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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

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.

Application

Pivalic acid can be employed:
  • As a co-catalyst with palladium for the arylation of unactivated arenes and N-heterocycles.
  • 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.
  • In the cyclization reaction of benzamides with alkynes to synthesize isoquinolones in the presence of 8-aminoquinoline ligand and cobalt catalyst.

Caution

Pungent odour/Stench

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Pricing

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

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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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
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
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
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)
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
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