Rhodanine

HCID 1201546

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

RHODANINE141-84-42-thioxothiazolidin-4-one2-Thioxo-4-thiazolidinone4-Thiazolidinone, 2-thioxo-Rhodaninic acidRhodaninRhodanic acid4-Oxo-2-thioxothiazoline2-Thio-4-ketothiazolidineRodaninUSAF HA-2
Show more names
AKOS BBS-00000851Argentonusafha-2RSOdanin
4-Thiazolidinone-2-thione4-Oxo-2-thionothiazolidine4-Oxo-2-thiothiazolidin4-Thioxo-4-thiazolidone2,4-Thiazolidinedione, 2-thio-7O50LKL2G8NSC-1899DTXSID4026002

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

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Organic Compounds
SpringerMaterials PropertiesCrystal structure
Density · 3 items

0.868 (NTP, 1992) - Less dense than water; will float

0.868

BULK DENSITY 0.617

Color/Form · 2 items

PALE YELLOW CRYSTALS (LONG BLADES) FROM GLACIAL ACETIC ACID OR WATER

LIGHT YELLOW PRISMS FROM ALCOHOL

Solubility · 4 items

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)

Endocrine DisruptorsPotential endocrine disrupting compound

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

Chemical: 4-Thiazolidinone, 2-thioxo-

2-Thioxo-4-thiazolidinone: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryEmergency treatment: Irritants; [HSDB] Toxic by ingestion; [Hawley] May explode from rapid heating; [Merck Index] An irritant that may cause serious eye injury; [MSDSonline]
Reactive GroupAmides and Imides
Reactivity ProfileRHODANINE may generate hydrogen sulfide with acids. May generate heat and hydrogen gas with alkali metals, nitrides, hydrides, and other strong reducing agents.
Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety & protection

First Aid · 1 item

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 · 1 item

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 · 1 item

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) · 1 item

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

Human Toxicity Excerpts...toxic by ingestion.
Non-Human Toxicity Excerpts · 1 item

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

Chemistry & industry

Uses & manufacturing

Uses · 4 items

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 · 2 items

(1977) No Data

(1979) No Data

U.S. Imports · 2 items

(1977) No Data

(1979) No Data

U.S. Production · 2 items

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

Methods of ManufacturingREACTION OF SODIUM CHLOROACETATE WITH AMMONIUM DITHIOCARBAMATE
General Manufacturing Information4-Thiazolidinone, 2-thioxo-: ACTIVE
Applications · 4 items

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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [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021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]

Additional notes

DefinitionChEBI: Rhodanine is a thiazolidinone.

Related reactions

341 records

Compound notes

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