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Cas Database

26661-13-2

26661-13-2

Identification

  • Product Name:Benzamide,N-(2,3-dihydro-2-oxo-4-pyrimidinyl)-

  • CAS Number: 26661-13-2

  • EINECS:628-907-2

  • Molecular Weight:215.211

  • Molecular Formula: C11H9N3O2

  • HS Code:29335990

  • Mol File:26661-13-2.mol

Synonyms:Benzamide,N-(1,2-dihydro-2-oxo-4-pyrimidinyl)- (8CI,9CI);Cytosine, N-benzoyl- (6CI);2(1H)-Pyrimidinone, 4-(benzoylamino)-;2-Hydroxy-4-benzamidopyrimidine;4-n-Benzoylcytosine;N-Benzoylcytosine;N4-Benzoylcytosine;NSC 211617;benzamide, N-(1,2-dihydro-2-oxo-4-pyrimidinyl)-;N-(2-Oxo-1,2-dihydropyrimidin-4-yl)benzamide;N4-Benzoyl Cytosine;N4-Benzoylcytosine;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH315 Causes skin irritation H319 Causes serious eye irritation H332 Harmful if inhaled H335 May cause respiratory irritation

  • 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
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  • Manufacture/Brand:Usbiological
  • Product Description:N4-Benzoylcytosine
  • Packaging:100g
  • Price:$ 333
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:N4-Benzoylcytosine
  • Packaging:100g
  • Price:$ 150
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:N4-Benzoylcytosine >97.0%(HPLC)(T)
  • Packaging:5g
  • Price:$ 18
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:N4-Benzoylcytosine
  • Packaging:5 g
  • Price:$ 48
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:N4-Benzoylcytosine 98%
  • Packaging:10g
  • Price:$ 62.3
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:N4-Benzoylcytosine >95%
  • Packaging:100g
  • Price:$ 78
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:N4-Benzoylcytosine >95%
  • Packaging:500g
  • Price:$ 245
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:N-(2-Oxo-1,2-dihydropyrimidin-4-yl)benzamide 97%
  • Packaging:100g
  • Price:$ 63
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  • Manufacture/Brand:Chemenu
  • Product Description:N-(2-oxo-1,2-dihydropyrimidin-4-yl)benzamide 98%
  • Packaging:1000g
  • Price:$ 72
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  • Manufacture/Brand:Chemcia Scientific
  • Product Description:N-(2-Hydroxy-pyrimidin-4-yl)-benzamide >95%
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Relevant articles and documentsAll total 17 Articles be found

Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds

Mondal, Santanu,Mugesh, Govindasamy

, p. 1773 - 1780 (2019/01/10)

Halogenated nucleosides, such as 5-iodo-2′-deoxyuridine and 5-iodo-2′-deoxycytidine, are incorporated into the DNA of replicating cells to facilitate DNA single-strand breaks and intra- or interstrand crosslinks upon UV irradiation. In this work, it is shown that the naphthyl-based organoselenium compounds can mediate the dehalogenation of halogenated pyrimidine-based nucleosides, such as 5-X-2′-deoxyuridine and 5-X-2′-deoxycytidine (X=Br or I). The rate of deiodination was found to be significantly higher than that of the debromination for both nucleosides. Furthermore, the deiodination of iodo-cytidines was found to be faster than that of iodo-uridines. The initial rates of the deiodinations of 5-iodocytosine and 5-iodouracil indicated that the nature of the sugar moiety influences the kinetics of the deiodination. For both the nucleobases and nucleosides, the deiodination and debromination reactions follow a halogen-bond-mediated and addition/elimination pathway, respectively.

Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine

Liu, Tongchao,Tang, Jiadeng,Liang, Jianpeng,Chen, Yabin,Wang, Xiaowen,Shen, Jingkang,Zhao, Dongmei,Xiong, Bing,Cen, Jun-Da,Chen, Yue-Lei

, p. 1203 - 1213 (2019/01/29)

Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.

