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700-57-2

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700-57-2 Usage

Chemical Properties

white to off-white crystalline powder

Uses

Different sources of media describe the Uses of 700-57-2 differently. You can refer to the following data:
1. The low-temperature X-ray structure of 2-adamantanol ester has been studied.2-Adamantanol was used to synthesize ester imides.
2. 2-Adamantanol was used to synthesize ester imides.

General Description

The low-temperature X-ray structure of 2-adamantanol ester has been studied.

Purification Methods

It can be purified by chromatography as for the 1-isomer. It crystallises from cyclohexane and has characteristic IR, max 3600, 1053, 1029 and 992cm-1 [Schleyer & Nicholas J Am Chem Soc 83 182 1961].

Check Digit Verification of cas no

The CAS Registry Mumber 700-57-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 0 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 700-57:
(5*7)+(4*0)+(3*0)+(2*5)+(1*7)=52
52 % 10 = 2
So 700-57-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H16O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-11H,1-5H2

700-57-2 Well-known Company Product Price

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  • Alfa Aesar

  • (A10697)  2-Adamantanol, 98%   

  • 700-57-2

  • 5g

  • 517.0CNY

  • Detail
  • Alfa Aesar

  • (A10697)  2-Adamantanol, 98%   

  • 700-57-2

  • 25g

  • 2423.0CNY

  • Detail

700-57-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name adamantan-2-ol

1.2 Other means of identification

Product number -
Other names 1-adamantanol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:700-57-2 SDS

700-57-2Relevant articles and documents

Decarbonylation of Adamantan-2-one by Two-photonic Excitation with XeCl Laser

Ichinose, Nobuyuki,Kawanishi, Shunichi

, p. 2017 - 2018 (1994)

Adamantan-2-one 1 in cyclohexane undergoes decarbonylation to give noradamantane 2 via two-photon absorption of XeCl laser light (308 nm).

Oxidation of Adamantane with H2O2–CF3COCF3 · 1.5 H2O in the Presence of VO(acac)2

Kislitsina,Shchadneva,Khusnutdinov

, p. 992 - 995 (2018)

The system hydrogen peroxide–hexafluoroacetone sesquihydrate effectively oxidizes adamantane in the presence of VO(acac)2 to afford 64% of adamantan-1-ol in tert-butyl alcohol or 76% of adamantan-2-one in a mixture of acetic acid with pyridine.

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Schleyer,P. von R.,Nicholas,R.D.

, p. 182 - 187 (1961)

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Definitive Identification of the C-5 and C-7 NMR Signals of Adamantan-2-ol

Srivastava, S.,Cheung, C. K.,Noble, W. J. de

, p. 232 - 235 (1985)

The E- and Z-5-deuterioadamantan-2-ols have been synthesized by an unambiguous route.The 13C NMR spectra show the familiar 1:1:1 splitting of one of the C-5 or C-7 signals, thus allowing a definite assignment of the δ-atoms to be made.This assignment is in accord with the conclusion of Duddeck and Islam.Revised assignments are offered for the reported configurations of the 5-bromo- and -chloro-adamantan-2-ols, and several unusual deuterium isotope shifts are reported.

Lenoir,Schleyer

, p. 941 (1970)

Hydroxylation of alkanes by molecular oxygen with dinuclear FeII macrocyclic complexes as catalysts

Wang, Zheng,Martell, Arthur E.,Motekaitis

, p. 1523 - 1524 (1998)

The iron(II) complexes of two new macrocyclic ligands: [24]RBPyBC (L24), a 24-membered macrocycle containing phenol, pyridine and amino donor groups, and [30]RBBPyBC (L30), a 30-membered macrocycle containing phenol, bipyridine, and amino donor groups, were found to be effective for the hydroxylation of alkanes, including cyclohexane and adamantane, with H2S as a two-electron reductant.

Epoxidation and hydroxylation reactions catalysed by β-Tetrahalogeno and β-octahalogeno manganese porphyrins

Baciocchi, Enrico,Boschi, Tristano,Cassioli, Luigi,Galli, Carlo,Lapi, Andrea,Tagliatesta, Pietro

, p. 7283 - 7286 (1997)

β-Tetrahalogenated manganese(III) porphyrins are more efficient catalysts than the β-octahalogenated ones in oxidations promoted by H2O2.

Activation of the C-H Bond in Hydrocarbons: the Isolation and Catalytic Activity of a Trinuclear Organoiron Carboxylate Cluster

Barton, Derek H. R.,Gastiger, Michel J.,Motherwell, William B.

, p. 731 - 733 (1983)

Tri-iron cluster compounds of type (1), in the presence of zinc powder, acetic acid, (aqueous) pyridine, and oxygen constitute an efficient and selective system for the oxidation of saturated hydrocarbons.

Catalytic Homogeneous Functionalization of Adamantane. Influence of Electronic and Structural Features of the Metalloporphyrin Catalyst on Atom Transfer Selectivity (Oxygenation versus Azidification/Halogenation)

Brown, Robert B.,Hill, Craig L.

