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FMOC-b-Ala-OH

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FMOC-b-Ala-OH Basic information
Product Name:FMOC-b-Ala-OH
Synonyms:3-Fmoc-aminopropanoic acid;Fmoc-β-alanine≥ 99% (HPLC);FMOC--ALA-OH Novabiochem;FMOC-GLY(C*CH2)-OH;FMOC-L-BETA-ALA-OH;FMOC-NH-(CH2)2-COOH;FMOC-BETA-ALANINE;FMOC-b-Ala-OH
CAS:35737-10-1
MF:C18H17NO4
MW:311.34
EINECS:
Product Categories:Amino Acids;β-Alanine [β-Ala];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
Mol File:35737-10-1.mol
FMOC-b-Ala-OH Structure
FMOC-b-Ala-OH Chemical Properties
Melting point 142-147 °C
Boiling point 451.38°C (rough estimate)
density 1.2626 (rough estimate)
refractive index 1.5100 (estimate)
storage temp. 2-8°C
solubility Soluble in water or 1% acetic acid
form powder to crystal
pka4.41±0.10(Predicted)
color White to Almost white
Water Solubility Soluble in water and 1% acetic acid.
BRN 2302327
Major Applicationpeptide synthesis
InChI1S/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)
InChIKeyLINBWYYLPWJQHE-UHFFFAOYSA-N
SMILESOC(=O)CCNC(=O)OCC1c2ccccc2-c3ccccc13
CAS DataBase Reference35737-10-1(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
HS Code 2924 29 70
HazardClass IRRITANT
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
FMOC-b-Ala-OH Usage And Synthesis
Chemical Propertieswhite to light yellow crystal powde
UsesIt is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.
reaction suitabilityreaction type: Fmoc solid-phase peptide synthesis
Synthesis
9-Fluorenylmethyl chloroformate

28920-43-6

β-Alanine

107-95-9

FMOC-b-Ala-OH

35737-10-1

Under stirring conditions, β-alanine (β-Ala, 0.5 g, 6.61 mmol) was dissolved in 10% aqueous Na2CO3 solution (12 ml) in a 50 ml flask. The flask was cooled in an ice bath followed by slow dropwise addition of Fmoc-Cl (1.45 g, 5.61 mmol) in dioxane (10 ml) solution. The reaction mixture was stirred continuously for 4 hours at room temperature. After completion of the reaction, the aqueous phase layer was separated by adding water (80 ml) for dilution and washed three times (75 ml each) with ether. The aqueous phase layer was acidified to pH=2 with 2N HCl aqueous solution and subsequently extracted with ethyl acetate three times (75 ml each). The organic phase layers were combined and concentrated to give 1.50 g of crude product. The crude product was recrystallized by a solvent mixture of ethyl acetate and hexane (1:2, 30 ml, v/v) and filtered under reduced pressure to obtain a white solid, Fmoc-β-Ala. yield: 1.41 g (81%). NMR (CDCl3) δ 2.6 (t, 2H, NHCH2CH2COOH), 3.47 (d, 2H, J = 7.0 Hz, NHCH2CH2COOH), 4.19 (t, 1H, J = 6.0 Hz, Fmoc-CH), 4.39 (d, 2H, J = 7.0 Hz, Fmoc-CH2), 7.29 (t, 2H , J = 7.3 Hz, Ar-H), 7.38 (t, 2H, J = 7.3 Hz, Ar-H), 7.56 (d, 2H, J = 7.0 Hz, Ar-H), 7.74 (d, 2H, J = 7.5 Hz, Ar-H).

References[1] Tetrahedron, 1991, vol. 47, # 14-15, p. 2389 - 2400
[2] Patent: US2009/131681, 2009, A1. Location in patent: Page/Page column 3
[3] Journal of Organic Chemistry, 1972, vol. 37, # 22, p. 3404 - 3409
[4] Bioorganic Chemistry, 1996, vol. 24, # 1, p. 50 - 58
[5] Russian Journal of General Chemistry, 2010, vol. 80, # 12, p. 2572 - 2589
Tag:FMOC-b-Ala-OH(35737-10-1) Related Product Information
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