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136824

Sigma-Aldrich

3,3-Dimethyl-2-butanol

98%

Synonym(s):

tert-Butyl methyl carbinol, Pinacoline alcohol, Pinacolyl alcohol

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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
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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.)

functional group

hydroxyl

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[1]. It is a synthetic analog of kairomone[2].

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.[3]
  • To prepare aryl ethers by reacting with aryl iodide using 4-pyrrolidinopyridine ligand via Cu-catalyzed Ullmann reaction.[4]
3,3-Dimethyl-2-butanol was used in conversion of ribose- and glucose-binding proteins into receptors for pinacolyl methyl phosphonic acid[5].

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS4550
MKCN9038
MKCK9690
MKCF4756
MKBX8203V

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J T James et al.
Journal of applied toxicology : JAT, 7(2), 135-142 (1987-04-01)
Four groups of male and female Sprague-Dawley rats were exposed for 13 weeks to 3,3-dimethyl-2-butanol (PA) at concentrations of 0.00, 0.20, 1.00 or 5.00 mg/l (1 mg/l = 240 ppm). Exposures were for 6 hr per day, 5 days per
3, 3-Dimethyl-1-butanol, a parakairomone component to Aleurodicus dispersus (Hemiptera: Aleyrodidae).
Zheng L-X, et al.
Arthropod-Plant Interactions, 7, 1-7 (2013)
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)
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
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)
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Questions

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  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/449/386/product-dating-information-mk.pdf

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  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

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