887144-94-7 | 1-Trifluoromethyl-1,2-benziodoxol-3-(1h)-one

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$6.00	$5.00
5g	98%	in stock	$25.00	$18.00
10g	98%	in stock	$50.00	$35.00
25g	98%	in stock	$70.00	$49.00
50g	98%	in stock	$140.00	$98.00
100g	98%	in stock	$239.00	$167.00

Description

• Catalog Number: AB47911
• Chemical Name: 1-Trifluoromethyl-1,2-benziodoxol-3-(1h)-one
• CAS Number: 887144-94-7
• Molecular Formula: C8H4F3IO2
• Molecular Weight: 316.0158
• MDL Number: MFCD18800706
• SMILES: O=C1O[I](c2c1cccc2)C(F)(F)F

Computed Properties

• Complexity: 254
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 14
• Hydrogen Bond Acceptor Count: 5
• XLogP3: 3.6

Upstream Synthesis Route

The upstream synthetic route for 1-Trifluoromethyl-1,2-benziodoxol-3(1H)-one involves the following steps:

1. Synthesis of 2-Iodobenzoic Acid:
Starting from commercially available anthranilic acid, diazotization is carried out using sodium nitrite (NaNO2) and hydrochloric acid (HCl) at 0-5°C to form the diazonium salt. The resulting diazonium salt is then reacted with potassium iodide (KI) to substitute the diazo group with an iodine, yielding 2-iodobenzoic acid.

2. Oxidation to 2-Iodobenzaldehyde:
The obtained 2-iodobenzoic acid is subjected to oxidative decarboxylation using a suitable oxidizing agent such as lead(IV) acetate or manganese dioxide (MnO2) in the presence of acetic acid to afford 2-iodobenzaldehyde.

3. Formation of 2-Iodo-Benzodioxole:
2-Iodobenzaldehyde is reacted with chloral hydrate and concentrated sulfuric acid resulting in the formation of 1,2-benziodoxole through a ketal formation/ring-closure mechanism.

4. Trifluoromethylation:
Finally, the trifluoromethyl group is introduced using a trifluoromethylating agent like Togni's reagent or Umemoto's reagent to yield the target 1-trifluoromethyl-1,2-benziodoxol-3(1H)-one through electrophilic aromatic substitution on the benziodoxole ring.

The choice of reagents and conditions for each step can vary, and the optimal route may require further optimization based on factors such as yield, purity, and scalability.

Literature

• Reactivity of a hypervalent iodine trifluoromethylating reagent toward THF: ring opening and formation of trifluoromethyl ethers.

  The Journal of organic chemistry 20100305

• Acid-mediated formation of trifluoromethyl sulfonates from sulfonic acids and a hypervalent iodine trifluoromethylating agent.

  Chemical communications (Cambridge, England) 20091028