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

pka

4.41±0.10(Predicted)

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Soluble in water and 1% acetic acid.

BRN 

2302327

CAS DataBase Reference

35737-10-1(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

FMOC-b-Ala-OH Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

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

FMOC-b-Ala-OH(35737-10-1)Related Product Information

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