2-Methyl-2-phenyloxirane

Base Information

• Chemical Name: 2-Methyl-2-phenyloxirane
• CAS No.: 2085-88-3
• Molecular Formula: C9H10 O
• Molecular Weight: 134.178
• Hs Code.: 2910900090
• European Community (EC) Number: 800-256-0
• NSC Number: 51065,36616
• DSSTox Substance ID: DTXSID10880779
• Nikkaji Number: J951B
• Mol file: 2085-88-3.mol

Synonyms:2-Phenylpropylene Oxide;2085-88-3;2-METHYL-2-PHENYLOXIRANE;alpha-Methylstyrene oxide;Oxirane, 2-methyl-2-phenyl-;2-Phenylpropene oxide;2-Phenyl-1,2-epoxypropane;1-Methyl-1-phenyloxirane;Propylene oxide, 2-phenyl-;alpha,beta-Epoxycumene;Propane, 1,2-epoxy-2-phenyl-;2-Phenyl-2-methyloxirane;NSC 36616;NSC 51065;alpha-Methyl styrene oxide;alpha-Methylstyrene epoxide;2-methyl-2-phenyl-oxirane;.alpha.-Methylstyrene oxide;Benzene, (1,2-epoxy-1-methylethyl)-;.alpha.-Methylstyrene epoxide;CCRIS 2731;Cumene, .alpha.,.beta.-epoxy-;BRN 0110135;Cumene,.beta.-epoxy-;Propane,2-epoxy-2-phenyl-;.alpha.-Methyl styrene oxide;Benzene,2-epoxy-1-methylethyl)-;2-PHENYLPROPYLENEOXIDE;.alpha.-methylepoxystyrene;Cumene, alpha,beta-epoxy-;1,2-Epoxy-2-phenylpropane;SCHEMBL123189;Cumol, .alpha.,.beta.-epoxy-;DTXSID10880779;CAA08588;NSC36616;NSC51065;MFCD00059156;NSC-36616;NSC-51065;AKOS002678727;AKOS016049066;LS-101077;CS-0449488;Cumene, alpha,beta-epoxy- (6CI,7CI,8CI);FT-0711260;P0833;EN300-61601;F52588;A924955;Z813010616

Chemical Property of 2-Methyl-2-phenyloxirane

Chemical Property:

• Vapor Pressure: 0.584mmHg at 25°C
• Refractive Index: 1.5180 to 1.5220
• Boiling Point: 195.6°Cat760mmHg
• Flash Point: 66.3°C
• PSA: 12.53000
• Density: 1.057g/cm³
• LogP: 1.93200
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

98%,99%, ^*data from raw suppliers

α-MethylstyreneOxide ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CO1)C2=CC=CC=C2
• Uses: α-Methylstyrene Oxide is structurally similar to rac Styrene Oxide (S687795) which is a major (toxic) metabolite of Styrene (S687790), catalyzed by epoxide hydrolase.

Technology Process of 2-Methyl-2-phenyloxirane

There total 121 articles about 2-Methyl-2-phenyloxirane 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: 88.0%

methyllithium lithium bromide + acetophenone (98-86-2) + 1,1-dibromomethane (74-95-3) → 2-methyl-2-phenyloxirane (2085-88-3) + 1-methyl-1-phenylethyl alcohol (617-94-7) + 1-bromo-2-phenylpropan-2-ol (31778-29-7)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -80 - 20 ℃; for 0.025h; Flow reactor;

DOI:10.1021/acs.orglett.9b04072

Reference yield: 86.0%

isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6) → 2-methyl-2-phenyloxirane (2085-88-3) + 2-phenylacrolein (4432-63-7) + 3-hydroxy-2-phenylpropene (6006-81-1)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 20 ℃; for 6h; Product distribution; Mechanism;

