Skip to Content
Merck

T71803

Pivalic acid

99%

Synonym(s):

2,2-Dimethylpropionic acid, Trimethylacetic acid

Sign In to View Organizational & Contract Pricing

Select a Size

5 ML

$47.20

100 ML

$101.00

500 ML

$112.00

$47.20

PRICE WITHOUT NATIONAL TAXES

Check Cart for Availability

Request a Bulk Order

About This Item

Linear Formula:
(CH3)3CCO2H
CAS Number:
Molecular Weight:
102.13
Beilstein:
969480
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Skip To

Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
P42800721611143502
assay

99%

assay

99%

assay

97%

assay

99%

reaction suitability

reaction type: C-H Activation

reaction suitability

-

reaction suitability

-

reaction suitability

-

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

density

0.889 g/mL at 25 °C (lit.)

density

-

density

-

density

0.918 g/mL at 25 °C (lit.)

bp

163-164 °C (lit.)

bp

-

bp

-

bp

193 °C (lit.)

mp

32-35 °C (lit.)

mp

139-142 °C (lit.)

mp

230-232 °C

mp

-

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]

Disclaimer

Pungent odour/Stench

comparable product

Product No.
Description
Pricing

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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
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
Guotao Li et al.
Journal of the American Chemical Society, 130(12), 3740-3741 (2008-03-04)
Propargylic pivalates with electronically unbiased internal alkynes are selectively transformed into (1Z,3E)-2-pivaloxy-1,3-dienes containing various functionalities. The unusual selectivity of 1,2-acyloxy migration over the structurally preferred 3,3-rearrangement is realized. This reaction is highly stereoselective and offers rapid access to dienes for
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)

Questions

1–2 of 2 Questions  
  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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  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

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service