Skip to the beginning of the images gallery

5-Bromouracil - 99%, high purity , CAS No.51-20-7

3 Citations

≥99%

CAS#: 51-20-7
Formula: C₄H₃BrN₂O₂
Molecular Weight: 190.98
Beilstein Registry Number: 127176
EC Number: 200-084-0
MDL number: MFCD00006017
PubChem CID: 5802
PubChem SID: 488179941

Item Number

B109680

Grouped product items
SKU	Size	Availability	Price
B109680-5g	5g	In stock	$17.90
B109680-25g	25g	In stock	$53.90
B109680-100g	100g	In stock	$168.90
B109680-500g	500g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$756.90

View related series

Halogenated heterocyclic block Pyrimidines

Basic Description

Synonyms	5-Bromouracil \| 51-20-7 \| BROMOURACIL \| 5-bromopyrimidine-2,4(1H,3H)-dione \| 5-Bromo-1H-pyrimidine-2,4-dione \| 5-Bromo-2,4(1H,3H)-pyrimidinedione \| Uracil, 5-bromo- \| 5-Bromo-2,4-dihydroxypyrimidine \| 5-bromopyrimidine-2,4-diol \| 2,4(1H,3H)-Pyrimidinedione, 5-bromo- \| MFCD00
Specifications & Purity	≥99%
Shipped In	Normal
Product Description	application： A major chemical mutagen. Incorporates into DNA, altering base-pair sequencing by replacing thymine.

Associated Targets(Human)

DPYD Tclin Dihydropyrimidine dehydrogenase [NADP(+)] (0 Activities)

Discover Target: DPYD

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Raji (5516 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

L1210 (27553 Activities)

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

DPYD Dihydropyrimidine dehydrogenase [NADP(+)] (7 Activities)

Discover Target: DPYD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Names and Identifiers

Pubchem Sid	488179941
Pubchem Sid Url	https://pubchem.ncbi.nlm.nih.gov/substance/488179941
IUPAC Name	5-bromo-1H-pyrimidine-2,4-dione
INCHI	InChI=1S/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChi Key	LQLQRFGHAALLLE-UHFFFAOYSA-N
Canonical SMILES	C1=C(C(=O)NC(=O)N1)Br
Isomeric SMILES	C1=C(C(=O)NC(=O)N1)Br
WGK Germany	3
RTECS	YQ9060000
PubChem CID	5802
UN Number	2811
Packing Group	I
Molecular Weight	190.98
Beilstein	127176
Reaxy-Rn	127176

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

To view the certificate results,please click on a Lot number.For Lot numbers from past orders,please use our order status section

20 results found

Lot Number	Certificate Type	Date	Item
K2225191	Certificate of Analysis	Aug 23, 2024	B109680
K2215080	Certificate of Analysis	Aug 23, 2024	B109680
D2416232	Certificate of Analysis	Mar 15, 2024	B109680
D2416231	Certificate of Analysis	Mar 15, 2024	B109680
D2416221	Certificate of Analysis	Mar 15, 2024	B109680
D2221073	Certificate of Analysis	Jan 08, 2024	B109680
D2221092	Certificate of Analysis	Jan 08, 2024	B109680
A2203227	Certificate of Analysis	Oct 11, 2023	B109680
G2128070	Certificate of Analysis	May 09, 2023	B109680
A2305451	Certificate of Analysis	Dec 06, 2022	B109680
A2305449	Certificate of Analysis	Dec 06, 2022	B109680
A2305445	Certificate of Analysis	Dec 06, 2022	B109680
A2305370	Certificate of Analysis	Dec 06, 2022	B109680
A2305369	Certificate of Analysis	Dec 06, 2022	B109680
A2305214	Certificate of Analysis	Dec 06, 2022	B109680
G2029019	Certificate of Analysis	Jun 11, 2022	B109680
G2029020	Certificate of Analysis	Jun 11, 2022	B109680
D2221091	Certificate of Analysis	Mar 09, 2022	B109680
B2210090	Certificate of Analysis	Feb 16, 2022	B109680
A2221057	Certificate of Analysis	Dec 16, 2021	B109680

Chemical and Physical Properties

Solubility	DMSO (Slightly), Water (Slightly)
Melt Point(°C)	>300 °C

Safety and Hazards(GHS)

