Product Name

  • Name

    3-NITROPHENETHYL ALCOHOL

  • EINECS 257-611-2
  • CAS No. 52022-77-2
  • Article Data20
  • CAS DataBase
  • Density 1.27 g/cm3
  • Solubility
  • Melting Point 47-50 °C(lit.)
  • Formula C8H9NO3
  • Boiling Point 298 °C at 760 mmHg
  • Molecular Weight 167.164
  • Flash Point 142.8 °C
  • Transport Information
  • Appearance
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 52022-77-2 (3-NITROPHENETHYL ALCOHOL)
  • Hazard Symbols IrritantXi
  • Synonyms Phenethylalcohol, m-nitro- (6CI);2-(3-Nitrophenyl)ethan-1-ol;2-(3-Nitrophenyl)ethanol;3-Nitrobenzeneethanol;3-Nitrophenethyl alcohol;3-Nitrophenylethyl alcohol;m-Nitrophenethyl alcohol;b-(m-Nitrophenyl)ethanol;
  • PSA 66.05000
  • LogP 1.65280

Synthetic route

1-nitro-3-vinyl-benzene
586-39-0

1-nitro-3-vinyl-benzene

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
With water In acetonitrile for 0.166667h; Quantum yield; Irradiation; var. cosolvent, var. H2O concentration, isotope effect (ΦOH/ΦOD);100%
With water In acetonitrile for 0.166667h; Irradiation;100%
With sulfuric acid In ethanol at 25℃; Mechanism;
With sulfuric acid In acetonitrile for 6h; Quantum yield; Irradiation; acidity dependence, other reagent, solvent isotope effect;
methyl 3-nitrophenylacetate
10268-12-9

methyl 3-nitrophenylacetate

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
Stage #1: methyl 3-nitrophenylacetate In tetrahydrofuran; methanol at 0 - 20℃;
Stage #2: With water In tetrahydrofuran; methanol		90%
With sodium tetrahydroborate In tetrahydrofuran; methanol for 6h; Reagent/catalyst; Solvent; Reflux;
With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃;
2-(3-chlorophenyl)ethanol
5182-44-5

2-(3-chlorophenyl)ethanol

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); t-BuBrettPhos; tris(3,5-dioxaheptyl)amine; sodium nitrite In tert-butyl alcohol at 130℃; for 24h; regioselective reaction;80%
3-nitro-benzeneacetic acid
1877-73-2

3-nitro-benzeneacetic acid

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
With borane-THF In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;68%
With dimethylsulfide borane complex In tetrahydrofuran Reflux;60%
With dimethylsulfide borane complex In tetrahydrofuran Reflux;60%
2-(4-amino-3-nitrophenyl)ethanol
15896-61-4

2-(4-amino-3-nitrophenyl)ethanol

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite anschliessendes Behandeln mit H3PO2;
methanol
67-56-1

methanol

1-nitro-3-vinyl-benzene
586-39-0

1-nitro-3-vinyl-benzene

A

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

B

1-(2-methoxyethyl)-3-nitrobenzene
110435-89-7

1-(2-methoxyethyl)-3-nitrobenzene

Conditions
ConditionsYield
With sulfuric acid In water; acetonitrile at 21℃; for 10h; Product distribution; Rate constant; Irradiation; investigation of the selectivity of the ring substituted phenethyl carbenium ion in the photoaddition of a binary aq. sol. of the corresponding alcohol; structural and nucleophilic effects are discussed;
...Expand
2-phenylethanol
60-12-8

2-phenylethanol

A

2-(4-nitrophenyl)ethanol
100-27-6

2-(4-nitrophenyl)ethanol

B

2-nitro-benzeneethanol
15121-84-3

2-nitro-benzeneethanol

C

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
With nitric acid; urea 1.) from -12 deg C to -5 deg C, 20 min, 2.) reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given;
With nitric acid; urea 1.) from -12 deg C to -5 deg C, 20 min, 2.) reflux, 5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
...Expand
4-acetamido-3-nitrophenethyl acetate
92959-73-4

4-acetamido-3-nitrophenethyl acetate

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous HCl
2: NaNO2; aqueous HCl / anschliessendes Behandeln mit H3PO2
View Scheme
1-bromomethyl-3-nitrobenzene
3958-57-4

1-bromomethyl-3-nitrobenzene

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 5 h / 50 °C
2: hydrogenchloride / methanol / 20 °C
3: tetrahydrofuran; methanol / 0 - 20 °C
View Scheme
(3-nitrophenyl)acetonitrile
621-50-1

