100349-67-5

Basic information

• Product Name: Benzenemethanol, a-(iodomethyl)-, (S)-
• Synonyms: 1-phenyl-2-iodo-ethanol;;2-iodo-1-phenylethan-1-ol;;1-hydroxy-2-iodo-1-phenylethane;;2-iodo-1-phenyl ethanol;;1-iodo-2-phenyl-2-ethanol;;2-iodo-1-phenylethanol
• CAS NO: 100349-67-5
• Molecular Formula: C8H9IO
• Molecular Weight: 248.063
• Mol File: 100349-67-5.mol
• Article Data: 82

Chemical Properties

• CAS DataBase Reference: Benzenemethanol, a-(iodomethyl)-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-(iodomethyl)-, (S)-(100349-67-5)
• EPA Substance Registry System: Benzenemethanol, a-(iodomethyl)-, (S)-(100349-67-5)

Safety Data

• Hazardous Substances Data: 100349-67-5(Hazardous Substances Data)

Usage

General Description

Benzenemethanol, a-(iodomethyl)-, (S)- is a chemical compound with the molecular formula C8H9IO. It is a chiral compound, with the (S)-enantiomer being the stereochemically preferred form. Benzenemethanol, a-(iodomethyl)-, (S)- is a derivative of benzenemethanol, with the addition of an iodomethyl group. It is commonly used in organic synthesis as a chiral building block for the preparation of biologically active molecules and pharmaceuticals. The (S)-enantiomer of benzenemethanol, a-(iodomethyl)- is particularly important for its role in the synthesis of chiral pharmaceuticals and agrochemicals. Benzenemethanol, a-(iodomethyl)-, (S)- is known for its ability to facilitate asymmetric synthesis and has applications in the production of various drugs and other important chemicals.

Upstream product

• 100-42-5 styrene 
• 67-56-1 methanol 
• 96-09-3 styrene oxide 
• 4636-16-2 iodoacetophenone 
• 127-65-1 chloroamine-T 
• 421-85-2 Trifluoromethanesulfonamide 
• 68-11-1 mercaptoacetic acid 
• 124-38-9 carbon dioxide 
• 1774-47-6 trimethylsulfoxonium iodide 
• 100-52-7 benzaldehyde 
• 66222-29-5 tri-n-butylstannylmethyl iodide 
• 68-12-2 N,N-dimethyl-formamide 
• 105581-82-6 (S)-2-(benzyloxy)-2-phenyl-1-ethanol 
• 134365-34-7 (S)-1-Benzyloxy-1-phenyl-2-(p-toluenesulfonyloxy)ethane 

Downstream Products

• 98-86-2 acetophenone 
• 96-09-3 styrene oxide 
• 98-85-1 1-Phenylethanol 
• 22383-53-5 2-ethoxy-1-phenylethanol 
• 122-78-1 phenylacetaldehyde 
• 14746-52-2 (2-hydroxy-2-phenylethyl)trimethylammonium iodide 
• 60-12-8 2-phenylethanol 
• 3587-84-6 2-methoxy-1-phenylethanol 
• 488785-29-1 (2S*,6R*)-2,6-diphenyl-4-tosylmorpholine 
• 124718-87-2 2-azido-1-phenylethan-1-ol 
• 87604-59-9 2-benzyloxy-2-phenyl ethanol 
• 17628-72-7 R-(-)-2-methoxy-2-phenyl ethanol 
• 111686-19-2 C₈H₁₁O₂⁽¹⁷⁾O⁽¹⁸⁾OPS 
• 20780-54-5 (S)-styrene oxide 

Relevant articles and documents

Envirocat (K10-MX)-catalyzed regioselective transformation of alkenes into iodohydrins and β-iodo ethers and further conversion of iodohydrins to epoxides using Al2O3-Na2Co3 under MWI

Commercial K10 clay was converted to extremely efficient and environmentally friendly catalyst K10-MX for the preparation of iodohydrins and β-iodo ethers from alkenes (terminal as well as internal) using microwave irradiation. This method was further extended for the conversion of alkenes to epoxides via iodohydrin intermediate in a one-pot reaction system. Copyright Taylor & Francis Group, LLC.

