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2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-5-(2-phenylethenyl)-, (E)- is a 5-substituted uracil derivative synthesized via palladium-catalyzed C-H olefination or cross-coupling reactions, where a styrene moiety is introduced at the C-5 position of the 1,3-dimethyluracil scaffold. 2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-5-(2-phenylethenyl)-, (E)- is typically obtained through oxidative coupling with styrene or cross-coupling of uracil triflates or iodonium salts with alkenyl reagents, demonstrating the versatility of palladium catalysis in modifying uracil derivatives. The (E)-configuration indicates the trans arrangement of the phenyl and uracil groups across the double bond. These methods provide efficient and selective routes to such alkenyluracil derivatives, which are of interest in medicinal and materials chemistry. Other names for 2,4(1H,3H)-Pyrimidinedione, 1,3-dimethyl-5-(2-phenylethenyl)-, (E)- may include: - (E)-1,3-Dimethyl-5-styryluracil - trans-1,3-Dimethyl-5-(2-phenylethenyl)uracil - 5-[(E)-Styryl]-1,3-dimethyluracil

100651-92-1

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100651-92-1 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 100651-92-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,0,6,5 and 1 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 100651-92:
(8*1)+(7*0)+(6*0)+(5*6)+(4*5)+(3*1)+(2*9)+(1*2)=81
81 % 10 = 1
So 100651-92-1 is a valid CAS Registry Number.

100651-92-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,3-dimethyl-5-<(E)-2-phenylethenyl>uracil

1.2 Other means of identification

Product number -
Other names 1,3-Dimethyl-5-((E)-styryl)-1H-pyrimidine-2,4-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100651-92-1 SDS

100651-92-1Downstream Products

100651-92-1Relevant academic research and scientific papers

Palladium-catalyzed C-H olefination of uracils and caffeines using molecular oxygen as the sole oxidant

Zhang, Xinyu,Su, Lv,Qiu, Lin,Fan, Zhenwei,Zhang, Xiaofeng,Lin, Shen,Huang, Qiufeng

, p. 3499 - 3506 (2017)

The palladium-catalyzed oxidative C-H olefination of uracils or caffeines with alkenes using an atmospheric pressure of molecular oxygen as the sole oxidant has been disclosed. This novel strategy offers an efficient and environmentally friendly method to

Palladium Catalyzed Alkenylation or Alkynylation at C-5 of Uracil Nucleosides Using Novel Phenyliodonium Triflate

Roh, Kyoung Rok,Kim, Joong Young,Kim, Yong Hae

, p. 1903 - 1906 (1999)

A new coupling reaction between novel uracil-5-iodonium triflate and unsaturated stannane or alkenyl boronic acid is described. The reaction is achieved via palladium catalyzed cross-coupling reaction under mild conditions within short reaction time.

PALLADIUM CATALYZED COUPLING OF 5-HYDROXYURACIL TRIFLUOROMETHANESULFONATES (TRIFLATES) WITH ALKENES AND ALKYNES

Hirota, Kosaku,Kitade, Yukio,Isobe, Yoshiaki,Maki, Yoshifumi

, p. 355 - 358 (1987)

Cross coupling of 5-hydroxyuracil triflates (1) with alkenes and alkynes in the presence of a palladium catalyst and triphenylphosphine affords 5-vinyluracils (2) and 5-alkynyluracils (3), respectively, in good yields.Coupling of the triflate (1a) with organocopper reagents is also described.

A Simple Synthesis of 5-(1-Alkenyl)uracil Derivatives by Palladium-Catalyzed Oxidative Coupling of Uracils With Olefins

Hirota, Kosaku,Isobe, Yoshiaki,Kitade, Yukio,Maki, Yoshifumi

, p. 495 - 496 (1987)

The oxidative coupling of uracil derivatives 1 with olefins, such as methyl acrylate, acrylonitrile, methyl vinyl ketone, and styrene, using one equivalent of palladium acetate leads to the corresponding 5-(1-alkenyl)uracil derivatives 2.

Dehydrogenative alkenylation of uracils via palladium-catalyzed regioselective C-H activation

Yu, Yi-Yun,Georg, Gunda I.

supporting information, p. 3694 - 3696 (2013/05/09)

A regioselective Pd-catalyzed cross-dehydrogenative coupling between uracils and alkenes is reported. This protocol provides easy access to a variety of 5-alkenyluracil structural motifs. The Royal Society of Chemistry 2013.

Synthesis of 5-substituted pyrimidine nucleosides through a palladium-catalyzed cross-coupling of alkenylhalosilanes

Matsuhashi, Hayao,Hatanaka, Yasuo,Kuroboshi, Manabu,Hiyama, Tamejiro

, p. 375 - 384 (2007/10/02)

Palladium-catalyzed cross-coupling of alkenylhalosilanes with 5-iodouracil and 5-iodouridine derivatives was described. 5-Iodo-1,3-dimethyluracil coupled with alkenylfluorodimethylsilanes to give the corresponding cross-coupled products in good yield. Ful

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