Welcome to LookChem.com Sign In|Join Free

Cas Database

21699-63-8

21699-63-8

Identification

  • Product Name:Oxirane, 2-ethenyl-3-phenyl-, (2R,3S)-rel-

  • CAS Number: 21699-63-8

  • EINECS:

  • Molecular Weight:146.189

  • Molecular Formula: C10H10O

  • HS Code:

  • Mol File:21699-63-8.mol

Synonyms:

Post Buying Request Now
Entrust LookChem procurement to find high-quality suppliers faster

Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
  • Delivery
  • Purchase

Relevant articles and documentsAll total 20 Articles be found

[2,3] Sigmatropic rearrangement of unstable sulfur ylides from allyl sulfonium salts. Comparative study of electrochemical reduction with the base method and mechanism elucidation by the MO method

Okazaki, Yuichi,Ando, Fumio,Koketsu, Jugo

, p. 1687 - 1695 (2004)

The cathodic reduction of sulfonium salts in acetonirile under the presence and absence of benzaldehyde were carried out and compared with the results of the base method. Under the presence of benzaldehyde, the electrochemical reduction gave epoxides as a

Tin(II)-mediated allylation. Asymmetric induction with a chiral tin(II) alkoxide

Auge, Jacques,Bourleaux, Guy

, p. 205 - 210 (1989)

In a study of tin-mediated allylation some tin(II) species including tin(II) halides, amides, acetonates, and alkoxides, have been shown to undergo oxidation of allyl halide in the presence of benzaldehyde to give the corresponding homoallyl alcohol.The first preparation of a chiral tin(II) alkoxide, tin(II) diethyltartrate is described; its 119Sn NMR spectrum exhibits two signals at high field, consistent with a trans dimer structure.This new reagent undergoes oxidative addition of 1,3-chloroiodopropene in the presence of benzaldehyde to give an optically active phenylvinyloxirane; this represents the first enantioselective preparation of cis- and trans-vinyloxiranes from aldehydes.

Novel reaction course of thiiranes to vinyloxiranes: Reaction of benzyne with thiiranes and aldehydes

Okuma, Kentaro,Qu, Yuxuan,Nagahora, Noriyoshi

, p. 1294 - 1300 (2021/07/19)

Reaction of 2 molar amount of 2-(trimethylsilyl)phenyl triflate with thiiranes and aldehydes in the presence of CsF afforded vinyloxiranes in one-pot operation. Reaction of benzyne with thiiranes gave the corresponding alkenyl phenyl sulfides, which furth

Synthesis of Epoxides from Alkyl Bromides and Alcohols with in Situ Generation of Dimethyl Sulfonium Ylide in DMSO Oxidations

Zhang, Zhi-Wei,Li, Hai-Bo,Li, Jin,Wang, Cui-Cui,Feng, Juan,Yang, Yi-Hua,Liu, Shouxin

, p. 537 - 547 (2020/01/02)

Direct conversion of the readily available alkyl bromides and alcohols to value-added epoxides using dimethyl sulfoxide (DMSO) under mild reaction conditions has been developed. Benzyl and allyl bromides, and activated and unactivated alcohols all proceeded smoothly to give epoxides in high to excellent yield. Dimethyl sulfide, generated by DMSO oxidations, was in situ elaborated to form the substituted dimethyl sulfonium ylide species that participates in the Corey-Chaykovsky epoxidation in a domino and one-pot fashion, respectively.

A One-Pot Reaction toward the Diastereoselective Synthesis of Substituted Morpholines

Aubineau, Thomas,Cossy, Janine

supporting information, p. 7419 - 7423 (2018/12/11)

The diastereoselective synthesis of various substituted morpholines has been achieved from vinyloxiranes and amino-alcohols under sequential Pd(0)-catalyzed Tsuji-Trost/Fe(III)-catalyzed heterocyclization. Using the same strategy, 2,6-, 2,5-, and 2,3-disubstituted as well as 2,5,6- and 2,3,5-trisubstituted morpholines were obtained in good to excellent yields and diastereoselectivities.