DOI:10.1021/jo971226w

Reference yield: 77.0%

isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6) → (R)-2-methyl-2-phenyloxirane (2085-88-3,2404-43-5,21019-52-3,100018-61-9) + benzaldehyde (100-52-7) + (2S)-2-methyl-2-phenyloxirane (2404-43-5)

Guidance literature:

With oxygen; isobutyraldehyde; In acetonitrile; at 45 ℃; for 8h; Reagent/catalyst; enantioselective reaction;

DOI:10.1016/j.jcat.2017.05.014

upstream raw materials:

1-iodo-2-phenyl-2-methyl-2-ethanol

1-chloro-2-phenylpropan-2-ol

peracetic acid

isopropenylbenzene

Downstream raw materials:

1,2-diphenyl-1-propanol

1-methyl-2-(dimethylamino)-1-phenylethanol

1-(N',N'-dimethyl-hydrazino)-2-phenyl-propan-2-ol

1-methyl-1-phenylethyl alcohol

Refernces

• 1、 Zarnegaryan, Ali,Pahlevanneshan, Zari,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammdpoor-Baltork, Iraj. "Copper(II) Schiff base complex immobilized on graphene nanosheets: a heterogeneous catalyst for epoxidation of olefins". . p. 747 - 756. Retrieved 2019.
• 2、 Rayati, Saeed,Zakavi, Saeed,Jafarzadeh, Parisa,Sadeghi, Omid,Amini, Mostafa M.. "Manganese meso-tetra-4-carboxyphenylporphyrin immobilized on MCM-41 as catalyst for oxidation of olefins with different oxygen donors in stoichiometric conditions". . p. 260 - 266. Retrieved 2012.
• 3、 Tangestaninejad,Moghadam,Mirkhani,Mohammadpoor-Baltork,Hoseini. "Efficient and selective hydrocarbon oxidation with sodium periodate catalyzed by supported manganese(III) porphyrin". . p. 663 - 672. Retrieved 2010.
• 4、 Yano et al.. "-". . p. 527. Retrieved 1973.
• 5、 Nooraeipour, Mehdi,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadpoor-Baltork, Iraj,Iravani, Nasir. "Multi-wall carbon nanotube supported tungsten hexacarbonyl: An efficient and reusable catalyst for epoxidation of alkenes with hydrogen peroxide". . p. 226 - 238. Retrieved 2012.
• 6、 Ghorbanloo, Massomeh,Bikas, Rahman,Ma?ecki, Grzegorz. "New molybdenum(VI) complexes with thiazole-hydrazone ligand: Preparation, structural characterization, and catalytic applications in olefin epoxidation". . p. 8 - 16. Retrieved 2016.
• 7、 Mori, Kohsuke,Watanabe, Kentaro,Terai, Yoshikazu,Fujiwara, Yasufumi,Yamashita, Hiromi. "Hybrid mesoporous-silica materials functionalized by PtII complexes: Correlation between the spatial distribution of the active center, photoluminescence emission, and photocatalytic activity". . p. 11371 - 11378,8. Retrieved 2012.
• 8、 Ghorbanloo, Massomeh,Bikas, Rahman,Jafari, Solmaz,Krawczyk, Marta S.,Lis, Tadeusz. "Synthesis, structural characterization and catalytic potential of oxidovanadium(IV) and dioxidovanadium(V) complexes with thiazole-derived NNN-donor ligand". . p. 1510 - 1525. Retrieved 2018.
• 9、 Zarrinjahan, Alireza,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj. "Graphene oxide nanosheets supported manganese(III) porphyrin: a highly efficient and reusable biomimetic catalyst for epoxidation of alkenes with sodium periodate". . p. 1509 - 1516. Retrieved 2016.
• 10、 Zhao, Jiquan,Zhang, Yuecheng,Han, Furong,Zhao, Shanshan. "Asymmetric epoxidation of unfunctionalized alkenes catalyzed by sugar moiety-modified chiral salen-Mn(III) complexes". . p. 61 - 66. Retrieved 2009.