52022-77-2

Basic information

• Product Name: 3-NITROPHENETHYL ALCOHOL
• Synonyms: 3-NITROPHENETHYL ALCOHOL;TIMTEC-BB SBB008558;2-(3-Nitrophenyl)ethanol;3-nitro-benzeneethano;3-Nitrobenzeneethanol;beta-(m-Nitrophenyl)ethanol;m-nitrophenethyl alcohol;3-Nitrophenylethylalcohol
• CAS NO: 52022-77-2
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• EINECS: 257-611-2
• Product Categories: Alcohols;C7 to C8;Oxygen Compounds;Building Blocks;C7 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 52022-77-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 47-50 °C(lit.)
• Boiling Point: 141-146 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.2917 (rough estimate)
• Vapor Pressure: 0.00171mmHg at 25°C
• Refractive Index: 1.5570 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.65±0.10(Predicted)
• CAS DataBase Reference: 3-NITROPHENETHYL ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITROPHENETHYL ALCOHOL(52022-77-2)
• EPA Substance Registry System: 3-NITROPHENETHYL ALCOHOL(52022-77-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 52022-77-2(Hazardous Substances Data)

Usage

Description

3-Nitrophenethyl alcohol, also known as 3-NPEA, is an organic compound with the chemical formula C8H9NO3. It is a colorless to pale yellow liquid with a characteristic odor. 3-NITROPHENETHYL ALCOHOL is characterized by the presence of a nitro group (-NO2) attached to a phenethyl alcohol backbone, which contributes to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
3-Nitrophenethyl alcohol is used as a substrate for the engineering of nitrobenzene dioxygenase, an enzyme that plays a crucial role in the production of hydroxytyrosol. Hydroxytyrosol is a highly potent antioxidant known for its various health benefits, including its antioxidant, anti-inflammatory, and neuroprotective properties. The use of 3-NPEA in this process aids in the development of novel and efficient methods for synthesizing hydroxytyrosol, which can be utilized in the pharmaceutical industry for the treatment and prevention of various diseases and conditions.
Used in Chemical Synthesis:
3-Nitrophenethyl alcohol can also be used as a versatile intermediate in the synthesis of various organic compounds, particularly those with pharmaceutical or chemical applications. Its unique structure allows for a range of chemical reactions, such as reduction, substitution, and condensation, which can lead to the formation of a diverse array of products. This makes 3-NPEA a valuable building block in the development of new drugs, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 3-nitrophenethyl alcohol is often employed in research and development settings. It can be used as a model compound to study various chemical reactions and mechanisms, as well as to develop new synthetic methods and techniques. Additionally, its use in the engineering of nitrobenzene dioxygenase for the production of hydroxytyrosol can provide valuable insights into enzyme catalysis and the development of biocatalytic processes for the synthesis of valuable compounds.

InChI:InChI=1/C8H9NO3/c1-6(10)7-3-2-4-8(5-7)9(11)12/h2-6,10H,1H3

Synthetic route

1-nitro-3-vinyl-benzene (586-39-0) → 2-(3-nitrophenyl)ethanol (52022-77-2)

Conditions	Yield
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) → 2-(3-nitrophenyl)ethanol (52022-77-2)

Conditions	Yield
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-nitrophenyl)ethanol (52022-77-2)

Conditions	Yield
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) → 2-(3-nitrophenyl)ethanol (52022-77-2)

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

Conditions	Yield
With hydrogenchloride; sodium nitrite anschliessendes Behandeln mit H3PO2;

methanol (67-56-1) + 1-nitro-3-vinyl-benzene (586-39-0) → 2-(3-nitrophenyl)ethanol (52022-77-2) + 1-(2-methoxyethyl)-3-nitrobenzene (110435-89-7)

Conditions	Yield
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;

2-phenylethanol (60-12-8) → 2-(4-nitrophenyl)ethanol (100-27-6) + 2-nitro-benzeneethanol (15121-84-3) + 2-(3-nitrophenyl)ethanol (52022-77-2)

Conditions	Yield
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;

4-acetamido-3-nitrophenethyl acetate (92959-73-4) → 2-(3-nitrophenyl)ethanol (52022-77-2)

