2-Nitro-l-propanol

The nitro alcohols in Table 1 are manufactured in commercial quantities however, three of the five of them are used only for the production of the corresponding amino alcohols. 2-Methyl-2-nitro-l-propanol (NMP) is available as the crystalline soHd or as a mixture with siHcon dioxide. 2-Hydroxymethyl-2-nitro-1,3-propanediol is available as the soHd ( 9.15/kg), a 50% solution in water ( 2.33/kg), a 25% solution in water ( 1.41/kg), or as... 

Polymers. AH nitro alcohols are sources of formaldehyde for cross-linking in polymers of urea, melamine, phenols, resorcinol, etc (see Amino RESINS AND PLASTICS). Nitrodiols and 2-hydroxymethyl-2-nitro-l,3-propanediol can be used as polyols to form polyester or polyurethane products (see Polyesters Urethane polymers). 2-Methyl-2-nitro-l-propanol is used in tires to promote the adhesion of mbber to tire cord (qv). Nitro alcohols are used as hardening agents in photographic processes, and 2-hydroxymethyl-2-nitro-l,3-propanediol is a cross-linking agent for starch adhesives, polyamides, urea resins, or wool, and in tanning operations (17—25). Wrinkle-resistant fabric with reduced free formaldehyde content is obtained by treatment with... 

Nltropropane. As much as 9100 t of 2-nitropropane once were consumed for use in coatings annually. Concern about toxicity and a general movement to low volatile organic compound (VOC) coatings have resulted in almost the complete disappearance of this use for 2-nitropropane. However, derivatives such as 2-meth5l-2-nitro-l-propanol (used in tire cord adhesive) and 2-amino-2-methyl-l-propanol (a pigment dispersant and buffer), have served as an outlet for 2-nitropropane production. 

Methyl-2-nitro-l-propanol [76-39-1] M 119.1, m 87-88 . Crystd from pet ether. 

MethyU2-Nitro-l-Propanol (2-Nitro-2-methyl-1 -propanol, /J-Nitroisobutylalcohol). (CH3)2.C(N02).CH20H, mw 119.12, N 11.76%, OB to C02 —127.60%, needles or plates from methanol, mp 90—91°, bp 94.5—95.5° at. 10mm. Easily sol in ethyl methyl ales, eth and w (350p in lOOp at 20°). May be prepd by treating 2-nitropropane with formaldehyde in the presence of an alkaline catalyst, such as K bicarbonate (Refs 1, 2, 3 4). On nitration, it yields an expl, 2-Methyl-2-Nitro-l-Propanol Nitrate (see below)... 

Nitro-l-propene Preparation is accomplished by dehydration of 2-nitro-l-propanol with phthalic anhydride (73%)45 or acetic anhydride-AcONa46 bp 56-57 °C/80 mmHg. 

The checkers purchased 2-nitro-l-propanol (ca. 98% purity) from EGA-Aldrich and used it without further purification. The submitters prepared this reagent from nitroethane and formalin according to the procedure of Feuer,2 yield 70-75%, bp 79-80°C (5 mm). 

The procedure described is essentially the same as that of Buck-ley and Scaife.3 The yield has been increased from 55.5% up to 72% by using 1.3 mol eq of phthalic anhydride and by carefully controlling the pressure and cooling the receiving flask. Although 2-nitropropene has previously been prepared by pyrolysis of 2-nitro-1-propyl benzoate in 72% overall yield from 2-nitro-l-propanol,4 the present method is preferred for its preparation since the procedure is much simpler and the product is directly obtainable from 2-nitro-l-propanol without first preparing its ester. It is also applicable to the preparation of 1-nitro-l-propene (58%),5-6 2-nitro-1 -butene (82%),7 and 2-nitro-2-butene (60%).6,7 In general, aliphatic nitroolefins have the tendency to polymerize readily with alkali. 

RC = CCH,X — RCX = C==CH,. /S.y- and 7,S-Acetylenic alcohols can be transformed to the halides in better yields by an alternative procedure, which consists in their esterification with p-toluenesulfonyl chloride and subsequent cleavage of the ester by the action of sodium iodide, lithium chloride, or calcium bromide in an appropriate solvent (60-90%). Halo ethers are prepared by the action of phosphorus tribromide on hydroxy ethers, as in the preparation of /3-ethoxyethyl bromide (66%). In a similar manner, /3-halo esters have been prepared without appreciable dehydration of the /3-hydroxy ester (40-60%). The reaction of cyanohydrins leads to a-halo nitriles. Treatment of 2-nitro-l-propanol with phosphorus pentachloride gives l-chloro-2-nitropropane (47%). ... 

Methyl-2-nitro-l-propanol [76-39-1] M 119.1, m 87-88 , b 94-95 /10mm. Distil it under vacuum and/or crystallise it from pet ether or MeOH. [Astle Abbott J Org Chem 21 1229 1956, Kambe Yasuda Bull Soc Chem Jpn 41 1444 1968, Beilstein 1 H 378,1 III 1546,1 IV 1604.]... 

Nitroethane and formalin react to form 2-nitro-l-propanol (847o yield), which is dehydrated with phthalic anhydride (727 yield). 

Nitro-l-propanol is a highly explosive colorless liquid with an aromatic odor, melting point of -21.4 °C, boiling point of 103 °C, refractive index of 1.465420. It is soluble in ether, but insoluble in water. It has five hydrogen bond acceptors, topological molecular polar surface area of 112, heavy atom number of 10, rotatable bond number of one, the number of hydrogen bond donor of 1, and the number of covalent bond units of one. 

Nitro-l-propanol is a slightly yellow liquid with boiling point of 72-74 °C (1 mmHg), density of 1.185 g/mL (25 °C), refractive index of ( >) 1.439 and flash point of 212 °F. 

Nitro-l-propanol should be stored in cylinders and stored in well-ventilated and dry environment at 2-8 °C. It cannot be stored together with acidic/basic materials, and must be far away from the fire, acidic chloride and acid anhydride. 

Methyl-2-nitro-l-propanol is a colorless liquid with a strong combustion performance. When it is combusted under confined conditions, an explosion will occur. It density is 1.135 g/cm with melting point of -1 °C, boiling point of 204.4 °C (760 mmHg), flash point of 92.1 °C, vapor pressure of 0.0634 mmHg (25 °C) and refractive index of 1.553. 

Nitropropane 3-Nitropropanoicacid 2-Nitro-l-propanol 1-Nitro-l-propene 2-Nitro-l-propene... 

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