147091-08-5

Basic information

• Product Name: (R)-a-isothiocyanato-Benzenepropanoic acid methyl ester
• Synonyms: (R)-a-isothiocyanato-Benzenepropanoic acid methyl ester;(R)-Alfa-isothiocyanato-Benzenepropanoic acid methyl ester
• CAS NO: 147091-08-5
• Molecular Formula: C11H11NO2S
• Molecular Weight: 221.28
• Mol File: 147091-08-5.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 335.2°C at 760 mmHg
• Flash Point: 156.5°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 0.000121mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: (R)-a-isothiocyanato-Benzenepropanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-a-isothiocyanato-Benzenepropanoic acid methyl ester(147091-08-5)
• EPA Substance Registry System: (R)-a-isothiocyanato-Benzenepropanoic acid methyl ester(147091-08-5)

Safety Data

• Hazardous Substances Data: 147091-08-5(Hazardous Substances Data)

Usage

General Description

(R)-a-isothiocyanato-Benzenepropanoic acid methyl ester is a chemical compound with the molecular formula C11H11NO2S. It is an ester derivative of a benzenepropanoic acid, with a substituted isothiocyanato group. (R)-a-isothiocyanato-Benzenepropanoic acid methyl ester is commonly used in organic synthesis and pharmaceutical research due to its ability to react with amino compounds to form stable thioureas, which are important building blocks in the development of various pharmaceutical drugs. It also has potential applications in the development of herbicides and insecticides due to its ability to inhibit the growth of certain plant and insect species. However, it is also important to handle this compound with caution, as excessive exposure or ingestion can result in harmful effects to human health.

InChI:InChI=1/C11H11NO2S/c1-14-11(13)10(12-8-15)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3/t10-/m1/s1

Upstream product

• 463-71-8 thiophosgene 
• 13033-84-6 D-phenylalanine methyl ester hydrochloride 
• 1428047-03-3 C₁₁H₁₃NO₂S₂ 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 75-15-0 carbon disulfide 
• 63-91-2 L-phenylalanine 
• 63526-79-4 methyl 2-isocyano-3-phenylpropanoate 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 15028-44-1 DL-phenylalanine methyl ester 

Relevant articles and documents

New mild and simple approach to isothiocyanates: A class of potent anticancer agents

In our current work, acetyl chloride-mediated synthesis of phenethyl isothiocyanate (PEITC) derivatives proves to be convenient and provides the expected products at good to excellent yields. Biological evaluation and structure-activity relationship analysis found that the novel compound 7 showed the best anticancer activity against human cancer cell line Panc1 and HGC27 compared with PEITC. Compounds 6 and 7 induced more apoptosis in pancreatic cancer cells but less toxicity in non-cancer cells. Further biological study demonstrated that 7 substantially increased intracellular reactive oxygen species (ROS) and depleted glutathione (GSH), leading to an oxidative stress to kill cancer cell.

A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur

Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is

Synthesis, biological activity and in silico pharmacokinetic prediction of a new 2-thioxo-imidazoldidin-4-one of primaquine

The discovery of novel antiparasitic drugs for neglected tropical diseases (NTDs) constitutes a global urgency and requires a range of innovative strategies to ensure a sustainable pipeline of lead compounds. Thus far, primaquine (PQ) is the only transmis

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.