35737-10-1

Basic information

• Product Name: FMOC-b-Ala-OH
• Synonyms: RARECHEM EM WB 0004;N-9-FLUORENYLMETHYLOXYCARBONYL-BETA-ALANINE;N-(9-FLUORENYLMETHOXYCARBONYL)-BETA-ALANINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-BETA-ALANINE;N-BETA-(9-FLUORENYLMETHOXYCARBONYL)-BETA-ALANINE;N-BETA-FMOC-BETA-ALANINE;N-FMOC-BETA-ALANINE;FMOC-NH-(CH2)2-COOH
• CAS NO: 35737-10-1
• Molecular Formula: C₁₈H₁₇NO₄
• Molecular Weight: 311.33
• Product Categories: Amino Acids;β-Alanine [β-Ala];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 35737-10-1.mol

Chemical Properties

• Melting Point: 142-147 °C
• Boiling Point: 451.38°C (rough estimate)
• Flash Point: 290 °C
• Appearance: white to light yellow crystal powder
• Density: 1.2626 (rough estimate)
• Vapor Pressure: 3.43E-13mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: 2-8°C
• PKA: 4.41±0.10(Predicted)
• Water Solubility: Soluble in water and 1% acetic acid.
• BRN: 2302327
• CAS DataBase Reference: FMOC-b-Ala-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-b-Ala-OH(35737-10-1)
• EPA Substance Registry System: FMOC-b-Ala-OH(35737-10-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 35737-10-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
FMOC-b-Ala-OH is used as a key intermediate for the synthesis of various organic compounds. Its chemical structure allows for the formation of new bonds and the creation of complex molecules, making it an essential component in the development of novel organic compounds.
Used in Pharmaceutical Industry:
FMOC-b-Ala-OH is used as a building block for the synthesis of pharmaceutical compounds. Its incorporation into drug molecules can enhance their efficacy, stability, and bioavailability, leading to the development of more effective medications.
Used in Agrochemicals:
In the agrochemical industry, FMOC-b-Ala-OH is used as a starting material for the development of new pesticides and herbicides. Its unique properties enable the creation of compounds with improved activity and selectivity, contributing to more effective and environmentally friendly agricultural products.
Used in Dyestuffs:
FMOC-b-Ala-OH is used as a raw material in the production of dyes and pigments. Its chemical structure can be modified to create a wide range of colors, making it a versatile component in the dyestuffs industry.

InChI:InChI=1/C18H17NO4/c20-17(21)9-10-19-18(22)23-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16H,9-11H2,(H,19,22)(H,20,21)/p-1

Upstream product

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Downstream Products

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• 176755-93-4 N-(9-fluorenylmethoxycarbonyl)-β-alanine p-nitrophenyl ester 
• 219803-84-6 (2-benzylcarbamoyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester 

Relevant articles and documents

Unwanted hydrolysis or α/β-peptide bond formation: How long should the rate-limiting coupling step take?

Nowadays, in Solid Phase Peptide Synthesis (SPPS), being either manual, automated, continuous flow or microwave-assisted, the reaction with various coupling reagents takes place via in situ active ester formation. In this study, the formation and stability of these key active esters were investigated with time-resolved 1H NMR by using the common PyBOP/DIEA and HOBt/DIC coupling reagents for both α- and β-amino acids. Parallel to the amide bond formation, the hydrolysis of the α/β-active esters, a side reaction that is a considerable efficacy limiting factor, was studied. Based on the chemical nature/constitution of the active esters, three amino acid categories were determined: (i) the rapidly hydrolyzing ones (t 24 h) in solution. The current insight into the kinetics of this key hydrolysis side reaction serves as a guide to optimize the coupling conditions of α- and β-amino acids, thereby saving time and minimizing the amounts of reagents and amino acids to be used-all key factors of more environmentally friendly chemistry.

Fmoc-OPhth, the reagent of Fmoc protection

Fmoc-OSu has been widely used for Fmoc protection of amino groups, especially amino acids, in solid phase peptide synthesis. However, it has been recognized that Fmoc-βAla-OH is formed as a by-product via the Lossen rearrangement during the reaction. Since we reconfirmed the formation of Fmoc-βAla-OH during the preparation of Fmoc-AA-OH by Fmoc-OSu, Fmoc-OPhth was designed and synthesized as a new Fmoc reagent to avoid the formation of Fmoc-βAla-OH. Furthermore, Fmoc protection by Fmoc-OPhth and Fmoc-SPPS were evaluated. The various Fmoc-amino acids prepared by Fmoc-OPhth were carried out in good yields and these are applicable in Fmoc-SPPS.