Nitrite, 2-methylbutyl

Isoamyl nitrite Nitrous acid, isopentyl ester (8) Nitrous acid, 3-methylbutyl ester (9) (110-46-3)... 

Methylbutyl Nitrite 3-Methylbutyraldehyde Methyl Carbitol Methyl Cellosolve Methyl Chloride Methyl Chlorocarbonate Methyl Chloroform Methyl Chlorofonnate... 

Figures 1 and 2 show the mass spectra (E.I.) of these compounds. High resolution mass spectra also gave their empirical formula. They were readily synthesized by reaction of 3-methylbutyl bromide or phenylethylbromide with sodium nitrite.

The addition of nitrosyl chloride to cyclohexene in sulfur dioxide at low temperature21 -25, or the reaction of cyclohexene with 3-methylbutyl nitrite and hydrochloric acid (producing nitrosyl chloride in situ)25 gave only the tram-adduct 1, isolated in high yield as a crystalline nitroso dimer (azodioxy compound) with E configuration at the N—N double bond. The trans configuration of the chloro and nitroso groups (mixture of diaxial and diequatorial conform-ers) was deduced by IR and H-NMR analyses (a mixture of conformers with both axial and both equatorial substituents is apparent)23-25 and by reduction with lithium aluminum hydride in tetrahydrofuran to yield tram-2-chloro-l-cyclohexanamine (trans-2)23. 

A single ra-stereomer 10 was obtained in low yield from y-terpinene, 3-methylbutyl nitrite and hydrochloric acid in acetic acid33. 

Nitrosyl formate, generated in situ from 3-methylbutyl nitrite in excess formic acid, underwent addition in a trans manner to cyclohexene to yield 1,1 -azobisi7ra .v-2-l ormyloxycyclohexane) A, Af-dioxide (1) in satisfactory yield70. The trans configuration was demonstrated by reduction to /nmv-aminocyclohcxanol as the hydrochloride salt (2-HCl), identified by comparison with an authentic sample. Saponification of the formyl-nitroso dimer afforded l,l -azabis(fraiw-2-hy-droxycyclohexane) A, A"-dioxide in 92% yield. 

To 100 m L of formic acid cooled at 5 °C is added with vigorous stirring over a 2 h period a solution of 16.4 g (0.2 mol) of cyclohexene in 48.6 g (0.4 mol) of 3-methylbutyl nitrite. The temperature is maintained at 5°C throughout the addition. The yellow-green solution is evaporated to dryness on a rotary evaporator (maximum temperature 25 °C, final pressure < 1 Torr) leaving a tan residue of crude l-formyloxy-2-nitro-socyclohexane dimer yield 22,7 g (72%). Crystallization from EtOAc (charcoal) yields a white crystalline solid (18.5 g, 59%), mp 149-150°C. 

Other photoinduced fluoro-dediazonizations have been described, and in some cases excellent yields of aryl fluorides are obtained as shown for 18 and 19.26 In these examples the aryl diazonium salts were prepared using 3-methylbutyl nitrite in boron trifluoride etherate and hydrogen fluoride (1 l).27... 

Methylbutyl nitrite. See Isoamyl nitrite 3-Methyl butyl octanoate. See Isoamyl octanoate... 

Nitrous acid, calcium salt. See Calcium nitrite Nitrous acid ethyl ester. See Ethyl nitrite Nitrous acid, isobutyl ester. See Isobutyl nitrite Nitrous acid, isopentyl ester Nitrous acid, 3-methylbutyl ester. Seejsoamyl nitrite Nitrous acid, 2-methylpropyl ester. See Isobutyl nitrite... 

Synonyms 3-Methylbutyl nitrous acid isopentyl nitrite Trade names ... 

Isopentyl nitrite (Isoamyl nitrite or 3-Methylbutyl nitrite) 110-46-3 X... 

Methyl-1,3-butadiene) see Isoprene (3-Methyl-1-butanol) see Isopentyl alcohol (4-Methyl-tert-butylbenzene) see p-tert-Butyltoluene (Methyl tert-butyl ether) see tert-Butyl methyl ether (3-Methylbutyl nitrite) see Isopentyl nitrite (3-Methylbutyraldehyde) see Isovaleraldehyde (Methyl CarbitoF ) see Methyldiglycol (Methyl Cellosolve ) see Methyl glycol... 

The compound (3) is a useful intermediate for the synthesis of mixed diesters of phosphoric acid (4). There are several methods of cleaving the N-P bond, of which the method of Ikehara is the most convenient. Reaction of (3) with a 40 molar excess of 3-methylbutyl nitrite in acetic acid-pyridine (1 1 v/v) is successful in removing the aniline protecting group from the phosphoryl moiety in almost quantitative yields, giving the O-alkyl/aryl-O-phenyl hydrogen phosphate. 

Nitrous acid 3-methylbutyl ester, 9CI. Amyl nitrite. Isopentyl... 

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