(3-nitrophenyl)acetonitrile

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / methanol / 20 °C
2: tetrahydrofuran; methanol / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; sulfuric acid / water / 110 °C
2: dimethylsulfide borane complex / tetrahydrofuran / Reflux
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; acetic acid / water / 110 °C
2: dimethylsulfide borane complex / tetrahydrofuran / Reflux
View Scheme
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
With palladium on carbon (10%) In tetrahydrofuran Cooling with ice; Inert atmosphere;100%
With hydrogen; palladium 10% on activated carbon In methanol under 2327.23 Torr;99%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 1.5h;98%
Pd-C
125620-28-2

Pd-C

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
In ethanol; water100%
acetic acid 2-(3-nitro-phenyl)-ethyl ester
68527-46-8

acetic acid 2-(3-nitro-phenyl)-ethyl ester

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

acetic acid 2-(3-amino-phenyl)-ethyl ester
690995-22-3

acetic acid 2-(3-amino-phenyl)-ethyl ester

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; under 2585.81 Torr; for 1h;99%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-(3-nitrophenyl)ethyl methanesulfonate
206874-43-3

2-(3-nitrophenyl)ethyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;98%
With pyridine In dichloromethane at 0 - 20℃;98%
With triethylamine In dichloromethane at 0 - 20℃; for 5h;84%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

1-(2-iodoethyl)-3-nitrobenzene
891855-81-5

1-(2-iodoethyl)-3-nitrobenzene

Conditions
ConditionsYield
With 1H-imidazole; iodine; triphenylphosphine In toluene at 20℃; for 3h; Inert atmosphere;98%
With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 20℃; for 15h;
With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 20℃; for 15h;
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

C14H23NO3Si

C14H23NO3Si

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h;94%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

Methanesulfonic anhydride
7143-01-3

Methanesulfonic anhydride

2-(3-nitrophenyl)ethyl methanesulfonate
206874-43-3

2-(3-nitrophenyl)ethyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 16h;90%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

methyl iodide
74-88-4

methyl iodide

1-(2-methoxyethyl)-3-nitrobenzene
110435-89-7

1-(2-methoxyethyl)-3-nitrobenzene

Conditions
ConditionsYield
Stage #1: 2-(3-nitrophenyl)ethanol With sodium hydride In tetrahydrofuran at 5 - 20℃;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 16h;		87%
Stage #1: 2-(3-nitrophenyl)ethanol With sodium hydride In tetrahydrofuran at 5 - 20℃; for 0.5h;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 16h;		87%
With sodium hydride In tetrahydrofuran at 0 - 20℃;81%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

methyl iodide
74-88-4

methyl iodide

A

1-(2-methoxyethyl)-3-nitrobenzene
110435-89-7

1-(2-methoxyethyl)-3-nitrobenzene

B

N-[3-(2-methoxyethyl)phenyl]-1,2,4-benzotriazin-3-amine 1-oxide
763131-61-9

N-[3-(2-methoxyethyl)phenyl]-1,2,4-benzotriazin-3-amine 1-oxide

Conditions
ConditionsYield
With NaH In tetrahydrofuranA n/a
B 87%
...Expand
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

acetic anhydride
108-24-7

acetic anhydride

acetic acid 2-(3-nitro-phenyl)-ethyl ester
68527-46-8

acetic acid 2-(3-nitro-phenyl)-ethyl ester

Conditions
ConditionsYield
In pyridine at 20℃;85%
With 4-pyrrolidin-1-ylpyridine; triethylamine at 20℃;
With 4-pyrrolidin-1-ylpyridine; triethylamine at 20℃;
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

toluene-4-sulfonic acid 2-(3-nitrophenyl)ethyl ester
69628-97-3

toluene-4-sulfonic acid 2-(3-nitrophenyl)ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 12h;83%
With triethylamine In dichloromethane at 20℃;79.8%
With dmap; triethylamine In chloroform at 20℃; for 63h;64%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

tolfenamic Acid
13710-19-5

tolfenamic Acid

2-(3-chloro-2-methyl-phenylamino)-benzoic acid 2-(3-nitro-phenyl)-ethyl ester

2-(3-chloro-2-methyl-phenylamino)-benzoic acid 2-(3-nitro-phenyl)-ethyl ester

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;80%
3,4,5-trimethoxyphenol
642-71-7

3,4,5-trimethoxyphenol

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

1,2,3-Trimethoxy-5-[2-(3-nitro-phenyl)-ethoxy]-benzene

1,2,3-Trimethoxy-5-[2-(3-nitro-phenyl)-ethoxy]-benzene

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In toluene for 1h;75%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

C16H18N2O2

C16H18N2O2

Conditions
ConditionsYield
With sodium hydroxide; zinc In ethanol; water Reflux;70%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

dimethyl sulfate
77-78-1

dimethyl sulfate

1-(2-methoxyethyl)-3-nitrobenzene
110435-89-7

1-(2-methoxyethyl)-3-nitrobenzene

Conditions
ConditionsYield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In benzene for 144h; Heating;60%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

