FMOC-4-AMINOBENZOIC ACID

Base Information

• Chemical Name: FMOC-4-AMINOBENZOIC ACID
• CAS No.: 185116-43-2
• Molecular Formula: C22H17NO4
• Molecular Weight: 359.381
• Hs Code.: 2924 29 70
• European Community (EC) Number: 689-942-7
• DSSTox Substance ID: DTXSID00373226
• Wikidata: Q72477779
• ChEMBL ID: CHEMBL46378
• Mol file: 185116-43-2.mol

Synonyms:4-(9-Fluorenylmethoxycarbonylamino)benzoicacid;

Chemical Property of FMOC-4-AMINOBENZOIC ACID

Chemical Property:

• Vapor Pressure: 1.05E-12mmHg at 25°C
• Melting Point: ~277 °C (dec.)
• Refractive Index: 1.684
• Boiling Point: 544.854 °C at 760 mmHg
• PKA: 4.29±0.10(Predicted)
• Flash Point: 283.318 °C
• PSA: 75.63000
• Density: 1.352 g/cm³
• LogP: 4.81880
• Storage Temp.: 2-8°C
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 359.11575802
• Heavy Atom Count: 27
• Complexity: 520

Purity/Quality:

99.3% ^*data from raw suppliers

Fmoc-4-aminobenzoic acid98+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC4=CC=C(C=C4)C(=O)O
• Uses: Fmoc-4-aminobenzoic acid is used in the improved rapid synthesis of oligo(benzamide) block copolymers.

Technology Process of FMOC-4-AMINOBENZOIC ACID

There total 2 articles about FMOC-4-AMINOBENZOIC ACID which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-(9H-fluoren-9-ylmethoxycarbonylamino)benzoic acid (185116-43-2)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; for 48h;

DOI:10.1002/ejoc.200701104

Reference yield: 94.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-(9H-fluoren-9-ylmethoxycarbonylamino)benzoic acid (185116-43-2)

Guidance literature:

for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.11.045

Reference yield: 85.0%

N-Fmoc-L-Pro Wang resin + 4-Fluorobenzoic acid (456-22-4) + 4-(9H-fluoren-9-ylmethoxycarbonylamino)benzoic acid (185116-43-2) → C19H18FN3O3 (1378484-08-2)

Guidance literature:

N-Fmoc-L-Pro Wang resin; With piperidine; In N,N-dimethyl-formamide; solid phase reaction;

4-(9H-fluoren-9-ylmethoxycarbonylamino)benzoic acid; With benzotriazol-1-ol; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; Inert atmosphere; solid phase reaction;

4-Fluorobenzoic acid; Further stages;

DOI:10.1016/j.bmcl.2012.03.078

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

4-amino-benzoic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

Downstream raw materials:

dimethyl N-(4-amino-benzoyl)-L-glutamate

N-<4-carbonyl>pyridin-2-ylmethyl)>aminobenzoyl>-L-glutamate

Refernces

• 1、 -. "N-aryl sulfanilamide-N-beta-D-glucopyranose diamide compound and application thereof". Paragraph 0029; 0034. . Retrieved 2021/06/26.
• 2、 Bandolik, Jan J.,Bhatia, Sanil,Borkhardt, Arndt,Hamacher, Alexandra,Hansen, Finn K.,Kassack, Matthias U.,Meiler, Jens,Roatsch, Martin,S?nnichsen, Melf,Sch?ler, Andrea,Schoeder, Clara T.,Sinatra, Laura. "Hydroxamic Acids Immobilized on Resins (HAIRs): Synthesis of Dual-Targeting HDAC Inhibitors and HDAC Degraders (PROTACs)". supporting information. p. 22494 - 22499. Retrieved 2020/10/12.