2-Nitrophenethyl alcohol Chemical Properties

Melting point:

2 °C(lit.)

Boiling point:

267 °C(lit.)

Density 

1.19 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5637(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

pka

14.63±0.10(Predicted)

Appearance

Light yellow to brown Oil

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

SLRIOXRBAPBGEI-UHFFFAOYSA-N

CAS DataBase Reference

15121-84-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneethanol, 2-nitro-(15121-84-3)

EPA Substance Registry System

2-Nitrobenzeneethanol (15121-84-3)

Safety Information

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

MSDS

• Language:English Provider:2-(2-Nitrophenyl)ethanol
• Language:English Provider:SigmaAldrich

2-Nitrophenethyl alcohol Usage And Synthesis

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

General Description

Needles dark brown liquid.

Air & Water Reactions

Insoluble in water.

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.

Fire Hazard

2-Nitrophenethyl alcohol is probably combustible.

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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