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Pinacol

CAS No.:
76-09-5
Catalog Number:
AG0035HM
Molecular Formula:
C6H14O2
Molecular Weight:
118.1742
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
25g
98%
In Stock USA
United States
$25
- +
100g
98%
In Stock USA
United States
$62
- +
500g
98%
In Stock USA
United States
$188
- +
Product Description
Catalog Number:
AG0035HM
Chemical Name:
Pinacol
CAS Number:
76-09-5
Molecular Formula:
C6H14O2
Molecular Weight:
118.1742
MDL Number:
MFCD00149294
IUPAC Name:
2,3-dimethylbutane-2,3-diol
InChI:
InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3
InChI Key:
IVDFJHOHABJVEH-UHFFFAOYSA-N
SMILES:
CC(C(O)(C)C)(O)C
EC Number:
200-933-5
UNII:
527QE7I5CO
NSC Number:
25943
Properties
Complexity:
72.5  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
118.099g/mol
Formal Charge:
0
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
118.176g/mol
Monoisotopic Mass:
118.099g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
40.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.1  
Literature
Title Journal
Frustrated Lewis pair inspired carbon dioxide reduction by a ruthenium tris(aminophosphine) complex. Angewandte Chemie (International ed. in English) 20121105
Pinacolborane as the boron source in nitrogen-directed borylations of aromatic N,N-dimethylhydrazones. The Journal of organic chemistry 20121102
Taking the F out of FLP: simple Lewis acid-base pairs for mild reductions with neutral boranes via borenium ion catalysis. Journal of the American Chemical Society 20121024
Ruthenium catalyzed hydroboration of terminal alkynes to Z-vinylboronates. Journal of the American Chemical Society 20120905
Synthesis and antimitotic and tubulin interaction profiles of novel pinacol derivatives of podophyllotoxins. Journal of medicinal chemistry 20120809
Beyond benzyl grignards: facile generation of benzyl carbanions from styrenes. Chemistry (Weinheim an der Bergstrasse, Germany) 20120723
Aerobic oxidation reactions catalyzed by vanadium complexes of bis(phenolate) ligands. Inorganic chemistry 20120702
Synthesis of taxane ABC tricyclic skeleton from lycoctonine. Natural product communications 20120601
Total syntheses of hopeanol and hopeahainol A empowered by a chiral Brønsted acid induced pinacol rearrangement. Angewandte Chemie (International ed. in English) 20120423
Regioselective synthesis of 1,2-dihydropyridines by rhodium-catalyzed hydroboration of pyridines. Journal of the American Chemical Society 20120227
Palladium-catalyzed synthesis of terminal acetals via highly selective anti-Markovnikov nucleophilic attack of pinacol on vinylarenes, allyl ethers, and 1,5-dienes. Chemical communications (Cambridge, England) 20120128
Catalytic non-conventional trans-hydroboration: a theoretical and experimental perspective. Chemistry (Weinheim an der Bergstrasse, Germany) 20120127
Ionic crystals [M3O(OOCC6H5)6(H2O)3]4[α-SiW12O40] (M = Cr, Fe) as heterogeneous catalysts for pinacol rearrangement. Inorganic chemistry 20120116
Highly selective trifluoromethylation of 1,3-disubstituted arenes through iridium-catalyzed arene borylation. Angewandte Chemie (International ed. in English) 20120109
Transition-metal-catalyzed synthesis of diboranes(4). Angewandte Chemie (International ed. in English) 20111223
Hydride as a leaving group in the reaction of pinacolborane with halides under ambient Grignard and Barbier conditions. One-pot synthesis of alkyl, aryl, heteroaryl, vinyl, and allyl pinacolboronic esters. The Journal of organic chemistry 20111202
Completing the puzzle of aurachin biosynthesis in Stigmatella aurantiaca Sg a15. Molecular bioSystems 20111201
Stereoselective construction of quaternary carbon stereocenters via a semipinacol rearrangement strategy. Accounts of chemical research 20111115
1,2-Bis(benz-yloxy)-1,2-bis-(4-chloro-phen-yl)-3,8-dimeth-oxy-acenaphthene. Acta crystallographica. Section E, Structure reports online 20111001
Alkoxide-catalyzed reduction of ketones with pinacolborane. The Journal of organic chemistry 20110805
An efficient copper(I)-catalyst system for the asymmetric hydroboration of β-substituted vinylarenes with pinacolborane. Chemistry, an Asian journal 20110801
4,4,5,5-Tetra-methyl-1,3,2λ-dioxa-phospho-lan-2-one. Acta crystallographica. Section E, Structure reports online 20110801
