phenyl

phenyl Chem.
  (ˈfiːnaɪl, ˈfiːnɪl, ˈfɛnɪl)
  [f. phen- + -yl, lit. ‘radical of benzene (phene)’.]
  1. The monovalent organic radical C₆H₅ (also symbolized Ph), which exists in the free state as diphenyl, H₅C₆–C₆H₅, and enters as a radical into benzene (phenyl hydride), phenol (phenyl hydroxyl), aniline (phenylamine), and a very extensive series of organic compounds.

1850 Daubeny Atom. The. viii. (ed. 2) 238 A compound radical called phenyle, a name given by Laurent to the supposed base of the volatile liquid, obtained by compressing oil gas, which was first examined by Faraday, and denominated by him benzole. 1857 Miller Elem. Chem. III. 563 Compounds..have been formed, which appear to contain oxide of phenyl in combination with acids. 1862 N. Syd. Soc. Year-bk. Med. 441 On some applications of Carbolic Acid or Oxide of Phenyle. 1880 E. Cleminshaw Wurtz' Atom. The. 220 Phenyl..wants but one atom of hydrogen to become benzene.

  2. attrib. and Comb., as phenyl acetate, phenyl carbonate, phenyl cyanide, phenyl ether, phenyl ketones, phenyl oxide, phenyl phosphate, phenyl sulphide; phenyl compounds, phenyl derivatives, etc.; phenyl-blue, dimethyl-amido-phenylimide of quinone; phenyl-brown, a colouring matter, possessing explosive properties.

1866 Odling Anim. Chem. 123 This relationship of salicic and phenyl compounds. 1872 Watts Dict. Chem. VI. 918 Phenyl carbonate... Phenyl phosphates [etc.]. 1875 Ibid. VII. 945 The explosive character of the phenyl-brown is..due to the dinitrophenol. 1899 J. Cagney tr. Jaksch's Clin. Diagn. vii. (ed. 4) 400 The exhibition of salol (phenyl-æther of salicylic acid).

  b. Freely combined (hyphened or written connectedly) with other chemical terms, denominating compounds into which phenyl enters as a radical, often replacing hydrogen or other monovalent element or group; such are, e.g.
  phenyl-aˈcetamide = acetanilide. phenyl-aˈcetic a.: see quot. 1877. phenyl-aˈcetylene: see quot. 1872. ˌphenylarˈsonic a. [arsonic a.], in phenylarsonic acid, a colourless, toxic, crystalline solid, C₆H₅AsO(OH)₂, which is used as a trypanocide; also, any derivative of this; phenyl-ˈglycol, a diatomic alcohol, C₆H₅·CHOH.CH₂OH. phenyl-ˈhydrazine: see quot. 1902. phenylˈhydrazone [ad. G. phenylhydrazon (O. Rudolph 1888, in Ann. d. Chem. u. Pharm. CCXLVIII. 99): see hydrazone], any of a class of compounds formed by condensation of an aldehyde or ketone with phenylhydrazine, which are usu. crystalline solids and are used to characterize the parent aldehyde or ketone; phenylˈmercury, used attrib. or absol. to denote compounds which contain a phenyl group bonded directly to a mercury atom; so ˌphenylmerˈcuric a., as phenylmercuric acetate, a white crystalline solid, CH₃COOHgC₆H₅, used mainly as a fungicide and herbicide; phenylmercuric nitrate, a white crystalline solid, C₆H₅HgNO₃.C₆H₅HgOH, used mainly as a fungicide and disinfectant. ˌphenylpyˈruvic a., phenylpyruvic acid, a colourless crystalline solid, C₆H₅CH₂CO·COOH, which in phenylketonuria is produced by the metabolism of phenylalanine and excreted in the urine; hence ˌphenylpyˈruvate, a salt or the anion of this acid. phenyl-sulˈphuric a., sulpho-carbolic: see quot. 1880. ˌphenylˌthioˈcarbamide, a white, crystalline solid, NH₂·CS·NH·C₆H₅, which has a bitter taste to persons possessing a certain dominant gene and is tasteless to those lacking it. ˌphenylthiouˈrea (-ˌθaɪəʊjʊˈriːə) = phenylthiocarbamide above.

