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532363

Sigma-Aldrich

(S)-(−)-1,2-Epoxybutane

98%

Synonym(s):

(2S)-Ethyloxirane

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About This Item

Empirical Formula (Hill Notation):
C4H8O
CAS Number:
Molecular Weight:
72.11
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

optical activity

[α]20/D −10°, neat

refractive index

n20/D 1.386 (lit.)

bp

63 °C (lit.)

density

0.837 g/mL at 25 °C (lit.)

SMILES string

CC[C@H]1CO1

InChI

1S/C4H8O/c1-2-4-3-5-4/h4H,2-3H2,1H3/t4-/m0/s1

InChI key

RBACIKXCRWGCBB-BYPYZUCNSA-N

Application

(S)-(−)-1,2-Epoxybutane can be used:
  • As a starting material to prepare (+)- and (−)-homononactic acids, which are used as intermediates in the total synthesis of a cyclic antibiotic tetranactin.
  • To prepare a chiral phosphorus synthon, which is applicable in the synthesis of phytoprostane B1 type I.
  • To prepare Eu3+-based precatalysts applicable in the Mukaiyama Aldol reaction in water.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

10.0 °F - closed cup

Flash Point(C)

-12.2 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis, spectroscopic characterization, and reactivity of water-tolerant Eu3+-based precatalysts
Averill DJ and Allen MJ
Inorganic Chemistry, 53(12), 6257-6263 (2014)
Synthesis of (+)-and (−)-homononactic acid from (S)-1, 2-epoxybutane. Total synthesis of tetranactin by ′reverse coupe du roi′
Schmidt U and Werner J
Journal of the Chemical Society. Chemical Communications, 996-998 (1986)
A flexible synthesis of the phytoprostanes B1 type I and II
El Fangour S, et al.
The Journal of Organic Chemistry, 70(3), 989-997 (2005)
1,2-Epoxybutane.
IARC monographs on the evaluation of carcinogenic risks to humans, 47, 217-228 (1989-01-01)
M Katz et al.
Journal of environmental pathology and toxicology, 3(5-6), 171-187 (1980-06-01)
Nitrosopiperidine, sodium nitrite and 1,2 epoxybutane were tested in the Ames agar incorporation assay in an attempt to establish exact criteria for detecting the activity of these weak mutagens. As regards minimum concentrations it was determined that at 500 microgram

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