172876-96-9 Usage
Molecular Weight
276.03 g/mol
Appearance
Pale yellow to off-white crystalline solid
Solubility
Soluble in organic solvents such as dichloromethane, acetone, and ethyl acetate
Reactivity
Hypervalent iodine compound, acts as an oxidizing agent
Applications
a. Selective oxidation of alcohols to aldehydes, ketones, and carboxylic acids
b. Oxidation of alkenes to epoxides
c. Oxidation of sulfides to sulfoxides and sulfones
d. Synthesis of pharmaceuticals and fine chemicals
Advantages
a. Environmentally friendly alternative to toxic oxidants like chromium or permanganate
b. Mild reaction conditions, avoiding harsh temperatures or pressures
c. High selectivity for various functional groups
d. Efficient and versatile reagent in organic synthesis
Safety
a. Use in a well-ventilated area or under a fume hood
b. Wear appropriate personal protective equipment (gloves, goggles, lab coat)
c. Dispose of waste according to local regulations and guidelines
Storage
Store in a cool, dry place, away from heat, light, and moisture
Stability
Stable under normal laboratory conditions, but sensitive to moisture and heat
Hazards
a. Irritant to eyes, skin, and respiratory system
b. Potential sensitizer
c. May cause allergic skin reaction
Incompatibilities
Incompatible with strong acids, strong bases, and reducing agents
Regulatory Information
Classified as a hazardous substance, subject to transportation and handling regulations
Synonyms
1,2-Benziodoxol-3(2H)-one 1-oxide, IBX, 1,2-Iodoxybenzene, 1,2-Diiodooxazole, O-Iodoxybenzoic acid, 1,2-Dihydro-1,2-benziodoxol-3-one 1-oxide
Check Digit Verification of cas no
The CAS Registry Mumber 172876-96-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,2,8,7 and 6 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 172876-96:
(8*1)+(7*7)+(6*2)+(5*8)+(4*7)+(3*6)+(2*9)+(1*6)=179
179 % 10 = 9
So 172876-96-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H4INO2/c10-5-9-7-4-2-1-3-6(7)8(11)12-9/h1-4H
172876-96-9Relevant articles and documents
N-Cyanation of Primary and Secondary Amines with Cyanobenzio-doxolone (CBX) Reagent
Chen, Zimin,Yuan, Weiming
supporting information, p. 14836 - 14840 (2021/09/30)
An efficient electrophilic N-cyanation of amines with a stable and less-toxic cyanobenziodoxole reagent towards the synthesis of cyanamides is disclosed. This synthetically practicable strategy allows the construction of a wide variety of cyanamides under very mild and simple conditions with a broad functional group compatibility, and showcases a huge potential in late-stage modification of complex molecules.
Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C
Bisai, Alakesh,Das, Mrinal Kanti,De, Subhadip,Maity, Arindam,Naskar, Malay,Roy, Avishek
supporting information, p. 1679 - 1684 (2020/03/05)
Efficient oxidative direct cyanations of 3-alkyl/aryl 2-oxindoles using Cyano-1,2-BenziodoXol-3(1H)-one (CBX) (2a) have been reported under 'transition metal-free' conditions to synthesize a wide variety of 3-cyano 3-alkyl/aryl 2-oxindoles sharing an all-carbon quaternary center under additive-free conditions. The application of this process is shown by the formal total synthesis of (±)-gliocladin C (11c) in a few steps.
A metal-free direct C (sp3)-H cyanation reaction with cyanobenziodoxolones
Sun, Ming-Xue,Wang, Yao-Feng,Xu, Bao-Hua,Ma, Xin-Qi,Zhang, Suo-Jiang
supporting information, p. 1971 - 1975 (2018/03/23)
A metal-free protocol of direct C(sp3)-H cyanation with cyanobenziodoxolones functioning as both cyanating reagents and oxidants was developed. Unactivated substrates, such as alkanes, ethers and tertiary amines, were thereby transformed to the corresponding nitriles in moderate to high yields. Mechanistic studies indicated that the cyanation proceeded with two potential pathways, which is highly dependent on the substrates: (1) a free radical case for alkanes and ethers and (2) an oxidative case for tertiary amines.
