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T76201

Sigma-Aldrich

Trimethylene oxide

97%

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Synonym(s):
1,3-Epoxypropane, 1,3-Propylene oxide, Cyclooxabutane, Oxacyclobutane, Oxetane
Empirical Formula (Hill Notation):
C3H6O
CAS Number:
Molecular Weight:
58.08
Beilstein/REAXYS Number:
102382
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

5.09 psi ( 20 °C)

Quality Level

assay

97%

refractive index

n20/D 1.388-1.396
n20/D 1.392 (lit.)

bp

50 °C (lit.)

density

0.893 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C1COC1

InChI

1S/C3H6O/c1-2-4-3-1/h1-3H2

InChI key

AHHWIHXENZJRFG-UHFFFAOYSA-N

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1 of 4

This Item
13956482320110205
vibrant-m

T76201

Trimethylene oxide

vibrant-m

139564

1,2,7,8-Diepoxyoctane

vibrant-m

82320

(±)-Propylene oxide

vibrant-m

110205

(±)-Propylene oxide

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

density

0.893 g/mL at 25 °C (lit.)

density

0.997 g/mL at 25 °C (lit.)

density

0.83 g/mL at 25 °C (lit.)

density

0.83 g/mL at 25 °C (lit.)

bp

50 °C (lit.)

bp

240 °C (lit.)

bp

34 °C (lit.)

bp

34 °C (lit.)

refractive index

n20/D 1.388-1.396, n20/D 1.392 (lit.)

refractive index

n20/D 1.445 (lit.)

refractive index

n20/D 1.366 (lit.)

refractive index

n20/D 1.366 (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

Application

  • Trimethylene oxide is a strained cyclic ether which can be used to replace carbonyl / gem-dimethyl groups during molecular modelling of bioactive molecules.
  • It can be incorporated in various bioactive molecule and drug substances for its improved physicochemical properties, via novel C-H activation methods.
  • Trimethylene oxide can also be used in the synthesis of poly(trimethylene oxide) and related polymer electrolytes.

pictograms

FlameExclamation mark

signalword

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

-4.0 °F - closed cup

flash_point_c

-20 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves


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Role of polar side chains in Li+ coordination and transport properties of polyoxetane-based polymer electrolytes.
Sai R, et al.
Physical Chemistry Chemical Physics, 19(7), 5185-5194 (2017)
Chun-Bao Miao et al.
The Journal of organic chemistry, 76(23), 9809-9816 (2011-10-27)
An efficient base-controlled selective conversion of the Michael adducts of malonates with enones in the presence of iodine is reported. Highly functionalized cyclopropane, oxetane, and α-hydroxylmalonate derivatives are obtained selectively using DBU, Na(2)CO(3), and NaOAc as the base, respectively. O(2)
Complex bioactive alkaloid-type polycycles through efficient catalytic asymmetric multicomponent aza-Diels-Alder reaction of indoles with oxetane as directing group.
Zhilong Chen et al.
Angewandte Chemie (International ed. in English), 52(7), 2027-2031 (2013-01-11)
Donato Ivan Coppi et al.
Chemical communications (Cambridge, England), 47(35), 9918-9920 (2011-08-05)
A valuable and direct method to access 2-substituted-2-phenyloxetanes by electrophilic quenching of the corresponding 2-lithiated derivative has, for the first time, been described. 2-Lithiated-2-phenyloxetane was found to be configurationally unstable. Evidence is presented to show that electron-transfer processes are also
Luciana Capece et al.
The journal of physical chemistry. B, 116(4), 1401-1413 (2011-12-27)
Indoleamine 2,3-dioxygenase (IDO) and tryptophan dioxygenase (TDO) are two heme proteins that catalyze the oxidation reaction of tryptophan (Trp) to N-formylkynurenine (NFK). Human IDO (hIDO) has recently been recognized as a potent anticancer drug target, a fact that triggered intense

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