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Cas Database

22050-10-8

22050-10-8

Identification

  • Product Name:2-Pyrrolidinone,5-phenyl-

  • CAS Number: 22050-10-8

  • EINECS:

  • Molecular Weight:161.203

  • Molecular Formula: C10H11 N O

  • HS Code:2933790090

  • Mol File:22050-10-8.mol

Synonyms:5-Phenyl-2-pyrrolidinone;5-Phenyl-2-pyrrolidone; NSC 28857; g-Phenyl-g-aminobutyricacid lactam

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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

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  • Manufacture/Brand:TRC
  • Product Description:5-phenylpyrrolidin-2-one
  • Packaging:100mg
  • Price:$ 330
  • Delivery:In stock
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  • Manufacture/Brand:CHESS?
  • Product Description:5-Phenylpyrrolidin-2-one 98
  • Packaging:5 g
  • Price:$ 60000
  • Delivery:In stock
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  • Manufacture/Brand:CHESS?
  • Product Description:5-Phenylpyrrolidin-2-one 98
  • Packaging:1 g
  • Price:$ 15000
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  • Manufacture/Brand:Chemenu
  • Product Description:5-Phenylpyrrolidin-2-one 95%
  • Packaging:1g
  • Price:$ 352
  • Delivery:In stock
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:5-PHENYLPYRROLIDIN-2-ONE 95.00%
  • Packaging:5MG
  • Price:$ 497.62
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  • Manufacture/Brand:Alichem
  • Product Description:5-phenyl-2-Pyrrolidinone
  • Packaging:1g
  • Price:$ 1685
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  • Manufacture/Brand:Alichem
  • Product Description:5-phenyl-2-Pyrrolidinone
  • Packaging:500mg
  • Price:$ 980
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  • Manufacture/Brand:Alichem
  • Product Description:5-phenyl-2-Pyrrolidinone
  • Packaging:250mg
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Relevant articles and documentsAll total 39 Articles be found

Synthesis of 3-phenyl- and 5- phenyl- 2- pyrrolidinone via rhodium catalysed carbonylation of allylamines

Bertozzi, Sergio,Salvadori, Piero

, p. 2959 - 2965 (1996)

The Rh4(CO)12 catalysed reaction with CO and H2 of 1-phenyl- and 3-phenyl allylamine gives 5-phenyl- and 3-phenyl-2-pyrrolidinone respectively, in good yield. A reasonable reaction pathway of the carbonylation reaction is

A mechanism-based cleavage of lactam-carbamates

Wei, Zhong-Yong,Knaus, Edward E.

, p. 847 - 848 (1994)

Magnesium methoxide is a simple, effective and highly selective reagent for the deprotection of N-alkoxycarbonyl lactams. The cleavage occurs via six-membered ring transition states involving coordination of magnesium ion with the oxygens of the carbamate and lactam carbonyl groups.

Tropylium-promoted Ritter reactions

Doan, Son H.,Hussein, Mohanad A.,Nguyen, Thanh Vinh

supporting information, p. 8901 - 8904 (2021/09/10)

The Ritter reaction used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuableN-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the tropylium ion to promote the Ritter reaction. This method works well on a range of alcohol and nitrile substrates, giving the corresponding products in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.

Highly Robust Iron Catalyst System for Intramolecular C(sp3)?H Amidation Leading to γ-Lactams

Kweon, Jeonguk,Chang, Sukbok

supporting information, p. 2909 - 2914 (2020/12/11)

Disclosed here is the use of an iron catalyst system for an intramolecular C?H amidation toward γ-lactam synthesis from dioxazolone precursors. (Phthalocyanine)FeIIICl was found to catalyze this cyclization with extremely high turnover numbers of up to 47 000 under mild and aerobic conditions. On the basis of experimental and computational mechanistic studies, the reaction is suggested to proceed by a stepwise radical pathway involving fast hydrogen atom abstraction followed by radical rebound. A plausible origin for the high turnover numbers along with air-compatibility is also rationalized.

Direct Synthesis of Chiral NH Lactams via Ru-Catalyzed Asymmetric Reductive Amination/Cyclization Cascade of Keto Acids/Esters

Shi, Yongjie,Tan, Xuefeng,Gao, Shuang,Zhang, Yao,Wang, Jingxin,Zhang, Xumu,Yin, Qin

supporting information, p. 2707 - 2713 (2020/03/30)

Lactams with a stereogenic center adjacent to the N atom have existed in many medicinal agents and bioactive alkaloids. Herein we report a broadly applicable synthesis of enantioenriched NH lactams through a one-pot asymmetric reductive amination/cyclization sequence of easily available keto acids/esters. Such cascade processes alleviate the demand for protecting group manipulations as well as intermediate purification. This strategy is capable of constructing enantioenriched lactams and benzo-lactams of a five-, six-, or seven-membered ring in generally high yield and with excellent enantioselectivities (up to 97% ee). Scalable and concise syntheses of key drug intermediates have further displayed the importance of this methodology.

Total syntheses of (?)-emestrin H and (?)-asteroxepin

Sakata, Juri,Tokuyama, Hidetoshi,Ueda, Yusuke,Umeki, Kanato

, (2020/11/02)

First total syntheses of (?)-emestrin H and (?)-asteroxepin are described. To find the appropriate protecting group on the amide nitrogen of the diketopiperazine core, we conducted model studies using a simple diketopiperazine derivative. As a result, allyloxymethyl (Allom) group was the most suitable protecting group, which tolerated Nicolaou's sulfenylation conditions, and was easily cleavable under the mild conditions using Pd(PPh3)4 and N,N-dimethylbarbituric acid leaving methylthioethers intact. The general utility of Allom group for protection of amides was studied using simple substrates. Finally, the effectiveness of Allom group was proved by the accomplishment of the first total synthesis of (?)-emestrin H. Allom group was robust enough during installation of two methylthioethers to the diketopiperazine core and easily removed at the final step. The first total synthesis of (?)-asteroxepin was also completed by acylation of (?)-emestrin H.

