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HomeProduct name list1-Naphthyl isothiocyanate

1-Naphthyl isothiocyanate

  • CAS NO.:551-06-4
  • Empirical Formula: C11H7NS
  • Molecular Weight: 185.24
  • MDL number: MFCD00003882
  • EINECS: 208-990-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-04 17:34:39
1-Naphthyl isothiocyanate Structural

What is 1-Naphthyl isothiocyanate?

Description

1-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 properties

white crystalline powder

The Uses of 1-Naphthyl isothiocyanate

1-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.

The Uses of 1-Naphthyl isothiocyanate

1-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.

The Uses of 1-Naphthyl isothiocyanate

1-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.

What are the applications of Application

1-Naphthyl isothiocyanate is a tool for the study of liver damage

Definition

ChEBI: 1-naphthyl isothiocyanate is an isothiocyanate. It has a role as an insecticide. It derives from a hydride of a naphthalene.

General Description

Odorless white needles or powder. Tasteless.

Air & Water Reactions

1-Naphthyl isothiocyanate is moisture sensitive. . Undergoes slow hydrolysis. Insoluble in water.

Reactivity Profile

Isocyanates 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 Hazard

Flash point data for 1-Naphthyl isothiocyanate is not available, but 1-Naphthyl isothiocyanate is probably combustible.

Environmental Fate

Naphthylisothiocyanate is moisture sensitive and insoluble in water. The hydrolysis rate is slow.

Purification Methods

Crystallise 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 evaluation

1-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.

Properties of 1-Naphthyl isothiocyanate

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 Reference 551-06-4(CAS DataBase Reference)
NIST Chemistry Reference Naphthalene, 1-isothiocyanato-(551-06-4)
EPA Substance Registry System 1-Naphthylisothiocyanate (551-06-4)

Safety information for 1-Naphthyl isothiocyanate

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Health Hazard
GHS08
GHS Hazard Statements H301:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H334:Sensitisation, respiratory
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 1-Naphthyl isothiocyanate

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