15448-47-2

Basic information

• Product Name: (R)-(+)-Propylene oxide
• Synonyms: (r)-(+)-propyleneoxid;(r)-epoxypropane;R(+)-METHYLOXIRANE;(R)-(+)-PROPYLENE OXIDE;(R)-PROPYLENE OXIDE;(R)-(+)-1,2-EPOXYPROPANE;(R)-1,2-EPOXYPROPANE;(R)-(+)-1,2-PROPYLENE OXIDE
• CAS NO: 15448-47-2
• Molecular Formula: C₃H₆O
• Molecular Weight: 58.08
• EINECS: 1806241-263-5
• Product Categories: chiral;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Oxiranes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Compound
• Mol File: 15448-47-2.mol
• Article Data: 77

Chemical Properties

• Melting Point: -111.91°C (estimate)
• Boiling Point: 33-34 °C(lit.)
• Flash Point: -31 °F
• Appearance: Colorless to light yellow liquid
• Density: 0.829 g/mL at 20 °C(lit.)
• Vapor Pressure: 572mmHg at 25°C
• Refractive Index: n20/D 1.366(lit.)
• Storage Temp.: 2-8°C
• Solubility: 405g/l
• Explosive Limit: 1.9-37%(V)
• Water Solubility: Miscible with water and many organic solvents.
• Merck: 14,7856
• BRN: 79764
• CAS DataBase Reference: (R)-(+)-Propylene oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-Propylene oxide(15448-47-2)
• EPA Substance Registry System: (R)-(+)-Propylene oxide(15448-47-2)

Safety Data

• Hazard Codes: F+,T
• Statements: 12-25-2017/12/25
• Safety Statements: 45
• RIDADR: UN 1280 3/PG 1
• WGK Germany: 3
• RTECS: UJ2650000
• HazardClass: 3
• PackingGroup: I
• Hazardous Substances Data: 15448-47-2(Hazardous Substances Data)

Usage

Description

(R)-(+)-Propylene oxide, a colorless to light yellow liquid, is an organic compound that plays a significant role in various industries due to its unique chemical properties and versatile applications.

Uses

Used in the Chemical Industry:
(R)-(+)-Propylene oxide is used as a key intermediate in the production of polyether polyols and propylene glycol, which are essential components in the manufacturing of polyurethane plastics. These plastics are widely used in various applications, including insulation materials, automotive parts, and furniture.
Used in the Food Industry:
As a fumigant, (R)-(+)-Propylene oxide is employed for the sterilization of packaged foods, ensuring the safety and quality of the products by eliminating harmful microorganisms.
Used in the Medical Industry:
(R)-(+)-Propylene oxide is utilized for the sterilization of plastic medical instruments, contributing to the maintenance of hygiene and safety in healthcare settings.
Used in the Scientific Research Industry:
When combined with ethanol, (R)-(+)-Propylene oxide is used in the preparation of biological samples for electron microscopy, aiding researchers in studying the structure and function of various biological entities.
Used in the Model Aircraft and Surface Vehicle Industry:
(R)-(+)-Propylene oxide is also used as a glow fuel in model aircraft and surface vehicles, providing a reliable and efficient source of energy for these applications.

InChI:InChI=1/C3H6O/c1-3-2-4-3/h3H,2H2,1H3/t3-/m1/s1

Synthetic route

tert-butyl carbamate (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)

Conditions	Yield
With air; 4-nitro-benzoic acid; (R,R)-((t-Bu)4-salen)Co(II) In various solvent(s) at 20℃; for 24h;	A 99% B n/a

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

Conditions	Yield
With epoxyhydrolase ECU1040 In water at 0 - 20℃; for 24h; Temperature; Enzymatic reaction;	92.3%
With (R,R)-Jacobsen catalyst; acetic acid In water; toluene at 0 - 20℃; for 20h;	76%
With bis(triphenylphosphine)iminium acetate; C64H74Cl2Co2N4O4 In toluene at 0℃; for 1.5h; Resolution of racemate; Inert atmosphere; optical yield given as %ee;	49%

Upstream product

• 113429-86-0 (R)-1-bromo-2-propanol 
• 40916-65-2 (S)-2-(dimethylamino)-1-propanol 
• 4254-15-3 (S)-1,2-Propanediol 
• 77965-71-0 (S)-2-(Mesyloxy)-1-propanol 
• 75-56-9 methyloxirane 
• 103775-61-7 (R)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 4248-19-5 tert-butyl carbazate 
• 124-38-9 carbon dioxide 
• 187737-37-7 propene 
• 19210-21-0 (S)-2-chloropropan-1-ol 
• 127-00-4 1-Chloro-2-propanol 
• 51-79-6 urethane 
• 687-47-8 (-)-ethyl lactate 
• 145021-03-0 (R)-1-(tertbutyl)thiopropan-2-ol 

