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Safety Information

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)

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.

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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Description
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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

T71803-5ML:
T71803-VAR:
T71803-BULK:
T71803-100G:
T71803-500ML:
T71803-100ML:
T71803-500G:

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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
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)
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
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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