1072-52-2

Basic information

• Product Name: 1-AZIRIDINEETHANOL
• Synonyms: 2-(1-Aziridinyl)ethanol;2-hydroxy-1-ethylaziridine;beta-hydroxy-1-ethylaziridine;Ethanol, 2-(1-aziridinyl)-;hydroxyethylethyleneimine;N-(2-Hydroxyethyl)ethylenimine;N-(beta-Hydroxyethyl)aziridine;N-(Hydroxyethyl)ethyleneimine
• CAS NO: 1072-52-2
• Molecular Formula: C₄H₉NO
• Molecular Weight: 87.12
• EINECS: 214-009-4
• Product Categories: Aziridines;Simple 3-Membered Ring Compounds
• Mol File: 1072-52-2.mol

Chemical Properties

• Boiling Point: 167-168°C
• Flash Point: 67°C
• Appearance: /
• Density: 1.088 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.542mmHg at 25°C
• Refractive Index: 1.4560
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.97±0.10(Predicted)
• Stability: Hygroscopic, Moisture Sensitive
• CAS DataBase Reference: 1-AZIRIDINEETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AZIRIDINEETHANOL(1072-52-2)
• EPA Substance Registry System: 1-AZIRIDINEETHANOL(1072-52-2)

Safety Data

• Hazard Codes: T
• Statements: 24/25-34
• Safety Statements: 26-36/37/39-45-23
• RIDADR: 2922
• RTECS: CM7000000
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1072-52-2(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Chemical intermediate.

Air & Water Reactions

Soluble in water. Hydrolyzes to give diethanolamine .

Reactivity Profile

1-AZIRIDINEETHANOL is an amino alcohol. Amines are chemical bases. They neutralize acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Hazard

Irritant to skin and eyes.

Fire Hazard

1-AZIRIDINEETHANOL is combustible.

Safety Profile

Poison by ingestion, skin contact, and intravenous routes. A sktn and eye irritant. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C4H9NO/c6-4-3-5-1-2-5/h6H,1-4H2/p+1

Synthetic route

oxirane (75-21-8) + ethyleneimine (151-56-4) → 2-(1-aziridine)ethanol (1072-52-2)

ethanolamine (141-43-5) → ethyleneimine (151-56-4) + 2-(1-aziridine)ethanol (1072-52-2) + 1,4-pyrazine (290-37-9)

Conditions	Yield
With (Cs2O)5.5-(P2O5)1.8/SiO2 at 420℃; Temperature;

2-(1-aziridine)ethanol (1072-52-2) + diethylzinc (557-20-0) → C2H5(1-)*Zn(2+)*C2H4NC2H4O(1-)=[(C2H5)Zn(C2H4NC2H4O)]

Conditions	Yield
In toluene Et2Zn and 1-aziridineethanol (1 equiv.) were reacted in toluene;	99%

2-(1-aziridine)ethanol (1072-52-2) + methyl (E)-5-[4-(2,2-dimethylpropanoyloxy)phenyl]-5-(4-hydroxyphenyl)-4-phenyl-pent-4-enoate → (E)-methyl 5-(4-(2-(aziridin-1-yl)ethoxy)phenyl)-4-phenyl-5-(4-(pivaloyloxy)phenyl)pent-4-enoate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; Mitsunobu Displacement;	99%

2-(1-aziridine)ethanol (1072-52-2) + 2-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (680199-30-8) → 2-[(2-chloroethyl)(2-hydroxyethyl)amino]-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (944088-69-1)

Conditions	Yield
With lithium chloride In various solvent(s) cooling;	97%
In 3-methyl-butan-2-one at 5 - 20℃; Product distribution / selectivity;	97%

2-(1-aziridine)ethanol (1072-52-2) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) → trans-(bis[(acetato-κO)-(2-(1-aziridinyl)ethanol-κ2-N,O)])cobalt(II) (1214883-04-1)

Conditions	Yield
In dichloromethane (Ar); Schlenk techniques; 2-(1-azirinyl)ethanol added to CH2Cl2 soln. ofCo(OAc)2; stirred at 21°C for 18 h; evapn.; dried in vac.; elem. anal.;	96%

2-(1-aziridine)ethanol (1072-52-2) + cobalt(II) chloride (7646-79-9) → cis-(bis[chlorido-(2-(1-aziridinyl)ethanol-κ2-N,O)])cobalt(II)

Conditions	Yield
In dichloromethane (Ar); Schlenk techniques; 2-(1-azirinyl)ethanol added to CH2Cl2 soln. ofCoCl2; stirred at 21°C for 18 h; evapn.; dried in vac.; stirred in dry acetone; decanted; dried in vac.; elem. anal.;	95%

2-(1-aziridine)ethanol (1072-52-2) → <2-<(2-hydroxyethyl)amino>ethyl>hydrazine (88303-65-5)

Conditions	Yield
With hydrazine In water at 113℃; for 44h;	94%
With hydrazine hydrate In water for 48h; Heating;	60%

2-(1-aziridine)ethanol (1072-52-2) + copper(ll) bromide (7789-45-9) → tetrakis(μ3-(2-aziridin-1-ylethanolato-κ2N,O)bromidocopper(II)) (1313430-51-1)

Conditions	Yield
In dichloromethane byproducts: HBr; (Ar); addn. of 1.2 equiv. of aziridine deriv. to suspn. of copper compd.in CH2Cl2, stirring for 18 h at room temp.; evapn., stirring in acetone overnight at room temp., decantation, dryingvac., elem. anal.;	93%

2-(1-aziridine)ethanol (1072-52-2) + 2-chloro-3,5-dinitrobenzamide (6266-51-9) → 2-[(2-chloroethyl)(2-hydroxyethyl)amino]-3,5-dinitrobenzamide

Conditions	Yield
With lithium chloride In tetrahydrofuran cooling;	92%
In tetrahydrofuran at 5 - 20℃;	92%

2-(1-aziridine)ethanol (1072-52-2) + (OC)4Re(η(3)-C3H5) → trans-bis[(μ2-O(η(2)-N,O)-2-aziridinylethoxy)tricarbonyl-rhenium(I)] (618885-13-5)

Conditions	Yield
In octane byproducts: C3H6, CO; all manipulations under Ar atm.; Re complex and 1 equiv. of aminoalc. dissolved in octane and refluxed for 2 h; solvent evapd., residue washed with pentane, dried in vac., elem. anal.;	92%

2-(1-aziridine)ethanol (1072-52-2) + di(tert-butyl) 2-[(2-chloro-3,5-dinitrobenzoyl)amino]ethyl phosphate (944088-64-6) → di(tert-butyl) 2-({2-[(2-chloroethyl)(2-hydroxyethyl)amino]-3,5-dinitrobenzoyl}amino)ethyl phosphate (944088-77-1)

Conditions	Yield
With triethylamine In 1,4-dioxane at 20℃;	90%

2-(1-aziridine)ethanol (1072-52-2) + 2-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (680199-30-8) → 2-[(2-bromoethyl)(2-hydroxyethyl)amino]-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (944088-70-4)

Conditions	Yield
With lithium bromide In 3-methyl-butan-2-one at 5 - 20℃; Product distribution / selectivity;	90%
With lithium bromide In various solvent(s) cooling;	80%

2-(1-aziridine)ethanol (1072-52-2) + N-benzyloxycarbonyl-2-(4-hydroxyphenyl)ethylamine (29655-46-7) → benzyl 4-(2-(aziridin-1-yl)ethoxy)phenethylcarbamate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at -5 - 20℃; Inert atmosphere;	89%

2-(1-aziridine)ethanol (1072-52-2) + (triphenylphosphine)gold(I) chloride (14243-64-2) + silver trifluoromethanesulfonate (2923-28-6) → [N-hydroxyethylaziridine-triphenylphosphanegold(I)]-trifluoromethylsulfonate (852989-12-9)

Conditions	Yield
In dichloromethane byproducts: AgCl; (Ar); Ag salt was added to soln. of Au complex (1 equiv.) in CH2Cl2; soln. was stirred for 15 min; centrifuged; soln. was decanted; aziridine (1equiv.) was added; soln. was stirred for 1 h; solvent evapd.; stirred in hexane; filtered; dried (vac.); elem. anal.;	88%

2-(1-aziridine)ethanol (1072-52-2) + 2-chloro-3,5-dinitrobenzamide (6266-51-9) → 2-[(2-bromoethyl)(2-hydroxyethyl)amino]-3,5-dinitrobenzamide (944088-67-9)

Conditions	Yield
With lithium bromide In various solvent(s) cooling;	87%
With lithium bromide In 3-methyl-butan-2-one at 5 - 20℃;	87%

2-(1-aziridine)ethanol (1072-52-2) + ((4-ethylpiperazin-1-yl)(5-fluoro-4-(methylsulfonyl)-2-nitrophenyl)methanone) → (5-((2-bromoethyl)(2-hydroxyethyl)amino)-4-(methylsulfonyl)-2-nitrophenyl)(4-ethylpiperazin-1-yl)methanone

Conditions	Yield
With lithium bromide In N,N-dimethyl-formamide at -5 - 0℃;	87%

2-(1-aziridine)ethanol (1072-52-2) + 2-chloro-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (680199-30-8) → 2-[(2-hydroxyethyl)(2-iodoethyl)amino]-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (944088-71-5)

Conditions	Yield
With sodium iodide In 3-methyl-butan-2-one at 5 - 20℃;	82%
With sodium iodide In various solvent(s) cooling;	63%

2-(1-aziridine)ethanol (1072-52-2) + 2-bromo-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide → 2-[(2-bromoethyl)(2-hydroxyethyl)amino]-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide (944088-70-4)

Conditions	Yield
sodium bromide In tetrahydrofuran for 44h; Product distribution / selectivity;	81%

2-(1-aziridine)ethanol (1072-52-2) + sodium tetrahydroborate (16940-66-2) → (HOC2H4)(CH2)2NBH3 (22557-95-5)

Conditions	Yield
With acetic acid In tetrahydrofuran filtration of filtrate, evapn., dissolving in THF, pptn. with hexane;;	76%

2-(1-aziridine)ethanol (1072-52-2) + carbon dioxide (124-38-9) → N-(2'-hydroxyethyl)-2-oxazolidone (3356-88-5)

Conditions	Yield
With 2,2':6,2''-terpyridine In methanol at 110℃; for 20h; Autoclave;	71%
With 1,3-bis(tert-butyl)-imidazolium-2-carboxylate In isopropyl alcohol at 90℃; under 37503.8 Torr; for 20h; Inert atmosphere; Autoclave;	40 %Spectr.

2-(1-aziridine)ethanol (1072-52-2) + 2-chloro-3,5-dinitrobenzamide (6266-51-9) → 2-[(2-hydroxyethyl)(2-iodoethyl)amino]-3,5-dinitrobenzamide (944088-68-0)

Conditions	Yield
With sodium iodide In various solvent(s) cooling;	70%
With sodium iodide In 3-methyl-butan-2-one at 5 - 20℃;	70%

2-(1-aziridine)ethanol (1072-52-2) + trifluoromethane sulfonyl chloride (421-83-0) → 2-(1-aziridinyl)ethyl trifluoromethanesulfonate (112599-15-2)

Conditions	Yield
With sodium hydride In tetrahydrofuran at -80℃; for 4h;	65%

2-(1-aziridine)ethanol (1072-52-2) + tert-butyl 2-chloro-3,5-dinitrobenzoate (87363-66-4) → tert-butyl 2-[(2-hydroxyethyl)(2-chloroethyl)amino]-3,5-dinitrobenzoate (944088-72-6)

Conditions	Yield
With lithium chloride In N,N-dimethyl-formamide cooling;	63%
With lithium chloride In N,N-dimethyl-formamide at 20℃; for 16h;	63%

2-(1-aziridine)ethanol (1072-52-2) + methyl 3-chloro-2,6-dinitrobenzoate (177035-51-7) → methyl 3-[(2-chloroethyl)(2-hydroxyethyl)amino]-2,6-dinitrobenzoate

Conditions	Yield
With lithium chloride In N,N-dimethyl-formamide cooling;	63%
With lithium chloride In N,N-dimethyl-formamide at 20℃; for 6h;	63%

2-(1-aziridine)ethanol (1072-52-2) + piperazine (110-85-0) → 1-(5-hydroxy-3-azapentyl)piperazine (134699-02-8)

Conditions	Yield
With hydrogenchloride In water at 50℃; for 3h;	60%

2-(1-aziridine)ethanol (1072-52-2) + tricarbonylcyclopentadienylmolybdenum(II) chloride (12128-23-3) + water (7732-18-5) → 1,1-dicarbonyl-(η(5)-cyclopentadienyl)-2-hydroxyethylmolybda(1)-aza(2)-cyclopentan(5)-one + [(N-hydroxyethyl-aziridine)(η(5)-cyclopentadienyl)Mo(CO)2]Cl

Conditions	Yield
In acetone byproducts: HOCl; Ar atmosphere, addn. of aziridine to soln. of of Mo complex with stirring, 60°C (1 h), cooling to room temp.; reductn. of volume (vacuum); elem. anal.;	A 60% B 0%

2-(1-aziridine)ethanol (1072-52-2) + hexanedioic acid dimethyl ester (627-93-0) → di[2-(1-aziridinyl)ethyl]adipate (6498-84-6)

Conditions	Yield
Stage #1: 2-(1-aziridine)ethanol With sodium hydride for 0.5h; Stage #2: hexanedioic acid dimethyl ester for 1h; Heating / reflux;	60%

2-(1-aziridine)ethanol (1072-52-2) + tert-butyl 2-chloro-3,5-dinitrobenzoate (87363-66-4) → C15H20BrN3O7 (1236199-90-8)

Conditions	Yield
With lithium bromide In N,N-dimethyl-formamide at 0 - 20℃;	60%

2-(1-aziridine)ethanol (1072-52-2) → methyl 3-[(2-hydroxyethyl)(2-iodoethyl)amino]-2,6-dinitrobenzoate (944088-75-9)

Conditions	Yield
Stage #1: methyl 3-chloro-2,6-dinitrobenzoate With sodium iodide In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 2-(1-aziridine)ethanol In N,N-dimethyl-formamide at 0 - 30℃; for 16h;	58%

2-(1-aziridine)ethanol (1072-52-2) + methyl 3-chloro-2,6-dinitrobenzoate (177035-51-7) → methyl 3-[(2-hydroxyethyl)(2-iodoethyl)amino]-2,6-dinitrobenzoate (944088-75-9)

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide cooling;	58%

2-(1-aziridine)ethanol (1072-52-2) + tert-butyldimethylsilyl chloride (18162-48-6) → 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-aziridine (192657-68-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	56%
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 15h;

Upstream product

• 75-21-8 oxirane 
• 151-56-4 ethyleneimine 
• 141-43-5 ethanolamine 

Downstream Products

• 41104-16-9 N-(2-Hydroxymethyl)-N-(2-chlorethyl)-2,6-dinitro-4-(trifluormethyl)anilin 
• 98896-97-0 2-thiazolidin-3-yl-ethanol 
• 73761-82-7 2-[2-(2-Hydroxy-ethylamino)-ethylsulfanyl]-benzoic acid 
• 73761-87-2 2-[2-(2-Amino-phenylsulfanyl)-ethylamino]-ethanol 
• 134699-02-8 1-(5-hydroxy-3-azapentyl)piperazine 
• 4185-47-1 nitro-bis-(2-nitryloxy-ethyl)-amine 
• 944088-77-1 di(tert-butyl) 2-({2-[(2-chloroethyl)(2-hydroxyethyl)amino]-3,5-dinitrobenzoyl}amino)ethyl phosphate 
• 944088-75-9 methyl 3-[(2-hydroxyethyl)(2-iodoethyl)amino]-2,6-dinitrobenzoate 
• 944088-70-4 2-[(2-bromoethyl)(2-hydroxyethyl)amino]-3,5-dinitro-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]benzamide 
• 944088-72-6 tert-butyl 2-[(2-hydroxyethyl)(2-chloroethyl)amino]-3,5-dinitrobenzoate 
• 156423-12-0 5--2,4-dinitrobenzamide 
• 944088-87-3 5-[(2-bromoethyl)(2-hydroxyethyl)amino]-2,4-dinitrobenzamide 
• 944088-74-8 methyl 3-[(2-bromoethyl)(2-hydroxyethyl)amino]-2,6-dinitrobenzoate 
• 944088-76-0 tert-butyl 3-[(2-chloroethyl)(2-hydroxyethyl)amino]-2,6-dinitrobenzoate 

Relevant articles and documents

Cyclization of monoethanolamine to aziridine over Cs2O-P 2O5/SiO2

Several commercially available supports were examined for cyclization of monoethanolamine to aziridine, and SiO2 was found to yield the best results. The obtained results indicated that selectivity of aziridine was mainly influenced by support. The catalysts were characterized by NH3-TPD and XRD. It was found that SiO2 with lower acidity could inhibit the intermolecular condensations, and thus favored the formation of aziridine. The Cs4P2O7 phase was confirmed as the active site in the supported cesium phosphate catalyst. The reaction parameters were also optimized and a yield of 52% aziridine was obtained over 200 h. Thus, a continuous process for the cyclization of monoethanolamine to aziridine has been established. Springer Science+Business Media B.V. 2012.

Cyclic oligomers of N-substituted aziridines

Novel cyclic oligomers of the formula STR1 ARE PREPARED BY CONTACTING (A) A STRONG PROTIC ACID WITH (B) AN N-substituted non-activated aziridine of the formula STR2 wherein R1 and R2 are independently hydrogen or lower alkyl and R3 is hydrogen, hydroxyl, cyano or an organic radical which is inert in the process. The process is typically conducted in an aqueous alkanol medium. E.g. the cyclic tetramer of N-phenethylaziridine was obtained as the predominant product by heating a solution of N-phenethylaziridine in aqueous ethanol at reflux temperatures in the presence of p-toluenesulfonic acid.