Pictogram(s)	GHS07
Signal	Warning
Hazard Statements	H302:Harmful if swallowed
Precautionary Statements	P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P270:Do not eat, drink or smoke when using this product. P330:Rinse mouth. P301+P317:IF SWALLOWED: Get medical help.
WGK Germany	3
RTECS	YQ9060000
Reaxy-Rn	127176
Class	6.1
Merck Index	1445

Citations of This Product

1. Hanwen Liu, Ying Liu, Ting Zhou, Penghui Zhou, Jianguo Li, Anping Deng. (2022) Ultrasensitive and Specific Detection of Anticancer Drug 5-Fluorouracil in Blood Samples by a Surface-Enhanced Raman Scattering (SERS)-Based Lateral Flow Immunochromatographic Assay. MOLECULES, 27 (13): (4019). [PMID:35807264]
2. Ting Zhou, Guangzhao He, Changjia Hu, Kang Wu, Ying Liu, Jianguo Li, Anping Deng. (2022) Development of a highly sensitive and specific monoclonal antibody-based ELISA coupled with immuno-affinity extraction for the detection of anticancer drug 5-fluorouracil in blood samples. TALANTA, 249 (123655). [PMID:35696979]
3. Su Xue-ling, Wang Shu-hui, Komal Sumra, Cui Liu-gen, Ni Rui-cong, Zhang Li-rong, Han Sheng-na. (2022) The caspase-1 inhibitor VX765 upregulates connexin 43 expression and improves cell–cell communication after myocardial infarction via suppressing the IL-1β/p38 MAPK pathway. ACTA PHARMACOLOGICA SINICA, 43 (9): (2289-2301). [PMID:35132192]

