BOC-3-AMINOBENZOIC ACID Chemical Properties

Melting point:

195 °C (dec.)

Boiling point:

339.8±25.0 °C(Predicted)

Density 

1.242±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.15±0.10(Predicted)

Appearance

White to off-white Solid

BRN 

5813611

CAS DataBase Reference

111331-82-9(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich

BOC-3-AMINOBENZOIC ACID Usage And Synthesis

Chemical Properties

Brown powder

Uses

Boc-3-Abz-OH, is an intermediate in the synthesis of various pharmaceutical compounds, including inhibitors, and therapeutic agents. It can also be used in the preparation of conformationally-constrained cyclic peptides with biarylamine linkers.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

GENERAL METHOD: To a stirred solution of m-aminobenzoic acid (5.00 g, 36.5 mmol) and sodium hydroxide (1.56 g, 39.3 mmol) in a solvent mixture of 1:1 water/dioxane (60 mL) at 0 °C was slowly added di-tert-butyl dicarbonate (14.3 g, 65.4 mmol). The reaction mixture was continued to be stirred at 0 °C for 3 h, followed by slow warming to room temperature and stirring overnight. After completion of the reaction, the reaction mixture was extracted with ethyl acetate (60 mL) and the extraction was repeated once (60 mL). The organic phases were combined and neutralized with 1 M aqueous KHSO4 to pH ≈ 7. The organic layer was separated, washed with water (60 mL) and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give 3-(N-Boc-amino)benzoic acid (7.53 g, 87% yield) as an off-white solid, which could be used in the next reaction without further purification.

References

[1] Journal of Medicinal Chemistry, 2001, vol. 44, # 3, p. 441 - 452
[2] Tetrahedron, 2012, vol. 68, # 6, p. 1790 - 1801
[3] Patent: US2014/194383, 2014, A1. Location in patent: Paragraph 0500; 0507-0508
[4] Chemical Communications, 2013, vol. 49, # 66, p. 7340 - 7342
[5] Bioorganic and Medicinal Chemistry, 2018,

BOC-3-AMINOBENZOIC ACID(111331-82-9)Related Product Information

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