112639-11-9

Basic information

• Product Name: 2-IODO-5-METHYLBENZENE-1,3-DIOL
• Synonyms: 2-IODO-5-METHYLBENZENE-1,3-DIOL
• CAS NO: 112639-11-9
• Molecular Formula: C₇H₇IO₂
• Molecular Weight: 250.03
• Mol File: 112639-11-9.mol

Chemical Properties

• Boiling Point: 219.2±35.0 °C(Predicted)
• Appearance: /
• Density: 2.006±0.06 g/cm3(Predicted)
• PKA: 8.11±0.15(Predicted)
• CAS DataBase Reference: 2-IODO-5-METHYLBENZENE-1,3-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IODO-5-METHYLBENZENE-1,3-DIOL(112639-11-9)
• EPA Substance Registry System: 2-IODO-5-METHYLBENZENE-1,3-DIOL(112639-11-9)

Safety Data

• Hazardous Substances Data: 112639-11-9(Hazardous Substances Data)

Upstream product

• 504-15-4 orcinol 

Downstream Products

• 1240403-17-1 (2R,2′R)-2,2′-((2-iodo-1,3-phenylene)bis(oxy))bis(N-mesitylpropanamide) 

Relevant articles and documents

First Total Synthesis of Dermocanarin 2

The first total synthesis of dermocanarin 2 is described. The synthesis features the construction of the anthraquinone and naphthoquinone frameworks through annulation reactions onto an axially chiral biphenyl intermediate, obtained by an enzyme-catalyzed enantioselective desymmetrization of a σ-symmetric precursor, followed by a stereoselective aldol reaction to construct the stereogenic center in the side chain.

Controlled Generation of 3-Triflyloxyarynes

The efficient generation of 3-triflyloxyarynes, including those bearing a transformable group, through an iodine-magnesium exchange reaction of 1,3-bis(triflyloxy)-2-iodoarenes was achieved by using finely tuned reaction conditions that efficiently suppre

N -annulated perylene-based push-pull-type sensitizers

Alkoxy-wrapped N-annulated perylene (NP) was synthesized and used as a rigid and coplanar ??-linker for three push-pull type metal-free sensitizers QB1-QB3. Their optical and electrochemical properties were tuned by varying the structure of acceptor. Thes

A Chiral Pentafluorinated Isopropyl Group via Iodine(I)/(III) Catalysis

An I(I)/(III) catalysis strategy to construct an enantioenriched fluorinated isostere of the iPr group is reported. The difluorination of readily accessible α-CF3-styrenes is enabled by the in situ generation of a chiral ArIF2 species to forge a stereocentre with the substituents F, CH2F and CF3 (up to 95 %, >20:1 vicinal:geminal difluorination). The replacement of the metabolically labile benzylic proton results in a highly preorganised scaffold as was determined by X-ray crystallography (π→σ* and stereoelectronic gauche σ→σ* interactions). A process of catalyst editing is disclosed in which preliminary validation of enantioselectivity is placed on a structural foundation.

Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization

1,1-Disubstituted styrenes with internal oxygen and nitrogen nucleophiles undergo oxidative fluorocyclization reactions with in situ generated chiral iodine(III)-catalysts. The resulting fluorinated tetrahydrofurans and pyrrolidines contain a tertiary carbon-fluorine stereocenter. Application of a new 1-naphthyllactic acid-based iodine(III)-catalyst allows the control of tertiary carbon-fluorine stereocenters with up to 96% ee. Density functional theory calculations are performed to investigate the details of the mechanism and the factors governing the stereoselectivity of the reaction.

Hypervalent Iodine(III)-Catalysed Enantioselective α-Acetoxylation of Ketones

An enantioselective catalytic synthesis of α-acetoxylated ketones through I(I)/I(III) catalysis using a resorcinol/lactamide-based chiral iodoarene is reported. Catalyst turnover by in situ generation of the active iodine(III) derivative is achieved by oxidation with mCPBA in the presence of acetic acid. The prior transformation of ketones to easily accessible acetyl enol ethers is beneficial and yields up to 97 percent with enantioselectivities up to 88 percent ee are obtained using only low catalyst loadings of only 5 mol percent under mild reaction conditions.

Enantioselective, Catalytic Vicinal Difluorination of Alkenes

The enantioselective, catalytic vicinal difluorination of alkenes is reported by II/IIII catalysis using a novel, C2-symmetric resorcinol derivative. Catalyst turnover via in situ generation of an ArIIIIF2 species is enabled by Selectfluor oxidation and addition of an inexpensive HF–amine complex. The HF:amine ratio employed in this process provides a handle for regioselective orthogonality as a function of Br?nsted acidity. Selectivity reversal from the 1,1-difluorination pathway (geminal) to the desired 1,2-difluorination (vicinal) is disclosed (>20:1 in both directions). Validation with electron deficient styrenes facilitates generation of chiral bioisosteres of the venerable CF3 unit that is pervasive in drug discovery (20 examples, up to 94:06 e.r.). An achiral variant of the reaction is also presented using p-TolI (up to >95 % yield).

Selective aryne formation via Grob fragmentation from the [2+2] cycloadducts of 3-triflyloxyarynes

A chemoselective ring-opening protocol of the formal [2+2] cycloadducts of 3-triflyloxyarynes was developed to generate 2,3-aryne intermediate via Grob fragmentation. A variety of 1,3-di- and 1, 2, 3-trisubstituted arenes could be readily accessed through this [2+2] cycloaddition-2,3-aryne formation sequence. The regioselectivity in these transformations originates from the steric repulsion of the aliphatic chain.

Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions

Molecular structures of the most prominent chiral non-racemic hypervalent iodine(III) reagents to date have been elucidated for the first time. The formation of a chirally induced supramolecular scaffold based on a selective hydrogen-bonding arrangement provides an explanation for the consistently high asymmetric induction with these reagents. As an exploratory example, their scope as chiral catalysts was extended to the enantioselective dioxygenation of alkenes. A series of terminal styrenes are converted into the corresponding vicinal diacetoxylation products under mild conditions and provide the proof of principle for a truly intermolecular asymmetric alkene oxidation under iodine(I/III) catalysis.