Tuning Triplet Energy Transfer of Hydroxamates as the Nitrene Precursor for Intramolecular C(sp3)-H Amidation

Chang, Sukbok,Jung, Hoimin,Keum, Hyeyun,Kweon, Jeonguk

supporting information, p. 5811 - 5818 (2020/04/10)

Reported herein is the design of a photosensitization strategy to generate triplet nitrenes and its applicability for the intramolecular C-H amidation reactions. Substrate optimization by tuning physical organic parameters according to the proposed energy transfer pathway led us to identify hydroxamates as a convenient nitrene precursor. While more classical nitrene sources, representatively organic azides, were ineffective under the current photosensitization conditions, hydroxamates, which are readily available from alcohols or carboxylic acids, are highly efficient in accessing synthetically valuable 2-oxazolidinones and γ-lactams by visible light. Mechanism studies supported our working hypothesis that the energy transfer path is mainly operative.

Process route upstream and downstream products

Process route

1-(4-methoxyphenyl)-5-phenylpyrrolidin-2-one
1048329-91-4

1-(4-methoxyphenyl)-5-phenylpyrrolidin-2-one

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
With ammonium cerium (IV) nitrate; In water; acetonitrile; at 5 ℃; for 0.5h;
85%
1-[(4-methoxyphenyl)methyl]-5-phenylpyrrolidin-2-one

1-[(4-methoxyphenyl)methyl]-5-phenylpyrrolidin-2-one

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
With trifluoroacetic acid; at 150 ℃; for 18h; Sealed tube;
70%
3-(3-phenylpropyl)-5H-1,4,2-dioxazol-5-one

3-(3-phenylpropyl)-5H-1,4,2-dioxazol-5-one

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
With C22H26ClIrN2O3; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; In dichloromethane; at 40 ℃; for 12h; Reagent/catalyst; Catalytic behavior;
95%
With C22H26ClIrN2O3; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; In dichloromethane; at 40 ℃; for 12h; Sealed tube;
94%
With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; 5-Nitro-1,10-phenanthroline; at 40 ℃; for 12h; Reagent/catalyst; Temperature; Catalytic behavior;
92%
With C18H24ClIrN3(1+)*Cl(1-); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; at 50 ℃; for 12h;
81%
With C18H24ClIrN3(1+)*Cl(1-); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; at 60 ℃; for 12h;
81%
With silver hexafluoroantimonate; chlorido(8-quinolinolato-κN1,κO8)(η6-p-cymene)ruthenium(II); In 1,2-dichloro-ethane; at 40 ℃; for 5h; Inert atmosphere; Glovebox;
78%
With silver hexafluoroantimonate; chlorido(8-quinolinolato-κN1,κO8)(η6-p-cymene)ruthenium(II); In 1,2-dichloro-ethane; at 40 ℃; for 5h; Solvent; Reagent/catalyst; chemoselective reaction; Catalytic behavior; Inert atmosphere; Glovebox;
78%
With iron(III)phthalocyanine chloride; at 40 ℃; for 12h; Reagent/catalyst; Catalytic behavior;
74%
N-[{3,5-bis(trifluoromethyl)benzoyl}oxy]-4-phenylbutanamide

N-[{3,5-bis(trifluoromethyl)benzoyl}oxy]-4-phenylbutanamide

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

3-phenylpropylisocyanate
68664-23-3

3-phenylpropylisocyanate

Conditions
Conditions Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; potassium carbonate; In 1,1,2,2-tetrachloroethane; at 25 ℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere; Irradiation;
75%
5%
C<sub>11</sub>H<sub>13</sub>NO<sub>2</sub>

C11H13NO2

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
With ammonium hydroxide; In methanol; at 20 ℃; for 0.666667h; Inert atmosphere;
19.3 mg
4-iodo-5-methoxy-2-phenyl-3,4-dihydro-2H-pyrrole

4-iodo-5-methoxy-2-phenyl-3,4-dihydro-2H-pyrrole

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 2h;
84%
(+/-)-4-hydroxy-4-phenylbutanenitrile
24241-74-5

(+/-)-4-hydroxy-4-phenylbutanenitrile

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
With tropylium tetrafluoroborate; In water; 1,2-dichloro-ethane; at 150 ℃; for 1h; Microwave irradiation;
79%
2-Oxo-5-phenyl-pyrrolidine-1-carboxylic acid methyl ester
76403-42-4

2-Oxo-5-phenyl-pyrrolidine-1-carboxylic acid methyl ester

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
With trimethylsilyl iodide; In chloroform; at 60 ℃; for 15h;
96%
3-benzoylpropionic acid methyl ester
25333-24-8

3-benzoylpropionic acid methyl ester

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
With ammonium acetate; sodium cyanoborohydride; In methanol; at 20 ℃; for 16h; Inert atmosphere;
74%
With ammonium acetate; sodium cyanoborohydride; In methanol; at 20 ℃; for 88h;
70%
phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

(+/-)-5-phenyl-2-pyrrolidinone
22050-10-8

(+/-)-5-phenyl-2-pyrrolidinone

Conditions
Conditions Yield
Succinimide; phenylmagnesium bromide; In tetrahydrofuran; dichloromethane; at -78 - 17 ℃;
With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; for 0.75h; pH=3 - 4;
30 g

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  • ENAO Chemical Co, Limited
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