A new protocol for the in situ generation of aromatic, heteroaromatic, and unsaturated diazo compounds and its application in catalytic and asymmetric epoxidation of carbonyl compounds. Extensive studies to map out scope and limitations, and rationalization of diastereo- and enantioselectivities

Aggarwal, Varinder K.,Alonso, Emma,Bae, Imhyuck,Hynd, George,Lydon, Kevin M.,Palmer, Matthew J.,Patel, Mamta,Porcelloni, Marina,Richardson, Jeffery,Stenson, Rachel A.,Studley, John R.,Vasse, Jean-Luc,Winn, Caroline L.

, p. 10926 - 10940 (2007/10/03)

A variety of metalated tosylhydrazone salts derived from benzaldehyde have been prepared and were reacted with benzaldehyde in the presence of tetrahydrothiophene (THT) (20 mol %) and Rh2(OAc)4 (1 mol %) to give stilbene oxide. Of the lithium, sodium, and potassium salts tested, the sodium salt was found to give the highest yield and selectivity. This study was extended to a wide variety of aromatic, heteroaromatic, aliphatic, α,β-unsaturated, and acetylenic aldehydes and to ketones. On the whole, high yields of epoxides with moderate to very high diastereoselectivities were observed. A broad range of tosylhydrazone salts derived from aromatic, heteroaromatic, and α,β-unsaturated rated aldehydes was also examined using the same protocol in reactions with benzaldehyde, and again, good yields and high diastereoselectivities were observed in most cases. Thus, a general process for the in situ generation of diazo compounds from tosylhydrazone sodium salts has been established and applied in sulfur-ylide mediated epoxidation reactions. The chiral, camphor-derived, [2.2.1] bicyclic sulfide 7 was employed (at 5-20 mol % loading) to render the above processes asymmetric with a range of carbonyl compounds and tosylhydrazone sodium salts. Benzaldehyde tosylhydrazone sodium salt gave enantioselectivities of 91 ± 3% ee and high levels of diastereoselectivity with a range of aldehydes. However, tosylhydrazone salts derived from a range of carbonyl compounds gave more variable selectivities. Although those salts derived from electron-rich or neutral aldehydes gave high enantioselectivities, those derived from electron-deficient or hindered aromatic aldehydes gave somewhat reduced enantioselectivities. Using α,β-unsaturated hydrazones, chiral sulfide 7 gave epoxides with high diastereoselectivities, but only moderate yields were achieved (12-56%) with varying degrees of enantioselectivity. A study of solvent effects showed that, while the impact on enantioselectivity was small, the efficiency of diazo compound generation was influenced, and CH3CN and 1,4-dioxane emerged as the optimum solvents. A general rationalization of the factors that influence both relative and absolute stereochemistry for all of the different substrates is provided. Reversibility in formation of the betaine intermediate is an important issue in the control of diastereoselectivity. Hence, where low diastereocontrol was observed, the results have been rationalized in terms of the factors that contribute to the reduced reversion of the syn betaine back to the original starting materials. The enantioselectivity is governed by ylide conformation, facial selectivity in the ylide reaction, and, again, the degree of reversibility in betaine formation. From experimental evidence and calculations, it has been shown that sulfide 7 gives almost complete control of facial selectivity, and, hence, it is the ylide conformation and degree of reversibility that are responsible for the enantioselectivity observed. A simple test has been developed to ascertain whether the reduced enantioselectivity observed in particular cases is due to poor control in ylide conformation or due to partial reversibility in the formation of the betaine.

Process route upstream and downstream products

Process route

benzylidene dichloride
98-87-3

benzylidene dichloride

potassium prop-2-enolate
33374-41-3

potassium prop-2-enolate

trans-2-phenyl-3-ethenyl oxirane
21699-64-9

trans-2-phenyl-3-ethenyl oxirane

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.333333h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
benzaldehyde
100-52-7

benzaldehyde

propenal tosylhydrazone sodium salt

propenal tosylhydrazone sodium salt

trans-2-phenyl-3-ethenyl oxirane
21699-64-9

trans-2-phenyl-3-ethenyl oxirane

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
With thiophene; dirhodium tetraacetate; N-benzyl-N,N,N-triethylammonium chloride; In various solvent(s); at 40 ℃; Title compound not separated from byproducts;
benzaldehyde
100-52-7

