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Pinacol information


Pinacol
Pinacol
Ball-and-stick model of pinacol
Names
Preferred IUPAC name
2,3-Dimethylbutane-2,3-diol
Other names
2,3-Dimethyl-2,3-butanediol
Tetramethylethylene glycol
1,1,2,2-Tetramethylethylene glycol
Pinacone
Identifiers
CAS Number
  • 76-09-5 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:131185 checkY
ChEMBL
  • ChEMBL3289669
ChemSpider
  • 21109330 checkY
ECHA InfoCard 100.000.849 Edit this at Wikidata
EC Number
  • 200-933-5
PubChem CID
  • 6425
UNII
  • 527QE7I5CO checkY
CompTox Dashboard (EPA)
  • DTXSID3058793 Edit this at Wikidata
InChI
  • InChI=1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3 checkY
    Key: IVDFJHOHABJVEH-UHFFFAOYSA-N checkY
SMILES
  • CC(C)(O)C(C)(C)O
  • CC(C)(O)C(C)(C)O
Properties
Chemical formula
C6H14O2
Molar mass 118.174 g/mol
Appearance White solid
Density 0.967 g/cm3
Melting point 40 to 43 °C (104 to 109 °F; 313 to 316 K)
Boiling point 171 to 173 °C (340 to 343 °F; 444 to 446 K)
Hazards
GHS labelling:
Pictograms
GHS05: CorrosiveGHS07: Exclamation mark
Signal word
Warning
Hazard statements
H228, H315, H319, H335
Precautionary statements
P210, P240, P241, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P405, P501
Flash point 77 °C (171 °F; 350 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
Pinacolone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms.

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Pinacol rearrangement

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The pinacol–pinacolone rearrangement is a method for converting a 1,2-diol to a carbonyl compound in organic chemistry. The 1,2-rearrangement takes place...

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Pinacol

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Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms. It may be produced by the pinacol coupling...

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Pinacol coupling reaction

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A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence...

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Boronic acid

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conjugate addition also in conjunction with a metal. In one study the pinacol ester of allylboronic acid is reacted with dibenzylidene acetone in such...

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Prins reaction

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reaction at room temperature. The Prins-pinacol reaction is a cascade reaction of a Prins reaction and a pinacol rearrangement. The carbonyl group in the...

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Semipinacol rearrangement

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rearrangements. While similar to the pinacol rearrangement, the semipinacol rearrangement differs from the pinacol rearrangement in that the cation is...

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Hamburg

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Wilhelm Rudolph Fittig (1835–1910), German chemist. He discovered the pinacol coupling reaction. Wilhelm Kühne (1837–1900), German physiologist. He coined...

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Phenaglycodol

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MeMgI are added to the ester give Phenaglycodol (7) crystals. A mixed Pinacol coupling rxn between 4-chloroacetophenone [99-91-2] and acetone with magnesium...

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Ring expansion and contraction

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carbon is a pinacol rearrangement. While this reaction refers specifically to a vicinal dihydroxide rearrangement, there are other pinacol type rearrangements...

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Migratory aptitude

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Baeyer-Villiger reaction, the more substituted group, in general, migrates. In the pinacol rearrangement, the order of migratory aptitude has not been determined...

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Pinacolone

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in the classroom, pinacolone arises by the pinacol rearrangement, which occurs by protonation of pinacol (2,3-dimethylbutane-2,3-diol). Industrially...

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Nicolaou Taxol total synthesis

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ring C. Two key chemical transformations are the Shapiro reaction and the pinacol coupling reaction. The overall synthesis was published in 1995 in a series...

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Dimethylbutadiene

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Dimethylbutadiene is readily prepared by an acid catalyzed dehydration reaction of pinacol: HO(CH3)2C−C(CH3)2OH → CH3(CH2=C−C=CH2)CH3 + 2 H2O The current industrial...

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Wilhelm Rudolph Fittig

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December 1835 – 19 November 1910) was a German chemist. He discovered the pinacol coupling reaction, mesitylene, diacetyl and biphenyl. Fittig studied the...

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Diol

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acid. Other routes to vic-diols are the hydrogenation of acyloins and the pinacol coupling reaction. 1,3-Diols are often prepared industrially by aldol condensation...

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McMurry reaction

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including potassium, zinc, and magnesium. This reaction is related to the Pinacol coupling reaction which also proceeds by reductive coupling of carbonyl...

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Ketyl

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soluble ketyl radical. Ketyls are also invoked as intermediates in the pinacol coupling reaction. The ketyl radicals derived from the reaction of sodium...

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Imine

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Furthermore, polyimines are known for their self-healing behaviour. Akin to pinacol couplings, imines are susceptible to reductive coupling leading to 1,2-diamines...

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Diethyl azodicarboxylate

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hydrogen by DEAD was demonstrated for isopropyl alcohol, resulting in pinacol and tetraethyl tetrazanetetracarboxylate, and for acetaldehyde yielding...

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Pivalic acid

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Pinacol rearrangement...

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List of organic reactions

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Pictet–Spengler reaction Piloty–Robinson pyrrole synthesis Pinacol coupling reaction Pinacol rearrangement Pinner amidine synthesis Pinner method for ortho...

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Carbenoid

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ISBN 0-534-07968-7 Iterative Stereospecific Reagent-Controlled Homologation of Pinacol Boronates by Enantioenriched -Chloroalkyllithium Reagents Paul R. Blakemore...

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Aldehyde

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performed as a one-pot reaction, giving the overall conversion RCH=O → RCH3. Pinacol coupling reaction Diol With reducing agents such as magnesium Wittig reaction...

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C6H14O2

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2-Butoxyethanol 1,1-Diethoxyethane 1,6-Hexanediol 2-Methyl-2,4-pentanediol (MPD) Pinacol This set index page lists chemical structure articles associated with the...

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Bismuth

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subcarbonate or subnitrate. As catalyst for the fluorination of arylboronic pinacol esters through a Bi(III)/Bi(V) catalytic cycle, mimicking transition metals...

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