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N4525

Sigma-Aldrich

1-Naphthyl isothiocyanate

95%

Synonym(s):

α-Naphthyl isothiocyanate, 1-Isothiocyanatonaphthalene, Naphthalen-1-yl isothiocyanate

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About This Item

Linear Formula:
C10H7NCS
CAS Number:
551-06-4
Molecular Weight:
185.24
EC Number:
208-990-8
MDL number:
MFCD00003882
UNSPSC Code:
12352100
PubChem Substance ID:
24897706
NACRES:
NA.22

assay

95%

form

solid

mp

55.5-57 °C (lit.)

SMILES string

S=C=Nc1cccc2ccccc12

InChI

1S/C11H7NS/c13-8-12-11-7-3-5-9-4-1-2-6-10(9)11/h1-7H

InChI key

JBDOSUUXMYMWQH-UHFFFAOYSA-N

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Application

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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Synthesis and antimicrobial activity of some pyridyl and naphthyl substituted 1, 2, 4-triazole and 1, 3, 4-thiadiazole derivatives.
Zamani K, et al.
Turkish Journal of Chemistry, 28(1), 95-100 (2004)
Calix [4] arenes containing thiourea and amide moieties: neutral receptors towards ?, ?-dicarboxylate anions.
Liu SY, et al.
Organic & Biomolecular Chemistry, 2(11), 1582-1586 (2004)
Bradley P Sullivan et al.
Toxicological sciences : an official journal of the Society of Toxicology, 115(1), 286-294 (2010-02-06)
Alpha-naphthylisothiocyanate (ANIT) causes cholestatic hepatitis characterized by intrahepatic bile duct epithelial cell injury and periportal hepatocellular necrosis. The progression of ANIT-induced hepatocyte injury is reported to involve extrahepatic cells including platelets. We showed recently that the procoagulant protein tissue factor
James P Luyendyk et al.
Toxicological sciences : an official journal of the Society of Toxicology, 119(1), 233-243 (2010-10-27)
Alpha-naphthylisothiocyanate (ANIT)-induced cholestatic liver injury causes tissue factor (TF)-dependent coagulation in mice, and TF deficiency reduces ANIT-induced liver injury. However, the mechanism whereby TF contributes to hepatotoxicity in this model is not known. Utilizing pharmacological and genetic strategies, we evaluated
Fan Yang et al.
Journal of ethnopharmacology, 144(3), 599-604 (2012-10-13)
To evaluate the hepatoprotective effect of the root and rhizome of Rhubarb (Rhei Radix et Rhizoma) against α-naphthylisothiocyanate (ANIT)-induced liver injury using metabolic profile of bile acids (BAs) along with biochemical parameters and histological alterations. Ultra-performance liquid chromatography coupled with
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