Structure-based design of novel boronic acid-based inhibitors of autotaxin. Journal of medicinal chemistry 20110714
Silver-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with β-boryl acrylates. The Journal of organic chemistry 20110318
New developments in aromatic halogenation, borylation, and cyanation. Chimia 20110101
Chiral Brønsted acid catalyzed pinacol rearrangement. Angewandte Chemie (International ed. in English) 20101210
Diols and anions can control the formation of an exciplex between a pyridinium boronic acid with an aryl group connected via a propylene linker. Chemical communications (Cambridge, England) 20101121
Catalytic activity of phosphine-copper complexes for hydroboration of styrene with pinacolborane: experiment and theory. The journal of physical chemistry. A 20101118
1-Bromo-3-(1',1'-dimethylalkyl)-1-deoxy-Δ(8)-tetrahydrocannabinols: New selective ligands for the cannabinoid CB(2) receptor. Bioorganic & medicinal chemistry 20101115
An opportunity for Mg-catalyzed Grignard-type reactions: direct coupling of benzylic halides with pinacolborane with 10 mol % of magnesium. Journal of the American Chemical Society 20100901
Isolation and reactivity of palladium hydrido complexes: intermediates in the hydrodefluorination of pentafluoropyridine. Dalton transactions (Cambridge, England : 2003) 20100828
C-H bond activation/borylation of furans and thiophenes catalyzed by a half-sandwich iron N-heterocyclic carbene complex. Chemistry, an Asian journal 20100705
The synthesis and NMR investigation on novel boron derivatives of stavudine. Bioorganic chemistry 20100601
Synthesis of notoamide J: a potentially pivotal intermediate in the biosynthesis of several prenylated indole alkaloids. The Journal of organic chemistry 20100507
Borinium cations as sigma-B-H ligands in osmium complexes. Journal of the American Chemical Society 20100428
Catalytic asymmetric conjugate addition of alpha-cyanoketones for the construction of a quaternary stereogenic center. Organic letters 20100402
Regio- and stereoselective Ni-catalyzed 1,4-hydroboration of 1,3-dienes: access to stereodefined (Z)-allylboron reagents and derived allylic alcohols. Journal of the American Chemical Society 20100303
Dramatic effect of Lewis acids on the rhodium-catalyzed hydroboration of olefins. Journal of the American Chemical Society 20100113
Highly regio- and stereoselective synthesis of (Z)-trisubstituted alkenes via propyne bromoboration and tandem Pd-catalyzed cross-coupling. Organic letters 20090917
Rationally improved chiral Brønsted acid for catalytic enantioselective allylboration of aldehydes with an expanded reagent scope. The Journal of organic chemistry 20090605
Synthesis of 1-borylisoindoles via palladium-catalyzed dehydrogenation/C-H borylation of isoindolines. Journal of the American Chemical Society 20090506
Unexpected Ti(III)/Mn-promoted pinacol coupling of ketones. The Journal of organic chemistry 20090501
Reduction of benzophenones with SmI2. Post electron transfer processes. The Journal of organic chemistry 20090306
Demonstration that CobG, the monooxygenase associated with the ring contraction process of the aerobic cobalamin (vitamin B12) biosynthetic pathway, contains an Fe-S center and a mononuclear non-heme iron center. The Journal of biological chemistry 20090220
Diastereoselective intramolecular pinacol couplings of sulfinyl iron(0) diene complexes. The Journal of organic chemistry 20090220
Aerobic oxidation of pinacol by vanadium(V) dipicolinate complexes: evidence for reduction to vanadium(III). Journal of the American Chemical Society 20090121
Selectivity control in Lewis acid catalyzed regiodivergent tandem cationic cyclization/ring expansion terminated by pinacol rearrangement. Angewandte Chemie (International ed. in English) 20090101
Activation of B-H bonds by an oxo-rhenium complex. Dalton transactions (Cambridge, England : 2003) 20081221
Asymmetric reductive Mannich reaction to ketimines catalyzed by a Cu(I) complex. Journal of the American Chemical Society 20081203
Diastereoselective addition of zincated hydrazones to alkenylboronates and stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles. Journal of the American Chemical Society 20081119
