21055-46-9

Basic information

• Product Name: METHYL L-2-ISOTHIOCYANATO-3-PHENYLPROPIONATE
• Synonyms: Benzenepropanoic acid, α-isothiocyanato-, methyl ester
• CAS NO: 21055-46-9
• Molecular Formula: C₁₁H₁₁NO₂S
• Molecular Weight: 221.28
• Mol File: 21055-46-9.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL L-2-ISOTHIOCYANATO-3-PHENYLPROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL L-2-ISOTHIOCYANATO-3-PHENYLPROPIONATE(21055-46-9)
• EPA Substance Registry System: METHYL L-2-ISOTHIOCYANATO-3-PHENYLPROPIONATE(21055-46-9)

Safety Data

• Hazardous Substances Data: 21055-46-9(Hazardous Substances Data)

Upstream product

• 63526-79-4 methyl 2-isocyano-3-phenylpropanoate 
• 5619-07-8 methyl 2-amino-3-phenylpropanoate hydrochloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 75-15-0 carbon disulfide 
• 15028-44-1 DL-phenylalanine methyl ester 

Relevant articles and documents

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

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.

Gas chromatography of amino acids as N-thiocarbonyl ester derivatives.

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