Conditions	Yield
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) → 2-(3-nitrophenyl)ethanol (52022-77-2)

Conditions	Yield
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) → 2-(3-nitrophenyl)ethanol (52022-77-2)

Conditions	Yield
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-aminophenyl)ethan-1-ol (52273-77-5)

Conditions	Yield
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) + 2-(3-nitrophenyl)ethanol (52022-77-2) → 2-(3-aminophenyl)ethan-1-ol (52273-77-5)

Conditions	Yield
In ethanol; water	100%

acetic acid 2-(3-nitro-phenyl)-ethyl ester (68527-46-8) + 2-(3-nitrophenyl)ethanol (52022-77-2) → acetic acid 2-(3-amino-phenyl)-ethyl ester (690995-22-3)

Conditions	Yield
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) + methanesulfonyl chloride (124-63-0) → 2-(3-nitrophenyl)ethyl methanesulfonate (206874-43-3)

Conditions	Yield
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) → 1-(2-iodoethyl)-3-nitrobenzene (891855-81-5)

Conditions	Yield
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) + tert-butyldimethylsilyl chloride (18162-48-6) → C14H23NO3Si

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h;	94%

2-(3-nitrophenyl)ethanol (52022-77-2) + Methanesulfonic anhydride (7143-01-3) → 2-(3-nitrophenyl)ethyl methanesulfonate (206874-43-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h;	90%

2-(3-nitrophenyl)ethanol (52022-77-2) + methyl iodide (74-88-4) → 1-(2-methoxyethyl)-3-nitrobenzene (110435-89-7)

Conditions	Yield
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) + methyl iodide (74-88-4) → 1-(2-methoxyethyl)-3-nitrobenzene (110435-89-7) + N-[3-(2-methoxyethyl)phenyl]-1,2,4-benzotriazin-3-amine 1-oxide (763131-61-9)

Conditions	Yield
With NaH In tetrahydrofuran	A n/a B 87%

2-(3-nitrophenyl)ethanol (52022-77-2) + acetic anhydride (108-24-7) → acetic acid 2-(3-nitro-phenyl)-ethyl ester (68527-46-8)

Conditions	Yield
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) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 2-(3-nitrophenyl)ethyl ester (69628-97-3)

Conditions	Yield
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) + tolfenamic Acid (13710-19-5) → 2-(3-chloro-2-methyl-phenylamino)-benzoic acid 2-(3-nitro-phenyl)-ethyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h;	80%

3,4,5-trimethoxyphenol (642-71-7) + 2-(3-nitrophenyl)ethanol (52022-77-2) → 1,2,3-Trimethoxy-5-[2-(3-nitro-phenyl)-ethoxy]-benzene

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In toluene for 1h;	75%

2-(3-nitrophenyl)ethanol (52022-77-2) → C16H18N2O2

Conditions	Yield
With sodium hydroxide; zinc In ethanol; water Reflux;	70%

2-(3-nitrophenyl)ethanol (52022-77-2) + dimethyl sulfate (77-78-1) → 1-(2-methoxyethyl)-3-nitrobenzene (110435-89-7)

Conditions	Yield
With sodium hydroxide; tetra-(n-butyl)ammonium iodide In benzene for 144h; Heating;	60%

2-(3-nitrophenyl)ethanol (52022-77-2) + 2,6-dibromo-1,5-naphthalenediol (84-59-3) → C26H20Br2N2O6 (1414857-97-8)

Conditions	Yield
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) + 2-(3-nitrophenyl)ethanol (52022-77-2) → 3'-nitrophenethyl (E)-3-(3,4-dihydroxyphenyl)acrylate

Conditions	Yield
With ytterbium(III) triflate In nitromethane at 120℃;	52%

morpholine (110-91-8) + 2-(3-nitrophenyl)ethanol (52022-77-2) → 1-morpholino-2-(3-nitrophenyl)ethane-1,2-dione (1391739-32-4)

Conditions	Yield
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) → 3-(2-Bromoethyl)nitrobenzene (16799-04-5)

Conditions	Yield
With phosphorus tribromide In diethyl ether Heating;

