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281697

Sigma-Aldrich

(R)-(−)-2-Pyrrolidinemethanol

99%

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Synonym(s):
(R)-(−)-2-(Hydroxymethyl)pyrrolidine, D-Prolinol
Empirical Formula (Hill Notation):
C5H11NO
CAS Number:
68832-13-3
Molecular Weight:
101.15
Beilstein:
1523669
MDL number:
MFCD00064321
PubChem Substance ID:
24856990
NACRES:
NA.22

Assay

99%

optical activity

[α]20/D −31°, c = 1 in toluene

refractive index

n20/D 1.4849 (lit.)

bp

74-76 °C/2 mmHg (lit.)

density

1.025 g/mL at 25 °C (lit.)

SMILES string

OC[C@H]1CCCN1

InChI

1S/C5H11NO/c7-4-5-2-1-3-6-5/h5-7H,1-4H2/t5-/m1/s1

InChI key

HVVNJUAVDAZWCB-RXMQYKEDSA-N

Related Categories

Application

Versatile reagent for asymmetric synthesis.

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)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Tetrahedron Asymmetry, 15, 519-523 (2004)
Silvia Dei et al.
Bioorganic & medicinal chemistry, 11(14), 3153-3164 (2003-06-24)
Four out of the eight possible stereoisomers of 1-methyl-2-(2-methyl-1,3-dioxolan-4-yl)pyrrolidine, 1-methyl-2-(2-methyl-1,3-oxathiolan-5-yl)pyrrolidine and the corresponding iodomethylates have been synthesised. They were formally derived from hybridisation of potent though unselective agonists studied before, such as 1,3-dioxolane 1 and 1,3-oxathiolane 2, with the structure
Emily M Christensen et al.
The Journal of biological chemistry, 295(52), 18316-18327 (2020-10-29)
Pyrroline-5-carboxylate reductase 1 (PYCR1) catalyzes the biosynthetic half-reaction of the proline cycle by reducing Δ1-pyrroline-5-carboxylate (P5C) to proline through the oxidation of NAD(P)H. Many cancers alter their proline metabolism by up-regulating the proline cycle and proline biosynthesis, and knockdowns of

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