References

1. Hameed P S, Solapure S, Patil V, Henrich PP, Magistrado PA, Bharath S, Murugan K, Viswanath P, Puttur J, Srivastava A et al.. (2015) Triaminopyrimidine is a fast-killing and long-acting antimalarial clinical candidate.. Nat Commun, 6 (3): (6715). [PMID:25823686]
2. F Hutchinson. (1973-05-01) The lesions produced by ultraviolet light in DNA containing 5-bromouracil.. Quarterly reviews of biophysics, 6 ((2)): (201-246). [PMID:4579676]
3. H E Jacob,E Golovinsky. (1983-01-01) [Effects of 5-bromouracil and 5-bromodeoxyuridine in combination with 8-aza-adenine on the UV sensitivity of bacteria].. Zeitschrift fur allgemeine Mikrobiologie, 23 ((8)): (495-501). [PMID:6419483]
4. P Metrangolo,G Resnati. (2008-08-16) Chemistry. Halogen versus hydrogen.. Science (New York, N.Y.), 321 ((5891)): (918-919). [PMID:18703728]
5. Shu-Shen Liu,Xiao-Qing Song,Hai-Ling Liu,Ya-Hui Zhang,Jing Zhang. (2009-02-14) Combined photobacterium toxicity of herbicide mixtures containing one insecticide.. Chemosphere, 75 ((3)): (381-388). [PMID:19215957]
6. Monika Kobyłecka,Annapaola Migani,David Asturiol,Janusz Rak,Lluís Blancafort. (2009-04-21) Benign decay vs. photolysis in the photophysics and photochemistry of 5-bromouracil. A computational study.. The journal of physical chemistry. A, 113 ((19)): (5489-5495). [PMID:19374393]
7. Fadi Al Mardini,Bernard Legube. (2009-06-23) Effect of the adsorbate (Bromacil) equilibrium concentration in water on its adsorption on powdered activated carbon. Part 1. Equilibrium parameters.. Journal of hazardous materials, 170 ((2-3)): (744-753). [PMID:19539425]
8. Fadi Al Mardini,Bernard Legube. (2009-06-30) Effect of the adsorbate (Bromacil) equilibrium concentration in water on its adsorption on powdered activated carbon. Part 2: Kinetic parameters.. Journal of hazardous materials, 170 ((2-3)): (754-762). [PMID:19560269]
9. Denis Fourches,Julie C Barnes,Nicola C Day,Paul Bradley,Jane Z Reed,Alexander Tropsha. (2009-12-18) Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.. Chemical research in toxicology, 23 ((1)): (171-183). [PMID:20014752]
10. Ajit K Sarmah,Murray E Close. (2010-02-26) Modelling the dissipation kinetics of six commonly used pesticides in two contrasting soils of New Zealand.. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes, 44 ((6)): (507-517). [PMID:20183056]
11. Kensuke Miki,Mitsuhiro Shimizu,Michihiko Fujii,Shinichi Takayama,Mohammad Nazir Hossain,Dai Ayusawa. (2010-11-03) 5-bromodeoxyuridine induces transcription of repressed genes with disruption of nucleosome positioning.. The FEBS journal, 277 ((21)): (4539-4548). [PMID:21040474]
12. Piotr Storoniak,Janusz Rak,Katarzyna Polska,Lluís Blancafort. (2011-03-30) Local excitation of the 5-bromouracil chromophore in DNA. Computational and UV spectroscopic studies.. The journal of physical chemistry. B, 115 ((15)): (4532-4537). [PMID:21443217]
13. Zejun Li,Pierre Cloutier,Léon Sanche,J Richard Wagner. (2011-09-10) Low-energy electron-induced damage in a trinucleotide containing 5-bromouracil.. The journal of physical chemistry. B, 115 ((46)): (13668-13673). [PMID:21902215]
14. Katarzyna Niedojadło,Szymon Pięciński,Dariusz Jan Smoliński,Elżbieta Bednarska-Kozakiewicz. (2012-02-02) Transcriptional activity of Hyacinthus orientalis L. female gametophyte cells before and after fertilization.. Planta, 236 ((1)): (153-169). [PMID:22293855]
15. Hironobu Morinaga,Tomohiro Takenaka,Fumitaka Hashiya,Seiichiro Kizaki,Kaori Hashiya,Toshikazu Bando,Hiroshi Sugiyama. (2013-02-27) Sequence-specific electron injection into DNA from an intermolecular electron donor.. Nucleic acids research, 41 ((8)): (4724-4728). [PMID:23439569]
16. Shu-Shen Liu,Cheng-Lin Wang,Jin Zhang,Xiang-Wei Zhu,Wei-Ying Li. (2013-07-03) Combined toxicity of pesticide mixtures on green algae and photobacteria.. Ecotoxicology and environmental safety, 95 (98-103). [PMID:23816361]
17. Shinji Kobuchi,Yukako Ito,Taro Hayakawa,Asako Nishimura,Nobuhito Shibata,Kanji Takada,Toshiyuki Sakaeda. (2014-07-23) Semi-physiological pharmacokinetic-pharmacodynamic (PK-PD) modeling and simulation of 5-fluorouracil for thrombocytopenia in rats.. Xenobiotica; the fate of foreign compounds in biological systems, 45 ((1)): (19-28). [PMID:25050790]
