4-Fluoroglutamic acid

Base Information

• Chemical Name: 4-Fluoroglutamic acid
• CAS No.: 2708-77-2
• Molecular Formula: C5H8FNO4
• Molecular Weight: 165.121
• Hs Code.: 2922499990
• European Community (EC) Number: 220-302-8
• DSSTox Substance ID: DTXSID40949843
• Nikkaji Number: J192.215G
• Mol file: 2708-77-2.mol

Synonyms:2-amino-4-(18F)-fluoropentanedioic acid;4-fluoroglutamic acid;4-fluoroglutamic acid, (D)-isomer;4-fluoroglutamic acid, (DL)-isomer;4-fluoroglutamic acid, (L)-isomer;BAY 85-8050;gamma-fluoroglutamic acid

Chemical Property of 4-Fluoroglutamic acid

Chemical Property:

• Vapor Pressure: 1.37E-05mmHg at 25°C
• Melting Point: 160.9 °C
• Refractive Index: 1.491
• Boiling Point: 342.4 °C at 760 mmHg
• PKA: 2.06±0.10(Predicted)
• Flash Point: 160.9 °C
• PSA: 100.62000
• Density: 1.498 g/cm³
• LogP: -0.08860
• XLogP3: -3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 165.04373590
• Heavy Atom Count: 11
• Complexity: 172

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Fluoro-DL-glutamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(=O)O)N)C(C(=O)O)F
• Uses: 4-Fluoro-DL-glutamic acid is used as a reagent to synthesize analogues of Methotrexate (M260675), a drug that is used to treat acute leukemia, breast carcinoma, and rheumatoid arthritis. The labelled form of 4-Fluoro-DL-glutamic acid is used in the medical field as an amino acid radiotracer for imaging of tumours.

Technology Process of 4-Fluoroglutamic acid

There total 11 articles about 4-Fluoroglutamic 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%

dimethyl thero-4-fluoroglutamate hydrochloride (148267-92-9) → D,L-erythro,threo-4-fluoroglutamic acid (2708-77-2,149117-03-3,91383-48-1,91383-47-0)

Guidance literature:

With hydrogenchloride; at 70 ℃; for 3h;

DOI:10.1016/S0022-1139(00)80033-0

Reference yield: 84.0%

γ-fluoroglutamic acid diisopropyl ester hydrochloride (95755-23-0) → D,L-erythro,threo-4-fluoroglutamic acid (2708-77-2,149117-03-3,91383-48-1,91383-47-0)

Guidance literature:

With hydrogenchloride; at 70 ℃; for 3h;

DOI:10.1016/S0022-1139(00)80033-0

Reference yield: 80.0%

C-Acetamino-C-<2-fluor-2-aethoxycarbonyl-aethyl>-malonsaeure-diaethylester (1652-64-8) → D,L-erythro,threo-4-fluoroglutamic acid (2708-77-2,149117-03-3,91383-48-1,91383-47-0)

Guidance literature:

With hydrogenchloride; for 5h; Heating;

DOI:10.1016/S0022-1139(00)80032-9

upstream raw materials:

ethyl 2-acetamidoacrylate

fluoromalonic acid diethyl ester

2-Acetamino-2,4-dicarboxy-4-fluor-glutarsaeuretetramethylester

1-Acetamino-3-fluor-propan-tetracarbensaeure-(1,1,3,3)-tetraethylester

Downstream raw materials:

γ-Fluor-N(-4-benzyloxycarbonylaminobenzoyl)glutaminaeure

(+/-)-2-Fluoro-4-aminobutanoic acid

(-)-D-erythro-4-fluoroglutamic acid

d-threo-(2R,4R)-4-Fluoroglutamic acid

Refernces

• 1、 Tolman, V.,Vlasakova, V.,Nemecek, J.. "Chemistry of 4-fluoroglutamic acid. Part 2. Separation of the diastereomers on a large scale. Preparation of cis- and trans-4-fluoro-5-pyrrolidone-2-carboxylic acids (4-fluoropyroglutamic acids)". . p. 185 - 191. Retrieved 2007/10/02.