1-Chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole

Base Information

• Chemical Name: 1-Chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole
• CAS No.: 69352-04-1
• Molecular Formula: C9H10ClIO
• Molecular Weight: 296.535
• Mol file: 69352-04-1.mol

Synonyms:1,2-Benziodoxole, 1-chloro-1,3-dihydro-3,3-dimethyl-;

Chemical Property of 1-Chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole

Chemical Property:

• Melting Point: 143-145 °C(Solv: carbon tetrachloride (56-23-5))
• PSA: 9.23000
• LogP: 3.69670

Purity/Quality:

95% ^*data from raw suppliers

1-?Chloro-?1,?3-?dihydro-?3,?3-?dimethyl-?1,?2-?benziodioxole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-?Chloro-?1,?3-?dihydro-?3,?3-?dimethyl-?1,?2-?benziodioxole is used as a reactant in one-pot preparation of hypervalent iodine(III)-CF3 reagent for the use in electrophilic trifluoromethylation reactions. 1-Chloro-3,3-dimethylbenziodoxole is a crystalline, air-stable, yellow chloroiodane compound which finds use as a starting material for production of other hypervalent iodine compounds. It can also be used as a mild chlorinating reagent. The compound shows good solubility in polar organic solvents, typically dichloromethane or ethyl acetate.

Technology Process of 1-Chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole

There total 6 articles about 1-Chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole 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: 92.0%

2-(2-iodophenyl)propan-2-ol (69352-05-2) → 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (69352-04-1)

Guidance literature:

With tert-butylhypochlorite; at 20 ℃; for 0.5h; Darkness; Inert atmosphere;

DOI:10.1002/adsc.201300266

Reference yield: 38.0%

o-iodo-methyl-benzoic acid (610-97-9) + methylmagnesium bromide (75-16-1) → 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (69352-04-1)

Guidance literature:

o-iodo-methyl-benzoic acid; methylmagnesium bromide; In diethyl ether; at 0 - 23 ℃; for 3h; Inert atmosphere;

With tert-butylhypochlorite; In tetrachloromethane; at 23 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja304401u

Reference yield:

o-iodo-methyl-benzoic acid (610-97-9) → 1-chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole (69352-04-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / diethyl ether / 1 h / Heating

2: 56.5 percent / tert-butyl hypochlorite / CCl₄ / 0.5 h

With tert-butylhypochlorite; In tetrachloromethane; diethyl ether;

DOI:10.1021/ja00183a038

upstream raw materials:

2-(2-iodophenyl)propan-2-ol

o-iodo-methyl-benzoic acid

2-Iodobenzoic acid

methylmagnesium bromide

Downstream raw materials:

3,3-dimethyl-1-(2,2,2-trifluoro-1-phenyl-1-trifluoromethyl-ethoxy)-1,3-dihydro-1λ³-benzo[d][1,2]iodoxole

1-hydroxy-3,3-dimethyl-1,3-dihydro-λ³-benzo[d][1,2]iodoxole

Togni's reagent

1-methyl-1-phenylethyl alcohol

Refernces

• 1、 Comito, Robert J.,Ghosh, Subrata K.,Hu, Mengnan. "One-Pot Synthesis of Primary and Secondary Aliphatic Amines via Mild and Selective sp3 C?H Imination". supporting information. p. 17601 - 17608. Retrieved 2021/11/03.
• 2、 Lucchetti, Nicola,Tkacheva, Anastasia,Fantasia, Serena,Mu?iz, Kilian. "Radical C?H-Amination of Heteroarenes using Dual Initiation by Visible Light and Iodine". supporting information. p. 3889 - 3893. Retrieved 2018/09/21.