A mechanistic study of the non-oxidative decarboxylation catalyzed by the radical S-adenosyl-l-methionine enzyme BlsE involved in blasticidin S biosynthesis

Liu, Lei,Ji, Xinjian,Li, Yongzhen,Ji, Wenjuan,Mo, Tianlu,Ding, Wei,Zhang, Qi

supporting information, p. 8952 - 8955 (2017/08/15)

Decarboxylation is a fundamentally important reaction in biology and involves highly diverse mechanisms. Here we report a mechanistic study of the non-oxidative decarboxylation catalyzed by BlsE, a radical S-adenosyl-l-methionine (SAM) enzyme involved in blasticidin S biosynthesis. Through a series of biochemical analysis with isotopically labeled reagents, we show that the BlsE-catalyzed reaction is initiated by the 5′-deoxyadenosyl (dAdo) radical-mediated hydrogen abstraction from a sugar carbon of the substrate cytosylglucuronic acid (CGA), and does not involve a carboxyl radical as has been proposed for 4-hydroxyphenylacetate decarboxylase (HPAD). Our study reveals that BlsE represents a mechanistically new type of radical-based decarboxylase.

Preparation method for N4-benzoylcytosine

-

Paragraph 0027; 0028, (2016/11/17)

The invention discloses a preparation method for N4-benzoylcytosine. According to the invention, with benzoic acid anhydride or benzoyl chloride and cytosine as raw materials and a highly-efficient acylating reagent, i.e., 4-dimethylaminopyridine, as a ca

PEPTIDE NUCLEIC ACID MONOMERS AND OLIGOMERS

-

, (2011/10/13)

Disclosed is a peptide nucleic acid monomer as well as a corresponding peptide nucleic acid molecule. The monomer comprises a terminal amino group and a terminal group A. The terminal amino group and the terminal group A are connected by an aliphatic moie

Process route upstream and downstream products

Process route

Cytosine
71-30-7

Cytosine

benzoyl chloride
98-88-4

benzoyl chloride

4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

Conditions
Conditions Yield
In pyridine; methanol;
90%
With pyridine; at 20 ℃; for 5h; Cooling with ice;
86%
Cytosine; benzoyl chloride; With pyridine; at 0 - 20 ℃; for 6h;
In ethanol; at 0 ℃; for 0.5h;
In water; at 20 ℃; for 15h;
86%
for 0.166667h; microwave irradiation;
58%
With pyridine;
With pyridine; for 3h;
4 g
In pyridine; methanol; isopropyl alcohol;
With dmap; triethylamine; In chloroform; for 16h; Reflux;
With dmap; triethylamine; In acetonitrile; at 5 - 45 ℃; for 3h; Solvent; Temperature; Inert atmosphere; Large scale;
40 kg
With pyridine; dmap; In dichloromethane; at 20 ℃; Inert atmosphere;
Cytosine
71-30-7

Cytosine

benzoic acid anhydride
93-97-0

benzoic acid anhydride

4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

Conditions
Conditions Yield
With dmap; In acetonitrile; for 7h; Heating;
91%
With dmap; triethylamine; In acetonitrile; at 5 - 50 ℃; for 3h; Solvent; Inert atmosphere; Large scale;
41 kg
N<sup>4</sup>-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine
123413-57-0

N4-benzoyl-2',3'-didehydro-2',3'-dideoxycytidine

4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

Cytosine
71-30-7

Cytosine

Conditions
Conditions Yield
In water; at 40 ℃; Rate constant; degradation in various buffers (acidic condition, < pH 6);
4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