2-(3-nitrophenyl)ethanol (52022-77-2) → formaldehyd (50-00-0) + 1-methyl-3-nitrobenzene (99-08-1)

Conditions	Yield
In water; acetonitrile Product distribution; Irradiation;

2-(3-nitrophenyl)ethanol (52022-77-2) → 1-methyl-3-nitrobenzene (99-08-1) + 3,3'-dinitrobibenzyl (19829-61-9)

Conditions	Yield
In water; acetonitrile for 2h; Mechanism; Product distribution; Quantum yield; Irradiation; variation of pH;

2-(3-nitrophenyl)ethanol (52022-77-2) + TsX → toluene-4-sulfonic acid 2-(3-nitrophenyl)ethyl ester (69628-97-3)

Upstream product

• 10268-12-9 methyl 3-nitrophenylacetate 
• 621-50-1 (3-nitrophenyl)acetonitrile 
• 3958-57-4 1-bromomethyl-3-nitrobenzene 
• 5182-44-5 2-(3-chlorophenyl)ethanol 
• 92959-73-4 4-acetamido-3-nitrophenethyl acetate 
• 60-12-8 2-phenylethanol 
• 586-39-0 1-nitro-3-vinyl-benzene 
• 67-56-1 methanol 
• 1877-73-2 3-nitro-benzeneacetic acid 
• 15896-61-4 2-(4-amino-3-nitrophenyl)ethanol 

Downstream Products

• 52273-77-5 2-(3-aminophenyl)ethan-1-ol 
• 110435-89-7 1-(2-methoxyethyl)-3-nitrobenzene 
• 172833-08-8 methyl 3-amino-4-[3-[(aminoiminomethyl)amino]phenyl]butanoate 
• 1308256-17-8 1-(2-fluoroethyl)-3-nitrobenzene 
• 1308256-18-9 3-(2-fluoroethyl)aniline 
• 1308256-19-0 2,2,2-trifluoro-N-(3-(2-fluoroethyl)phenyl)acetamide 
• 1331896-47-9 2-(2-fluoroethyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride 
• 1308256-20-3 2,2,2-trifluoro-N-(3-(2-fluoroethyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenyl)acetamide 
• 1308254-88-7 4-amino-2-(2-fluoroethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide 
• 1308256-30-5 methyl(3-nitrophenethyl)sulfane 
• 1308256-31-6 3-(2-(methylthio)ethyl)aniline 
• 1308256-32-7 2,2,2-trifluoro-N-(3-(2-(methylthio)ethyl)phenyl)acetamide 
• 1308256-33-8 2,2,2-trifluoro-N-(3-(2-(methylsulfonyl)ethyl)phenyl)acetamide 
• 1308256-34-9 2-(2-(methylsulfonyl)ethyl)-4-(2,2,2-trifluoroacetamido)benzenesulfonic acid 

Relevant articles and documents

CHEMICAL COMPOUNDS

The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to FormμLa (I): wherein R, R1,P, X, Y, and Z are as defined herein; or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be usefμL in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety

A series of CAPE derivatives with mono-substituted phenylethanols moiety were synthesized and evaluated by MTT assay on growth of 4 human cancer cell lines (Hela, DU-145, MCF-7 and ECA-109). The substituent effects on the antiproliferative activity were systematically investigated for the first time. It was found that electron-donating and hydrophobic substituents at 2′-position of phenylethanol moiety could significantly enhance CAPE's antiproliferative activity. 2′-Propoxyl derivative, as a novel caffeic acid ester, exhibited exquisite potency (IC50?=?0.4?±?0.02 & 0.6?±?0.03?μM against Hela and DU-145 respectively).

N, N-disubstituted benzo-nitrogen heterocycles-2-amine compound and use thereof

The invention mainly relates to an N,N-double substituted benzoazacyclo-2-amide compound and an application thereof. The N,N-double substituted benzoazacyclo-2-amide compound is a compound shown as formula I or a salt formed by a medical acid or alkali. The compound provided by the invention has strong inhibition activity on RhoA protease which is tightly related with cardiovascular and cerebrovascular diseases. The compound provided by the invention is hopeful to be developed into a RhoA protease small-molecule inhibitor type cardiovascular and cerebrovascular disease treatment medicine.