Skip to Content
Merck
All Photos(2)

Documents

136824

Sigma-Aldrich

3,3-Dimethyl-2-butanol

98%

Synonym(s):

tert-Butyl methyl carbinol, Pinacoline alcohol, Pinacolyl alcohol

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
(CH3)3CCH(OH)CH3
CAS Number:
464-07-3
Molecular Weight:
102.17
Beilstein:
1718948
EC Number:
207-347-9
MDL number:
MFCD00004522
UNSPSC Code:
12352100
PubChem Substance ID:
24848296
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.415 (lit.)

bp

119-121 °C (lit.)

mp

4.8 °C (lit.)

density

0.812 g/mL at 25 °C (lit.)

SMILES string

CC(O)C(C)(C)C

InChI

1S/C6H14O/c1-5(7)6(2,3)4/h5,7H,1-4H3

InChI key

DFOXKPDFWGNLJU-UHFFFAOYSA-N

General description

3,3-Dimethyl-2-butanol is a potential precursor for prohibited chemical weapons such as soman, a nerve agent. It is a synthetic analog of kairomone.

Application

3,3-Dimethyl-2-butanol (pinacolyl alcohol) can be used as a substrate:
  • To study the oxidation of secondary alcohols to ketones using cyclic microwave heating technique.
  • To prepare aryl ethers by reacting with aryl iodide using 4-pyrrolidinopyridine ligand via Cu-catalyzed Ullmann reaction.
3,3-Dimethyl-2-butanol was used in conversion of ribose- and glucose-binding proteins into receptors for pinacolyl methyl phosphonic acid.

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

78.8 °F - closed cup

Flash Point(C)

26 °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’.

Already Own This Product?

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

Visit the Document Library

Fast oxidation of secondary alcohols by the bromate-bromide system using cyclic microwave heating in acidic water
Paakkonen S, et al.
Tetrahedron Letters, 51(51), 6695-6699 (2010)
Chemical ionization mass spectral analysis of pinacolyl alcohol and development of derivatization method using p-tolyl isocyanate.
Murty MRVS, et al.
Analytical Methods : Advancing Methods and Applications, 2(10), 1599-1605 (2010)
J T James et al.
Journal of applied toxicology : JAT, 7(5), 307-312 (1987-10-01)
Sprague-Dawley rats were given 15, 70 and 140 min exposures to 15 mg/l 3,3-dimethyl-2-butanol, pinacolyl alcohol (PA), or 6-hour exposures to 0.2, 1.0 and 5.0 mg/l PA (1 mg/l = 240 ppm). A 50% mortality rate was obtained at the
Ullmann CO coupling of sterically hindered secondary alcohols using excess amount of strongly coordinating monodentate ligands
Sugata H, et al.
Tetrahedron Letters, 58(10), 1015-1019 (2017)
W E Luttrell et al.
Biochemical pharmacology, 46(11), 2083-2092 (1993-12-03)
Soman (pinacolyl methylphosphonofluoridate), a highly toxic organophosphate compound, has been found to be a strong inhibitor of hepatic microsomal carboxylesterase in vitro, but an enhancer of carboxylesterase when administered in vivo. In response to this paradoxical observation, the objective of
View All Related Papers

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