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H41544

Sigma-Aldrich

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
Beilstein:
1740440
EC Number:
204-626-7
MDL number:
MFCD00004471
UNSPSC Code:
12352100
PubChem Substance ID:
24895626
NACRES:
NA.22

vapor density

4 (vs air)

Quality Level

200

vapor pressure

<1 mmHg ( 20 °C)

Assay

99%

form

liquid

expl. lim.

6.9 %

refractive index

n20/D 1.423 (lit.)

bp

166 °C (lit.)

density

0.931 g/mL at 25 °C (lit.)

SMILES string

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

InChI

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

InChI key

SWXVUIWOUIDPGS-UHFFFAOYSA-N

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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.

Signal Word

Warning

Hazard Statements

H226,H319,H335,H361fd

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

136.4 °F - closed cup

Flash Point(C)

58 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

H41544-4L:4548173949543
H41544-1L:
H41544-VAR:
H41544-2.5L:
H41544-500ML:4548173949550
H41544-BULK:
H41544-25ML:4548173949536

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Tandem aldol-transfer-Tischtschenko reaction of aldehydes and ?-hydroxyketones catalyzed by trimethylaluminum
Simpura I and Nevalainen V
Tetrahedron Letters, 42(23), 3905-3907 (2001)
Harriet L R Cooper et al.
Archives of biochemistry and biophysics, 507(1), 111-118 (2010-11-16)
The diagnostic substrate tetramethylcyclopropane (TMCP) has been reexamined as a substrate with three drug- and xenobiotic-metabolizing cytochrome P450 enzymes, human CYP2E1, CYP3A4 and rat CYP2B1. The major hydroxylation product in all cases was the unrearranged primary alcohol along with smaller
I Magneron et al.
Environmental science & technology, 37(18), 4170-4181 (2003-10-04)
The OH-initiated oxidation of two VOCs directly emitted to the atmosphere through their use as industrial solvents, hexylene glycol (HG, (CH3)2C(OH)CH2CH(OH)CH3) and diacetone alcohol (DA, (CH3)2C(OH)CH2C(O)CH3), has been studied in two photoreactors: a 140 L Teflon bag irradiated by lamps
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.
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