Coiodination of styrene with commercial clays: A convenient preparation of styrene oxide

Styrene oxide is easily prepared in 82-91% yield by the reaction of styrene with iodine/water in the presence of commercial clays, followed by in situ addition of KOH in n-hexane/water.

Regioselective synthesis of vic-halo alcohols and symmetrical or unsymmetrical vic-dihalides from epoxides using triphenylphosphine -N-halo imides

A simple, novel, and highly regioselective cleavage of epoxides into vicinal halo alcohols and symmetrical or unsymmetrical dihalides is described using different stoichiometries of triphenylphosphine (PPh3) and N-halo succinimide (NXS) or N-halo saccharine (NXSac).

Selenium-catalyzed iodohydrin formation from alkenes

A new simple method for catalyzed iodohydroxylation of alkenes using stoichiometric amounts of water is described. The iodohydrins were prepared in good yields from the corresponding alkenes using N-iodosuccinimide, 2 equiv of H2O, and catalytic amounts of diphenyl diselenide in MeCN.

Benzyl(triphenyl)phosphonium Dichloroiodate: A New Reagent for Coiodination of Alkenes

A mild, efficient, and regio- and stereoselective method for iodoalkoxylation and iodohydroxylation of olefins has been developed using benzyl(triphenyl)phosphonium dichloroiodate as iodine source. This procedure led to the corresponding iodoalkoxylated and iodohydroxylated products in moderate to excellent yields.

Cleavage of epoxides into halohydrins with elemental iodine and bromine in the presence of 2,6-bis[2-(o-aminophenoxy)methyl]-4-bromo-1-methoxybenzene (BABMB) as catalyst

The ring opening of epoxides with elemental iodine and bromine in the presence of 2,6-bis[2-(o-aminophenoxy)methyl]-4-bromo-1-methoxybenzene as a new catalyst affords vicinal iodo alcohols and bromo alcohols in high yields. This new procedure occurs regioselectively under neutral and mild conditions in various aprotic solvents even when sensitive functional groups are present.

Formation of unexpected products in the attempted aziridination of styrene with trifluoromethanesulfonyl nitrene

The reaction of styrene with trifluoromethanesulfonyl nitrene generated from trifluoromethanesulfonamide in the system (t-BuOCl+NaI) results in the formation of trifluoro-N-[2-phenyl-2-(trifluoromethylsulfonyl)aminoethyl] methanesulfonamide, 1-phenyl-2-io

Convenient, easy and highly regioselective preparation of haloalcohols from the reaction of epoxides with elemental halogen catalyzed by hexamethylenetetramine (HMTA)

The highly regioselective cleavage of epoxides into corresponding vicinal haloalcohols with elemental halogen has been catalyzed by hexamethylenetetramine (HMTA). This method occurred under neutral and mild conditions with high yields and short reaction times in various aprotic solvents even when sensitive functional groups were present.

o-Phenylenediamine as a new catalyst in the highly regioselective conversion of epoxides to halohydrins with elemental halogens

The regioselective ring opening of epoxides using elemental iodine and bromine in the presence of o-phenylenediamine as a new catalyst affords vicinal iodo alcohols and bromo alcohols in high yields. The major advantages of this method are versatility, high regioselectivity, a cheap and commercially available catalyst, mild and neutral reaction conditions, and short reaction times. Fourier transform Raman spectroscopy was used to study the reaction of iodine with o-phenylenediamine. The results indicate that the complex [(Diamine)I]+·I5- is formed, and we suggest that the major nucleophile is the pentaiodide ion. This bulky nucleophile has a fundamental role in the high regioselectivity observed attacking the less sterically hindered epoxide carbon. Springer-Verlag 2004.

IBX-I2 redox couple for facile generation of IOH and I +: Expedient protocol for iodohydroxylation of olefins and iodination of aromatics

(Chemical Equation Presented) IBX is readily reduced to IBAin the presence of molecular iodine in DMSO to generate hypoiodous acid (IOH), which reacts with a variety of olefins as well as R, β-unsaturated ketones leading to their respective iodohydrins with anti stereochemistry. The same redox chemistry in acetonitrile containing TFA produces iodonium ions for facile iodination of a variety of aromatic compounds in respectable isolated yields.

