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T76201

Sigma-Aldrich

Trimethylene oxide

97%

Synonym(s):

1,3-Epoxypropane, 1,3-Propylene oxide, Cyclooxabutane, Oxacyclobutane, Oxetane

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About This Item

Empirical Formula (Hill Notation):
C3H6O
CAS Number:
503-30-0
Molecular Weight:
58.08
Beilstein:
102382
EC Number:
207-964-3
MDL number:
MFCD00005167
UNSPSC Code:
12352100
PubChem Substance ID:
24900463
NACRES:
NA.22

vapor pressure

5.09 psi ( 20 °C)

Quality Level

200

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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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
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H302 + H312 + H332

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

-4.0 °F - closed cup

Flash Point(C)

-20 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7231
BCCL7230
BCCK8047
BCCJ8682
BCCH1805

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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)
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
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
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)
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