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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
Pricing and availability is not currently available.

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.[1]

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.[2]
  • Aldol-transfer products such as β-hydroxy ketones by reacting with various aldehydes in the presence of L-proline as a catalyst.[3]
  • Mono-α-arylated ketones and esters via Pd catalyzed reaction with aryl halides and aryl triflates, respectively.[4]

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.[5]

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

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB2468
SDBB2466
SDBB1202
STBL3099
STBL1301

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C-C Activation by Retro-Aldol Reaction of Two ?-Hydroxy Carbonyl Compounds: Synergy with Pd-Catalyzed Cross-Coupling To Access Mono-?-arylated Ketones and Esters
Zhang SL and Yu ZL
The Journal of Organic Chemistry, 81(1), 57-65 (2015)
M Kitulagodage et al.
Ecotoxicology and environmental safety, 71(2), 597-600 (2007-12-25)
Fipronil, a phenyl pyrazole pesticide, is aerially applied in eastern Australia to control locust outbreaks, usually as "Adonis 3UL Insecticide" (BASF), an ultra low (UL) volume formulation containing 0.3% active pesticide. We tested the toxicities of technical-grade fipronil, the Adonis
Atsumi Wakabayashi et al.
Langmuir : the ACS journal of surfaces and colloids, 22(22), 9260-9263 (2006-10-18)
A novel method to prepare transparent antistatic films by trapping nanoparticles in thin surface layers is proposed, and high performance of the product is demonstrated. Coating solutions consisting of surface-active antimony-doped tin oxide (ATO) nanoparticles, an organic solvent mixture of
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)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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