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Pietro Biginelli (25 July 1860 – 15 January 1937) was an Italian chemist, who discovered a three-component reaction between
urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...
, acetoacetic ester and
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
s (
Biginelli reaction The Biginelli reaction is a multiple-component chemical reaction that creates 3,4-dihydropyrimidin-2(1''H'')-ones 4 from ethyl acetoacetate 1, an aryl aldehyde (such as benzaldehyde 2), and urea 3. It is named for the Italian chemist Pietro Bigi ...
). He also studied various aspects of sanitation chemistry and chemical products' quality control.


Biography

Biginelli is born on 25 July 1860 in
Palazzolo Vercellese Palazzolo Vercellese (''Palasseu'' in Piedmontese) is a ''comune'' (municipality) in the Province of Vercelli in the Italian region Piedmont, located about northeast of Turin and about southwest of Vercelli. As of 31 December 2004, it had a popu ...
which was back then the Kingdom of
Piedmont-Sardinia The Kingdom of Sardinia,The name of the state was originally Latin: , or when the kingdom was still considered to include Corsica. In Italian it is , in French , in Sardinian , and in Piedmontese . also referred to as the Kingdom of Savoy-S ...
. He attended the
University of Turin The University of Turin (Italian language, Italian: ''Università degli Studi di Torino'', UNITO) is a public university, public research university in the city of Turin, in the Piedmont (Italy), Piedmont region of Italy. It is one of the List ...
, studying under
Icilio Guareschi Icilio Guareschi (24 December 1847 – 20 June 1918) was an Italian chemist. Icilio Guareschi studied at the University of Bologna and received his Ph.D there in 1871. He became professor at the University of Siena and in 1879 at the Universi ...
, a well-known Italian chemist and chemistry historian.Istituto Superiore di Sanitа. Microanalisi elementare organica. Collezione di strumenti a cura di Anna Farina e Cecilia Bedetti. 2007, I beni storico-scientifi ci dell’Istituto Superiore di Sanitа, p 24 In 1885, he was already a 4th-year student. By 1891, Biginelli worked at the chemical laboratory at the
University of Florence The University of Florence (Italian: ''Università degli Studi di Firenze'', UniFI) is an Italian public research university located in Florence, Italy. It comprises 12 schools and has around 50,000 students enrolled. History The first universi ...
,Biginelli P. Ueber Aldehyduramide des Acetessigaethers. ''
Berichte der Deutschen Chemischen Gesellschaft ''Chemische Berichte'' (usually abbreviated as ''Ber.'' or ''Chem. Ber.'') was a German-language scientific journal of all disciplines of chemistry founded in 1868. It was one of the oldest scientific journals in chemistry, until it merged with ...
'', 1891, vol. 24, pp. 1317–1319.
where 2 years later he developed a method which later would be known as Biginelli Pyrimidine synthesis.'' J. Chem. Soc.'', Abstr., 1893, p. 645 In 1897, he was already in Rome, as a privatdozent. In 1901, Biginelli, as coadjutor, moved to the Chemical Laboratory of State Medicine in Rome, where he was working as an assistant of
Bartolomeo Gosio Bartolomeo Gosio (17 March 1863 – 13 April 1944) was an Italian medical scientist. He discovered a toxic fume, eponymously named "Gosio gas", which is produced by microorganisms, that killed many people. He identified the chemical nature of the g ...
, a chemist known for his discovery of arsenic-containing volatile gas known as "Gosio gas".Gosio, B., Action de quelques moisissures sure les composés fixes d’ársenic. '' Arch. Ital. Biol.'', 1893, vol. 18, pp. 253–265. From 1925 to 1928, Biginelli worked as a director of the above-mentioned chemical laboratory.Istituto Superiore di Sanitа. Microanalisi elementare organica. Collezione di strumenti a cura di Anna Farina e Cecilia Bedetti. 2007, I beni storico-scientifi ci dell’Istituto Superiore di Sanitа, p 26 He died in Rome on 15 January 1937.


