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T71803

Sigma-Aldrich

Pivalic acid

99%

Synonym(s):

2,2-Dimethylpropionic acid, Trimethylacetic acid

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5 ML
$35.80
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500 ML
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About This Item

Linear Formula:
(CH3)3CCO2H
CAS Number:
75-98-9
Molecular Weight:
102.13
Beilstein/REAXYS Number:
969480
EC Number:
200-922-5
MDL number:
MFCD00004194
UNSPSC Code:
12352100
PubChem Substance ID:
24900421
NACRES:
NA.22

$35.80

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vapor density

3.6 (vs air)

Quality Level

200

vapor pressure

9.75 mmHg ( 60 °C)

assay

99%

reaction suitability

reaction type: C-H Activation

bp

163-164 °C (lit.)

mp

32-35 °C (lit.)

density

0.889 g/mL at 25 °C (lit.)

functional group

carboxylic acid

SMILES string

OC(C(C)(C)C)=O

InChI

1S/C5H10O2/c1-5(2,3)4(6)7/h1-3H3,(H,6,7)

InChI key

IUGYQRQAERSCNH-UHFFFAOYSA-N

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General description

Pivalic acid is a carboxylic acid, employed as a ligand to synthesize cerium(IV) hexanuclear clusters.[1]

Application

Pivalic acid can be employed:
  • As a co-catalyst with palladium for the arylation of unactivated arenes[2] and N-heterocycles.[3]
  • As an additive to facilitate the carbonylative suzuki reactions to synthesize biaryl ketones from aryl iodides and arylboronic acids by using palladium nanoparticles as catalyst.[4]
  • In the cyclization reaction of benzamides with alkynes to synthesize isoquinolones in the presence of 8-aminoquinoline ligand and cobalt catalyst.[5]

Caution

Pungent odour/Stench

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GHS07

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Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

147.2 °F - closed cup

flash_point_c

64 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6422
MKCW6928
MKCR6547
MKCN8445
MKCN2710

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Tobias Illg et al.
ChemSusChem, 4(3), 392-398 (2011-02-09)
The two-step synthesis of tert-butyl peroxypivalate is performed in a single-channel microreactor. The first step, the deprotonation of tert-butyl hydroperoxide, is done in a simple mixer tube setup. The residence time section for the second reaction step is equipped with
Toshiaki Shimasaki et al.
Angewandte Chemie (International ed. in English), 49(16), 2929-2932 (2010-03-17)
Catalytic amination: The title reaction demonstrates the use of aryl carboxylates as suitable electrophilic coupling substrates in catalytic amination reactions. N-heterocyclic carbene ligands and NaOtBu promote the amination of aryl pivalates through the cleavage of normally unreactive aryl carbon-oxygen bonds
Phosphine-free, palladium-catalyzed arylation of heterocycles through C-H bond activation with pivalic acid as a cocatalyst.
Dongbing Zhao et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(6), 1337-1340 (2008-12-31)
Qi Zhou et al.
Journal of the American Chemical Society, 135(9), 3307-3310 (2013-02-22)
We have developed a stereospecific nickel-catalyzed cross-coupling of benzylic pivalates with arylboroxines. The success of this reaction relies on the use of Ni(cod)2 as the catalyst and NaOMe as a uniquely effective base. This reaction has broad scope with respect
Lukas J Goossen et al.
Angewandte Chemie (International ed. in English), 48(20), 3569-3571 (2009-03-13)
Crucial breakthroughs in the activation of the C(aryl)-O bond of phenol derivatives were achieved almost simultaneously by two research groups (see scheme; Cy = cyclohexyl). Garg et al. coupled a range of aryl pivalates with arylboronic acids to give unsymmetrical
View All Related Papers

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    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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  2. 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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