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ChemicalBook--->CAS DataBase List--->1820-81-1

1820-81-1

1820-81-1 Structure

1820-81-1 Structure
IdentificationMore
[Name]

5-Chlorouracil
[CAS]

1820-81-1
[Synonyms]

5-CHLORO-2,4-DIHYDROXYPYRIMIDINE
5-CHLORO-5-URACIL
5-CHLOROPYRIMIDINE-2,4(1H,3H)-DIONE
5-CHLOROURACIL
TIMTEC-BB SBB004103
2,4(1H,3H)-Pyrimidinedione,5-chloro-
2,4-Pyrimidinediol,5-chloro-
3h)-pyrimidinedione,5-chloro-4(1h
5-Chlor-2,4-dihydroxypyrimidin
5-Chloro-1H-pyrimidine-2,4-dione
5-Chloro-2,4-pyrimidinedione
5-chloro-uraci
Uracil,5-chloro-
5-CHLOROURACIL CRYSTALLINE
5-Chlorouracil,98%
2,4(1H,3H)-Pyrimidinedione, 5-chloro-(9CI)
5-Chloro-2,4(1H,3H)-pyrimidinedione
NSC 28172
5-CHLOROURACIL,5-CHLORO-2,4-DIHYDROXYPYRIMIDINE
5-Chloro-1,2,3,4-tetrahydropyrimidine-2,4-dione
[EINECS(EC#)]

217-339-7
[Molecular Formula]

C4H3ClN2O2
[MDL Number]

MFCD00006019
[Molecular Weight]

146.53
[MOL File]

1820-81-1.mol
Chemical PropertiesBack Directory
[Appearance]

white to light beige crystalline powder
[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
[form ]

Solid
[pka]

6.77±0.10(Predicted)
[color ]

White to Off-White
[Water Solubility ]

2.501g/L(25 ºC)
[Usage]

Used for the experimental and clinical treatment of neoplastic and viral diseases
[Detection Methods]

HPLC,NMR
[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]

1820-81-1(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[RTECS ]

YQ9410000
[HS Code ]

29335995
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

5-Chlorouracil(1820-81-1).msds
Hazard InformationBack Directory
[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.
[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.
Spectrum DetailBack Directory
[Spectrum Detail]

5-Chlorouracil(1820-81-1)MS
5-Chlorouracil(1820-81-1)1HNMR
5-Chlorouracil(1820-81-1)IR1
5-Chlorouracil(1820-81-1)IR2
5-Chlorouracil(1820-81-1)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

5-Chlorouracil, 99%(1820-81-1)
[Alfa Aesar]

5-Chlorouracil, 98%(1820-81-1)
[Sigma Aldrich]

1820-81-1(sigmaaldrich)
[TCI AMERICA]

5-Chlorouracil,>98.0%(T)(1820-81-1)
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