, p. 5762 - 5768 (1988)

Upon treatment of the two-phase systems, Mn tetraarylporphyrin, and alkane (organic phase)/Na+X- (aqueous phase), with iodosylarenes, both alcohols and alkyl azides (or halides), X- = halide or azide, are formed from the alkane substrates.The Mn porphyrin functions as a catalyst for alkane oxygenation and a phase transfer catalyst for X-.Catalytic functionalization of the exemplary caged alkane, adamantane, by a variety of these two-phase systems as function of the reaction conditions has been examined.The results reported here allow, for the first time, an assessment of the relathionship between the electronic and structural features of the metalloporphyrin catalysts and their selectivity with respect to the replacement of unactivated alkane carbon-hydrogen bonds with oxygen versus non-oxygen (halide or azide) functional groups.Of the first-row transition metal matalloporphyrins, only those of manganese are active for both the cleavage of unactivated alkane C-H bonds and replacement of these bonds by halogen or nitrogen-based groups.The oxygen donors that give the highest yields of these non-oxygenated products are the iodosylarenes.Examination of adamantane functionalization by iodosylarenes catalyzed by eight different manganese tetraphenylporphyrin derivatives, whose porphyrin ligands vary widely in electron-donating ability, establishes that the relative tertiary-secondary C-H cleavage selectivities are minimally affected by such electronic effects.In contrast, the selectivity for incorporation of the non-oxygen versus oxygen functions is substantially affected by the electron-donating ability of the catalyst porphyrin rings.The more electron withdrawing the porphyrin ring, and consequently the more anodic the potential of the ligated, S = 2, manganese(III) ion, the lower the selectivity for incorporation of the non-oxygen functions.Functionalization of adamantane catalyzed by the most electron poor manganese porphyrin complex, MnIII(F20TPP)X, is effectively selective for oxygenation.All the metalloporphyrins examined here eventually succumb to deactivation by irreversible oxidative degradation of the organic porphyrin ligand.

Solvolysis of 2-adamantyl p-toluenesulfonate in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate

Okazaki, Takao,Ito, Koji,Kitagawa, Toshikazu

, p. 6066 - 6068 (2015)

The solvolytic rate constants of 2-adamantyl p-toluenesulfonate were determined in [BMIM][BF4] in the presence/absence of 2,6-lutidine by NMR measurements. The activation parameters suggest that the reaction proceeded by kc mechanism. The solvolysis quantitatively gave 2-adamantanol as a product by the reaction with the water present in the ionic liquid. The solvent ionizing power of [BMIM][BF4] was found to be similar to that of ethanol.

π-Face diastereoselection: Stereochemistry and reactivity of reduction reactions on conformationally rigid substrates: 5-X-adamantan-2-ones and trans-10-X-decal-2-ones

Di Maio, Giorgio,Innella, Carolina,Vecchi, Elisabetta

, p. 7403 - 7407 (2001)

Stereochemistry and relative rates kax and keq of reduction reactions on title compounds have been measured under four different reaction conditions (NaBH4 in i-PrOH, LiBH4 and NaAlH4 in THF and LiAlH4 in Et2O). Reaction sensitivities show that the Group III element has a prominent role in determining the structure of the transition state shape.

Functional aspects of Gif-type oxidation of hydrocarbons mediated by iron picolinate H2O2-dependent systems: Evidence for the generation of carbon- and oxygen-centered radicals

Kiani, Salma,Tapper, Amy,Staples, Richard J.,Stavropoulos, Pericles

, p. 7503 - 7517 (2000)

The present investigation explores the functional features of several novel and other previously ill-defined ferrous and ferric complexes of the picolinic acid anion (Pic), which are used to mediate Gif-type oxidation of hydrocarbons by H2O2. Complexes [Fe(Pic)2(py)2], [Fe(Pic)3]·0.5py, [Fe2O(Pic)4(py)2], [Fe2(μ-OH)2(Pic)4], and FeCl3 have been employed in oxygenations of adamantane by H2O2 mostly in py/AcOH to reveal that tert- and sec-adamantyl radicals are generated in Gif solutions. The alleged absence of sec-adamantyl radicals from Gif product profiles has been previously interpreted as compelling evidence in support of a non-radical mechanism for the activation of secondary C-H sites in Gif chemistry. The product profile is entirely dictated by trapping of the diffusively free adamantyl radicals, since authentic tert- and sec-adamantyl radicals are shown to partition between dioxygen and protonated pyridine at 4% O2 (in N2), or between dioxygen and TEMPO at 100% O2, in a manner analogous to that observed in Gif oxygenations of adamantane. The low tert/sec selectivity (2.2-4.5) obtained, increasing with increasing dioxygen partial pressure, and the small intramolecular kinetic isotope effect values revealed by employing adamantane-1,3-d2 (1.06(6) (Ar); 1.73(2) (4% O2 in N2)), indicate the presence of an indiscriminate oxidant under inert atmosphere, coupled to a more selective oxidant at higher partial pressures of dioxygen. Gif oxygenation of DMSO by H2O2 mediated by [Fe(Pic)2(py)2] provides pyridine-trapped methyl radicals under argon, as expected for the addition reaction of hydroxyl radicals to DMSO. The reaction is progressively inhibited by increasing amounts of EtOH, generating pyridine-captured CH3·CHOH and ·CH2CH2OH radicals. Quantification of the DMSO- versus EtOH-derived alkyl radicals affords an estimate of k(EtOH)/k(DMSO) equal to 0.34(3), in reasonable agreement with the kinetics of radiolytically produced hydroxyl radicals (k(EtOH)/k(DMSO) = 0.29). The formation of methyl radicals in Gif oxygenation of DMSO is also supported by the quantitative generation of tert-adamantyl radicals in the presence of 1-iodoadamantane. These results are consistent with the action of hydroxyl radicals in Gif oxygenations by Fe(II/III)/H2O2 (Ar), most likely coupled to substrate-centered alkoxyl radicals under O2. The oxygen-centered radicals perform H-atom abstractions from Gif substrates to generate diffusively free carbon-centered radicals, in accord with previously reported findings.

