4-methyl-pentanoic acid methyl ester 

Relevant articles and documents

Development of potent and selective Cathepsin C inhibitors free of aortic binding liability by application of a conformational restriction strategy

Cathepsin C plays a key role in the activation of several degradative enzymes linked to tissue destruction in chronic inflammatory and autoimmune diseases. Therefore, Cathepsin C inhibitors could potentially be effective therapeutics for the treatment of diseases such as chronic obstructive pulmonary disease (COPD) or acute respiratory distress syndrome (ARDS). In our efforts towards the development of a novel series of Cathepsin C inhibitors, we started working around AZD5248 (1), an α-amino acid based scaffold having potential liability of aortic binding. A novel series of amidoacetonitrile based Cathepsin C inhibitors were developed by the application of a conformational restriction strategy on 1. In particular, this work led to the development of a potent and selective Cathepsin C inhibitor 3p, free of aortic binding liability.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Synthesis and Explosion Hazards of 4-Azido- l -phenylalanine

A reliable, scalable, cost-effective, and chromatography-free synthesis of 4-azido-l-phenylalanine beginning from l-phenylalanine is described. Investigations into the safety of the synthesis reveal that the Ullman-like Cu(I)-catalyzed azidation step does not represent a significant risk. The isolated 4-azido-l-phenylalanine product, however, exhibits previously undocumented explosive characteristics.