30608-62-9

Basic information

• Product Name: (S)-(-)-1,2-Epoxybutane
• Synonyms: (S)-(-)-1,2-EPOXYBUTANE;(S)-1,2-EPOXYBUTANE;2S-ETHYLOXIRANE;(S)-1-Butene oxide;(S)-Ethyloxirane;(S)-()-1,2-Epoxybutane,(2S)-Ethyloxirane;(S)-1,2-Butylene oxide;(2S)-(-)-1,2-Epoxybutane, (2S)-(-)-3-Methyl-1,2-propenoxide
• CAS NO: 30608-62-9
• Molecular Formula: C₄H₈O
• Molecular Weight: 72.11
• Product Categories: Chiral Compounds;Epoxides
• Mol File: 30608-62-9.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 63 °C(lit.)
• Flash Point: 10 °F
• Appearance: /
• Density: 0.837 g/mL at 25 °C(lit.)
• Vapor Pressure: 184mmHg at 25°C
• Refractive Index: n20/D 1.386(lit.)
• CAS DataBase Reference: (S)-(-)-1,2-Epoxybutane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-1,2-Epoxybutane(30608-62-9)
• EPA Substance Registry System: (S)-(-)-1,2-Epoxybutane(30608-62-9)

Safety Data

• Hazard Codes: F,T
• Statements: 20/21/22-34-40
• Safety Statements: 16-26-27-36/37/39-45
• RIDADR: UN 3022 3/PG 2
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 30608-62-9(Hazardous Substances Data)

Usage

Description

(S)-(-)-1,2-Epoxybutane, also known as (S)-butylene oxide, is a colorless liquid that serves as an epoxide reagent in organic synthesis. It is characterized by its reactive epoxide ring, which allows for various chemical transformations and applications in different industries.

Uses

Used in Pharmaceutical Industry:
(S)-(-)-1,2-Epoxybutane is used as a synthetic building block for the production of α-ethyltryptamines, which are dual dopamine-serotonin releasers. These compounds have potential applications in the treatment of neurological and psychiatric disorders.
Used in Antibiotic Synthesis:
(S)-(-)-1,2-Epoxybutane is used as a starting material to prepare (+)and (?)-homononactic acids. These acids are essential intermediates in the total synthesis of tetranactin, a cyclic antibiotic with potent antibacterial properties.
Used in Chiral Synthesis:
(S)-(-)-1,2-Epoxybutane is used to prepare a chiral phosphorus synthon, which is applicable in the synthesis of phytoprostane B1 type I. (S)-(-)-1,2-Epoxybutane has potential applications in the development of new chiral molecules and pharmaceuticals.
Used in Catalyst Preparation:
(S)-(-)-1,2-Epoxybutane is used to prepare Eu3+-based precatalysts that are applicable in the Mukaiyama Aldol reaction in water. This reaction is an important carbon-carbon bond-forming process in organic synthesis, and the use of (S)-(-)-1,2-Epoxybutane in the preparation of precatalysts can enhance the reaction's efficiency and selectivity.

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

Upstream product

• 106-88-7 ethyloxirane 
• 70379-72-5 (R)-2-acetoxy-1-bromobutane 
• 40348-66-1 (R)-1,2-butanediol 
• 93246-17-4 ((R)-2-Hydroxy-butyl)-trimethyl-ammonium; hydroxide 
• 136656-75-2 (R)-(-)-1-(benzenesulfanyl)-2-butanol 
• 72952-76-2 S-(-)-1-bromo-2-acetoxy-butane 
• 145021-04-1 (R)-1-tert-Butylsulfanyl-butan-2-ol 
• 56536-49-3 (2S)-2-chlorobutan-1-ol 
• 51-79-6 urethane 
• 917-61-3 sodium isocyanate 
• 124-38-9 carbon dioxide 
• 111873-09-7 (2R,3R)-2,3-Bis-benzoyloxy-3-carboxy-propionate((S)-2-hydroxy-butyl)-dimethyl-sulfonium; 
• 72952-75-1 (S)-1,3-butanediol acetonide 
• 93246-18-5 ((S)-2-Hydroxy-butyl)-trimethyl-ammonium; hydroxide 

Downstream Products

• 4476-77-1 (S)-3-tetradecanol 
• 16460-75-6 (R)-2-phenyl-butan-1-ol 
• 2031-46-1 (3S)-3-phenylbutan-1-ol 
• 1873-25-2 1-chloro-butan-2-ol 
• 38401-84-2 (2S,5R,S)-Chalcogran 
• 93246-20-9 (S)-2-(3,5-Bisphenyl)-2-(2-hydroxybutyl)-1,3-dithiane 
• 89497-71-2 (S:R)-N-benzyl-1,1'-iminobis-2-butanol 
• 89479-95-8 (S:S)-N-benzyl-1,1'-iminobis-2-butanol 
• 89479-94-7 (R)(-)-1-N-benzylaminobutan-2-ol 
• 89479-93-6 (S)(+)-1-N-benzylaminobutan-2-ol 
• 93246-19-6 (R)-2-(3,5-Bisphenyl)-2-(2-hydroxybutyl)-1,3-dithiane 
• 176165-02-9 (S)-1-(2-Methoxymethoxy-phenylamino)-butan-2-ol 
• 42558-50-9 methyl (S)-3-hydroxyvalerate 

Relevant articles and documents

Enantioselective Resolution Copolymerization of Racemic Epoxides and Anhydrides: Efficient Approach for Stereoregular Polyesters and Chiral Epoxides

Herein we report an efficient strategy for preparing isotactic polyesters and chiral epoxides via enantioselective resolution copolymerization of racemic terminal epoxides with anhydrides, mediated by enantiopure bimetallic complexes in conjunction with a nucleophilic cocatalyst. The chirality of both the axial linker and the diamine backbones of the ligand are responsible for the chiral induction of this kinetic resolution copolymerization process. The catalyst systems exhibit exceptional levels of enantioselectivity with a kinetic resolution coefficient exceeding 300 for various racemic epoxides, affording highly isotactic copolymers (selectivity factors of more than 300) with a completely alternating structure and low polydispersity index. Most of the produced isotactic polyesters are typical semicrystalline materials with melting temperatures in the range from 77 to 160 °C.

OXYSTEROLS AND METHODS OF USE THEREOF

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R2, R3, R4, R5, and and R6 are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.