18. Can Huang,Na-Mei Li,Pei Gao,Sa Yang,Qian Ning,Wen Huang,Zhi-Ping Li,Peng-Ju Ye,Li Xiang,Dong-Xiu He,Xiang-Wen Tan,Cui-Yun Yu. (2017-02-22) In vitro and in vivo evaluation of macromolecular prodrug GC-FUA based nanoparticle for hepatocellular carcinoma chemotherapy.. Drug delivery, 24 ((1)): (459-466). [PMID:28219253]
19. J Poštulka,P Slavíček,J Fedor,M Fárník,J Kočišek. (2017-09-01) Energy Transfer in Microhydrated Uracil, 5-Fluorouracil, and 5-Bromouracil.. The journal of physical chemistry. B, 121 ((38)): (8965-8974). [PMID:28858504]
20. Shinji Kobuchi,Yukiko Yazaki,Yukako Ito,Toshiyuki Sakaeda. (2017-11-28) Circadian variations in the pharmacokinetics of capecitabine and its metabolites in rats.. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 112 (152-158). [PMID:29175408]
21. Yoko Akune,Masakazu Yamada,Chika Shigeyasu. (2018-06-23) Determination of 5-fluorouracil and tegafur in tear fluid of patients treated with oral fluoropyrimidine anticancer agent, S-1.. Japanese journal of ophthalmology, [PMID:29931401]
22. Shinji Kobuchi,Yukako Ito,Daiki Takamatsu,Toshiyuki Sakaeda. (2018-08-06) Circadian variations in the pharmacokinetics of the oral anticancer agent tegafur-uracil (UFT) and its metabolites in rats.. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 123 (452-458). [PMID:30077713]
23. Santanu Mondal,Govindasamy Mugesh. (2018-11-07) Dehalogenation of Halogenated Nucleobases and Nucleosides by Organoselenium Compounds.. Chemistry (Weinheim an der Bergstrasse, Germany), 25 ((7)): (1773-1780). [PMID:30398293]
24. Teodora Todorova,Daniela Miteva,Stephka Chankova. (2019-03-16) DNA susceptibility of Saccharomyces cerevisiae to Zeocin depends on the growth phase.. International microbiology : the official journal of the Spanish Society for Microbiology, 22 ((4)): (419-428). [PMID:30875034]
25. Ramon Bonte,Michiel Bongaerts,Serwet Demirdas,Janneke G Langendonk,Hidde H Huidekoper,Monique Williams,Willem Onkenhout,Edwin H Jacobs,Henk J Blom,George J G Ruijter. (2019-11-30) Untargeted Metabolomics-Based Screening Method for Inborn Errors of Metabolism using Semi-Automatic Sample Preparation with an UHPLC- Orbitrap-MS Platform.. Metabolites, 9 ((12)): [PMID:31779119]
26. Shuhei Sakai,Shinji Kobuchi,Yukako Ito,Toshiyuki Sakaeda. (2021-02-20) A Physiologically Based Pharmacokinetic-Pharmacodynamic Model for Capecitabine in Colorectal Cancer Rats: Simulation of Antitumor Efficacy at Various Administration Schedules.. European journal of drug metabolism and pharmacokinetics, 46 ((2)): (301-315). [PMID:33606175]
27. G Alavi,M Sanda,B Loo,R E Green,C Ray. (2008-04-01) Movement of bromacil in a Hawaii soil under pineapple cultivation - a field study.. Chemosphere, 72 ((1)): (45-52). [PMID:18374966]
28. Giordano Pula,Ursula Mayr,Colin Evans,Marianna Prokopi,Dina S Vara,Xiaoke Yin,Zoe Astroulakis,Qingzhong Xiao,Jonathan Hill,Qingbo Xu,Manuel Mayr. (2008-11-22) Proteomics identifies thymidine phosphorylase as a key regulator of the angiogenic potential of colony-forming units and endothelial progenitor cell cultures.. Circulation research, 104 ((1)): (32-40). [PMID:19023133]
29. Victor I Danilov,Tanja van Mourik,Noriyuki Kurita,Hajime Wakabayashi,Takayuki Tsukamoto,Dmytro M Hovorun. (2009-02-17) On the mechanism of the mutagenic action of 5-bromouracil: a DFT study of uracil and 5-bromouracil in a water cluster.. The journal of physical chemistry. A, 113 ((11)): (2233-2235). [PMID:19216504]
30. Pierre Daublain,Arun K Thazhathveetil,Vladimir Shafirovich,Qiang Wang,Anton Trifonov,Torsten Fiebig,Frederick D Lewis. (2010-02-04) Dynamics and efficiency of electron injection and transport in DNA using pyrenecarboxamide as an electron donor and 5-bromouracil as an electron acceptor.. The journal of physical chemistry. B, 114 ((45)): (14265-14272). [PMID:20121242]
31. Guangxin Lin,Jing Zhang,Yu Zeng,Hai Luo,Yinsheng Wang. (2010-02-20) Conformation-dependent formation of the G[8-5]U intrastrand cross-link in 5-bromouracil-containing G-quadruplex DNA induced by UVA irradiation.. Biochemistry, 49 ((11)): (2346-2350). [PMID:20166754]
32. Fadi Al Mardini,Bernard Legube. (2010-07-14) Effect of the adsorbate (Bromacil) equilibrium concentration in water on its adsorption on powdered activated carbon. Part 3: Competition with natural organic matter.. Journal of hazardous materials, 182 ((1-3)): (10-17). [PMID:20619963]
33. P Chris Wilson,Sandra B Wilson. (2010-09-08) Toxicity of the herbicides bromacil and simazine to the aquatic macrophyte, Vallisneria americana Michx.. Environmental toxicology and chemistry, 29 ((1)): (201-211). [PMID:20821436]
