Basic information
- CAS
696-07-1- Standard SMILES
O=c1[nH]cc(I)c(=O)[nH]1- InChIKey
KSNXJLQDQOIRIP-UHFFFAOYSA-N- Molecular formula
- C4H3IN2O2
- Average molar mass
- 237.98 g/mol
- Monoisotopic mass
- 237.92392534
Overview
5-iodouracil is an organoiodine compound consisting of uracil having an iodo substituent at the 5-position. It has a role as an antimetabolite. It is functionally related to a uracil.
Names & identifiers
- Preferred name
- 5-Iodouracil
- IUPAC
- 5-iodo-1H-pyrimidine-2,4-dione
- English name
- 5-Iodouracil
- Molecular formula
- C4H3IN2O2
- Molecular weight
- 237.98
Names & synonyms
5-Iodouracil696-07-15-iodopyrimidine-2,4(1H,3H)-dione2,4(1H,3H)-Pyrimidinedione, 5-iodo-Uracil, 5-iodo-2,4-Dihydroxy-5-iodopyrimidineNSC 57848H59BRK500MCHEBI:43636NSC-57848DTXSID3061009RefChem:102973
Show more names
5IU5-Iodouracl5-iodo-uraci5-iodine uracil5-Iodouracil>5-Iodouracil,97%5-Iodouracil ,99%
DTXCID9046526211-788-25-iodo-1H-pyrimidine-2,4-dione5-iodopyrimidine-2,4-diolMFCD000060205-iodo-1,2,3,4-tetrahydropyrimidine-2,4-dione5-Iodo-uracilCHEMBL1173
Database identifiers
- CAS
696-07-1- PubChem CID
- 69672
- DTXSID
DTXSID3061009- ChEMBL
CHEMBL1173- ChEBI
CHEBI:43636- UNII
- H59BRK500M
- EC Number
- 211-788-2
- Nikkaji
- J49.056C
Properties
Computed structural properties
- XLogP
- 0
- Topological polar surface area
- 58.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 199
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Physicochemical properties
- Melting point
- 274 · 274-276 °C (dec.) (lit.)
- Density
- 2.2076 · 2.2076 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 3 aq · Very faint turbidity in NH3aq. Soluble in 1M NaOH.
- pka
- 7.02 · 7.02±0.10(Predicted)
- form
- Fluffy Powder
- color
- White to light yellow
- Water Solubility
- SOLUBLE IN COLD WATER
- Sensitive
- Light Sensitive
- BRN
- 4891 · 4891
- InChI
- InChI=1S/C4H3IN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (91.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information2,4(1H,3H)-Pyrimidinedione, 5-iodo-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (91.5%)
Safety data
- PPE
- Eyeshields, Gloves, type P2 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- YR0525000
- ridadr
- 2811
- hs_code
- 29335990
- risk_code
- 46-20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- T,Xi
- hazard_note
- Irritant/Carcinogenic/Light Sensitive
- safety_code
- 53-22-26-36/37/39-45
Chemistry & industry
Uses & manufacturing
General Manufacturing Information2,4(1H,3H)-Pyrimidinedione, 5-iodo-: INACTIVE
Applications
Uses5-Iodouracil is a halogenated pyrimidine that can be used in nucleoprotein photo-crosslinking via RNA substitution. 5-Iodouracil is used in thymidine phosphorylase targeted imaging and therapy. Studies show that DNA N-glycosylase MED1 exhibited higher preference for 5-Iodouracil and halogenated bases over non-halogenated ones.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
常州帝通化工有限公司+86-0519-88298848 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司
Related reactions
35 records
Compound notes
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