(R)-(+)-Propylene oxide

Base Information

• Chemical Name: (R)-(+)-Propylene oxide
• CAS No.: 15448-47-2
• Molecular Formula: C3H6O
• Molecular Weight: 58.08
• Hs Code.: 2910 20 00
• European Community (EC) Number: 604-958-6
• DSSTox Substance ID: DTXSID201320388
• Nikkaji Number: J471.948D
• Wikidata: Q27104006
• Metabolomics Workbench ID: 51916
• ChEMBL ID: CHEMBL1901974
• Mol file: 15448-47-2.mol

Synonyms:d-Propylene oxide;Oxirane,methyl-, (2R)- (9CI);Oxirane, methyl-, (R)-;Propylene oxide, (R)-(+)- (8CI);(+)-(R)-Propylene oxide;(+)-Methyloxirane;(+)-Propylene oxide;(2R)-2-Methyloxirane;(2R)-Methyloxirane;(R)-(+)-1,2-Epoxypropane;(R)-(+)-Methyloxirane;(R)-(+)-Propylene oxide;(R)-1,2-Epoxypropane;(R)-2-Methyloxirane;(R)-Methyloxirane;(R)-Propenoxide;(R)-Propylene oxide;

Chemical Property of (R)-(+)-Propylene oxide

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 572mmHg at 25°C
• Melting Point: -111.91°C (estimate)
• Refractive Index: n20/D 1.366(lit.)
• Boiling Point: 32.899 °C at 760 mmHg
• Flash Point: -31 °F
• PSA: 12.53000
• Density: 0.904 g/cm³
• LogP: 0.40510
• Storage Temp.: 2-8°C
• Solubility.: 405g/l
• Water Solubility.: Miscible with water and many organic solvents.
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 58.041864811
• Heavy Atom Count: 4
• Complexity: 26.5

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-Propylene oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F+, T
• Hazard Codes: F+,T
• Statements: 12-25-2017/12/25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CO1
• Isomeric SMILES: C[C@@H]1CO1
• General Description: (R)-(+)-Propylene oxide, also known as (R)-(+)-methyloxirane or (R)-1,2-epoxypropane, is a chiral epoxide with high enantiomeric purity (>99% e.e.), widely used as a synthon in organic synthesis. It can be obtained through stereoselective methods such as Jacobsen's hydrolytic kinetic resolution (HKR) of racemic propylene oxide or via microbial conversion of glucose to (R)-propylene glycol followed by chemical transformation. (R)-(+)-Propylene oxide serves as a key intermediate in the synthesis of enantiomerically pure compounds, including pharmaceuticals like leodomycin C and D, and is also employed in copolymerization with CO2 to form polycarbonates with high enantioselectivity. Its practical synthesis from L- or D-threonine further highlights its versatility as a chiral building block.

Technology Process of (R)-(+)-Propylene oxide

There total 56 articles about (R)-(+)-Propylene oxide 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: 99.0%

tert-butyl carbazate (4248-19-5) + methyloxirane (75-56-9,16033-71-9) → tert-butyl [(2S)-2-hydroxypropyl]carbamate (167938-56-9) + (R)-propylene oxide (15448-47-2)

Guidance literature:

With air; 4-nitro-benzoic acid; (R,R)-((t-Bu)4-salen)Co(II); In various solvent(s); at 20 ℃; for 24h;

DOI:10.1021/ol048322l

Reference yield: 92.3%

methyloxirane (75-56-9,16033-71-9) → (R)-propylene oxide (15448-47-2)

Guidance literature:

With epoxyhydrolase ECU₁₀₄₀; In water; at 0 - 20 ℃; for 24h; Temperature; Enzymatic reaction;

Reference yield: 65.0%

(S)-1,2-propanediol 2-tosylate (96882-98-3) → (R)-propylene oxide (15448-47-2)

Guidance literature:

With potassium hydroxide; In water; at 70 - 80 ℃;

DOI:10.1016/S0040-4020(01)96497-X

upstream raw materials:

(R)-1-bromo-2-propanol

(2R)-hydroxypropylamine

(2R)-propane-1,2-diol

2-chloro-1-propanol

Downstream raw materials:

(R)-1-bromo-2-propanol

(R)-(-)-1-chloro-2-propanol

(R)-(-)-Heptyn-2-ol

(R)-1-(3-Methoxymethoxy-phenyl)-propan-2-ol