ChemicalBook > CAS DataBase List > 5-Chlorouracil

5-Chlorouracil

Product Name
5-Chlorouracil
CAS No.
1820-81-1
Chemical Name
5-Chlorouracil
Synonyms
5-CHLOROPYRIMIDINE-2,4(1H,3H)-DIONE;Fluorouracil EP Impurity E;5-Chloro-1H-pyrimidine-2,4-dione;NSC 28172;5-chloro-uraci;5-CHLOROURACIL;Uracil,5-chloro-;5-CHLORO-5-URACIL;5-Chlorouracil,99%;5-Chlorouracil,98%
CBNumber
CB6216858
Molecular Formula
C4H3ClN2O2
Formula Weight
146.53
MOL File
1820-81-1.mol
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5-Chlorouracil Property

Melting point:
>300 °C (lit.)
Density 
1.6838 (rough estimate)
refractive index 
1.6550 (estimate)
storage temp. 
2-8°C
solubility 
1 M NH4OH: soluble50mg/mL
pka
6.77±0.10(Predicted)
form 
Solid
color 
White to Off-White
Water Solubility 
2.501g/L(25 ºC)
BRN 
127173
InChI
InChI=1S/C4H3ClN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
InChIKey
ZFTBZKVVGZNMJR-UHFFFAOYSA-N
SMILES
C1(=O)NC=C(Cl)C(=O)N1
CAS DataBase Reference
1820-81-1(CAS DataBase Reference)
EPA Substance Registry System
5-Chlorouracil (1820-81-1)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25-36-26
WGK Germany 
3
RTECS 
YQ9410000
HS Code 
29335995
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

H341Suspected of causing genetic defects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
224588
Product name
5-Chlorouracil
Purity
99%
Packaging
5g
Price
$92.1
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR2867
Product name
Fluorouracil Related Compound E
Purity
certified reference material, pharmaceutical secondary standard
Packaging
50MG
Price
$608
Updated
2024/03/01
Sigma-Aldrich
Product number
1279054
Product name
Fluorouracil Related Compound E
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
25mg
Price
$1210
Updated
2024/03/01
TCI Chemical
Product number
C0969
Product name
5-Chlorouracil
Purity
>98.0%(T)
Packaging
5g
Price
$62
Updated
2024/03/01
TCI Chemical
Product number
C0969
Product name
5-Chlorouracil
Purity
>98.0%(T)
Packaging
25g
Price
$180
Updated
2024/03/01
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5-Chlorouracil Chemical Properties,Usage,Production

Description

5-Chlorouracil (5-CU) may have advantages for the inhibition of undesired fibroblast proliferation taking place after surgery for glaucoma and results in filtration failure. A comparison of 5-CU and 5-fluorouracil (5-FU) cytotoxicity shows that 5-CU is approximately 1000 times less toxic to nonproliferative cells while maintaining good antimitotic activity. In addition, 5-CU induces apoptotic-controlled cell death, whereas the influence of 5-FU is by apoptonecrosis. The 5-CU apoptotic mechanism is driven mainly by the nuclear translocation of AIF and activation of the LEI/L-DNase II pathways, which are caspase-independent. In conclusion, even though 5-CU is a weaker antiproliferating agent than 5-FU, its reduced toxic side effects on the epithelium and sclera allow for its enhanced efficacy and extended reduction of IOP after filtering surgery for glaucoma. 5-CU is an effective mutagen, clastogen and toxicant, and an effective inducer of sister-chromatid exchange, and is not as sensitive to ionizing radiation as other thymine analogues[1].

Chemical Properties

white to light beige crystalline powder

Uses

5-Chlorouracil was used as a control in resazurin-based cytotoxicity assay for screening of cytotoxicity in hepatocytes and liver cell lines.

Uses

5-Chlorouracil can be used for the experimental and clinical treatment of neoplastic and viral diseases.

Definition

ChEBI: An organochlorine compound consisting of uracil having an chloro substituent at the 5-position. It is functionally related to a uracil.

General Description

The shape resonance spectra of 5-chlorouracil, obtained from fixed-nuclei elastic scattering calculations by the Schwinger multichannel method with pseudopotentials, was studied.

Purification Methods

It recrystallises from hot H2O (4g/500mL) using charcoal. [McOmie et al. J Chem Soc 3478 1955, West & Barrett J Am Chem Soc 76 3146 1954, Beilstein 24 III/IV 1231.]

References

[1] Marianne Berdugo Polak. “Controlled delivery of 5-chlorouracil using poly(ortho esters) in filtering surgery for glaucoma.” Investigative ophthalmology & visual science (2008): 2993–3003.

