15121-84-3

Basic information

• Product Name: 2-Nitrophenethyl alcohol
• Synonyms: o-nitro-phenethylalcoho;o-nitrophenethyl alcohol;ORTHO-NITROPHENETHYLALCOHOL;o-Nitrophenylethanol;2-nitrophenethyl alchol;Ncgc00090875-01;2-(2-Nitrophenyl)ethan-1-ol;2-nitro-2-phenylethan-1-ol
• CAS NO: 15121-84-3
• Molecular Formula: C₈H₉NO₃
• Molecular Weight: 167.16
• EINECS: 239-178-1
• Product Categories: Alcohols;C7 to C8;Oxygen Compounds;Building Blocks;C7 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Piperazines
• Mol File: 15121-84-3.mol

Chemical Properties

• Melting Point: 2 °C(lit.)
• Boiling Point: 267 °C(lit.)
• Flash Point: >230 °F
• Appearance: brown liquid
• Density: 1.19 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00416mmHg at 25°C
• Refractive Index: n20/D 1.5637(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.63±0.10(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2-Nitrophenethyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Nitrophenethyl alcohol(15121-84-3)
• EPA Substance Registry System: 2-Nitrophenethyl alcohol(15121-84-3)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: SG8601000
• HazardClass: IRRITANT
• Hazardous Substances Data: 15121-84-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Nitrophenethyl alcohol is used as an intermediate in the synthesis of indoles, which are important for the development of pharmaceutical compounds. Indoles have a wide range of biological activities, including anti-inflammatory, analgesic, and anti-cancer properties. The use of 2-Nitrophenethyl alcohol in the synthesis of these compounds contributes to the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
2-Nitrophenethyl alcohol is also used as a reagent in various chemical synthesis processes. Its unique chemical properties allow it to be employed in the production of a variety of compounds, including those with potential applications in the fields of materials science, agrochemicals, and specialty chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 438, 1984 DOI: 10.1021/jo00177a010

Air & Water Reactions

Insoluble in water.

Fire Hazard

2-Nitrophenethyl alcohol is probably combustible.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C8H9NO3/c10-6-5-7-3-1-2-4-8(7)9(11)12/h1-4,10H,5-6H2

Upstream product

• 103-45-7 acetic acid phenethyl ester 
• 31912-02-4 ethyl 2-nitrophenylacetate 
• 50-00-0 formaldehyd 
• 88-72-2 1-methyl-2-nitrobenzene 
• 60-12-8 2-phenylethanol 
• 7697-37-2 nitric acid 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 109-63-7 trifluoroborane diethyl ether 
• 579-71-5 2-nitrostyrene 
• 552-89-6 2-nitro-benzaldehyde 
• 1969-73-9 (2-nitrophenyl)acetaldehyde 
• 30095-98-8 methyl (2-nitrophenyl)acetate 
• 24393-59-7 (E)-ethyl 3-(2-nitrophenyl)acrylate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 16793-89-8 (2-bromoethyl)-2-nitrobenzene 
• 69628-96-2 p-toluenesulfonic acid o-nitrophenethyl ester 
• 33100-15-1 2-(2-aminoethyl)nitrobenzene 
• 179691-21-5 2-nitrophenethyl chloroformate 
• 5339-85-5 2-aminophenethyl alcohol 
• 118311-01-6 1-(2-tert-butyldimethylsilyloxy)ethyl-2-nitrobenzene 
• 179691-36-2 5'-O-(2-(2-nitrophenyl)ethoxycarbonyl)thymidine 
• 215600-56-9 2-(2-Nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 215600-60-5 2-(2-Nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{4-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-2-oxo-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethyl ester 
• 199122-98-0 2-(2-Nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 
• 215600-73-0 2-(2-Nitro-phenyl)-ethanesulfonic acid (2R,3S,5R)-3-hydroxy-5-{6-[2-(4-nitro-phenyl)-ethoxy]-2-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl ester 
• 791-28-6 Triphenylphosphine oxide 
• 833-44-3 2-(2-nitrophenyl)ethyl nitrate 
• 88-72-2 1-methyl-2-nitrobenzene 

Relevant articles and documents

Direct Arylation of Distal and Proximal C(sp3)-H Bonds of t-Amines with Aryl Diazonium Tetrafluoroborates via Photoredox Catalysis

A visible light-mediated arylation protocol for t-amines has been reported through the coupling of γ- and α-amino alkyl radicals with different aryl diazonium salts using Ru(bpy)3Cl2·6H2O as a photocatalyst. Structurally different 9-aryl-9,10-dihydroacridine, 1-aryl tetrahydroisoquinoline, hexahydropyrrolo[2,1-a]isoquinoline, and hexahydro-2H-pyrido[2,1-a]isoquinoline frameworks with different substitution patterns have been synthesized in good yield using this methodology.

