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309753

Sigma-Aldrich

(R)-(−)-3-Hydroxytetrahydrofuran

98%

Synonym(s):

(R)-(-)-Tetrahydro-3-furanol

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About This Item

Empirical Formula (Hill Notation):
C4H8O2
CAS Number:
86087-24-3
Molecular Weight:
88.11
MDL number:
MFCD00067101
UNSPSC Code:
12352005
PubChem Substance ID:
24858751
NACRES:
NA.22

€38.50

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Quality Level

100

Assay

98%

form

liquid

optical activity

[α]20/D −18°, c = 2.4 in methanol

refractive index

n20/D 1.45 (lit.)

bp

181 °C (lit.)

density

1.097 g/mL at 25 °C (lit.)

functional group

ether
hydroxyl

SMILES string

O[C@@H]1CCOC1

InChI

1S/C4H8O2/c5-4-1-2-6-3-4/h4-5H,1-3H2/t4-/m1/s1

InChI key

XDPCNPCKDGQBAN-SCSAIBSYSA-N

Application

(R)-(-)-3-Hydroxytetrahydrofuran may be used as building block in the synthesis of potent HIV protease inhibitors.[1]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

179.6 °F - closed cup

Flash Point(C)

82 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000346987
0000346987
0000268840
0000268840
0000183712

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Diethyl zinc catalyzed diastereoselective addition of ketenes to (S)-(+)-3-hydroxytetrahydrofuran.
Tandon VK.
Tetrahedron Letters, 42(34), 5985-5987 (2001)
Angle-Resolved Photoelectron Spectroscopy of Randomly Oriented 3-Hydroxytetrahydrofuran Enantiomers.
Giardini A, et al.
ChemPhysChem, 6(6), 1164-1168 (2005)
Matt Hrapchak et al.
Journal of labelled compounds & radiopharmaceuticals, 57(12), 687-694 (2014-10-22)
Empagliflozin, (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol was recently approved by the FDA for the treatment of chronic type 2 diabetes mellitus. Herein, we report the synthesis of carbon-13 and carbon-14 labeled empagliflozin. Carbon-13 labeled empagliflozin was prepared in five steps and in 34% overall

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  1. 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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  2. 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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