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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

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.

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

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.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

309753-1G:
309753-250MG:
309753-VAR:
309753-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM6158
WXBC8200V
32796KM
40796PK
06496CK

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Angle-Resolved Photoelectron Spectroscopy of Randomly Oriented 3-Hydroxytetrahydrofuran Enantiomers.
Giardini A, et al.
ChemPhysChem, 6(6), 1164-1168 (2005)
Diethyl zinc catalyzed diastereoselective addition of ketenes to (S)-(+)-3-hydroxytetrahydrofuran.
Tandon VK.
Tetrahedron Letters, 42(34), 5985-5987 (2001)
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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