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221171

Sigma-Aldrich

Pinacol

98%

Synonym(s):

2,3-Dimethyl-2,3-butanediol, Tetramethylethylene glycol

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About This Item

Linear Formula:
HOC(CH3)2C(CH3)2OH
CAS Number:
76-09-5
Molecular Weight:
118.17
Beilstein/REAXYS Number:
1340501
EC Number:
200-933-5
MDL number:
MFCD00004462
UNSPSC Code:
12352100
PubChem Substance ID:
24853219
NACRES:
NA.22

Quality Level

200

assay

98%

form

solid

bp

171-172 °C/739 mmHg (lit.)

mp

40-43 °C (lit.)

solubility

alcohol: freely soluble
diethyl ether: freely soluble
hot water: freely soluble

functional group

hydroxyl

SMILES string

CC(C)(O)C(C)(C)O

InChI

1S/C6H14O2/c1-5(2,7)6(3,4)8/h7-8H,1-4H3

InChI key

IVDFJHOHABJVEH-UHFFFAOYSA-N

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General description

The pinacol coupling reaction with the inorganic electride [Ca2N](+)·e(−) as an electron donor in organic solvents was studied.

Application

Pinacol is a 1,2-diol that can be used:
  • As a ligand to prepare uranyl complexes by reacting with uranyl nitrate and acetate hydrates.
  • To prepare pinacolone and 2,3-dimethyl-1,3-butadiene by typical pinacol rearrangement reaction.
  • As a reactant to synthesize 4-(4,4,5,5-tetramethyl-1,3,2-bioxaborolan-2-yl)benzoic acid, which is used to prepare derivatives of 4-acetoxy-3-phenylbenzaldehyde.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

170.6 °F - closed cup

flash_point_c

77 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB5170
BCBZ4309
BCBX4292
WXBC6969V
WXBC6694V

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Uranyl complexes with 1, 2-diols and tetrahydrofurfuryl alcohols
Villiers C, et al.
Polyhedron, 46(1), 133-138 (2012)
Fe-substituted molecular sieves as catalysts in liquid phase pinacol rearrangement
Hsien M, et al.
J. Mol. Catal. A: Chem., 181(1-2), 189-200 (2002)
Ye Ji Kim et al.
Chemical communications (Cambridge, England), 50(37), 4791-4794 (2014-04-02)
The scalable pinacol coupling reaction is realized utilizing the inorganic electride [Ca2N](+)·e(-) as an electron donor in organic solvents. The bond cleavages of the [Ca2N](+) layers by methanol play a vital role in transferring anionic electrons to electrophilic aldehydes, accompanying
Egor V Verbitskiy et al.
Journal of fluorescence, 25(3), 763-775 (2015-03-31)
Novel donor-π-acceptor dyes bearing the pyrimidine unit as an electron-withdrawing group have been synthesized by using combination of two processes, based on the microwave-assisted Suzuki cross-coupling reaction and nucleophilic aromatic substitution of hydrogen. Spectral properties of the obtained dyes in

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