Photoinduced reduction of cytochrome c in the presence of hydroperoxide derivative of biphenyl

Matsugo,Kayamori-Sato,Konishi

, p. 415 - 420 (1994)

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Rate and product studies with 2-adamantyl fluoroformate under solvolytic conditions

Kyong, Jin Burm,Rhu, Chan Joo,Kim, Yong-Gun,Kevill, Dennis N.

, p. 525 - 531 (2007)

The specific rates of solvolysis of 2-adamantyl fluoroformate have been measured at 25.0°C in 20 pure and binary solvents. These are well correlated using the extended Grunwald-Winstein equation, with incorporation of the N T solvent nucleophilicity scale and the YCl solvent ionizing power scale. The sensitivities (l = 2.15±0.17 and m = 0.95±0.07) toward the changes in solvent nucleophilicity and solvent ionizing power, and the kF/kCl values are very similar to those previously observed for solvolyses of n-octyl fluoroformate, consistent with the addition step of an addition-elimination pathway being rate-determining. For aqueous ethanol, measurement of the product ratio allowed selectivity values (5) to be determined. The results are compared with those reported earlier for 2-adamantyl chloroformate and mechanistic conclusions are drawn. Copyright

OXONE AS OXYGEN DONOR IN THE CATALYTIC HYDROXYLATION OF SATURATED HYDROCARBONS.

Poorter, Bertha de,Ricci, Marko,Meunier, Bernard

, p. 4459 - 4462 (1985)

Manganese porphyrin complexes catalyze the hydroxylation of saturated hydrocarbons by potassium hydrogen persulfate (or Oxone) at room temperature.High conversions of hydrocarbons are obtained.

Non-Heme-Iron-Mediated Selective Halogenation of Unactivated Carbon?Hydrogen Bonds

Bleher, Katharina,Comba, Peter,Faltermeier, Dieter,Gupta, Ashutosh,Kerscher, Marion,Krieg, Saskia,Martin, Bodo,Velmurugan, Gunasekaran,Yang, Shuyi

supporting information, (2021/12/09)

Oxidation of the iron(II) precursor [(L1)FeIICl2], where L1 is a tetradentate bispidine, with soluble iodosylbenzene (sPhIO) leads to the extremely reactive ferryl oxidant [(L1)(Cl)FeIV=O]+ with a cis disposition of the chlorido and oxido coligands, as observed in non-heme halogenase enzymes. Experimental data indicate that, with cyclohexane as substrate, there is selective formation of chlorocyclohexane, the halogenation being initiated by C?H abstraction and the result of a rebound of the ensuing radical to an iron-bound Cl?. The time-resolved formation of the halogenation product indicates that this primarily results from sPhIO oxidation of an initially formed oxido-bridged diiron(III) resting state. The high yield of up to >70 % (stoichiometric reaction) as well as the differing reactivities of free Fe2+ and Fe3+ in comparison with [(L1)FeIICl2] indicate a high complex stability of the bispidine-iron complexes. DFT analysis shows that, due to a large driving force and small triplet-quintet gap, [(L1)(Cl)FeIV=O]+ is the most reactive small-molecule halogenase model, that the FeIII/radical rebound intermediate has a relatively long lifetime (as supported by experimentally observed cage escape), and that this intermediate has, as observed experimentally, a lower energy barrier to the halogenation than the hydroxylation product; this is shown to primarily be due to steric effects.

Cationic nickel(II) pyridinophane complexes: Synthesis, structures and catalytic activities for C-H oxidation

Nishimura, Tsubasa,Ando, Yuki,Shinokubo, Hiroshi,Miyake, Yoshihiro

supporting information, p. 1049 - 1052 (2021/05/19)

A series of nickel(II) pyridinophane complexes were synthesized and characterized by X-ray crystallographic analysis. Their IR spectra supported the existence of mononuclear nickel(II) complexes in solution. Furthermore, we conducted catalytic CH oxidation of cyclooctane with nickel(II) pyridinophanes as the catalysts. The activity of nickel(II) pyridinophanes was affected by steric hindrance around the nitrogen atoms.

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