Diastereoselective synthesis of cyclopentanediols by InCl 3/Al mediated intramolecular pinacol coupling reaction in aqueous media. Molecules (Basel, Switzerland) 20081027
Ionic-liquid-promoted decaborane olefin-hydroboration: a new efficient route to 6-R-B10H13 derivatives. Inorganic chemistry 20081020
Total syntheses of (+)- and (-)-peribysin E. Journal of the American Chemical Society 20081015
Synthesis, characterization, and reactivity of rhodium(I) acetylacetonato complexes containing pyridinecarboxaldimine ligands. Inorganic chemistry 20081006
Analysis of recognition of fructose by imprinted polymers. Talanta 20080915
Pinacol macrocyclization-based route to the polyfused medium-sized CDE ring system of lancifodilactone G. Organic letters 20080904
Sigma-borane complexes of iridium: synthesis and structural characterization. Journal of the American Chemical Society 20080813
9,9-Dioctyl-2,7-bis-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene. Acta crystallographica. Section E, Structure reports online 20080801
An expeditious one-step entry to the tetracyclic core of integrastatins. Chemical communications (Cambridge, England) 20080721
An improved system for the palladium-catalyzed borylation of aryl halides with pinacol borane. The Journal of organic chemistry 20080718
Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol x SnCl4 complexes. optimization, substrate scope and mechanistic investigations. Journal of the American Chemical Society 20080702
rac-(2R,3S)-2-Phenyl-3-(3-phenyl-1,2,3,4-tetra-hydro-quinoxalin-2-yl)quinoxaline. Acta crystallographica. Section E, Structure reports online 20080701
Gold(I)-catalyzed divergence in the reactivity of 3-silyloxy 1,6-enynes: pinacol-terminated vs claisen-terminated cyclization cascades. Organic letters 20080619
Sequential Ni-catalyzed borylation and cross-coupling of aryl halides via in situ prepared neopentylglycolborane. Organic letters 20080619
Stereochemical nonrigidity of a chiral rhodium boryl hydride complex: a sigma-borane complex as transition state for isomerization. Journal of the American Chemical Society 20080402
Efficient amide-directed catalytic asymmetric hydroboration. Journal of the American Chemical Society 20080326
On the role of samarium/HMPA in the post electron-transfer steps in SmI2 reductions. Organic letters 20080306
Thermometric MIP sensor for fructosyl valine. Biosensors & bioelectronics 20080227
Stepwise oxygenation of pinacolborane by a rhodiumperoxo complex: detection of an intermediate metal borate and perborate. Angewandte Chemie (International ed. in English) 20080101
Enantioselective pinacol coupling of aryl aldehydes catalyzed by chiral Salan-Mo(IV) complexes. The Journal of organic chemistry 20071221
The skeletal rearrangement of gold- and platinum-catalyzed cycloisomerization of cis-4,6-dien-1-yn-3-ols: pinacol rearrangement and formation of bicyclo[4.1.0]heptenone and reorganized styrene derivatives. Journal of the American Chemical Society 20071219
Samarium(ii) iodide-mediated intramolecular pinacol coupling reactions with cyclopropyl ketones. Chemical communications (Cambridge, England) 20071207
Room temperature-stable electride as a synthetic organic reagent: application to pinacol coupling reaction in aqueous media. Organic letters 20071011
Theoretical study of the role of solvent H2O in neopentyl and pinacol rearrangements. Journal of computational chemistry 20070715
Palladium-catalyzed cyclization of 1,omega-dienols: multiple ways to intramolecularly trap a carbocation. The Journal of organic chemistry 20070622
Development of fructosyl valine binding polymers by covalent imprinting. Biosensors & bioelectronics 20070615
One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes. Organic letters 20070301
Catalyzed tandem reaction of 3-silyloxy-1,5-enynes consisting of cyclization and pinacol rearrangement. Angewandte Chemie (International ed. in English) 20070101
Synthetic studies toward (-)-FR901483 using a conjugate allylation to install the C-1 quaternary carbon. The Journal of organic chemistry 20061208
Luminescence tuning of organoboron quinolates through substituent variation at the 5-position of the quinolato moiety. Organic letters 20061109
TADDOL-derived phosphites and phosphoramidites for efficient rhodium-catalyzed asymmetric hydroboration. Organic letters 20060706