34. E Itälä,D T Ha,K Kooser,E Rachlew,M A Huels,E Kukk. (2010-10-26) Fragmentation patterns of core-ionized thymine and 5-bromouracil.. The Journal of chemical physics, 133 ((15)): (154316-154316). [PMID:20969395]
35. Martin D Shetlar,Vladimir J Basus. (2010-10-27) A (6-4) photoproduct of 5-bromouracil.. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 10 ((1)): (76-83). [PMID:20976373]
36. María Ibáñez,Juan V Sancho,Oscar J Pozo,Félix Hernández. (2011-09-29) Use of quadrupole time-of-flight mass spectrometry to determine proposed structures of transformation products of the herbicide bromacil after water chlorination.. Rapid communications in mass spectrometry : RCM, 25 ((20)): (3103-3113). [PMID:21953966]
37. S Yamada,T Kuroda,B C Fuchs,X He,J G Supko,A Schmitt,C M McGinn,M Lanuti,K K Tanabe. (2011-11-15) Oncolytic herpes simplex virus expressing yeast cytosine deaminase: relationship between viral replication, transgene expression, prodrug bioactivation.. Cancer gene therapy, 19 ((3)): (160-170). [PMID:22076044]
38. Hironobu Morinaga,Seiichiro Kizaki,Tomohiro Takenaka,Shuhei Kanesato,Yuta Sannohe,Ryu Tashiro,Hiroshi Sugiyama. (2012-12-26) Photoreactivities of 5-bromouracil-containing RNAs.. Bioorganic & medicinal chemistry, 21 ((2)): (466-469). [PMID:23266180]
39. Shinji Kobuchi,Yukako Ito,Taro Hayakawa,Asako Nishimura,Nobuhito Shibata,Kanji Takada,Toshiyuki Sakaeda. (2014-07-30) Pharmacokinetic-pharmacodynamic (PK-PD) modeling and simulation of 5-fluorouracil for erythropenia in rats.. Journal of pharmacological and toxicological methods, 70 ((2)): (134-144). [PMID:25072509]
40. Vijay Kumar,Virender Kumar,Neerja Thakur,Tek Chand Bhalla. (2015-04-26) Bench scale synthesis of p-hydroxybenzoic acid using whole-cell nitrilase of Gordonia terrae mutant E9.. Bioprocess and biosystems engineering, 38 ((7)): (1267-1279). [PMID:25911422]
41. Bart A W Jacobs,Dick Pluim,Pia van der Laan,Anna Tzani,Jos H Beijnen,Jan H M Schellens. (2018-10-05) Development and validation of a quantitative method for thymidine phosphorylase activity in peripheral blood mononuclear cells.. Nucleosides, nucleotides & nucleic acids, 37 ((8)): (436-454). [PMID:30285552]
42. E Rossignol,M B Amiand,J Sorrieul,J M Bard,C Bobin-Dubigeon. (2019-11-18) A fully validated simple new method for environmental monitoring by surface sampling for cytotoxics.. Journal of pharmacological and toxicological methods, 101 (106652-106652). [PMID:31734280]
43. Shuhei Sakai,Shinji Kobuchi,Yukako Ito,Toshiyuki Sakaeda. (2020-04-03) Assessment of pharmacokinetic variations of capecitabine after multiple administration in rats: a physiologically based pharmacokinetic model.. Cancer chemotherapy and pharmacology, 85 ((5)): (869-880). [PMID:32240335]
44. Shinji Kobuchi,Eisuke Matsumura,Yukako Ito,Toshiyuki Sakaeda. (2020-04-21) Population Pharmacokinetic Model-Based Evaluation of Circadian Variations in Plasma 5-Fluorouracil Concentrations During Long-Term Infusion in Rats: A Comparison With Oral Anticancer Prodrugs.. Journal of pharmaceutical sciences, 109 ((7)): (2356-2361). [PMID:32311368]
45. Hanwen Liu, Ying Liu, Ting Zhou, Penghui Zhou, Jianguo Li, Anping Deng. (2022) Ultrasensitive and Specific Detection of Anticancer Drug 5-Fluorouracil in Blood Samples by a Surface-Enhanced Raman Scattering (SERS)-Based Lateral Flow Immunochromatographic Assay. MOLECULES, 27 (13): (4019). [PMID:35807264]
46. Ting Zhou, Guangzhao He, Changjia Hu, Kang Wu, Ying Liu, Jianguo Li, Anping Deng. (2022) Development of a highly sensitive and specific monoclonal antibody-based ELISA coupled with immuno-affinity extraction for the detection of anticancer drug 5-fluorouracil in blood samples. TALANTA, 249 (123655). [PMID:35696979]
47. Su Xue-ling, Wang Shu-hui, Komal Sumra, Cui Liu-gen, Ni Rui-cong, Zhang Li-rong, Han Sheng-na. (2022) The caspase-1 inhibitor VX765 upregulates connexin 43 expression and improves cell–cell communication after myocardial infarction via suppressing the IL-1β/p38 MAPK pathway. ACTA PHARMACOLOGICA SINICA, 43 (9): (2289-2301). [PMID:35132192]

Solution Calculators

Molarity Calculator

Determine the necessary mass, volume, or concentration for preparing a solution.

Dilution Calculator

Determine the dilution needed to prepare a stock solution.