| Identification | More | [Name]
2-Nitrophenethyl alcohol | [CAS]
15121-84-3 | [Synonyms]
2-(2-NITROPHENYL)ETHANOL
2-NITROPHENETHYL ALCOHOL
2-(o-nitrophenyl)ethanol
2-(o-nitrophenyl)ethylalcohol
2-nitro-benzeneethano
2-Nitrobenzeneethanol
o-nitro-phenethylalcoho
o-nitrophenethyl alcohol
ORTHO-NITROPHENETHYLALCOHOL
o-Nitrophenylethanol | [EINECS(EC#)]
239-178-1 | [Molecular Formula]
C8H9NO3 | [MDL Number]
MFCD00007192 | [Molecular Weight]
167.16 | [MOL File]
15121-84-3.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
24/25 | [WGK Germany ]
3
| [RTECS ]
SG8601000
| [HazardClass ]
IRRITANT | [HS Code ]
29062990 | [Toxicity]
mic-sat 3333 mLg/plate EMMUEG 19(Suppl 21),2,1992 |
| Hazard Information | Back Directory | [General Description]
Needles dark brown liquid. | [Reactivity Profile]
A nitrated alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. | [Air & Water Reactions]
Insoluble in water. | [Fire Hazard]
This chemical is probably combustible. | [Chemical Properties]
brown liquid | [Uses]
2-Nitrophenethyl alcohol was used in the synthesis of indoles. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 49, p. 438, 1984 DOI: 10.1021/jo00177a010 | [Safety Profile]
Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx. | [Synthesis]
Example 26: Synthesis of 2-(2-nitrophenyl)ethanol (8a)
To a stirred solution of ethyl (E)-3-(2-nitrophenyl)acrylate (9) (7.0 g, 31.7 mmol) in 95% ethanol (100 mL) was added CO2Cl2-6H2O (377 mg, 5 mol%) and diisopropylamine (320 mg, 10 mol%) at 25 °C, followed by the slow addition of NaBH4 (4.8 g 126.8 mmol). The reaction mixture was stirred at 50 °C for 24 hours. Upon completion of the reaction (monitored by TLC), the reaction was quenched by the addition of water (20 mL) and ethyl acetate (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2 x 50 mL). The combined organic layers were washed with brine (2 × 20 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using petroleum ether/ethyl acetate (7:3 v/v) as eluent to give alcohol 8a (5.74 g) as a gel.
Yield: 85%;
IR (CHCl3): νmax 857, 968, 1029, 1060, 1245, 1440, 1507, 3430 cm-1;
1H NMR (200 MHz, CDCl3): δ 1.85-1.99 (m, 2H), 2.14 (br s, 1H), 2.98 (t, J = 7.6 Hz, 2H), 3.70 (t, J = 6.2 Hz, 2H), 7.31-7.55 (m, 3H), 7.86 (d, J = 7.7 Hz, 1H);
13C NMR (50 MHz, CDCl3): δ 29.1, 33.2, 61.6, 64.4, 126.8, 131.8, 132.8, 136.7, 149.1;
Elemental analysis (C9H11NO3) calculated values: C, 59.66; H, 6.12; N, 7.73; measured values: C, 59.71; H, 6.15; N, 7.79%. | [References]
[1] Patent: WO2013/140419, 2013, A1. Location in patent: Page/Page column 32-33
[2] Patent: US2015/38714, 2015, A1. Location in patent: Paragraph 0047; 0082; 0083 |
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