Basic information
- CAS
141-84-4- Standard SMILES
O=C1CSC(=S)N1- InChIKey
KIWUVOGUEXMXSV-UHFFFAOYSA-N- Molecular formula
- C3H3NOS2
- Average molar mass
- 133.2 g/mol
- Monoisotopic mass
- 132.96560572
Overview
Rhodanine appears as light yellow crystals. Density 0.868 g / cm3. Melting point 168.5 °C. May explode on rapid heating.
Names & identifiers
- Preferred name
- Rhodanine
- IUPAC
- 2-sulfanylidene-1,3-thiazolidin-4-one
- English name
- Rhodanine
- Molecular formula
- C3H3NOS2
- Molecular weight
- 133.19
Names & synonyms
Show more names
Database identifiers
- CAS
141-84-4、6913-23-1- PubChem CID
- 1201546
- DTXSID
DTXSID4026002- ChEMBL
CHEMBL224633- ChEBI
CHEBI:8830- UNII
- 7O50LKL2G8
- EC Number
- 205-505-1
- Nikkaji
- J5.808D
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 86.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 122
Experimental & physicochemical properties
Density
0.868 (NTP, 1992) - Less dense than water; will float
0.868
BULK DENSITY 0.617
Color/Form
PALE YELLOW CRYSTALS (LONG BLADES) FROM GLACIAL ACETIC ACID OR WATER
LIGHT YELLOW PRISMS FROM ALCOHOL
Solubility
Very soluble (NTP, 1992)
FREELY SOL IN BOILING WATER, IN METHANOL, ETHANOL, DIMETHYLFORMAMIDE, ETHER, ALKALIES, AMMONIA, HOT ACETIC ACID
SLIGHTLY SOL IN WATER; INSOL IN PETROLEUM ETHER
>20 [ug/mL] (The mean of the results at pH 7.4)
Melting Point
335.3 °F (NTP, 1992)
168.5 °C (CAPILLARY); 170.5-171 °C (HOT STAGE)
Physical Description
Rhodanine appears as light yellow crystals. Density 0.868 g / cm3. Melting point 168.5 °C. May explode on rapid heating.
Pale yellow solid; [Merck Index] Light yellow powder; [MSDSonline]
Physicochemical properties
- Melting point
- 165 · 165-169 °C(lit.)
- Density
- 0.868 · 0.868
- refractive index
- 1.5231 · 1.5231 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 0.5 g/10 · methanol: soluble0.5g/10 mL, clear, colorless to greenish-yellow
- form
- Fine Crystalline Powder
- pka
- pK (25°) 5.52
- color
- Light yellow to beige
- Water Solubility
- SOLUBLE IN HOT WATER
- Merck
- 14 · 14,8184
- BRN
- 110701 · 110701
- InChI
- InChI=1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6)
- InChIKey
- KIWUVOGUEXMXSV-UHFFFAOYSA-N
- SMILES
- S1CC(=O)NC1=S
- CAS DataBase Reference
- 141 · 141-84-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 7 O50LKL2G8 · 7O50LKL2G8
- NIST Chemistry Reference
- 2 · 2-Thioxo-4-thiazolidinone(141-84-4)
- EPA Substance Registry System
- Rhodanine (141-84-4)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H319
- Precautionary statements
- 301 · P301+P312+P330-P305+P351+P338
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-41
- Safety Statements
- 22 · 22-26-39
- RIDADR
- 3288 · 3288
- WGK Germany
- 3 · 3
- RTECS
- 7700000 · VI7700000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- II
- HS Code
- 29341000 · 29341000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2
- Hazardous Substances Data
- 141 · 141-84-4(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 4-Thiazolidinone, 2-thioxo-
2-Thioxo-4-thiazolidinone: Does not have an individual approval but may be used under an appropriate group standard
Safety & protection
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Storage Conditions
MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED...
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Dampen spilled material with alcohol to avoid dust, then transfer material to a suitable container. Use absorbent paper dampened with alcohol to pick up remaining material. Wash surface well with soap and water. Seal all wastes in vapor-tight plastic bags for eventual disposal.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Non-Human Toxicity Excerpts
Rhodanine was tested for mutagenicity in the Salmonella/microsome preincubation assay using a protocol approved by the National Toxicology Program. Rhodanine was tested over a wide range of doses (0, 10, 33, 100, 333, and 1000 ug/plate) in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. Rhodanine was negative in these tests and the highest ineffective dose level tested in any Salmonella tester strain was 1000 ug/plate.
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- VI7700000
- ridadr
- 3288
- hs_code
- 29341000
- risk_code
- 22-41
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-26-39
- hazard_class
- 6.1(a)
- Storage Class
- 11 - Combustible Solids
- packing_group
- II
- Hazard statements
- H302-H319
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2
- Precautionary statements
- P301+P312+P330-P305+P351+P338
- Hazardous Substances Data
- 141-84-4(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as a fungicide, laboratory reagent, and intermediate for phenylalanine and cyanine dyes; Not produced commercially in the US; [HSDB]
Farming (Pesticides) [Category: Industry]
FUNGICIDE
CHEMICAL INTERMEDIATE FOR PHENYLALANINE & CYANINE DYES; LABORATORY REAGENT
U.S. Exports
(1977) No Data
(1979) No Data
U.S. Imports
(1977) No Data
(1979) No Data
U.S. Production
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
Applications
Usesthiadiazole pharmaceutical intermediate
UsesIn the case of reagents containing several potential donor atoms, one of the first steps in the study of complex formation is the specification of the functional groups which actually participate in the complexation reaction. The literature on rhodanine derivatives provides a good example of such examinations.
UsesIn the synthesis of phenylalanine.
General DescriptionLight yellow crystals. Density 0.868 g / cm3. Melting point 168.5°C. May explode on rapid heating.
Upstream & downstream products
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: Rhodanine is a thiazolidinone.
Related reactions
Compound notes
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