1- Nitro-2-Butanol

The purification of Hquid nitro alcohols by distillation should be avoided because violent decompositions and detonation have occurred when distillation was attempted. However, if the distillation of a nitro alcohol cannot be avoided, the utmost caution should be exercised. Reduced pressure should be utilised, ie, ca 0.1 kPa (<1 mm Hg). The temperature of the Hquid should not exceed 100°C hot water should be used as the heating bath. A suitable explosion-proof shield should be placed in front of the apparatus. At any rise in pressure, the distillation should be stopped immediately. The only commercially produced Hquid nitro alcohol, 2-nitro-1-butanol, is not distilled because of the danger of decomposition. Instead, it is isolated as a residue after the low boiling impurities have been removed by vacuum treatment at a relatively low temperature. 

Acute oral LD q data for nitro alcohols in mice are given in Table 1. Because of their low volatiHty, the nitro alcohols present no vapor inhalation ha2ard. They are nonirritating to the skin and, except for 2-nitro-1-butanol, are nonirritating when introduced as a 1 wt % aqueous solution in the eye of a rabbit. When 0.1 mL of 1 wt % commercial-grade 2-nitro-1-butanol in water is introduced into the eyes of rabbits, severe and permanent corneal scarring results. This anomalous behavior may be caused by the presence of a nitro-olefin impurity in the unpurifted commercial product. 

Stabilizers. Nitro alcohols can be used to prevent the decomposition of phenylenediarnine color-developing agents (27). 2-Hydroxymethyl-2-nitro-l,3-propanediol and 2-nitro-1-butanol have been used as additives for the stabilization of 1,1,1-trichloroethane. 

Other. 2-Nitro-1-butanol is an excellent solvent for many polyamide resins, cellulose acetate butyrate, and ethylceUulose. It can be utilized in paint removers for epoxy-based coatings. 2-Hydroxymethyl-2-nitro-l,3-propanediol is usebil for control of odors in chemical toilets. Its slow release of formaldehyde ensures prolonged action to control odor, and there is no reodorant problem which sometimes is associated with the use of free formaldehyde. 2-Hydroxymethyl-2-nitro-l,3-propanediol solutions are effective preservative and embalming fluids. The slow Uberation of formaldehyde permits thorough penetration of the tissues before hardening. 

Furalazine, Acetylfuratrizine, Panfuran-S. Heating nitrovin in butanol or dimethylformamide at 100—130°C affords furalazine, 6-[2-(5-nitro-2-furanyl)ethenyl]-l,2,4-triazine-3-amine (34). An improved synthesis originates with 5-nitro-2-furancarboxaldehyde and acetone, proceeds through 4-(5-nitro-2-furanyl)-3-buten-2-one followed by a selenium dioxide oxidation to the pymvaldehyde hydrate, and subsequent reaction with aininoguariidine (35). Furalazine, acetylfuratrizine (36), and the A[-A/-bis(hydroxymethyl) derivative, Panfuran-S, formed from the parent compound and formaldehyde (37), are systemic antibacterial agents. 

Methyl-2-nitro-l,3-propanediol [77-49-6] M 135.1, m 145 . Crystd from n-butanol. 

Chloro-3-nitro-5 Sulfamyl Benzoic Acid n-Butanol... 

Nitrobutano 1 Nitrats (Nitrobutylic Nitrate, 2-Nitro-butanol-(l)-nitrate). 02N.CH(C2H5).CH2(0N02), mw 164.12, N 17.07%, OB to C02 -68.2%, yellowish, somewhat vise liq, d 1.242g/cc at 15.5°, Prepd by Pauwels (Ref 2) by nitrating secondary nitro-normal bu-... 

Nitro-phenyl)-butanol-(2) — 2-(4-Nitro-phenyl)-butan 100%d.Th. 

A variety of para-substituted 2-phenyl-2-butanols undergo quick and efficient reductions to the corresponding 2-phenylbutanes when they are dissolved in dichloromethane and a 2-10% excess of phenylmethylneopentylsilane and boron trifluoride is introduced at 0° (Eq. 30).126 Several reactions deserve mention. For example, when R = CF3, use of trifluoroacetic acid produces no hydrocarbon product, even after two hours of reaction time. In contrast, addition of boron trifluoride catalyst provides an 80% yield of product after only two minutes. When R = MeO, both trifluoroacetic acid and boron trifluoride produce a quantitative yield of the hydrocarbon within two minutes. However, when R = NO2, attempts to promote the reduction with either trifluoroacetic acid or even methanesulfonic acid fail even after reaction periods of up to eight hours, only recovered starting alcohol is obtained. Use of boron trifluoride provides a quantitative conversion into 2-(/ -nitrophenyl)butane after only ten minutes. It is significant that the normally easily reducible nitro group survives these conditions entirely intact.126129 Triethylsilane may be used as the silane.143... 

Benzene represents aromatics and olefins. Pentanone represents keto compounds and esters. Butanol represents alcohols and weak acids. Nitropropane represents nitro- and nitrile compounds. Pyridine represents N-heterocyles. 

Reactions are successful for hindered compounds 3,3-dinitro-2-butanol is obtained from the oxidative nitration of 3-nitro-2-butanol. ... 

Bei der Hydrierung von aromatischen bzw. heteroaromatischen Nitro-alkenen mit in situ aus Benzaldehyd und 1,2-Diamino-benzol in Butanol hergestelltem 2-Phenyl-2,3-dihydro-benzimidazol werden keine Nebenprodukte gebildet und man erhalt selektiv l-Aryl-2-nitro- bzw. l-Hetaryl-2-nitro-alkane in Ausbeuten von 70-90% ... 

Trinitro-l-butanol 2,2,2-Trinitroethyl-2-nitroxyethyl ether N-Nitro-N-methylhydroxy acetamidenitrate... 

Prepd by reacting formaldehyde with 2-nitro-butanol-1 or with nitiopropane, and potassium... 

A similar approach, involving condensation of 4-nitro-2-butanol with sodium glyoxylate309 in the presence of sodium hydrogencarbon-ate offers a route to 3-amino-3,4,6-trideoxy-DL-hexopyranoses. Two lactones, 552 and 553, were formed during the reaction (overall yield, 42%) in the ratio of 3 1 these lactones may be considered to be potential precursors of a variety of isomeric 3-amino sugars. The synthesis... 

Amino-l,2,4-triazole was alkylated with 4-nitrobenzyl bromide by simply refluxing the mixture in isopropanol to give SO in excellent yield. The aminotriazole SO was deaminated with NaNOa in aqueous HCI and the nitro group was reduced with ammonium formate catalyzed by 10% Pd/C to deliver 47 in an improved yield over the route shown in Scheme 17. Diazotization of 47, reduction of the diazonium salt with sodium sulphite and Fischer indolization of the resulting hydrazine with 4-( /, /-dimethylamino)butanol dimethyl acetal was performed in a single step to afford rizatriptan (4) in 45% yield. 

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