Mechanisms of glycerol dehydration. The journal of physical chemistry. A 20060511
Novel calixarene hemisphere synthesized via pinacol rearrangement of [2.1.2.1]metacyclophane. Organic letters 20060511
The uptake of methyl vinyl ketone, methacrolein, and 2-methyl-3-butene-2-ol onto sulfuric acid solutions. The journal of physical chemistry. A 20060223
Studies of low-coordinate iron dinitrogen complexes. Journal of the American Chemical Society 20060125
Formation of arylboronates by a CuI-catalyzed coupling reaction of pinacolborane with aryl iodides at room temperature. Organic letters 20060119
New enantioselective entry to cycloheptane amino acid polyols. The Journal of organic chemistry 20060106
Stereoselective pinacol coupling of chiral formylferrocene using divalent samarium triflate: preparation of a new chiral bisferrocenyl oxazoline ligand and its application to asymmetric Diels-Alder reactions. Organic letters 20051222
The unusual phases of anhydrous and hydrated pinacol. Acta crystallographica. Section B, Structural science 20051201
A density functional study of propylene glycol conversion to propanal and propanone of various acid-catalyzed reaction models: a water-addition effect. Journal of computational chemistry 20051130
Samarium diiodide-induced intramolecular pinacol coupling of dinitrones: synthesis of cyclic cis-vicinal diamines. Chemical communications (Cambridge, England) 20051121
Novel multichiral diols and diamines by highly stereoselective pinacol coupling of planar chiral [2.2]paracyclophane derivatives. Chemistry (Weinheim an der Bergstrasse, Germany) 20051118
Nickel-catalyzed trans-alkynylboration of alkynes via activation of a boron-chlorine bond. Journal of the American Chemical Society 20051116
Vanadium-catalyzed pinacol coupling reaction in water. The Journal of organic chemistry 20051014
Preparation and Suzuki-Miyaura coupling reactions of tetrahydropyridine-2-boronic acid pinacol esters. The Journal of organic chemistry 20050902
Tetracyanoanthraquinodimethanes with a chiral amide group: preparation, properties, and charge-transfer photochirogenetic reaction with 1,2-dianisylacenaphthene-1,2-diol. The Journal of organic chemistry 20050708
Syntheses and reactions of the bis-boryloxide O(Bpin)2(pin = O2C2Me4). Dalton transactions (Cambridge, England : 2003) 20050621
Steric effects in metathesis and reduction reactions of phosphinimines with catechol- and pinacolboranes. Inorganic chemistry 20050613
Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling. Organic letters 20050609
Highly functionalised cyclobutanols via samarium(II) iodide-induced pinacol cyclisations of carbohydrate-derived 1,4-diketones. Carbohydrate research 20050523
Ketone-imide versus ketone-oxime reductive cross-coupling promoted by samarium diiodide: new mechanistic insight gained from a failed aminocyclopentitol synthesis. The Journal of organic chemistry 20050513
Samarium diiodide-catalyzed diastereoselective pinacol couplings. Organic letters 20050512
A chelation effect on the pathway between intramolecular hydrodimerization and pinacol coupling. Organic letters 20050414
Pinacol coupling of aromatic aldehydes and ketones using TiCl3-Mg under ultrasound irradiation. Ultrasonics sonochemistry 20050401
Rhodium boryl complexes in the catalytic, terminal functionalization of alkanes. Journal of the American Chemical Society 20050302
Six- and eightfold palladium-catalyzed cross-coupling reactions of hexa- and octabromoarenes. Chemistry (Weinheim an der Bergstrasse, Germany) 20041217
Ring expansion-annulation strategy for the synthesis of substituted azulenes and oligoazulenes. 2. Synthesis of azulenyl halides, sulfonates, and azulenylmetal compounds and their application in transition-metal-mediated coupling reactions. The Journal of organic chemistry 20041210
In quest of factors that control the enantioselective catalytic Markovnikov hydroboration/oxidation of vinylarenes. Chemistry (Weinheim an der Bergstrasse, Germany) 20041203
Efficient analyte oxidation in an electrospray ion source using a porous flow-through electrode emitter. Journal of the American Society for Mass Spectrometry 20041201
Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis. Organic letters 20041125
