15448-47-2

Usage

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

• 687-47-8 (S)-Ethyl lactate 
• 40916-65-2 (S)-2-(dimethylamino)-1-propanol 
• 4248-19-5 tert-butyl carbazate 
• 75-56-9 methyloxirane 
• 124-38-9 carbon dioxide 
• 687-47-8 (-)-ethyl lactate 
• 145021-03-0 (R)-1-(tertbutyl)thiopropan-2-ol 
• 108033-49-4 (S)-2-(phenylthio)-1-propanol 
• 96882-98-3 (S)-1,2-propanediol 2-tosylate 
• 67253-47-8 (R)-2-hydroxypropane-1-phenylsulfide 
• 99457-42-8 (R)-(+)-2-acetoxy-1-bromopropane 
• 77965-71-0 (S)-2-(Mesyloxy)-1-propanol 
• 4254-15-3 (S)-1,2-Propanediol 
• 57057-80-4 ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate 

Downstream Products

• 113429-86-0 (R)-1-bromo-2-propanol 
• 19141-39-0 (R)-(-)-1-chloro-2-propanol 
• 90192-97-5 (R)-(-)-Heptyn-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 

Relevant academic research and scientific papers

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

In-Situ Monitoring of Enantiomeric Excess during a Catalytic Kinetic Resolution

Vibrational Circular Dichroism combined with FTIR spectroscopy (VCD-IR) is demonstrated as a viable tool for the in situ measurement of enantiomeric excess during asymmetric catalytic transformations. Employing the Jacobsen (salen)Co-catalyzed hydrolytic kinetic resolution of racemic epoxides as a proof-of-concept case study, methodology is developed to monitor the enantiomeric excess of the epoxide substrate as a function of conversion of the limiting reactant, water. Comparison of results for monomeric and oligomeric catalysts probes the molecularity of the catalyst by investigating nonlinear effects in catalyst enantiopurity. These results are in excellent agreement with previous mechanistic investigations of this reaction based on kinetic measurements and computational studies.

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.

Alternating copolymerization of CO2 and propylene oxide catalyzed by CoIII(salen)/Lewis base

The use of CoIII(salen)/Lewis base catalyst system for copolymerization of CO2 and propylene oxide was analyzed. The ratio of catalyst to Lewis base cocatalyst influenced the TOF. The use of Lewis base cocatalyst enables high catalytic activity at low CO2 pressure and affords superior enantioselectivity. The results show that the use of cocatalyst produced a highly alternating monodisperse polycarbonate product without concomitant cyclic carbonate production.

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.

Chiral catalysts for the asymmetric cycloaddition of carbon dioxide with epoxides

Several chiral BINADCo(III)X (BINAD = Bis(1,1′-2-hydroxy-2′-alkoxy-3-naphthylidene)-1,2-cyclohexanediamine, X = OAc, CF3CO2, CCl3CO2, OTs, p-NO2PhCO2) complexes were synthesized and used to

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.

Total synthesis of the proposed structures of eushearilide

Total synthesis of (3R,16Z,20E,23S)- and (3R,16Z,20E,23R)-eushearilide was accomplished in 15 steps, respectively. Using either enantiomer of one of the four building blocks to assemble the phosphonium salt for the latter Wittig reaction, two diastereomers of eushearilide were prepared. Shiina macrolactonization (2-methyl-6-nitrobenzoic anhydride) was a key step in production of the 24-membered lactone in high yield.

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)