Nin-Formyl-D-tryptophan hydrochloride
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Nin-Formyl-D-tryptophan hydrochloride

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Category
D-Amino Acids
Catalog number
BAT-003540
CAS number
367453-01-8
Molecular Formula
C12H12N2O3·HCl
Molecular Weight
268.74
Nin-Formyl-D-tryptophan hydrochloride
IUPAC Name
(2R)-2-amino-3-(1-formylindol-3-yl)propanoic acid;hydrochloride
Synonyms
D-Trp(For)-OH HCl; H-D-TRP(FOR)-OH HCl
Appearance
Off-white powder
Purity
≥ 99% (HPLC)
Melting Point
214-220 °C (dec.)
Storage
Store at 2-8 °C
InChI
InChI=1S/C12H12N2O3.ClH/c13-10(12(16)17)5-8-6-14(7-15)11-4-2-1-3-9(8)11;/h1-4,6-7,10H,5,13H2,(H,16,17);1H/t10-;/m1./s1
InChI Key
GWYUYJDIFZXFJT-HNCPQSOCSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(=CN2C=O)CC(C(=O)O)N.Cl
1. 1-Haloacylpiperazines
S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.
By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.
2. Metal-free and regiospecific synthesis of 3-arylindoles
Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.
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