Conditions
Conditions Yield
cytosine monohydrate
6020-40-2

cytosine monohydrate

benzoyl chloride
98-88-4

benzoyl chloride

4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

Conditions
Conditions Yield
With hydrogenchloride; sodium hydroxide; In pyridine; ethanol; water;
16.1 g product (75%)
With hydrogenchloride; sodium hydroxide; In ethanol; water;
16.1 g product (75%)
With hydrogenchloride; sodium hydroxide; In pyridine; ethanol; water;
16.1 g product (75%)
benzoyl cyanide
613-90-1

benzoyl cyanide

N<sup>4</sup>-Benzoylcytosine
26661-13-2

N4-Benzoylcytosine

Conditions
Conditions Yield
With triethylamine; In acetonitrile; Ambient temperature;
76.5%
bromoacetic acid <i>tert</i>-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

N<sub>4</sub>-Benzoyl-1-tert-butyloxycarbonylmethylcytosine
168263-85-2

N4-Benzoyl-1-tert-butyloxycarbonylmethylcytosine

Conditions
Conditions Yield
With potassium carbonate; caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 36h;
68%
With potassium carbonate; In chloroform; water; N,N-dimethyl-formamide;
With potassium carbonate; In chloroform; water; N,N-dimethyl-formamide; toluene;
15.23 g (46%)
4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

1,2-di-O-acetyl-3-azido-5-[(benzyloxycarbonyl)methyl]-3,5-dideoxy-D-ribofuranose

1,2-di-O-acetyl-3-azido-5-[(benzyloxycarbonyl)methyl]-3,5-dideoxy-D-ribofuranose

2'-O-acetyl-3'-azido-5'-[(benzyloxycarbonyl)methyl]-N4-benzoyl-3',5'-dideoxycytidine

2'-O-acetyl-3'-azido-5'-[(benzyloxycarbonyl)methyl]-N4-benzoyl-3',5'-dideoxycytidine

Conditions
Conditions Yield
4-N-benzoylcytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; Inert atmosphere; Reflux;
1,2-di-O-acetyl-3-azido-5-[(benzyloxycarbonyl)methyl]-3,5-dideoxy-D-ribofuranose; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 0 ℃; Inert atmosphere; Reflux;
89%
4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

5-O-(o-toluoyl)-1,2-diacetyl-3-deoxyxylofuranose

5-O-(o-toluoyl)-1,2-diacetyl-3-deoxyxylofuranose

5'-O-(o-toluoyl)-2'-O-acetyl-3'-deoxy-4-N-benzoylcytidine

5'-O-(o-toluoyl)-2'-O-acetyl-3'-deoxy-4-N-benzoylcytidine

5'-O-(o-toluoyl)-2'-O-acetyl-3'-deoxy-4-N-benzoylcytidine

5'-O-(o-toluoyl)-2'-O-acetyl-3'-deoxy-4-N-benzoylcytidine

Conditions
Conditions Yield
4-N-benzoylcytosine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 20 ℃; for 0.333333h;
5-O-(o-toluoyl)-1,2-diacetyl-3-deoxyxylofuranose; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -20 - 70 ℃; for 2h; stereoselective reaction;
69%
10%
4-N-benzoylcytosine
26661-13-2

4-N-benzoylcytosine

(4S)-4-ethoxycarbonyl-3-(N-benzyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine

(4S)-4-ethoxycarbonyl-3-(N-benzyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine

(S)-ethyl 3-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(((benzyloxy)carbonyl)amino)propanoate

(S)-ethyl 3-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-(((benzyloxy)carbonyl)amino)propanoate

Conditions
Conditions Yield
4-N-benzoylcytosine; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;
(4S)-4-ethoxycarbonyl-3-(N-benzyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine; In acetonitrile; at 20 ℃; for 72h; Inert atmosphere;
61%

Global suppliers and manufacturers

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  • Hangzhou Dingyan Chem Co., Ltd
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  • Amadis Chemical Co., Ltd.
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  • Shaanxi BLOOM TECH Co.,Ltd
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  • Shanghai Upbio Tech Co.,Ltd
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  • Chemwill Asia Co., Ltd.
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