(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
• Uses: (R)-(+)-Propylene oxide is widely utilized in the manufacture of polyether polyols and propylene glycol, which is used to make the polyurethane plastics. It finds application as a fumigant for the sterilization of packaged foods and plastic medical instruments. Combine with ethanol, it used to make biological samples for electron microscopy. It also used in model aircraft and surface vehicles as a glow fuel.

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)-7-Benzyloxy-2-heptanol

Refernces

• 1、 Koppenhoefer, Bernhard,Weber, Roland,Schurig, Volker. "A Useful Route to (R)-Alkyloxiranes of Defined Enantiomeric Purity from (S)-Amino Acids". . p. 316 - 318. Retrieved 1982.
• 2、 Mower, Matthew P.,Blackmond, Donna G.. "In-Situ Monitoring of Enantiomeric Excess during a Catalytic Kinetic Resolution". . p. 5977 - 5982. Retrieved 2018.
• 3、 Paddock, Robert L.,Nguyen, SonBinh T.. "Alternating copolymerization of CO2 and propylene oxide catalyzed by CoIII(salen)/Lewis base". . p. 6251 - 6253. Retrieved 2005.
• 4、 Jin, Lili,Huang, Yongzhong,Jing, Huanwang,Chang, Tao,Yan, Peng. "Chiral catalysts for the asymmetric cycloaddition of carbon dioxide with epoxides". . p. 1947 - 1953. Retrieved 2008.
• 5、 Yamauchi, Takayasu,Takidaira, Jun-Ichi,Okamoto, Kenya,Sugiura, Takaya,Horikoshi, Hiroki,Kudo, Shintaro,Sasaki, Shigeru,Mizushima, Noriko,Higashiyama, Kimio. "Total synthesis of the proposed structures of eushearilide". . p. 1175 - 1189. Retrieved 2014.
• 6、 -. "A (R)- single thio propylene carbonate preparation method (by machine translation)". Paragraph 0007-0008; 0028-0029; 0031-0032. . Retrieved 2018/03/28.