FMOC-4-AMINOBENZOIC ACID

FMOC-4-AMINOBENZOIC ACID Property

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

Safety Statements 

22-24/25

WGK Germany 

3

F 

10

HS Code 

2924 29 70

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

FMOC-4-AMINOBENZOIC ACID Chemical Properties,Usage,Production

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