62129-39-9

Basic information

• Product Name: (S)-N-BOC-4-Bromophenylalanine
• Synonyms: BOC-PHE(4-BR)-OH;BOC-P-BROMO-L-PHE-OH;BOC-P-BROMO-PHENYLALANINE;BOC-P-BROMO-PHE-OH;BOC-PHE(P-BR)-OH;BOC-L-PHE(4-BR)-OH;BOC-(S)-2-AMINO-3-(4'-BROMOPHENYL)PROPANOIC ACID;BOC-4'-BROMO-L-PHE
• CAS NO: 62129-39-9
• Molecular Formula: C₁₄H₁₈BrNO₄
• Molecular Weight: 344.2
• EINECS: 1592732-453-0
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;a-amino
• Mol File: 62129-39-9.mol

Chemical Properties

• Melting Point: 118 °C
• Boiling Point: 475.3 °C at 760 mmHg
• Flash Point: 241.2 °C
• Appearance: off-white powder
• Density: 1.5311 (rough estimate)
• Vapor Pressure: 7.71E-10mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: Store at RT.
• PKA: 3.83±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: (S)-N-BOC-4-Bromophenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-BOC-4-Bromophenylalanine(62129-39-9)
• EPA Substance Registry System: (S)-N-BOC-4-Bromophenylalanine(62129-39-9)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 62129-39-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-N-Boc-4-Bromophenylalanine is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique chemical structure allows it to be a key component in the development of new pharmaceuticals, contributing to the advancement of medical treatments and therapies.
As a building block in the synthesis of complex organic molecules, (S)-N-Boc-4-Bromophenylalanine can be utilized in the creation of a wide range of pharmaceutical compounds, including those with potential applications in the treatment of various diseases and conditions. Its versatility and importance in the pharmaceutical industry make it a valuable asset in the development of new and innovative medications.

InChI:InChI=1/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 24250-84-8 H-p-BrPhe-OH 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 122839-59-2 (S)-2-amino-3-(4-bromophenyl)propanoic acid hydrochloride 

Downstream Products

• 949885-93-2 [2-(4-bromo-phenyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester 
• 854760-84-2 1,1-dimethylethyl [(1S)-2-(4-bromophenyl)-1-(hydroxymethyl)ethyl]carbamate 
• 99359-32-7 (S)-2-amino-3-(4-bromophenyl)propionic acid methyl ester hydrochloride 
• 1378243-23-2 C₂₆H₄₀BrN₃O₆S 
• 1378243-33-4 C₂₂H₃₂BrN₃O₅S 
• 266306-18-7 (S)-3-(4-Bromo-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester 
• 1398718-23-4 C₉H₉BrN₂ 
• 1398717-93-5 (S)-D₆-1-amino-N-(1-cyano-2-(4'-((4-methyl-piperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide 
• 1398717-97-9 (R)-1-amino-N-(1-cyano-2-(4'-((4-propylpiperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide 
• 1398717-99-1 (R)-1-amino-N-(1-cyano-2-(4'-((4-cyclopropyl-piperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide 
• 1398718-01-8 (R)-1-amino-N-(1-cyano-2-(4'-((4-(cyanomethyl)piperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclohexanecarboxamide 
• 869569-99-3 tert-butyl (S)-(1-amino-3-(4-bromophenyl)-1-oxopropan-2-yl)carbamate 
• 869570-00-3 tert-butyl (S)-[2-(4-bromophenyl)-1-cyanoethyl]carbamate 
• 1398718-36-9 (S)-(9H-fluoren-9-yl)methyl 1-(1-cyano-2-(4'-((4-methylpiperazin-1-yl)methyl)-biphenyl-4-yl)ethylcarbamoyl)cyclohexylcarbamate 

Relevant articles and documents

Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins

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Chemoenzymatic Synthesis of Optically Pure l- and d-Biarylalanines through Biocatalytic Asymmetric Amination and Palladium-Catalyzed Arylation

A chemoenzymatic approach was developed and optimized for the synthesis of a range of N-protected nonnatural l- and d-biarylalanine derivatives. Starting from 4-bromocinnamic acid and 4-bromophenylpyruvic acid using a phenylalanine ammonia lyase (PAL) and an evolved d-amino acid dehydrogenase (DAADH), respectively, both enantiomers of 4-bromophenylalanine were obtained and subsequently coupled with a panel of arylboronic acids to give the target compounds in high yield and optical purity under mild aqueous conditions.

PEPTIDYL NITRIL COMPOUNDS AS DIPEPTIDYL PEPTIDASE I INHIBITORS

The invention relates to compounds of Formula (I) and its use as a selective dipeptidyl peptidase I inhibitor, as well as pharmaceutical compositions comprising said compounds, and methods of treatment involving said compounds.

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Asymmetric synthesis of N-protected amino acids by the addition of organolithium carboxyl synthons to ROPHy/SOPHy-derived aldoximes and ketoximes.

A new asymmetric synthesis of alpha-amino acids is described in which the key step is the highly diastereoselective addition of organolithium carboxyl synthons (2-furyllithium, phenyllithium, vinyllithium) to (R)- and (S)-O-(1-phenylbutyl) oximes to give hydroxylamines, with vinyllithium being the most satisfactory nucleophilic reagent. Subsequent reductive cleavage of the N-O bond in hydroxylamines, followed by N-protection, and oxidative cleavage of the carboxyl precursor gave a range of N-protected amino acids and esters. The method was exemplified by the synthesis of a range of derivatives of non-proteinogenic amino acids such as 4-bromophenylalanine, tert-leucine, norvaline, cyclohexyl- and aryl-glycines, 2-amino-8-oxodecanoic acid (Aoda) and alpha-methylvaline.