1866 Watts Dict. Chem. IV. 418 *Phenyl-acetamide or Acetanilide..Produced by the action of aniline upon acetic anhydride or chloride of acetyl. 1885–8 Fagge & Pye-Smith Princ. Med. (ed. 2) I. 205 Antifebrin (..phenyl-acetamide) is said to be more useful, more agreeable, and more safe than any.

1877 Watts Fownes' Chem. (ed. 12) II. 528 Alpha-toluic or *phenyl-acetic acid, C6H5·CH2·CO2H. 1885 Klein Micro-Organisms 73 Antiseptics, such as carbolic acid..strong solutions of phenyl-propionic acid and phenyl⁓acetic acid.

1872 Watts Dict. Chem. VI. 920 *Phenyl⁓acetylene. Syn. with Acetenyl-benzene. 1885 I. Remsen Org. Chem. (1888) p. ix, Phenyl-acetylene and Derivatives.

1905 Amer. Chem. Jrnl. XXXIII. 104 The reduction takes place with equal ease in the aromatic series, monophenyl arsine..being obtained from *phenyl arsonic acid. 1937 Thorpe's Dict. Appl. Chem. (ed. 4) I. 488/1 The introduction of an amino group into the para-position in phenylarsonic acid decreases its toxicity and increases its trypanocidal activity. 1959 Times 7 Dec. (Agric. Suppl.) p. vii/1 So far as arsenicals are concerned, two phenylarsonic acids have received attention [as growth stimulants for poultry].

1897 Allbutt's Syst. Med. III. 213 The property of *phenyl⁓hydrazin to form with grape-sugar a characteristic crystalline compound called phenyl-glucosagon. 1902 Encycl. Brit. XXVI. 721/2 E. Fischer [in] 1884, made the all-important discovery of phenylhydrazine, C6H5·NH.NH2 or Ph.NH.NH2.

1889 Jrnl. Chem. Soc. LVI. 251 (heading) *Phenylhydrazones. 1938 [see hydrazone]. 1966 McGraw-Hill Encycl. Sci. & Technol. VII. 62/2 When the starting material is the phenylhydrazone of acetone, the product is 2-methylindole.

1920 Chem. Abstr. XIV. 2181 There at once sep. leaflets of *phenylmercuric chloride, PhHgCl, m. 250°. 1921 F. C. Whitmore Org. Compounds Mercury iii. 65 Phenyl mercuric acetate reacts with ammonium hydroxide giving a substance (C6H5Hg)2NH2OAc. Ibid. ix. 177 Phenylmercuric nitrate forms rhombic tablets, insoluble in cold water. 1951 A. Grollman Pharmacol. & Therapeutics xxv. 510 The first of these compounds used as an antiseptic was phenylmercuric chloride but..this was supplanted by the more soluble basic phenylmercuric nitrate. 1966 McGraw-Hill Encycl. Sci. & Technol. I. 483/1 The most important of the organic mercurials are phenylmercuric nitrate and acetate. 1972 Phenylmercuric [see phenylmercury below].

1931 Jrnl. Infectious Dis. XLIX. 440 *Phenyl-mercury-nitrate was first prepared by Otto in 1870, but its biologic characteristics have..never been studied. 1955 G. J. Rose Crop Protection vi. 103 Bacterial canker of cherries has been controlled by applications of a formulation containing the phenyl mercury salt of naphthyl methane sulphonic acid. 1969 Johnels & Westermark in Miller & Berg Chem. Fallout x. 224 There is no indication..that the use of..phenylmercury from 1930 to 1940 has caused an increase in the mercury content of these terrestrial bird species. 1971 Nature 20 Aug. 535/1 The death of birds in Sweden was traced to the use of phenylmercury compounds in the pulp and paper industry. 1972 F. Matsumura Environmental Toxicol. Pesticides 532 In the U.S. the source of contamination of many rivers has been suspected to be by phenylmercuries, because of the extensive use of phenylmercuric acetate as a slime treatment agent in paper mills.

1932 Jrnl. Biol. Chem. XCVI. 628 In one experiment, after 2·5 gm. of sodium *phenylpyruvate had been fed for 2 successive days, it was possible to isolate from the urine 0·4 gm. of phenaceturic acid. 1970 R. W. McGilvery Biochem. xvii. 387 People with phenylketonuria also excrete some other aromatic compounds.., representing aberrations of the normal process of metabolism due to the high concentration of phenylpyruvate.

