FMOC-4-AMINOBENZOIC ACID Chemical Properties

Melting point:

~277 °C (dec.)

Boiling point:

544.9±33.0 °C(Predicted)

Density 

1.352±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

4.29±0.10(Predicted)

form 

powder

Appearance

White to off-white Solid

BRN 

7722986

CAS DataBase Reference

185116-43-2(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

F 

10

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

FMOC-4-AMINOBENZOIC ACID Usage And Synthesis

Chemical Properties

White powder

Uses

Fmoc-4-aminobenzoic acid is used in the improved rapid synthesis of oligo(benzamide) block copolymers.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

Under an inert atmosphere, p-aminobenzoic acid (10 g, 73 mmol) was dissolved in anhydrous N-methylpyrrolidone (NMP, 50 mL). Subsequently, a solution of anhydrous NMP (50 mL) of 9-fluorenylmethyl chloroformate (Fmoc-Cl, 18.9 g, 73 mmol) was slowly added dropwise. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the mixture was slowly poured into 400 mL of water to precipitate the product. The colorless precipitate was collected by filtration and washed with plenty of water. Finally, the product was dried under vacuum at 120 °C to afford N-Fmoc-p-aminobenzoic acid (24.8 g, 94% yield). The melting point of the product was 215 °C (decomposition). Nuclear magnetic resonance hydrogen spectrum (1H-NMR, 300 MHz, DMSO-d6): δ 4.33 (t, J = 6.25 Hz, 1H), 4.54 (d, J = 6.25 Hz, 2H), 7.33-7.45 (m, 4H), 7.57 (d, J = 7.35 Hz, 2H), 7.76 (d, J = 7.35 Hz, 2H), and 7.89 (m, 4H), 10.08 (s, 1H), 12.69 (s, 1H). NMR carbon spectrum (13C-NMR and DEPT, 300 MHz, DMSO-d6): δ 46.61 (CH2), 65.83 (CH), 117.5 (CH), 120.22 (CH), 124.48 (C), 125.14 (CH), 127.17 (CH), 127.74 (CH), 130.48 ( CH), 140.86 (C), 143.31 (C), 143.74 (C), 153.31 (C), 167.03 (C). Infrared spectra (IR, ν, cm-1): 3344, 2970, 2887, 2660, 2544, 1709, 1673, 1610, 1592, 1526, 1511, 1411, 1311, 1282, 1221, 1052, 850, 736. reversed-phase high performance liquid chromatography (RP-HPLC) retention time: 26.6 Minutes. Mass spectrometry (FD-MS): m/z (%) = 359.1 (100), 360.1 (17.4); calculated value [C22H17NO4] = 359.1.

References

[1] Tetrahedron Letters, 2013, vol. 54, # 8, p. 753 - 756
[2] Chemical Communications, 2013, vol. 49, # 40, p. 4555 - 4557
[3] Journal of Chemical Research, Miniprint, 1998, # 10, p. 2736 - 2753
[4] Chemical Communications, 2014, vol. 50, # 14, p. 1691 - 1693

FMOC-4-AMINOBENZOIC ACID(185116-43-2)Related Product Information

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