Exploring the Potential of 2-(2-Nitrophenyl)ethyl-Caged N-Hydroxysulfonamides for the Photoactivated Release of Nitroxyl (HNO)

The emergence of nitroxyl (HNO) as a biological signaling molecule is attracting increasing attention. HNO-based prodrugs show considerable potential in treating congestive heart failure, with HNO reacting rapidly with metal centers and protein-bound and free thiols. A new class of 2-(2-nitrophenyl)ethyl (2-NPE)-photocaged N-hydroxysulfonamides has been developed, and the mechanisms of photodecomposition have been investigated. Three photodecomposition pathways are observed: The desired concomitant C-O/N-S bond cleavage to generate HNO, sulfinate, and 2-nitrostyrene, C-O bond cleavage to give the parent sulfohydroxamic acid and 2-nitrostyrene, and O-N bond cleavage to release a sulfonamide and 2-nitrophenylacetaldehyde. Laser flash photolysis experiments provide support for a Norrish type II mechanism involving 1,5-hydrogen atom abstraction to generate an aci-nitro species. A mechanism is proposed in which the (Z)-aci-nitro intermediate undergoes either C-O bond cleavage to release RSO2NHO(H), concerted C-O/N-S bond cleavage to generate sulfinate and HNO, or isomerization to the (E)-isomer prior to O-N bond cleavage. The pKa of the N(H) of the N-hydroxysulfonamide plays a key role in determining whether C-O or concerted C-O/N-S bond cleavage occurs. Deprotonating this site favors the desired C-O/N-S bond cleavage at the expense of an increased level of undesired O-N bond cleavage. Triplet state quenchers have no effect on the observed photoproducts.

Synthesis of thioethers, arenes and arylated benzoxazoles by transformation of the C(aryl)-C bond of aryl alcohols

Transformation of aryl alcohols into high-value functionalized aromatic compounds by selective cleavage and functionalization of the C(aryl)-C(OH) bond is of crucial importance, but very challenging by far. Herein, for the first time, we report a novel and versatile strategy for activation and functionalization of C(aryl)-C(OH) bonds by the cooperation of oxygenation and decarboxylative functionalization. A diverse range of aryl alcohol substrates were employed as arylation reagents via the cleavage of C(aryl)-C(OH) bonds and effectively converted into corresponding thioether, arene, and arylated benzoxazole products in excellent yields, in a Cu based catalytic system using O2 as the oxidant. This study offers a new way for aryl alcohol conversion and potentially offers a new opportunity to produce high-value functionalized aromatics from renewable feedstocks such as lignin which features abundant C(aryl)-C(OH) bonds in its linkages.

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).

Pd-Catalyzed Selective Synthesis of Cyclic Sulfonamides and Sulfinamides Using K2S2O5 as a Sulfur Dioxide Surrogate

A variety of cyclic sulfonamides and sulfinamides could be selectively synthesized under Pd catalysis using haloarenes bearing amino groups and a sulfur dioxide (SO2) surrogate. The amount of base was key in determining the selectivity. Mechanistic studies revealed that sulfinamides were initially formed via an unprecedented formal insertion of sulfur monoxide and were oxidized to sulfonamides in the presence of an iodide ion and DMSO.

Process for Synthesis of Chiral 3-Substituted Tetrahydroquinoline Derivatives

The present invention relates to novel and concise process for the construction of chiral 3-substituted tetrahyroquinoline derivatives based on proline catalyzed asymmetric α-functionalization of aldehyde, followed by in situ reductive cyclization of nitro group under catalytic hydrogenation condition with high optical purities. Further the invention relates to conversion of derived chiral 3-substituted tetrahydroquinoline derivatives into therapeutic agents namely (?)-sumanirole (96% ee) and 1-[(S)-3-(di-methylamino)-3,4-dihydro-6,7-dimethoxy-quinolin-1(2H)-yl]propanone[(S)-903] (92% ee).

Asymmetric Intramolecular Conjugate Addition Nitro-Mannich Route to cis-2-Aryl-3-nitrotetrahydroquinolines

Reductive cyclization of 2-iminonitrostyrenes (from the condensation of 2-aminostyrenes with an aldehyde and subsequent nitration of the alkene) using a bifunctional thiourea catalyst and tert-butyl-Hantzsch ester leads to an intramolecular conjugate hydride addition nitro-Mannich reaction to give the corresponding cis-2-aryl-3-nitrotetrahydroquinolines as single diastereoisomers in high yields and enantioselectivities.

Palladium-catalyzed direct coupling of 2-vinylanilines and isocyanides: An efficient synthesis of 2-aminoquinolines

Palladium-catalyzed oxidative coupling of 2-vinylanilines and isocyanides constitutes a direct, facile, and efficient approach to 2-aminoquinolines. The procedure, employing palladium acetate and silver carbonate, is attractive in terms of assembly efficiency, functional group tolerance, and operational simplicity. A variety of 2-aminoquinolines were prepared in good to excellent yields.

CERTAIN PROTEIN KINASE INHIBITORS

Provided are certain EGFR mutant selective inhibitors, pharmaceutical compositions thereof, and methods of use therefor.

Synthesis of indolines via a SmI2 promoted domino nitro reduction-intramolecular aza-Michael reaction

A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza-Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2-(2-nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This "one pot" strategy also permitted the expeditious synthesis of a 1,2,3,4-tetrahydroquinoline, whereas the seven-membered 2,3,4,5-tetrahydrobenzoazepines compounds were not formed under these reaction conditions.