1887 Jrnl. Chem. Soc. LII. 142 The author..advances the view that the compound is probably *phenylpyruvic acid. 1935 [see phenylketonuria]. 1968 Passmore & Robson Compan. Med. Stud. I. xi. 24/2 Presence of phenylpyruvic acid in the blood leads to mental retardation. Arrangements to test the urine of every child soon after birth for phenylpyruvic acid have been made in many places.

1880 Garrod & Baxter Mat. Med. 177 Sulphocarbolic or *phenylsulphuric acid is formed by the direct union of pure carbolic acid with sulphuric acid.

1879 Jrnl. Chem. Soc. XXXVI. 804 Mono- and di-*phenylthiocarbamide..are soluble in caustic soda or potash. 1932 [see PTC s.v. P II]. 1976 Nature 20 May 223/2 This report concerns two dermatoglyphic traits, fingerprint pattern index and total ridge-count, both strongly heritable. In addition, phenylthiocarbamide (PTC) taster ability..and skin colour were studied.

1896 Jrnl. Chem. Soc. LXIX. 857 If dilute hydrochloric acid be now added to the clear solution, a white solid at once separates, which..forms white prisms..consisting of *phenylthiourea. 1959 Listener 3 Dec. 968/2 People who can taste phenylthiourea seem to be slightly more liable to get one form of thyroid disease and slightly less liable to get another. 1971 J. Z. Young Introd. Study Man xxxviii. 553 A minimal yet striking example [of genetic variation of the nervous system] is the inheritance of the capacity to taste the substance phenylthiourea.

  Hence phenyˈlamic a. = anilic. ˈphenylaˌmide = anilide. ˈphenylaˌmine, the systematic name of aniline (monophenylamine), NH₂·C₆H₅, and of a large series of compounds of the same type, ‘organic bases derived from ammonia by the substitution of one or more atoms of phenyl for an equivalent quantity of hydrogen’ (Watts); e.g. diphenylamine, NH(C₆H₅)₂, triphenylamine, N(C₆H₅)₃; so azophenylamine, NH₂·C₆H₂N, bromophenylamine, NH₂·C₆H₄Br, chloro-phenylamine, iodo-phenylamine, nitrophenylamine, etc. ˈphenylate, a salt of phenylic acid.† pheˈnylia, obs. synonym of phenylamine (aniline). phenylic (fɪˈnɪlɪk) a., of or derived from phenyl; phenylic acid, phenylic alcohol, other names for Phenol or Carbolic acid; also formerly called ˈphenylous acid. ˈphenyliˌmide (imide): see quot. 1866. phenyˈlurea = carbanilamide.

1866 Watts Dict. Chem. IV. 419 *Phenylamic acids. Anilic acids.

1857 Miller Elem. Chem. III. 255 Aniline, Kyanol, *Phenylamide, Phenylia, Crystalline, or Benzidam (C12H7N)... This remarkable base may be prepared from several sources, and by a variety of reactions.

1866 Roscoe Elem. Chem. xxxix. 338 Aniline has been called *Phenylamine..but it cannot be prepared like an amine. 1880 Friswell in Jrnl. Soc. Arts 16 Apr. 442/1 The earliest violets obtained by artificial means were those produced by the action of pure aniline, or phenylamine, on roseine.

1880 Athenæum 27 Nov. 713/1 The authors..have thus prepared aluminic methylate,..*phenylate, &c.

1857 *Phenylia [see phenylamide].

1858 Thudichum Urine 339 *Phenylic acid was discovered, by Runge, in tar obtained by the distillation of coal. 1897 Allbutt's Syst. Med. II. 944 Carbolic acid is obtained from phenic acid or phenylic alcohol, a product of coal-tar distillation.

1866 Watts Dict. Chem. IV. 419 *Phenylimides or Anils, tertiary monamides..which..may be regarded as aniline in which 2 atoms of H[ydrogen] are replaced by a diatomic radicle: e.g. C6H5·(C4H4O2){pp}·N, phenyl-succinimide. 1852 *Phenylous acid [see phenic].

1857 Miller Elem. Chem. III. 616 *Phenyl-urea (carbanilamide).

Oxford English Dictionary