| Identification | More | [Name]
4-Nitrobenzeneethanol | [CAS]
100-27-6 | [Synonyms]
2-(4-NITROPHENYL)ETHANOL
2-(4-NITROPHENYL)ETHYL ALCOHOL
2-(p-Nitrophenyl)ethanol
3,5-DIMETHOXY-4-HYDROXYBENZOIC ACID
4-nitrobenzeneethanol
4-NITROPHENETHYL ALCOHOL
AKOS 90322
AURORA KA-7063
BETA-(P-NITROPHENYL)ETHANOL
P-NITROPHENETHYL ALCOHOL
4-nitro-benzeneethano
Phenethyl alcohol, p-nitro-
p-nitro-phenethylalcoho
beta-(p-Nitrophenyl)alcohol
β-P-nitrophenylenthanol
SS-P-NITROPHENYLENTHANOL
SS-P-NITROPHENYLETHANOL
PARA-NITROPHENETHYLALCOHOL
p-Nitrophenylethanol
4-NITROBENETHYL ALCOHOL | [EINECS(EC#)]
202-835-8 | [Molecular Formula]
C8H9NO3 | [MDL Number]
MFCD00010202 | [Molecular Weight]
167.16 | [MOL File]
100-27-6.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to orange crystalline powder | [Melting point ]
59-62 °C(lit.)
| [Boiling point ]
177 °C16 mm Hg(lit.)
| [density ]
1.2917 (rough estimate) | [refractive index ]
1.5570 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, Methanol (Slightly) | [form ]
Solid | [pka]
14.57±0.10(Predicted) | [color ]
White to Light Brown | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. | [Water Solubility ]
<0.01 g/100 mL at 18 ºC | [BRN ]
1866148 | [CAS DataBase Reference]
100-27-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzeneethanol, 4-nitro-(100-27-6) | [EPA Substance Registry System]
100-27-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
R40:Limited evidence of a carcinogenic effect.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
SG8602000
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [HS Code ]
29062990 |
| Hazard Information | Back Directory | [General Description]
Yellow needles (from aqueous methanol) or orange solid. | [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. | [Health Hazard]
SYMPTOMS: Structurally similar chemicals may cause methemoglobinemia. | [Fire Hazard]
Flash point data for this chemical are not available; however, P-NITROPHENETHYL ALCOHOL(100-27-6) is probably combustible. | [Chemical Properties]
yellow to orange crystalline powder | [Uses]
4-Nitro-benzeneethanol is a useful synthetic intermediate. It can be used to synthesize N-phenylethylindole carboxamides as SAR study of allosteric modulators of CB1 receptor. It can also be used to prepare 2-aza-2''-deoxyinosine-containing oligodeoxyribonucleotide duplexes. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 38, p. 2786, 1973 DOI: 10.1021/jo00956a011 | [Synthesis]
(1) Dissolve p-nitrophenylacetic acid in ether and heat under nitrogen protection to 50°C. Slowly add lithium aluminium hydride (mass ratio of lithium aluminium hydride to p-nitrophenylacetic acid 1:2) and make sure that the mixture is homogeneous. Subsequently, water was added dropwise (the mass ratio of the amount of water added dropwise to lithium aluminum hydride was 1:1) and the reaction continued to be stirred for 3 hours. Upon completion of the reaction, the reaction mixture was cooled to 0°C, and a 12% sodium hydroxide solution (the mass ratio of sodium hydroxide to lithium aluminum hydride was 3:2) and water (the mass ratio of water to lithium aluminum hydride for the second addition was 5:2) were slowly added. After standing for 20 minutes, it was gradually warmed to room temperature and dried by adding anhydrous MgSO4. After stirring for 30 minutes, filter and distill to remove the solvent in the filtrate to obtain p-nitrophenylethanol. (2) Dissolve p-nitrophenyl ethanol in ethanol and add catalyst (a mixture of CeO2, MnO and ZnO in the ratio of 1:2:5; the mass ratio of p-nitrophenyl ethanol to catalyst was 3:167). The reaction system was warmed up to 80°C under nitrogen atmosphere. hydrogen was introduced at atmospheric pressure and the reaction was carried out for 3 h. The reaction was carried out at atmospheric pressure and the reaction was carried out at atmospheric pressure and the reaction was carried out at atmospheric pressure. After completion of the reaction, it was cooled to room temperature and the catalyst was removed by filtration. Ethanol was removed by distillation and the resulting solid was purified by recrystallization to give p-aminophenethyl alcohol. | [References]
[1] Patent: CN108033888, 2018, A. Location in patent: Paragraph 0019-0057
[2] European Journal of Organic Chemistry, 2011, # 17, p. 3178 - 3183
[3] Journal of Medicinal Chemistry, 1990, vol. 33, # 11, p. 3008 - 3014
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 109 - 114
[5] Patent: WO2004/29066, 2004, A2. Location in patent: Page/Page column 302 |
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