2,6-dibromo-1,5-naphthalenediol
84-59-3

2,6-dibromo-1,5-naphthalenediol

C26H20Br2N2O6
1414857-97-8

C26H20Br2N2O6

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;58%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran
caffeic acid
331-39-5

caffeic acid

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

3'-nitrophenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate

3'-nitrophenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate

Conditions
ConditionsYield
With ytterbium(III) triflate In nitromethane at 120℃;52%
morpholine
110-91-8

morpholine

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

1-morpholino-2-(3-nitrophenyl)ethane-1,2-dione
1391739-32-4

1-morpholino-2-(3-nitrophenyl)ethane-1,2-dione

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate; copper(I) bromide In dimethyl sulfoxide at 70℃; for 12h;39%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

3-(2-Bromoethyl)nitrobenzene
16799-04-5

3-(2-Bromoethyl)nitrobenzene

Conditions
ConditionsYield
With phosphorus tribromide In diethyl ether Heating;
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

A

formaldehyd
50-00-0

formaldehyd

B

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

Conditions
ConditionsYield
In water; acetonitrile Product distribution; Irradiation;
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

A

1-methyl-3-nitrobenzene
99-08-1

1-methyl-3-nitrobenzene

B

3,3'-dinitrobibenzyl
19829-61-9

3,3'-dinitrobibenzyl

Conditions
ConditionsYield
In water; acetonitrile for 2h; Mechanism; Product distribution; Quantum yield; Irradiation; variation of pH;
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

TsX

TsX

toluene-4-sulfonic acid 2-(3-nitrophenyl)ethyl ester
69628-97-3

toluene-4-sulfonic acid 2-(3-nitrophenyl)ethyl ester

Benzeneethanol,3-nitro- Specification

The CAS register number of Benzeneethanol,3-nitro- is 52022-77-2. It also can be called as 3-Nitrobenzeneethanol and the IUPAC name about this chemical is 2-(3-nitrophenyl)ethanol. The molecular formula about this chemical is C8H9NO3 and the molecular weight is 167.16. It belongs to the following product categories which include Alcohols; C7 to C8; Oxygen Compounds and so on.

Physical properties about Benzeneethanol,3-nitro- are: (1)ACD/LogP: 1.09; (2)ACD/LogD (pH 5.5): 1.09; (3)ACD/LogD (pH 7.4): 1.09; (4)ACD/BCF (pH 5.5): 3.96; (5)ACD/BCF (pH 7.4): 3.96; (6)ACD/KOC (pH 5.5): 93.21; (7)ACD/KOC (pH 7.4): 93.21; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 55.05 Å2; (12)Index of Refraction: 1.581; (13)Molar Refractivity: 43.88 cm3; (14)Molar Volume: 131.5 cm3; (15)Polarizability: 17.39x10-24cm3; (16)Surface Tension: 53.6 dyne/cm; (17)Density: 1.27 g/cm3; (18)Flash Point: 142.8 °C; (19)Enthalpy of Vaporization: 56.8 kJ/mol; (20)Boiling Point: 298 °C at 760 mmHg; (21)Vapour Pressure: 0.000585 mmHg at 25 °C.

Preparation: this chemical can be prepared by 1-nitro-3-vinyl-benzene. This reaction needs irradiation. This reaction will need reagent of H2O and solvent of acetonitrile. The reaction time is 10 mins. The yield is about 100%.

Uses of Benzeneethanol,3-nitro-: it can be used to produce Methyl-3-nitrophenethylether with sulfuric acid dimethyl ester. This reaction will need reagent of tetra-n-butylammonium iodide, 50percent aq. NaOH and solvent of benzene. This reaction needs heating. The reaction time is 6 days. The yield is about 60%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It may cause inflammation to the skin or other mucous membranes. If you want to use it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to store it, you should keep the container tightly sealed in dry, cool places. If you store and use this chemical according the rule, it will not be decomposed.

You can still convert the following datas into molecular structure:
(1)SMILES: [O-][N+](=O)c1cccc(c1)CCO
(2)InChI: InChI=1/C8H9NO3/c10-5-4-7-2-1-3-8(6-7)9(11)12/h1-3,6,10H,4-5H2
(3)InChIKey: PWZWTSYUZQZFKE-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C8H9NO3/c10-5-4-7-2-1-3-8(6-7)9(11)12/h1-3,6,10H,4-5H2
(5)Std. InChIKey: PWZWTSYUZQZFKE-UHFFFAOYSA-N

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