benzaldehyde

propenal 2,4,6-triisopropylbenzenesulfonyl hydrazone

propenal 2,4,6-triisopropylbenzenesulfonyl hydrazone

trans-2-phenyl-3-ethenyl oxirane
21699-64-9

trans-2-phenyl-3-ethenyl oxirane

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
propenal 2,4,6-triisopropylbenzenesulfonyl hydrazone; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;
benzaldehyde; With thiophene; dirhodium tetraacetate; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran; toluene; at 20 ℃; for 12h; Title compound not separated from byproducts;
benzaldehyde
100-52-7

benzaldehyde

(Z-3-chloroprop-2-enyl)tri-n-butyl stannane
113662-35-4

(Z-3-chloroprop-2-enyl)tri-n-butyl stannane

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium(II) iodide; In tetrahydrofuran; at 63 ℃; for 24h;
58%
benzaldehyde
100-52-7

benzaldehyde

propenal 2,4,6-triisopropylbenzenesulfonyl hydrazone

propenal 2,4,6-triisopropylbenzenesulfonyl hydrazone

(2S,3S)-3-ethenyl-2-phenyloxirane
203397-84-6

(2S,3S)-3-ethenyl-2-phenyloxirane

(2R,3R)-2-phenyl-3-ethenyloxirane
190315-22-1

(2R,3R)-2-phenyl-3-ethenyloxirane

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
propenal 2,4,6-triisopropylbenzenesulfonyl hydrazone; With sodium hexamethyldisilazane; In 1,4-dioxane; at -78 ℃; for 1h;
benzaldehyde; With thiophene; dirhodium tetraacetate; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran; at 20 ℃; for 12h; Title compound not separated from byproducts;
(1S,2S)-2-Chloro-1-phenyl-but-3-en-1-ol
88086-64-0,113501-08-9,113501-09-0

(1S,2S)-2-Chloro-1-phenyl-but-3-en-1-ol

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
With potassium ethoxide;
98%
With potassium carbonate; In methanol; Yield given;
benzoyl chloride
98-88-4

benzoyl chloride

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 71 percent / AlCl3 / CH2Cl2 / 2 h / -20 °C
2: 1.) NaBH4, 2.)H2O/MeOH/NaOH / 1.) MeOH, 0 deg C
With methanol; sodium hydroxide; sodium tetrahydroborate; water; aluminium trichloride; In dichloromethane;
1-allyl-tetrahydrothiophenium bromide
66713-38-0

1-allyl-tetrahydrothiophenium bromide

benzaldehyde
100-52-7

benzaldehyde

trans-2-phenyl-3-ethenyl oxirane
21699-64-9

trans-2-phenyl-3-ethenyl oxirane

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
With tetraethylammonium perchlorate; In acetonitrile; at 22 ℃; Title compound not separated from byproducts; Electrochemical reaction;
benzaldehyde
100-52-7

benzaldehyde

1-allyldiethylsulfonium bromide

1-allyldiethylsulfonium bromide

trans-2-phenyl-3-ethenyl oxirane
21699-64-9

trans-2-phenyl-3-ethenyl oxirane

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
With tetraethylammonium perchlorate; In acetonitrile; at 22 ℃; Title compound not separated from byproducts; Electrochemical reaction;
benzaldehyde
100-52-7

benzaldehyde

allyl bromide
106-95-6

allyl bromide

trans-2-phenyl-3-ethenyl oxirane
21699-64-9

trans-2-phenyl-3-ethenyl oxirane

cis-2-phenyl-3-ethenyl oxirane
21699-63-8

cis-2-phenyl-3-ethenyl oxirane

Conditions
Conditions Yield
With caesium carbonate; di-isobutyl telluride; In tetrahydrofuran; diethyl ether; at 50 ℃; for 19h; Mechanism; predominant cis stereoselectivity;
With caesium carbonate; di-isobutyl telluride; In tetrahydrofuran; diethyl ether; water; at 50 ℃; for 19h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With lithium diisopropyl amide; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) THF, -78 deg C, 0.5 h, 2.) -78 deg C to room temperature;
With thiophene; potassium carbonate; In tert-butyl alcohol; Overall yield = 85 %; Overall yield = 3.5 g; diastereoselective reaction; Reflux; Inert atmosphere;
40 % de

Global suppliers and manufacturers

Global( 0) Suppliers
  • Company Name
  • Business Type
  • Contact Tel
  • Emails
  • Main Products
  • Country
close
Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 21699-63-8
Post Buying Request Now
close
Remarks: The blank with*must be completed