Metal-Free, N-Iodosuccinimide-Induced Regioselective Iodophosphoryloxylation of Alkenes with P(O)?OH Bonds

A simple and efficient method for the regioselective iodophosphoryloxylation of alkenes with P(O)?OH bonds has been established by using NIS (N-iodosuccinimide) as the iodination reagent under transition-metal-free conditions. The present protocol is compatible with different functional groups, and suitable for various alkenes and P(O)?OH compounds. A variety of functionalized β-iodo-1-ethyl phosphinic/phosphoric acid esters are obtained in good to excellent yields, which could be further transformed to diversified building blocks for the synthesis of bioactive compounds, pharmaceuticals and functional materials.

ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE HALOHYDRINS AND OXIRANES BY ENANTIOSELECTIVE REDUCTION OF PROCHIRAL α-HALOKETONES WITH CHIRALLY MODIFIED LITHIUM BOROHYDRIDE

Prochiral α-haloketones are reduced enantioselectively with the asymmetric reducing system lithium borohydride N,N'-dibenzoylcystine /t-butyl alcohol to give the corresponding halohydrins with up to 86percent enantiomeric excess, some of which are converted to optically active oxiranes.

Schiff-base complexes of metal(II) as new catalysts in the high- regioselective conversion of epoxides to halo alcohols by means of elemental halogen

The ring opening of epoxides with elemental iodine and bromine in the presence of some Schiff-base complexes of the first-row transition metal(II) as new catalysts affords vicinal iodo alcohols and bromo alcohols in high yields. This new procedure occurs regioselectively under mild conditions in various aprotic solvents. The catalysts are easily recovered and can be reused several times.

Regioselective vicinal functionalization of unactivated alkenes with sulfonium iodate(i) reagents under metal-free conditions

Metal-free, molecular iodine-free direct 1,2-difunctionalization of unactivated alkenes has been reported. The sulfonium iodate(i) reagent efficiently promoted the intermolecular vicinal iodo-functionalization of a diverse range of olefins in a stereo and regioselective manner. This method enables the divergent and straightforward preparation of synthetically useful functionalities; β-iodocarboxylates, β-iodohydrins, and β-iodoethers in a one-step process. Further interconversion of iodo-functionalized derivatives allows easy access to valuable synthetic intermediates en route to biologically active molecules.

Synthesis and Stereochemical Analysis of Chiral Inorganic Thiophosphate

The enantiomers of inorganic thiophosphate have prepared and a procedure has been developed which allows them to be distinguished by 31P n.m.r. spectroscopy.

Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties

Iodination of protoporphyrin IX dimethyl ester using phenyliodine bis(trifluoroacetate) (PIFA) and I2 was studied. Iodine added to both the C3- and C8-vinyl groups equally to afford the iodohydrin or iodoether in the presence of water or alcohol, respectively. Any meso-hydrogen atom was not substituted by an iodine atom under these conditions, although both the vinyl group and one of the meso positions of methyl pyropheophorbide-a bearing a chlorin π-system, a chlorophyll-a derivative, was modified with PIFA and I2. The reaction intermediates derived from the porphyrin were more reactive than those from the chlorin and liable to form intermolecular linkages. The obtained 2-iodo-1-hydroxyethyl group was transformed into a formyl group by a mild treatment. The corresponding iodoether moiety was readily converted into the acetyl group under basic conditions. These transformations were also applicable to smaller olefins such as styrene.

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Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides

The palladium-catalyzed intermolecular Heck-type reaction of both cyclic and acyclic epoxides is reported with tolerance of typical polar groups and acidic protons. Suitable alkenes include styrenes, conjugate dienes, and some electron-deficient olefins. In reactions of aliphatic terminal epoxides, ring opening occurs selectively at terminal positions, and stereocenters of epoxides are fully retained. Mechanistic studies provide evidence for in situ conversion of epoxides to β-halohydrins, generation of alkyl radicals, and radical addition to alkenes as key steps. Cyclovoltammetric determination of reduction potentials suggests that during activation of alkyl iodides by palladium(0) complexes, inner-sphere halogen abstraction is more likely than outer-sphere single electron transfer.