138769-92-3

Basic information

• Product Name: (+)-CIS-2(S),3(S)-2,3-DIHYDROXY-2,3-DIHYDROIODOBENZENE
• Synonyms: CIS-(1S,2S)-3-IODO-3,5,CYCLOHEXADIENE-1,2- DIOL;(+)-CIS-2(S),3(S)-2,3-DIHYDROXY-2,3-DIHYDROIODOBENZENE
• CAS NO: 138769-92-3
• Molecular Formula: C₆H₇IO₂
• Molecular Weight: 238.02
• Mol File: 138769-92-3.mol

Chemical Properties

• Boiling Point: 319.0±42.0 °C(Predicted)
• Appearance: /
• Density: 2.12±0.1 g/cm3(Predicted)
• PKA: 12.57±0.60(Predicted)
• CAS DataBase Reference: (+)-CIS-2(S),3(S)-2,3-DIHYDROXY-2,3-DIHYDROIODOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-CIS-2(S),3(S)-2,3-DIHYDROXY-2,3-DIHYDROIODOBENZENE(138769-92-3)
• EPA Substance Registry System: (+)-CIS-2(S),3(S)-2,3-DIHYDROXY-2,3-DIHYDROIODOBENZENE(138769-92-3)

Safety Data

• Hazardous Substances Data: 138769-92-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is utilized as a key intermediate in organic synthesis for the production of various complex organic molecules. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is used as a chiral compound for the development of enantiomerically pure drugs. Its stereochemistry plays a crucial role in the biological activity of the resulting pharmaceuticals, ensuring targeted effects and minimizing side effects.
Used in Chemical Industry:
(+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is employed in the chemical industry for the production of specialty chemicals, such as dyes, pigments, and polymers. Its unique properties contribute to the development of innovative materials with specific characteristics, catering to various applications.
Used in Asymmetric Synthesis:
As a chiral compound with two stereocenters, (+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is used in asymmetric synthesis to produce enantiomerically enriched products. This is crucial for the development of single-enantiomer drugs, which can exhibit improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Chiral Ligand Development:
(+)-CIS-2(S),3(S)-2,3-Dihydroxy-2,3-Dihydroiodobenzene is also used in the development of chiral ligands for catalysis. These ligands are essential in enantioselective catalysis, enabling the production of enantiomerically pure compounds with high selectivity and efficiency.

Upstream product

• 591-50-4 iodobenzene 

Downstream Products

• 114763-29-0 (2R,3S)-2,3-dihydroxy-1-ethynylcyclohexa-4,6-diene 
• 138769-94-5 cis-(1S,2R)-1,2-dihydroxy-3-allylcyclohexa-3,5-diene 
• 138769-97-8 (1S,2S)-1,2-dihydroxy-3-methylsulfanylcyclohexa-3,5-diene 
• 138769-93-4 cis-(1S,2R)-3-Butylcyclohexa-3,5-diene-1,2-diol 
• 138769-95-6 (1S,2R)-3-Trimethylsilanylethynyl-cyclohexa-3,5-diene-1,2-diol 
• 176166-16-8 cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohex-3-ene 
• 166191-22-6 (1S,7S,10S,11S)-10,11-Dihydroxy-1-iodo-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione 
• 300830-78-8 (1S,6S)-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}-2-iodocyclohexa-2,4-dien-1-ol 
• 320410-60-4 (1R,2R,3S,4S)-5-iodocyclohex-5-ene-1,2,3,4-tetraol 
• 320410-59-1 (1S,2S,3S,4S)-5-iodo-5-cyclohexene-1,2,3,4-tetraol 
• 638163-81-2 (1S,2S)-3-iodocyclohexa-3,5-dien-1,2-diyl bis-crotonate 
• 19337-60-1 3-iodo-1,2-benzenediol 
• 900792-05-4 (1S,2R,5S,6S)-6-(acetyloxy)-2,5-dibromo-3-iodo-3-cyclohexenyl acetate 
• 910564-72-6 (1S,2S,3S,6R)-6-Benzyloxy-4-iodo-cyclohex-4-ene-1,2,3-triol 

Relevant articles and documents

Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin

Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.

Medium-scale preparation of useful metabolites of aromatic compounds via whole-cell fermentation with recombinant organisms

The whole-cell fermentation of aromatic coumpounds with Escherichia coli JM109 (pDTG601) on a medium scale (10-15L) produces enantiopure cyclohexadienediols. A detailed procedure for the fermentation is described, and yields for several metabolites are provided. A similar procedure using E. coli JM109 (pDTG602) affords catechols. The dienediols are useful for asymmetric synthesis, and several important targets originating from these metabolites are tabulated.

Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes

Toluene dioxygenase-catalysed oxidation of mono-substituted benzene substrates (R = F, Cl, Br, I, Me, Et, CH2OAc, CH=CH2, C=CH, CF3, CN, OMe, OEt, SMe) in growing cultures of Pseudomonas putida UV4 yielded the corresponding cis-dihydrodiol metabolites. Palladium-catalysed cross-coupling of cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene with a range of tributyltin compounds provided a chemoenzymatic route to a further series of cis-dihydrodiol derivatives of monosubstituted benzenes (R = D, CH2CH=CH2, Bun, SEt, SPr1, SBu1, SPh, SC6H4Me-4). The enantiopurities and absolute configurations of the cis-dihydrodiols, obtained by both enzymatic and chemoenzymatic routes, were determined by several new methods including 1H NMR spectroscopic analysis of the bis-MTPA esters of the 4-phenyl-1,2,4-triazoline-3,5-dione cycloadducts, X-ray crystallography, circular dichroism spectroscopy and stereochemical correlation.

Enzymatic and Chemical Syntheses of cis-Dihydrodiol Derivatives of Monocyclic Arenes

Metabolism of bromobenzene and iodobenzene by growing cultures of Pseudomonas putida UV4 gave the corresponding cis-dihydrodiol products 1 and 2 in high yields; subsequent direct chemical substitution of the halogen atoms in these metabolites provided a new range of enantiomerically pure cis-dihydrodiols of known absolute configuration.