1-Naphthyl isothiocyanate

1-Naphthyl isothiocyanate Basic information
Product Name:1-Naphthyl isothiocyanate
Synonyms:1-Isothiocyanatenaphthalene;1-isothiocyanate-naphthalene;1-NAPHTHYL ISOTHIOCYANATE >95%;1-NAPHTHYL ISOTHIOCYANATE 98%;1-Naphthyl senfoel;1-Naphthyl isothiocyanate,98%;1-NAPTHYL ISOTHIOCYANATE;1-Naphthyl isothiocyanate, 98% 5GR
CAS:551-06-4
MF:C11H7NS
MW:185.24
EINECS:208-990-8
Product Categories:Thiocyanates/IsothiocyanatesDerivatization Reagents;Derivatization Reagents HPLC;Organic Building Blocks;Sulfur Compounds;UV-VIS
Mol File:551-06-4.mol
1-Naphthyl isothiocyanate Structure
1-Naphthyl isothiocyanate Chemical Properties
Melting point 55.5-57 °C(lit.)
Boiling point 190 °C(Press: 20 Torr)
density 1.1142 (rough estimate)
refractive index 1.5500 (estimate)
storage temp. 2-8°C
form Fine Crystalline Powder
color Yellow
Water Solubility insoluble
Sensitive Moisture Sensitive
Merck 14,6411
BRN 637868
Stability:Stable, but moisture sensitive. Incompatible with strong oxidizing agents.
CAS DataBase Reference551-06-4(CAS DataBase Reference)
NIST Chemistry ReferenceNaphthalene, 1-isothiocyanato-(551-06-4)
EPA Substance Registry System1-Naphthylisothiocyanate (551-06-4)
Safety Information
Hazard Codes T
Risk Statements 20/21-25-36/37/38-42-23/24/25
Safety Statements 22-26-36/37-45-24/25
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS NX9100000
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29309090
MSDS Information
ProviderLanguage
1-Naphthyl isothiocyanate English
SigmaAldrich English
ACROS English
ALFA English
1-Naphthyl isothiocyanate Usage And Synthesis
Description1-Napthylisothiocyanate is a toxic chemical that has been used to create experimental cholestasis in rodents. Laboratory studies have also shown that 1-napthylisothiocyanate can act as a chemoprotectant in rodents challenged with a tumorinducing agent such as phorbol-12 myristate 13-acetate.
Chemical Propertieswhite crystalline powder
Uses1-Naphthylisothiocyanate is used as an ingredient in insecticides. It is also found in cyanamide, which is used in many industrial applications. It is commonly used in medical and drug studies in animals as a model hepatotoxicant producing experimental cholestasis in rats and mice.
Uses1-Naphthyl isothiocyanate is a tool for the study of liver damage which causes bile stasis and hyperbilirubinemia acutely and bile duct hyperplasia and biliary cirrhosis chronically, with changes in hepatocyte function.
Uses1-Naphthyl isothiocyanate (NITC) can be used as a source of thiourea moiety to synthesize derivatives of calix[4]arenes to be used as anion acceptors. It can also be used for the synthesis of naphthyl substituted 1,2,4-triazoles and 1,3,4-thiadiazoles.
DefinitionChEBI: 1-naphthyl isothiocyanate is an isothiocyanate. It has a role as an insecticide. It derives from a hydride of a naphthalene.
General DescriptionOdorless white needles or powder. Tasteless.
Air & Water Reactions1-Naphthyl isothiocyanate is moisture sensitive. . Undergoes slow hydrolysis. Insoluble in water.
Reactivity ProfileIsocyanates and thioisocyanates, such as 1-Naphthyl isothiocyanate, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].
Fire HazardFlash point data for 1-Naphthyl isothiocyanate is not available, but 1-Naphthyl isothiocyanate is probably combustible.
Environmental FateNaphthylisothiocyanate is moisture sensitive and insoluble in water. The hydrolysis rate is slow.
Purification MethodsCrystallise the isothiocyanate from hexane (1g in 9 mL). It forms white needles and is soluble in most organic solvents but is insoluble in H2O. It is absorbed through the skin and may cause dermatitis. [Cymmerman-Craig et al. Org Synth Coll Vol IV 700 1963, Beilstein 12 H 1244, 12 III 2948.]
Toxicity evaluation1-Naphthylisothiocyanate causes separation of extracellular tight junctions that seal bile canaliculi, impairing bile formation. 1-Naphthylisothiocyanate inhibits microsomal drug-metabolizing activity. In rats, 1-naphthylisothiocyanteglutathione complex is formed in hepatocytes, then transported to the bile ducts, where it is released from the glutathione, and then selectively injures biliary epithelial cells, resulting in reduced bile flow.
6-CHRYSENYLISOTHIOCYANATE ISOTHIOCYANATE, POLYMER-BOUND, 200-400 9-PHENANTHRYLISOTHIOCYANATE 1-PYRENEISOTHIOCYANATE Fluorescein isothiocyanate Phenyl isocyanate Liranaftate 1,4-PHENYLENE DIISOTHIOCYANATE 1-(1-NAPHTHYL)-2-THIOUREA ISOCYANIC ACID Phenyl isothiocyanate 6-BENZO[A]PYRENYLISOTHIOCYANATE Chlorosulfonyl isocyanate Isocyanatocyclohexane 5-HYDROXYNAPHTHYLISOTHIOCYANATE 1-Naphthyl isothiocyanate Allyl isothiocyanate 8-ISOTHIOCYANATOPYRENE-1,3,6-TRISULFONIC ACID TRISODIUM SALT

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