(S)-(-)-1,2-Epoxybutane

Base Information

• Chemical Name: (S)-(-)-1,2-Epoxybutane
• CAS No.: 30608-62-9
• Molecular Formula: C4H8O
• Molecular Weight: 72.1069
• Hs Code.: 29109000
• European Community (EC) Number: 608-509-5
• DSSTox Substance ID: DTXSID801315723
• Nikkaji Number: J389.769I
• Wikidata: Q72470926
• Mol file: 30608-62-9.mol

Synonyms:(S)-(-)-1,2-Epoxybutane;30608-62-9;(2S)-2-ethyloxirane;(S)-1,2-Epoxybutane;(S)-2-ethyloxirane;Oxirane, ethyl-, (2S)-;Oxirane, 2-ethyl-, (2S)-;2beta-Ethyloxirane;(S)-(-)-Ethyloxirane;(s)-1,2-epoxy-butane;(S)-(-)-Butylene Oxide;(S)-(-)-Ethylethylene Oxide;RBACIKXCRWGCBB-BYPYZUCNSA-N;DTXSID801315723;MFCD02683445;AKOS015918476;(S)-(-)-1,2-Epoxybutane, 98%;B3833;D89036;EN300-107870;J-018034

Chemical Property of (S)-(-)-1,2-Epoxybutane

Chemical Property:

• Vapor Pressure: 184mmHg at 25°C
• Refractive Index: n20/D 1.386(lit.)
• Boiling Point: 63.4 °C at 760 mmHg
• Flash Point: 10 °F
• PSA: 12.53000
• Density: 0.88 g/cm³
• LogP: 0.79520
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 72.057514874
• Heavy Atom Count: 5
• Complexity: 34.6

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)?-?(-?)?-?1,?2-?Epoxybutane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 20/21/22-34-40
• Safety Statements: 16-26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CO1
• Isomeric SMILES: CC[C@H]1CO1
• Uses: (S)?-?(-?)?-?1,?2-?Epoxybutane is an epoxide reagent used in organic synthesis. Used in the synthesis of α-ethyltryptamines as dual dopamine-serotonin releasers. (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.

Technology Process of (S)-(-)-1,2-Epoxybutane

There total 37 articles about (S)-(-)-1,2-Epoxybutane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

((R)-2-Hydroxy-butyl)-trimethyl-ammonium; hydroxide (93246-17-4) → (R)-(+)-1,2-epoxybutane (106-88-7,3760-95-0,30608-62-9,55555-96-9)

Guidance literature:

at 130 ℃; for 0.5h;

DOI:10.1055/s-1984-30884

Reference yield: 71.0%

S-(-)-1-bromo-2-acetoxy-butane (72952-76-2) → (R)-(+)-1,2-epoxybutane (106-88-7,3760-95-0,30608-62-9,55555-96-9)

Guidance literature:

With potassium pentanolate; In pentan-1-ol; for 0.5h; Ambient temperature;

DOI:10.1021/ja00217a044

Reference yield: 49.0%

ethyloxirane (106-88-7) → (R)-(+)-1,2-epoxybutane (106-88-7,3760-95-0,30608-62-9,55555-96-9)

Guidance literature:

With bis(triphenylphosphine)iminium acetate; C₆₄H₇₄Cl₂Co₂N₄O₄; In toluene; at 0 ℃; for 52h; optical yield given as %ee; Resolution of racemate; Inert atmosphere;

DOI:10.1021/ja807709j

upstream raw materials:

ethyloxirane

(R)-2-acetoxy-1-bromobutane

(R)-1,2-butanediol

((R)-2-Hydroxy-butyl)-trimethyl-ammonium; hydroxide

Downstream raw materials:

(S)-3-tetradecanol

(R)-2-(3,5-Bisphenyl)-2-(2-hydroxybutyl)-1,3-dithiane

(S)-1-(2-Methoxymethoxy-phenylamino)-butan-2-ol

methyl (S)-3-hydroxyvalerate

Refernces

• 1、 Liang, Jian,Soucie, Luke N.,Blechschmidt, Daniel R.,Yoder, Aaron,Gustafson, Addie,Liu, Yu. "Aromatic Donor-Acceptor Interaction-Based Co(III)-salen Self-Assemblies and Their Applications in Asymmetric Ring Opening of Epoxides". supporting information. p. 513 - 518. Retrieved 2019/01/14.
• 2、 Xie, Shengming,Zhang, Junhui,Fu, Nan,Wang, Bangjin,Hu, Cong,Yuan, Liming. "Application of homochiral alkylated organic cages as chiral stationary phases for molecular separations by capillary gas chromatography". . . Retrieved 2016/12/03.