Scientific interests

Biginelli's first known scientific work, in which he was a co-author of his mentor
Icilio Guareschi Icilio Guareschi (24 December 1847 – 20 June 1918) was an Italian chemist. Icilio Guareschi studied at the University of Bologna and received his Ph.D there in 1871. He became professor at the University of Siena and in 1879 at the Universi ...
, was focused on synthesis and reactivity of chlorobromonaphthalene. Already in the University of Florence, Biginelli described a three-component reaction between
urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...
,
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
, and
ethyl acetoacetate The organic compound ethyl acetoacetate (EAA) is the ethyl ester of acetoacetic acid. It is a colorless liquid. It is widely used as a chemical intermediate in the production of a wide variety of compounds. It is used as a flavoring for food. ...
, which was at first incorrectly interpreted as one leading to the formation of alpha-benzuramido-crotonacetic ester, or ethyl-alpha-salicyluramido-
crotonate Crotonic acid ((2''E'')-but-2-enoic acid) is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. It is called crotonic acid because it was erroneously thought to be a saponification product of croton oil. It cryst ...
with open-chain acyclic structures. However, later he corrected himself this interpretation and expanded his initial studies, showing that the end products actually were pyrimidines. However, Biginelli did not change the chemical names presented earlier. Another scope of his research interests emerged when he was assistant of Bartolomeo Gosio. At that time, it was known that certain poisonous volatile arsenic species tend to form at
mold A mold () or mould () is one of the structures certain fungi can form. The dust-like, colored appearance of molds is due to the formation of spores containing fungal secondary metabolites. The spores are the dispersal units of the fungi. Not ...
s growing on wallpapers painted by arsenic-containing paints. Finally, Gosio and Biginelli succeeded in isolating and analyzing the species: when Gosio gas was passed into a solution of
mercuric chloride Mercury(II) chloride (or mercury bichloride, mercury dichloride), historically also known as sulema or corrosive sublimate, is the inorganic chemical compound of mercury and chlorine with the formula HgCl2. It is white crystalline solid and is a ...
in dilute HCl (Biginelli's solution) a crystalline precipitate was formed. A small vial of the Gosio/Biginelli mercurichloride is to this day preserved at The Museum of the History of Medicine (Museo di Storia della Medicina) in Rome, Italy. Under the printed name "Laboratorio Batteriologico della Sanità Pubblica" is handwritten, "arsina penicillare comp. mercurico". From analysis of this material and of the gas itself it appeared that the gas was diethyl
arsine Arsine (IUPAC name: arsane) is an inorganic compound with the formula As H3. This flammable, pyrophoric, and highly toxic pnictogen hydride gas is one of the simplest compounds of arsenic. Despite its lethality, it finds some applications in ...
. Later, however, it was found that gas discovered by Gosio and Biginelli was in fact
trimethylarsine Trimethylarsine (abbreviated TMA or TMAs) is the chemical compound with the formula (CH3)3As, commonly abbreviated As Me3 or TMAs. This organic derivative of arsine has been used as a source of arsenic in microelectronics industry, a building bloc ...
. Biginelli stated in 1911 that
tannin Tannins (or tannoids) are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids. The term ''tannin'' (from Anglo-Norman ''tanner'' ...
has the formula C41H32O25 and that it was probably a glucoside. These conclusions were based on the property shown by tannin of forming additive products with water, alcohol, and ether, (which are stable even in vacuum) and also on the loss of
carbon dioxide Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is trans ...
and water with formation of hexa-hydroxy-
benzophenone Benzophenone is the organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. It is a white solid that is soluble in organic solvents. Benzophenone is a widely used building block in organic chemistry, being the parent diarylket ...
, when tannin is heated in aqueous solution with
lead dioxide Lead(IV) oxide is the inorganic compound with the formula PbO2. It is an oxide where lead is in an oxidation state of +4. It is a dark-brown solid which is insoluble in water. It exists in two crystalline forms. It has several important applicatio ...
(the amount of carbon dioxide liberated was estimated). In 1914, Biginelli showed that aristoquinine and
quinine Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to '' Plasmodium falciparum'' that is resistant to chloroquine when artesunate is not available. While sometimes used for nocturnal le ...
carbonate placed in market by Bayer and Zimmer in 1898 were not the salts of carbonic acid, that true quinine carbonate is very bitter, that their action on the organism is slight and slow compared with that of quinine, and that euquinine is ethyl quinine carboxylate, C20H23O2N2 ·COOC2H5, and aristochin, carbonylquinine, (C20H23O2N2 ) 2CO. After leaving his post as a director of the Chemical Laboratory of State Medicine, Biginelli, as he himself stated,Marotta D. Camillo Manuelli e Pietro Biginelli. ''La Chimica e l’Industria'', 1937, vol. 19, pp. 216-217. focused mainly on the problems of chemical commodity research, e.g. distinguishing between true and false tannates of commercial quinine, artificial tannins, etc.


References

{{DEFAULTSORT:Biginelli, Pietro 1860 births 1937 deaths Italian chemists University of Turin alumni People from Palazzolo Vercellese