(5-Amino-1,2,4-thiadiazol-3-yl)[(fluoromethoxy)imino]acetic acid

Base Information

• Chemical Name: (5-Amino-1,2,4-thiadiazol-3-yl)[(fluoromethoxy)imino]acetic acid
• CAS No.: 116833-10-4
• Molecular Formula: C₅H₅FN₄O₃S
• Molecular Weight: 220.184
• DSSTox Substance ID: DTXSID60699575
• Mol file: 116833-10-4.mol

Synonyms:116833-10-4;DTXSID60699575;(5-Amino-1,2,4-thiadiazol-3-yl)[(fluoromethoxy)imino]acetic acid;2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl) acetic acid

Chemical Property of (5-Amino-1,2,4-thiadiazol-3-yl)[(fluoromethoxy)imino]acetic acid

Chemical Property:

• Boiling Point: 442.0±47.0 °C(Predicted)
• PKA: 2.03±0.41(Predicted)
• PSA: 139.66000
• Density: 1.93±0.1 g/cm3(Predicted)
• LogP: -0.21730
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 220.00663937
• Heavy Atom Count: 14
• Complexity: 251

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(ON=C(C1=NSC(=N1)N)C(=O)O)F

Technology Process of (5-Amino-1,2,4-thiadiazol-3-yl)[(fluoromethoxy)imino]acetic acid

There total 6 articles about (5-Amino-1,2,4-thiadiazol-3-yl)[(fluoromethoxy)imino]acetic 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: 84.0%

methyl (Z)-2-(5-formylamino-1,2,4-thiadiazol-3-yl)-2-<(fluoromethoxy)imino>acetate (127930-01-2) → 2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid (116833-10-4)

Guidance literature:

With sodium hydroxide; at 22 ℃; for 6h;

DOI:10.1246/bcsj.66.2335

Reference yield: 60.5%

methyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-<(fluoromethoxy)imino>acetate (127929-83-3) → 2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid (116833-10-4) + (5-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-fluoromethoxyimino]-acetylamino}-[1,2,4]thiadiazol-3-yl)-[(Z)-fluoromethoxyimino]-acetic acid

Guidance literature:

With sodium hydroxide; In methanol; for 1h; Ambient temperature;

DOI:10.1246/bcsj.66.2335

Reference yield:

(E)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-<(fluoromethoxy)imino>acetonitrile (126483-43-0) → 2-fluoromethoxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)-acetic acid (116833-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / methanol / 24 h / 20 °C

2: 84 percent / 4 M H₂SO₄ / acetone / 2 h / 20 °C

3: 84 percent / acetic anhydride / 12 h / 25 °C

4: 84 percent / 1 M aq. NaOH / 6 h / 22 °C

With sodium hydroxide; sulfuric acid; acetic anhydride; In methanol; acetone;

DOI:10.1246/bcsj.66.2335

upstream raw materials:

methyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-<(fluoromethoxy)imino>acetate

methyl (Z)-2-(5-formylamino-1,2,4-thiadiazol-3-yl)-2-<(fluoromethoxy)imino>acetate

(E)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-<(fluoromethoxy)imino>acetonitrile

methyl (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-<(fluoromethoxy)imino>acetimidate

Downstream raw materials:

(6R,7R)-7-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-fluoromethoxyimino]-acetylamino}-3-iodomethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

p-methoxybenzyl (6R,7R)-7-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-fluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

(6R,7R)-7-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-fluoromethoxyimino]-acetylamino}-3-[(E)-2-((R)-2-methyl-isoxazolidin-5-yl)-vinyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester