122-98-5

Basic information

• Product Name: 2-Anilinoethanol
• Synonyms: 2-anilino-ethano;Aniline, N-(2-hydroxyethyl)-;Aniline, N-(beta-hydroxyethyl)-;Benzenamine, N-(2-hydroxyethyl)-;Emery 5700;emery5700;Ethanol, 2-anilino-;Ethanol,2-(phenylamino)-
• CAS NO: 122-98-5
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 204-588-1
• Product Categories: Intermediates of Dyes and Pigments;Hydroxyethylamines;Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 122-98-5.mol
• Article Data: 69

Chemical Properties

• Melting Point: -30 °C
• Boiling Point: 150-152 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear yellow to brown liquid
• Density: 1.094 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.578(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 4.5g/l
• PKA: 14.39±0.10(Predicted)
• Explosive Limit: 1-6.8%(V)
• Water Solubility: 53 g/L (20 ºC)
• BRN: 774672
• CAS DataBase Reference: 2-Anilinoethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Anilinoethanol(122-98-5)
• EPA Substance Registry System: 2-Anilinoethanol(122-98-5)

Safety Data

• Hazard Codes: T
• Statements: 24-41-48/20/21/22-36-R36-R24
• Safety Statements: 26-36/37/39-45-28A-S45-S36/37/39-S28A-S26
• RIDADR: UN 2810 6.1/PG 2
• WGK Germany: 1
• RTECS: KJ7175000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 122-98-5(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW TO BROWN LIQUID

Uses

Different sources of media describe the Uses of 122-98-5 differently. You can refer to the following data:
1. N-Phenylethanolamine is used as an intermediate for dyes and other organic compounds. Further, it is used as a substrate for human olfactory uridine 5'-diphospho-glucuronosyltransferase.
2. N-(2-Hydroxyethyl)aniline was employed as substrate for human olfactory UDP-glucuronosyltransferase.

Synthesis Reference(s)

Different sources of media describe the Synthesis Reference(s) of 122-98-5 differently. You can refer to the following data:
1. Journal of Medicinal Chemistry, 11, p. 87, 1968 DOI: 10.1021/jm00307a019Journal of the American Chemical Society, 74, p. 5514, 1952Tetrahedron Letters, 10, p. 4555, 1969 DOI: 10.1017/S0009838800024678
2. Synthetic Communications, 24, p. 1415, 1994 DOI: 10.1080/00397919408011745

Flammability and Explosibility

Notclassified

Safety Profile

Poison by skin contact, intraperitoneal, and intravenous routes. Moderately toxic by ingestion. A skin and severe eye irritant. Combustible when exposed to heat or flame. To fight fire, use dry chemical, water mist. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C8H11NO/c10-7-6-9-8-4-2-1-3-5-8/h1-5,9-10H,6-7H2

Synthetic route

iodobenzene (591-50-4) + ethanolamine (141-43-5) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With copper(l) chloride; potassium hydroxide at 20℃; for 8h; Neat (no solvent);	99%
With aluminum oxide; copper; potassium hydroxide for 0.5h;	98%
With copper(l) iodide; bis(tetrabutylammonium) adipate; L-proline In N,N-dimethyl-formamide at 25℃; for 24h; Inert atmosphere;	96%

bromobenzene (108-86-1) + ethanolamine (141-43-5) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With copper(l) chloride; potassium hydroxide at 90℃; for 8h; Neat (no solvent);	99%
With potassium phosphate; copper(l) iodide In diethylene glycol at 70℃; for 14h; Sealed tube;	98%
With copper(l) iodide; potassium carbonate In water at 80℃; for 15h;	91.1%
With chitosan Cu2+ complex In acetonitrile for 6h; Reflux; Green chemistry;	87%

ethanolamine (141-43-5) + phenylboronic acid (98-80-6) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With [copper(II)]2-β-cyclodextrin complex In water at 20℃; for 24h; chemoselective reaction;	96%
With Fe3O4 magnetic nanoparticles-supported EDTA-copper(II) complex In water at 50℃; for 2h; Green chemistry;	96%

[1,3]-dioxolan-2-one (96-49-1) + aniline (62-53-3) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With Na-Y zeolite In Triethylene glycol dimethyl ether at 160℃; for 0.5h;	94%
With 1-n-butyl-3-methylimidazolim bromide

oxirane (75-21-8) + aniline (62-53-3) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With samarium(III) chloride In tetrahydrofuran at 0℃; for 12h;	93.1%
With zinc(II) chloride In acetonitrile at -20℃; for 20h;	87.3%
In acetone for 15h; Cooling with ice;	82%

Iodoethanol (624-76-0) + aniline (62-53-3) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
at 90℃; for 6h; Inert atmosphere;	90%

aniline (62-53-3) + 2-bromoethanol (540-51-2) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
at 90℃; for 4h; Inert atmosphere;	89%
at 80℃; for 1h;	3 g

thiophenol (108-98-5) + 3-phenyl-1,2,3-oxadiazolinium trifluoromethanesulfonate → diphenyl sulfide (139-66-2) + diphenyldisulfane (882-33-7) + Azobenzene (1227476-15-4) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
In phosphate buffer; acetonitrile at 25℃; for 4h; pH=7.4; Oxidation; Ring cleavage; Further byproducts given;	A 3% B 85% C 7.5% D 1.7%

2-phenoxyethanamine (1758-46-9) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate In 2,2,2-trifluoroethanol at 29℃; for 24h; Reagent/catalyst; Solvent; Sealed tube; Irradiation; Inert atmosphere;	85%

ethylene glycol (107-21-1) + aniline (62-53-3) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With Fe3O4/FeO In water at 40℃; for 24h; Time; Green chemistry;	76%
With palladium on activated charcoal; zinc(II) oxide In water at 150℃; for 24h; Sealed tube;	65%
In o-xylene at 150℃; for 30h; Inert atmosphere; Sealed tube;	39%
tiveTMNano*MgO*Plus*(NAP-MgO,*Aerogel*prepared) at 125℃; for 1h;

[1,3]-dioxolan-2-one (96-49-1) + aniline (62-53-3) → 2,2'-(phenylimino)bis[ethanol] (120-07-0) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
With tri-i-butyl(methyl)phosphonium tosylate at 170℃; for 8h; Ionic liquid; Neat (no solvent);	A 74% B n/a
With Na-Y zeolite In Triethylene glycol dimethyl ether at 160℃; for 2h;	A 19% B 63%
In neat (no solvent) at 140℃; for 14h;

Glycolaldehyde (141-46-8) + aniline (62-53-3) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
Stage #1: Glycolaldehyde; aniline In 1,2-dichloro-ethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 4h;	72%

Diphenyliodonium triflate (66003-76-7) + ethanolamine (141-43-5) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With potassium phosphate; copper diacetate In 1,4-dioxane at 40℃; for 24h; Inert atmosphere;	60%

triphenylbismuth(V) diacetate (28899-97-0) + ethanolamine (141-43-5) → N,N-diphenyl-N-(2-hydroxyethyl)amine (6315-51-1) + N-(2-phenoxyethyl)aniline (622-18-4) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
	A 8% B 17% C 51%

bromobenzene (108-86-1) + (2-hydroxy-ethyl)ammonium acetate (54300-24-2) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With copper In N,N-dimethyl-formamide Reflux;	46%

aniline (62-53-3) + 2-chloro-ethanol (107-07-3) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With potassium carbonate; potassium iodide at 80℃; for 12h; Inert atmosphere;	41%
at 110℃;

3-phenylcyclohexanospiro-2-oxazolidine (74255-58-6) → 1-phenyl-4,5,6,7-tetrahydro-1H-indole (68394-64-9) + 2-Anilinoethanol (122-98-5) + cyclohexanol (108-93-0)

Conditions	Yield
With potassium hydroxide Heating; CH3ONa as reagent;	A 38% B n/a C n/a

methanol (67-56-1) + formaldehyd (50-00-0) + aniline (62-53-3) → 2,2'-(phenylimino)bis[ethanol] (120-07-0) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
With tert.-butylhydroperoxide; titanium(III) chloride at 20℃; for 0.5h; Acidic aq. solution; Inert atmosphere;	A 15% B 30%

N-(2-aminoethyl)benzeneamine (1664-40-0) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With [Ir(κ2O,O-CH3COO)(I)2{κC,C'-methylenebis(N-methyl)imidazole-2-ylidene}]; water; glycerol; potassium hydroxide at 120℃; for 16h;	22%

N-methyl-2-phenoxyethan-1-amine (37421-04-8) → N-(2-hydroxyethyl)-N-methylaminobenzene (93-90-3) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate In 2,2,2-trifluoroethanol at 29℃; for 24h; Sealed tube; Irradiation; Inert atmosphere;	A 15% B 8%

N-phenylglycine ethyl ester (2216-92-4) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With ethanol; sodium

1-chloro-2-phenylcarbamoyloxy-ethane (3747-48-6) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With alkaline solution; water
With ethanol; alkaline solution

4-((2-hydroxyethyl)amino)benzoic acid (117821-34-8) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
at 210 - 260℃;

4-((2-hydroxyethyl)amino)benzoic acid (117821-34-8) → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
at 210 - 260℃;

ethylene glycol (107-21-1) + aniline (62-53-3) → 2,2'-(phenylimino)bis[ethanol] (120-07-0) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
With boron trifluoride at 190℃;

N-Phenylglycine (103-01-5) → 2-Anilinoethanol (122-98-5)

Conditions	Yield
With lithium aluminium tetrahydride

aniline (62-53-3) + 2-chloro-ethanol (107-07-3) → 1,4-diphenyl-piperazine (613-39-8) + 2,2'-(phenylimino)bis[ethanol] (120-07-0) + N,N'-diphenylethylenediamine (150-61-8) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
at 110℃;
at 110℃;

aniline (62-53-3) + 2-chloro-ethanol (107-07-3) → 1,4-diphenyl-piperazine (613-39-8) + 2,2'-(phenylimino)bis[ethanol] (120-07-0) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
at 110℃;

aniline (62-53-3) + 2-chloro-ethanol (107-07-3) → N,N'-diphenylethylenediamine (150-61-8) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
at 180℃;

aniline (62-53-3) + 2-chloro-ethanol (107-07-3) → 2,2'-(phenylimino)bis[ethanol] (120-07-0) + 2-Anilinoethanol (122-98-5)

Conditions	Yield
With water; calcium carbonate
With sodium carbonate
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 6h; Time; Temperature; Concentration;

Upstream product

• 75-21-8 oxirane 
• 62-53-3 aniline 
• 6326-87-0 N-(2-hydroxyethyl)-2-phenoxyacetamide 
• 73178-24-2 2-<4-(Dimethylamino)styryl>-N-phenyl-1,3-oxazolidine 
• 74-85-1 ethene 
• 2216-92-4 N-phenylglycine ethyl ester 
• 64-17-5 ethanol 
• 3747-48-6 1-chloro-2-phenylcarbamoyloxy-ethane 
• 107-21-1 ethylene glycol 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 108-86-1 bromobenzene 
• 54300-24-2 (2-hydroxy-ethyl)ammonium acetate 
• 141-46-8 Glycolaldehyde 

Downstream Products

• 703-56-0 N-phenyl-2-oxazolidinone 
• 474414-72-7 N-(2-hydroxy-ethyl)-N-phenyl-N'-p-tolyl-thiourea 
• 16285-78-2 2,3-Diphenyl-1,3-oxazolidine 
• 2166-93-0 3,6-diphenyl-3,6-diazaoctane-1,8-diol 
• 32974-54-2 (3-phenyl-oxazolidin-2-ylidene)-m-tolyl-amine 
• 32974-55-3 (4-chloro-phenyl)-(3-phenyl-oxazolidin-2-ylidene)-amine 
• 32974-53-1 (3-phenyl-oxazolidin-2-ylidene)-p-tolyl-amine 
• 13468-08-1 (3-phenyl-oxazolidin-2-ylidene)-o-tolyl-amine 
• 5679-73-2 2,3-diphenyl-1,3,2-oxazaphospholidine 
• 31707-09-2 N,N-diethyl-3-phenyl-1,3,2-oxazaphospholidin-2-amine 
• 126480-68-0 N-(hydroxy-2' ethyl) anilinomethylene-5 dimethyl-2,2 dioxanne-1,3 dione-4,6 
• 115334-90-2 N-Phenyl-N-(2-phenylsulfanyl-ethyl)-acetamide 
• 85687-78-1 2-ethoxy-2-oxo-3-phenyl-1,3,2-oxazaphospholan 
• 13534-87-7 N-(2-acetoxyethyl)acetanilide 

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A new easily accessible chiral phosphite–phosphoramidite ligand based on 2-Anilinoethanol (cas 122-98-5) and R-BINOL moieties for Rh-catalyzed asymmetric olefin hydrogenation09/07/2019

A novel chiral phosphite–phosphoramidite ligand based on 2-anilinoethanol and R-BINOL moieties has been synthesized in one-pot. The ligand was evaluated in the rhodium-catalyzed enantioselective hydrogenation of α- and β-dehydroamino acid derivatives and dimethyl itaconate in three different ...detailed

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