5-Chlorouracil Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 5-Chlorouracil manufacturers

Hebei Mujin Biotechnology Co.,Ltd
Product
5-Chlorouracil 1820-81-1
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-08-22
Hebei Weibang Biotechnology Co., Ltd
Product
5-Chlorouracil 1820-81-1
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-12-05
Zhuozhou Wenxi import and Export Co., Ltd
Product
5-chlorouracil 1820-81-1
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-26

1820-81-1, 5-ChlorouracilRelated Search:

Uracil Difluorochloromethane 5-Chlorouridine Terbacil 5-CHLORO-6-METHYLURACIL 4-AMINOPYRAZOLO[3,4-D]PYRIMIDINE 6-Chlorouracil 6-methyl-5-chlorouracil 1,3-Dimethyl-4-chlorouracil,1,3-DIMETHYL-6-CHLOROURACIL 3-Methyl-6-chlorouracil, GC 97%,3-METHYL-6-CHLOROURACIL 2,4(1H,3H)-Pyrimidinedione,5-chloro-6-(chloromethyl)-(9CI) 5-CHLORO-2'-DEOXYURIDINE 1-(3-Fluoro-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-chlorouracil 5-Chloro-2',3'-O-isopropylidene-D-uridine 5-Chloro-5'-deoxy-5'-iodo-2',3'-O-isopropylidene-D-uridine 5-Chlorouracil-15N2,13C 1,3,5-TRICHLOROURACIL 5-CHLORO-5'-DEOXYURIDINE

  • TIMTEC-BB SBB004103
  • 2,4(1H,3H)-Pyrimidinedione,5-chloro-
  • 2,4-Pyrimidinediol,5-chloro-
  • 3h)-pyrimidinedione,5-chloro-4(1h
  • 5-Chloro-1,2,3,4-tetrahydropyrimidine-2,4-dione
  • 5-Chloropyrimidine-2,4-diol
  • 5-Chlorouracil,99%
  • Fluorouracil Related CoMpound E
  • 5-Chlorouracil ReagentPlus(R), 99%
  • Fluorouracil Related Compound E (25 mg) (5-Chloropyrimidine-2,4(1H,3H)-dione)
  • 5-Chlorouracil Vetec(TM) reagent grade, 98%
  • Fluorouracil Impurity 5（Fluorouracil EP Impurity E）
  • Fluorouracil EP Impurity E
  • 5-Chlor-2,4-dihydroxypyrimidin
  • 5-Chloro-1H-pyrimidine-2,4-dione
  • 5-Chloro-2,4-pyrimidinedione
  • 5-chloro-uraci
  • Uracil,5-chloro-
  • 5-CHLORO-2,4-DIHYDROXYPYRIMIDINE
  • 5-CHLORO-5-URACIL
  • 5-CHLOROURACIL
  • 5-CHLOROPYRIMIDINE-2,4(1H,3H)-DIONE
  • 5-CHLOROURACIL,5-CHLORO-2,4-DIHYDROXYPYRIMIDINE
  • 2,4(1H,3H)-Pyrimidinedione, 5-chloro- (9CI)
  • 5-Chloro-2,4(1H,3H)-pyrimidinedione
  • NSC 28172
  • 5-CHLOROURACIL CRYSTALLINE
  • 5-Chlorouracil,98%
  • Fluorouracil BP Impurity E
  • 5-Chlorouracil &gt
  • 5-Chlorouracil USP/EP/BP
  • 5-Chlorouracil (Fluorouracil Impurity)
  • 4(1H,3H)-Pyrimidinedione,5-chloro-
  • Fluorouracil EP Impurity E (5-Chlorouracil)
  • 5-ChlorouracilQ: What is 5-Chlorouracil Q: What is the CAS Number of 5-Chlorouracil Q: What is the storage condition of 5-Chlorouracil Q: What are the applications of 5-Chlorouracil
  • Fluorouracil Related Compound E (5-Chloropyrimidine-2,4(1H,3H)-dione) (1279054)
  • Fluorouracil USP Related Compound E
  • 5-chloro-2,4-dioxopyrimidine
  • Fluorouracil Related Compound E (5-Chloropyrimidine-2,4(1H,3H)-dione)
  • Fluorouracil EP Impurity E (Fluorouracil USP Related Compound E)
  • 5-Chloropyrimidine-2,4(1H,3H)-dione (5-Chlorouracil)
  • 1820-81-1
  • 156-2-19
  • C4H3ClN2O2
  • Building Blocks
  • Pyrimidines
  • Heterocyclic Building Blocks
  • Halogenated Heterocycles
  • Pyrimidine series
  • Heterocyclic Compounds
  • Biochemistry
  • Nucleobases and their analogs
  • Nucleosides, Nucleotides & Related Reagents
  • Nucleic acids
  • Bases & Related Reagents
  • Heterocycles
  • Nucleotides
  • PYRIMIDINE