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Merck

H41544

4-Hydroxy-4-methyl-2-pentanone

99%

Synonym(s):

Diacetone alcohol

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About This Item

Linear Formula:
(CH3)2C(OH)CH2COCH3
CAS Number:
123-42-2
Molecular Weight:
116.16
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24895626
EC Number:
204-626-7
Beilstein/REAXYS Number:
1740440
MDL number:
MFCD00004471
Assay:
99%
Form:
liquid

Key Documents

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form

liquid

InChI

1S/C6H12O2/c1-5(7)4-6(2,3)8/h8H,4H2,1-3H3

InChI key

SWXVUIWOUIDPGS-UHFFFAOYSA-N

SMILES string

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

vapor density

4 (vs air)

vapor pressure

<1 mmHg ( 20 °C)

assay

99%

expl. lim.

6.9 %

refractive index

n20/D 1.423 (lit.)

bp

166 °C (lit.)

density

0.931 g/mL at 25 °C (lit.)

Quality Level

200

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General description

4-Hydroxy-4-methyl-2-pentanone is commonly used as a solvent in various industries, including paints, coatings, adhesives, and printing inks.

Application

4-Hydroxy-4-methyl-2-pentanone can be used to synthesize:
  • Diolmonoesters by reacting with aldehydes via tandem aldol-transfer–Tischtschenko reaction catalyzed by trimethylaluminum.
  • Aldol-transfer products such as β-hydroxy ketones by reacting with various aldehydes in the presence of L-proline as a catalyst.
  • Mono-α-arylated ketones and esters via Pd catalyzed reaction with aryl halides and aryl triflates, respectively.

It can also be used as a complexing agent to synthesize double-metal cyanide (DMC) catalysts by reacting with metal salt (MX) and cyanometalate compounds.

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Repr. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

136.4 °F - closed cup

flash_point_c

58 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB7604
SDBB5372
SDBB4064
SDBB2468
SDBB2466

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Daniel Rios et al.
Inorganic chemistry, 51(23), 12768-12775 (2012-11-14)
Combined collision-induced dissociation mass spectrometry experiments with DFT and MP2 calculations were employed to elucidate the molecular structures and energetics of dissociation reactions of uranyl species containing acetone and diacetone alcohol ligands. It is shown that solutions containing diacetone alcohol
L-Proline catalyzed asymmetric transfer aldol reaction between diacetone alcohol and aldehydes
Ramakrishna R, et al.
Chemical Communications (Cambridge, England), 42(21), 2450-2451 (2004)
S Chandrasekhar et al.
Chemical communications (Cambridge, England), (21)(21), 2450-2451 (2004-10-30)
We demonstrate for the first time, L-proline as a chiral catalyst for transfer aldol reaction between aldehydes and diacetone alcohol.
Synthesis of Polycarbonate Polyols by Double-Metal Cyanide Catalyzed Copolymerization of Epoxide with Carbon Dioxide
Lim J, et al.
Journal of Nanoscience and Nanotechnology, 17(10), 7507-7514 (2017)
Tandem aldol-transfer-Tischtschenko reaction of aldehydes and ?-hydroxyketones catalyzed by trimethylaluminum
Simpura I and Nevalainen V
Tetrahedron Letters, 42(23), 3905-3907 (2001)
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