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T71803

Sigma-Aldrich

Pivalic acid

99%

Synonym(s):

2,2-Dimethylpropionic acid, Trimethylacetic acid

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About This Item

Linear Formula:
(CH3)3CCO2H
CAS Number:
75-98-9
Molecular Weight:
102.13
Beilstein:
969480
EC Number:
200-922-5
MDL number:
MFCD00004194
UNSPSC Code:
12352100
PubChem Substance ID:
24900421
NACRES:
NA.22
Pricing and availability is not currently available.

vapor density

3.6 (vs air)

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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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

147.2 °F - closed cup

Flash Point(C)

64 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6422
MKCW6928
MKCR6547
MKCN8445
MKCN2710

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In situ generation of palladium nanoparticles: ligand-free palladium catalyzed pivalic acid assisted carbonylative Suzuki reactions at ambient conditions.
Zhou Q, et al.
The Journal of Organic Chemistry, 79(3), 1454-1460 (2014)
Asit K Chakraborti et al.
The Journal of organic chemistry, 71(15), 5785-5788 (2006-07-15)
Magnesium bistrifluoromethanesulfonimide catalyzed the acetylation of phenols, alcohols, and thiols under solvent-free conditions at room temperature and in short times. Electron-deficient and sterically hindered phenols provided excellent yields. The catalyst was found to be general for acylation with other anhydrides
Vishal Kandathil et al.
Carbohydrate polymers, 223, 115060-115060 (2019-08-21)
The core characteristics of a perfect catalyst include good activity, simple design, excellent stability, easy recovery from reaction mixture, recyclability, and have the provision for easy scale up. The ease in synthesis, recyclability and scale up makes the dip catalyst
Cross-coupling of aryl/alkenyl pivalates with organozinc reagents through nickel-catalyzed C-O bond activation under mild reaction conditions.
Bi-Jie Li et al.
Angewandte Chemie (International ed. in English), 47(52), 10124-10127 (2008-11-19)
Cerium (IV) hexanuclear clusters from cerium (III) precursors: Molecular models for oxidative growth of ceria nanoparticles
L Mathey, et al.
Chemistry?A European Journal , 21, 13454-13461 (2015)
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Questions

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  1. 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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  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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