201For the reconstruction of shooting events, gunshot residues are an indispensable aid in forensic investigations. For example, the analysis of gunshot residues provides evidence for the type of ammunition used. The area distribution of residues around the target is a measure for the shooting distance.The gunshot residue is in many cases invisible for the naked eye. Its detection is performed by measuring certain typical components of the ammunition (leading elements) in residues by chemical or spectroscopic means. For common ammunition, these leading elements are typically heavy metals such as lead, barium, or antimony. Preferentially, sensitive wet-chemistry colour reactions with certain complex-forming agents have been used for visualizing the area distribution of these compounds on a target (e.g., rhodizonic acid, disodium salt, C 6 Na 2 O 6 , for lead and barium [1]). Physical methods are also used for the detection of residues (e.g., X-ray fluorescence analysis, scanning electron microscopy, and ICP mass spectrometry [2]).For more than ten years a new ammunition is available, the so-called 'toxin-reduced' or 'lead-free' ammunition. For this type of ammunition, the classical methods for analysis of gunshot residues are naturally not applicable. The bullets have lead cores that are surrounded by a copper/zinc alloy and do not leave behind traces of lead or of other heavy metals typical for conventional ammunition. However, such ammunition leaves behind copper and zinc as telltale metals, sometimes boron. For the detection of copper and zinc, the azo dye Chlorindazone DS 1 has been used in criminology as a suitable reagent [2]. The coloured reaction products are highly specific for these elements: Chlorindazone DS 1 generates a purple complex with zinc ions and a blue one with copper ions [3]. Chlorindazone DS 1 was first described in 1969 as a reagent for the formation of coloured metal ion complexes including of copper and zinc [3]. These complexes were measured by spectrophotometric methods [4]. Besides these applications, indicator strips containing Chlorindazone DS 1 subsequently have been used for measuring calcium and magnesium ions in water [5]. Abstract. Recently, Chlorindazone DS 1 has become an important analytical reagent for the detection of gunshot residues from newly introduced ammunition. A simplified synthesis of the precursor of the azo dye 1, 3-amino-6-chloroindazole (2), from commercially available 2,4-dichlorobenzonitrile (3a) has been described. The physical and spectroscopiChlorindazone DS 1 can be readily prepared from 3-amino-6-chloroindazole (2) (see [6] for applications) and 2-hydroxynaphthalene-3,6-disulfonic acid, disodium salt (Fluka). However, the amine 2 is not easily obtained [7]. We present a substantially simplified preparation of 2 by using the commercially available 2,4-dichlorobenzonitrile (3a) (Merck) as starting material.cal properties of the known compounds 1 and 2 have been completed. 2-Chloro-4-hydrazinobenzonitrile (4a), 2-bromo-4-hydrazinobenzonitrile (4b) and a ne...