Downstream Products

• 113429-86-0 (R)-1-bromo-2-propanol 
• 19141-39-0 (R)-(-)-1-chloro-2-propanol 
• 139403-83-1 (2R)-10-<2'-(Methoxymethoxy)phenyl>decan-2-ol 
• 3620-18-6 (4R)-(+)-2-acetyl-4-pentanolide 
• 135561-78-3 (R)-1-(3’-trifluoromethylphenyl)-2-propanol 
• 95657-20-8 (R,αR)-N-acetyl-(2-hydroxypropyl)-L-cysteine methyl ester 
• 128301-93-9 1-<2,6-Dimethoxyphenyl>propan-2-ol 
• 64584-92-5 (R)-pent-4-en-2-ol 
• 132840-93-8 (R)-1-[2-((2S,3R,4S,5R,6R)-3,4,5-Trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexa-2,5-dienyl]-propan-2-ol 
• 83515-85-9 (-)-(R)-11-Benzyloxy-2-undecanol 
• 67253-47-8 (R)-2-hydroxypropane-1-phenylsulfide 
• 121959-26-0 (2S)-12-<2'-(Methoxymethoxy)phenyl>dodecan-2-ol 
• 152037-54-2 (3R,5R)-3-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-9-trimethylsilanyl-non-8-ynyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 158139-63-0 2-<3,5-bis(tert-butyldimethylsilyloxy)benzyl>-2-<2-(R)-hydroxypropyl>-1,3-dithiane 

Relevant articles and documents

Stereoselective concise total synthesis of leodomycin C and D

Stereoselective concise total synthesis of leodomycin C and D from commercially available propylene oxide using Jacobsens hydrolytic kinetic resolution (HKR), base-promoted alkyne zipper reaction, TPP-promoted enyne ester (ynoate) to diene ester (dienoate

Improved Preparation of (+)-(R)-Methyloxirane

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A practical synthesis of both enantiomers of 1-amino-2-propanol and propylene oxide

A practical large-scale synthesis of both enantiomers of 1-amino-2-propanol 1 from L- and D-threonine is described. Greater than 99% e.e. propylene oxide 2 is obtained from 1 through a diazotization under basic conditions.

A Combined Microbial/Chemical Synthesis of (+)-(R)-Methyloxirane Having High Enantiomeric Excess

Clostridium thermosaccharolyticum (ATCC 31960) converts glucose to (-)-(R)-propylene glycol; standard procedures transform this substance to (+)-(R)-methyloxirane ((+)-(R)-propylene oxide) with enantiomeric excess >99percent.This procedure is capable of generating this useful chiral synthon on a large scale.

Regioselective Cyclodehydration of Chiral Diols with Diethoxytriphenylphosphorane, Triphenylphosphine-Tetrachloromethane-Potassium Carbonate, and Triphenylphosphine-Diethyl Azodicarboxylate Reagents. A Comparative Study

The regioselectivity of cyclodehydration of chiral diols has been examined with the reagents diethoxytriphenylphosphorane, triphenylphosphine-tetrachloromethane-potassium carbonate, and triphenylphosphine-diethyl azodicarboxylate. (S)-(+)-Propane-1,2-diol and (R)-(-)-pentane-1,4-diol afford 80-87percent retention of stereochemistry at the chiral carbon in the ether while (S)-(+)-phenylethane-1,2-diol affords essentially racemic styrene oxide with all three reagents.

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.

The Rickiols: 20-, 22-, and 24-membered Macrolides from the Ascomycete Hypoxylon rickii

In preceding studies the neotropical ascomycete Hypoxylon rickii turned out to be a prolific source of new secondary metabolites, considering that we had obtained terpenoids with five different scaffolds along with a series of terphenyls. From the mycelial extracts of a 70 L scale fermentation of this strain we additionally isolated nine new macrolides (1–9) by RP-HPLC. The planar structures were elucidated by NMR spectroscopy complemented by HR-ESIMS. The relative configurations were assigned by J-based configuration analyses and confirmed by Kishi′s Universal Database. Subsequently, the absolute configurations were assigned by Mosher′s method using the shift analysis of a tetra-MTPA derivative. For rickiol A (1) and E (5) we observed transesterification of 20-membered ring structures to 22-membered isomers rickiol A2 (6) and E2 (7), and to 24-membered isomers rickiol A3 (8) and rickiol E3 (9), respectively. Cytotoxic effects and moderate antibiotic activity against Gram-positive bacteria were observed for 1–8 and 1–6 and 8, respectively. The total synthesis of rickiol E3 (9) established easier access to these compounds.

Bimetallic Chromium Catalysts with Chain Transfer Agents: A Route to Isotactic Poly(propylene oxide)s with Narrow Dispersities

Bimetallic chromium catalysts are investigated for the enantioselective polymerization of propylene oxide. The catalyst is composed of two salen chromium species linked by an alkyl chain, the length of which significantly impacts the rate of polymerization. While the use of a chloride initiator on the catalyst resulted in bimodal molecular weight distributions, switching to a trifluoroacetate initiating group and adding a diol chain transfer agent afforded polymers of controllable molecular weight with low, unimodal dispersities.