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Merck
CN

T71803

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24900421
EC Number:
200-922-5
Beilstein/REAXYS Number:
969480
MDL number:
MFCD00004194

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Product Name

Pivalic acid, 99%

InChI

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

InChI key

IUGYQRQAERSCNH-UHFFFAOYSA-N

SMILES string

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

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

Quality Level

200

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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.

Disclaimer

Pungent odour/Stench

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk

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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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
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
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)
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
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