4430-47-1

Basic information

• Product Name: 3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE
• Synonyms: 5-ISOTHIOCYANATOMETHYL-BENZO[1,3]DIOXOLE;3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE;1,3-BENZODIOXOL-5-YLMETHYL ISOTHIOCYANATE;5-Isothiocyanatomethyl-1,3-benzodioxole;1,3-Benzodioxol-5-ylmethyl isothiocyanate, 95%+;3,4-(Methylenedioxy)benzyl isothiocyanate, (1,3-Benzodioxol-5-yl)methyl isocyanate;3,4-Methylenedioxybenzyl isothiocyate, 99%
• CAS NO: 4430-47-1
• Molecular Formula: C₉H₇NO₂S
• Molecular Weight: 193.22
• EINECS: -0
• Mol File: 4430-47-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 140 °C
• Flash Point: 139-140°C/1mm
• Appearance: /
• Density: 1.32
• Vapor Pressure: 0.000596mmHg at 25°C
• Refractive Index: 1.6150
• Water Solubility: Hydrolyses in water.
• Sensitive: Moisture Sensitive
• BRN: 1428941
• CAS DataBase Reference: 3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE(4430-47-1)
• EPA Substance Registry System: 3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE(4430-47-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2810
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 4430-47-1(Hazardous Substances Data)

Usage

Description

3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE is an organic compound characterized by the presence of a methylenedioxybenzyl group and an isothiocyanate functional group. It is known for its reactivity in various chemical reactions, particularly nucleophilic addition reactions, making it a versatile building block in the synthesis of different organic molecules.

Uses

Used in Chemical Synthesis:
3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE is used as an intermediate in the chemical synthesis of various organic compounds. Its unique structure allows it to participate in nucleophilic addition reactions, which are crucial for the formation of new chemical bonds and the creation of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE is used as a key intermediate in the synthesis of bioactive molecules with potential therapeutic applications. Its ability to undergo nucleophilic addition reactions enables the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE is also utilized in the agrochemical industry for the synthesis of compounds with pesticidal properties. Its reactivity in nucleophilic addition reactions allows for the creation of new molecules with enhanced insecticidal, herbicidal, or fungicidal activities.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE serves as an intermediate for the production of various colored compounds. Its unique structure contributes to the development of dyes and pigments with improved color intensity, stability, and application properties.
Overall, 3,4-(METHYLENEDIOXY)BENZYL ISOTHIOCYANATE is a valuable compound in various industries due to its reactivity and versatility in chemical synthesis, making it a crucial component in the development of new molecules with diverse applications.

InChI:InChI=1/C9H7NO2S/c13-5-10-4-7-1-2-8-9(3-7)12-6-11-8/h1-3H,4,6H2

Upstream product

• 1158178-28-9 C₆H₁₅N*C₉H₉NO₂S₂ 
• 2620-50-0 1,3-benzodioxol-5-ylmethyl amine 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 75-15-0 carbon disulfide 

Downstream Products

• 1001554-37-5 C₁₆H₁₅BrN₂O₂S 
• 206761-70-8 4-piperonyl thiosemicarbazide 
• 107057-26-1 [1,4]benzoquinone-carbamimidoylhydrazone-(4-piperonyl thiosemicarbazone) 

Relevant articles and documents

A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide

A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.

Synthesis and structure-activity relationship of non-peptidic antagonists of neuropilin-1 receptor

Neuropilins (NRPs) are VEGF-A165 co-receptors over-expressed in tumor cells, and considered as targets in angiogenic-related pathologies. We previously identified compound 1, the first non-peptidic antagonist of the VEGF-A165/NRP binding, which exhibits in vivo anti-angiogenic and anti-tumor activities. We report here the synthesis and biological evaluations of new antagonists structurally-related to compound 1. Among these molecules, 4a, 4c and 4d show cytotoxic effects on HUVEC and MDA-MB-31 cells, and antagonize VEGF-A165/NRP-1 binding. This study confirmed our key structure-activity relationships hypothesis and paved the way to compound 1 'hit to lead' optimization.

Synthesis and cytotoxic evaluation of quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or N-methyldithiocarbamate side Chains

We have previously found that the dithiocarbamate derivatives of quinazolin-4(3H)-one could act as cytotoxic agents against a panel of human tumor cell lines. To investigate the contribution of dithiocarbamate moiety to the cytotoxic activity, three series of novel quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or Nmethyldithiocarbamate side chains were synthesized and tested for their cytotoxic activity against human cancer cell lines A549, MCF-7, HeLa, HT29 and HCT-116 by MTT assay. The results showed that transformation of the dithiocarbamate moiety in lead compound I to thiocarbamate or thiourea led to a decrease or loss of cytotoxic activity. Some N-alkylated analogs of lead compound II preferentially inhibited the proliferation of A549 cells, although their potencies were not improved in comparison with the unalkylated counterparts. The structure-activity relationship obtained in this research will be beneficial for further synthesis and discovery of effective cytotoxic agents.