Catalytic, highly enantio- and diastereoselective pinacol coupling reaction with a new tethered bis(8-quinolinolato) ligand. Journal of the American Chemical Society 20041020
The potential of photochemical transition metal reactions in prebiotic organic synthesis. I. Observed conversion of methanol into ethylene glycol as possible prototype for sugar alcohol formation. Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life 20041001
Regio- and enantiocontrol in the room-temperature hydroboration of vinyl arenes with pinacol borane. Journal of the American Chemical Society 20040804
Theoretical study of reaction pathways for the rhodium phosphine-catalysed borylation of C-H bonds with pinacolborane. Dalton transactions (Cambridge, England : 2003) 20040521
Reaction of tin porphyrins with vicinal diols. Inorganic chemistry 20040405
Photochemical pinacol rearrangements of unsymmetrical diols. The Journal of organic chemistry 20040319
Palladium-catalyzed cross-coupling of stereospecific potassium cyclopropyl trifluoroborates with aryl bromides. Organic letters 20040205
Metal-catalyzed reactions of diborons for synthesis of organoboron compounds. Chemical record (New York, N.Y.) 20040101
Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent. Chemical communications (Cambridge, England) 20031207
Synthesis of 2,3-substituted thienylboronic acids and esters. The Journal of organic chemistry 20031128
Synthesis of arylboronates by the palladium catalysed cross-coupling reaction in ionic liquids. Organic & biomolecular chemistry 20031007
Waste-free and facile solid-state protection of diamines, anthranilic acid, diols, and polyols with phenylboronic acid. Chemistry (Weinheim an der Bergstrasse, Germany) 20030905
Truly catalytic and enantioselective pinacol coupling of aryl aldehydes mediated by chiral Ti(III) complexes. The Journal of organic chemistry 20030711
New mixed phosphonate esters by transesterification of pinacol phosphonates and their use in aldehyde and ketone coupling reactions with nonstabilized phosphonates. The Journal of organic chemistry 20030221
A novel, solventless reductive coupling of carbonyl compounds by alkali metals, catalysed by bromobenzene. Chemical communications (Cambridge, England) 20030221
Pinacol coupling reaction of beta-halo-alpha,beta-unsaturated aldehydes promoted by TiI4. Organic letters 20021114
Mechanistic insight into fragmentation reactions of titanapinacolate complexes. Journal of the American Chemical Society 20021016
A sigma 4, lambda 5-phosphinine palladium complex: a new type of phosphorus ligand and catalyst. Application to the Pd-catalyzed formation of arylboronic esters. Chemical communications (Cambridge, England) 20020807
Novel Brønsted acidic ionic liquids and their use as dual solvent-catalysts. Journal of the American Chemical Society 20020529
sigma-Borane and dihydroborate complexes of ruthenium. Journal of the American Chemical Society 20020522
Efficient synthesis and hydrolysis of cyclic oxalate esters of glycols. Chemical & pharmaceutical bulletin 20020301
Microwave-assisted synthesis of pinacol boronates from aryl chlorides catalyzed by a palladium/imidazolium salt system. Organic letters 20020221
Rhodium-catalyzed, regiospecific functionalization of polyolefins in the melt. Journal of the American Chemical Society 20020220
Enantioselective pinacol coupling of aldehydes mediated and catalyzed by chiral titanium complexes. Organic letters 20011129
Synthesis of novel, potent, diol-based HIV-1 protease inhibitors via intermolecular pinacol homocoupling of (2S)-2-benzyloxymethyl-4-phenylbutanal. Journal of medicinal chemistry 20011011
Photochemical reactions and on-line UV detection in microfabricated reactors. Lab on a chip 20010901
Reactions of aliphatic ketones R2CO (R=Me, Et, iPr and tBu) with the MCI4/Li(Hg) system (M=U or Ti): mechanistic analogies between the McMurry, Wittig, and Clemmensen reactions. Chemistry (Weinheim an der Bergstrasse, Germany) 20010716
Diastereoselective inter- and intramolecular pinacol coupling of aldehydes promoted by monomeric titanocene(II) complex Cp(2)TiPh. The Journal of organic chemistry 20010601
Hydroboration of unsaturated phosphonic esters: synthesis of boronophosphonates and trisubstituted vinylphosphonates. Organic letters 20010125
Properties