551-06-4 Usage
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
Uses
Different sources of media describe the Uses of 551-06-4 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 551-06-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 551-06:
(5*5)+(4*5)+(3*1)+(2*0)+(1*6)=54
54 % 10 = 4
So 551-06-4 is a valid CAS Registry Number.
InChI:InChI=1/C11H7NS/c13-8-12-11-7-3-5-9-4-1-2-6-10(9)11/h1-7H
551-06-4Relevant articles and documents
Tetrabutylammonium Iodide/I2 Mediated Convenient and Green Synthesis of Substituted Organic Isothiocyanates
Srivastava, Nitin
, p. 562 - 570 (2021/10/07)
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Design, synthesis, and biological evaluation of novel substituted thiourea derivatives as potential anticancer agents for NSCLC by blocking K-Ras protein-effectors interactions
Cheng, Minghui,Meng, Xin,Tang, Haikang,Xu, Wenqing,Yang, Fujun,Zhang, Yuan
, p. 344 - 353 (2019/12/30)
Mutation of the proto-oncogene K-Ras is one of the most common molecular mechanisms in non-small cell lung cancer. Many drugs for treating lung cancer have been developed, however, due to clinical observed K-Ras mutations, corresponding chemotherapy and targeted therapy for such mutation are not efficient enough. In this study, on the basis of the crystal structure of K-Ras, 21 analogues (TKR01–TKR21) containing urea or thiourea were rationally designed, which can effectively inhibit the lung cancer cell A549 growth. The designing of these compounds was based on the structure of K-Ras protein, and the related groups were replaced by bioisosteres to improve the affinity and selectivity. Biological testing revealed that compound TKR15 could significantly inhibit the proliferation of A549 cell with IC50 of 0.21 μM. Docking analysis showed that the TKR15 can effectively bind to the hydrophobic cavity and form a hydrogen bond with the Glu37. In addition, through flow apoptosis assay and immunofluorescence staining assay, it confirmed that this compound can inhibit A549 cell proliferation with the mechanism of blocking K-RasG12V protein and effector proteins interactions through the apoptotic pathway. In conclusion, our studies in finding novel potent compound (TKR15) with confirmed mechanism showed great potential for further optimisation and other medicinal chemistry relevant studies.
Isothiocyanate synthesized by three components and preparation method of isothiocyanate
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Paragraph 0034, (2019/04/26)
The invention discloses isothiocyanate and a preparation method thereof. The method comprises the steps that primary amine, sodium difluorobromoacetate and elemental sulfur are taken as reactants forreaction; the reaction is carried out under the action of a copper catalyst, wherein the copper catalyst is any one of cuprous chloride, copper bromide, cuprous iodide, copper chloride and copper trifluoromethanesulfonate; an alkali is also added, wherein the alkali is any one of sodium bicarbonate, potassium carbonate, cesium carbonate, potassium phosphate, DABCO and sodium tert-butoxide; the whole reaction is carried out in a solvent, wherein the solvent is acetonitrile or dimethyl sulfoxide, the reaction temperature is 80-120 DEG C, and the reaction time is 10-14 hours. The method can directly synthesize the target product, does not need to separate intermediate products and only needs stirring and heating reaction under normal pressure to obtain the target product, and the yield can beup to 87%; a waste solution is fewer during the reaction, and the method protects the environment and ensures the health of an operator; in addition, a series of isothiocyanate derivatives can be prepared, and the method has a stronger substrate universality.
