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

Chemical Properties

Colorless to light yellow liqui

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.

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 
• 2799-16-8 (2R)-hydroxypropylamine 
• 4254-14-2 (2R)-propane-1,2-diol 
• 78-89-7 2-chloro-1-propanol 
• 19210-21-0 (S)-2-chloropropan-1-ol 
• 4254-15-3 (S)-1,2-Propanediol 
• 75-56-9 methyloxirane 
• 51-79-6 urethane 
• 124-38-9 carbon dioxide 
• 99457-42-8 (R)-(+)-2-acetoxy-1-bromopropane 
• 57057-80-4 ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate 
• 40916-65-2 (S)-2-(dimethylamino)-1-propanol 
• 687-47-8 (S)-Ethyl lactate 
• 187737-37-7 propene 

Downstream Products

• 139403-83-1 (2R)-10-<2'-(Methoxymethoxy)phenyl>decan-2-ol 
• 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 
• 143251-29-0 1--N-benzyl>amino-(R)-(-)-2-propyl alcohol 
• 128573-05-7 (2S,4R,2'R)-4-Hydroxy-1-(2'-hydroxypropyl)proline 
• 89401-28-5 (2R)-1-(benzyloxy)propan-2-ol 

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

-

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.

A (R)- single thio propylene carbonate preparation method (by machine translation)

The invention relates to a (R)- single thio propylene carbonate preparation method, including: (1) epoxy propane, epoxy hydrolase ECU1040 is mixed with water, for 0 - 5 °C reaction 10 - 40 hours, stopping the reaction, normal pressure is distilled to produce (R)- propylene oxide; (2) the above the resulting (R)- propylene oxide is mixed with organic solvent, adding carbonylation and alkali and organic amine, in the 10 - 30 °C under stirring into the carbonyl sulfide gas, until the oxysulfide until the gas does not absorb, the total reaction time is 15 - 30 hours, to obtain the (R)- single thio propylene carbonate ester. Preparation method of the invention normal pressure operation, high yield, simple and practical, low risk, less equipment investment, optical purity of the product to achieve 99% e.e value or more, and has excellent industrial prospect. (by machine translation)

Stereoselective synthesis of 5′-hydroxyzearalenone

A first stereoselective total synthesis of 14-memebered β-resorcylic macrolactone 5′-hydroxyzearalenone (1) has been achieved. The key steps are Jocobsen hydrolytic kinetic resolution, Sharpless asymmetric dihydroxylation, Vilsmeier-Haack reaction, Mitsunobu esterification and ring-closing metathesis.