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Cas Database

151-56-4

151-56-4

Identification

  • Product Name:Ethyleneimine

  • CAS Number: 151-56-4

  • EINECS:205-793-9

  • Molecular Weight:43.0684

  • Molecular Formula: C2H5N

  • HS Code:2921300040

  • Mol File:151-56-4.mol

Synonyms:Azacyclopropane;Aziran;Binary Ethyleneimine;Dimethylenimine;EI;Q 043;Q 043 (amine);Soluol XC 100;Aziridina;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,ToxicT

  • Hazard Codes:F;T,T,F,N,T+

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH300 Fatal if swallowed H310 Fatal in contact with skin H314 Causes severe skin burns and eye damage H330 Fatal if inhaled H340 May cause genetic defects H350 May cause cancer H411 Toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention . Ethyleneimine is classified as extremely toxic with a probable oral lethal dose of 5-50 mg/kg which is approximately 7 drops to 1 teaspoonful for a 70 kg (150 lb.) person. Ethyleneimine gives inadequate warning when over-exposure is by inhalation or skin absorption. It is a severe blistering agent, causing third degree chemical burns of the skin. Also, it has a corrosive effect on mucous membranes and may cause scarring of the esophagus. It is corrosive to eye tissue and may cause permanent corneal opacity and conjunctival scarring. Severe exposure may result in overwhelming pulmonary edema. Renal damage has been described. Hemorrhagic congestion of all internal organs has been observed. (EPA, 1998) Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mg/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin bums with dry sterile dressings after decontamination ... . /Organic bases/Amines and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use dry chemical, "alcohol resistant" foam, carbon dioxide, or water spray. Water may be ineffective. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors & toxic decomp products. Explosive decomp may occur under fire conditions. Fight fire from protected location or maximum possible distance. Irritating vapors are generated when heated. Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. May polymerize in fires with evolution of heat and container rupture. Runoff to sewer may create fire or explosion hazard. Ethyleneimine vapors are not inhibited and may form polymers in vents or flame arresters, resulting in stopping of the vents. Toxic oxides of nitrogen are produced during combustion. Upon treatment with sodium hypochlorite, it gives off the explosive compound 1-chloroazidine. Avoid acids, sodium hypochlorite. If heated under pressure, instability may result. Hazardous polymerization may occur. Avoid contact with silver or aluminum. Explosive polymerization may occur upon contact with acids. Polymerization is catalyzed by carbon dioxide. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Remove all ignition sources. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Cover with a 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Fireproof. Separated from acids, oxidants and food and feedstuffs. Dry. Store only if stabilized.Can be stored for some time over a few pellets of sodium hydroxide. /In a closed container/

  • Exposure controls/personal protection:Occupational Exposure limit valuesNIOSH considers ethyleneimine to be a potential occupational carcinogen.NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn.Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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Relevant articles and documentsAll total 42 Articles be found

Inverse-Electron-Demand Palladium-Catalyzed Asymmetric [4+2] Cycloadditions Enabled by Chiral P,S-Ligand and Hydrogen Bonding

Wang, Ya-Ni,Xiong, Qin,Lu, Liang-Qiu,Zhang, Qun-Liang,Wang, Ying,Lan, Yu,Xiao, Wen-Jing

, p. 11013 - 11017 (2019)

Catalytic asymmetric cycloadditions of ambident Pd-containing dipolar species with nucleophilic dipolarophiles, namely, inverse-electron-demand cycloadditions, are challenging and underdeveloped. Possibly, the inherent linear selectivity of Pd-catalyzed intermolecular allylations and the lack of efficient chiral ligands are responsible for this limitation. Herein, two cycloadditions of such intermediates with deconjugated butenolides and azlactones were accomplished by using a novel chiral hybrid P,S-ligand and hydrogen bonding. By doing so, highly functionalized, optically active dihydroquinol-2-ones were produced with generally high reaction efficiencies and selectivities. Preliminary DFT calculations were performed to explain the high enantio- and diastereoselectivities.

-

Wystrach,Schaefer

, p. 1263 (1956)

-

Thermogravimetric Analyzer(TG)-Gas Chromatography(GC)/Mass Spectrometry(MS) and Pyrolytic Studies of 1,6-Bis(2-oxooxazolidin-3-ylcarbonylamino)hexane

Shimasaki, Choichiro,Murai, Atsuko,Sakai, Yukiko,Tsukumirichi, Eiichi

, p. 1009 - 1012 (1988)

1,6-Bis(2-oxooxazolidin-3-ylcarbonylamino)hexane (1) was prepared from 2-oxazolidinone and hexamethylenediisocyanurate using triethylenediamine as a catalyst in benzene.A TG effluent gas is collected in a cold trap and then directly injected into a GC for separation, the MS for unequivocal identification.The 13 effluent compounds from the thermal degradation of 1 were identified.

Cyclodehydration of N- and C-Substituted β-Amino Alcohols to the Corresponding Aziridines with Diethoxytriphenylphosphorane

Kelly, Jeffery W.,Eskew, Nita L.,Evans, Slayton A.

, p. 95 - 97 (1986)

-

Vapor-phase transport as a novel route to hyperbranched polyamine-oxide hybrid materials

Chaikittisilp, Watcharop,Didas, Stephanie A.,Kim, Hyung-Ju,Jones, Christopher W.

, p. 613 - 622 (2013)

A new method to prepare hyperbranched polyamine-oxide hybrid materials by means of a vapor-phase transport is developed. In this method, hybrid materials having hyperbranched amine polymers covalently bound to an oxide support are formed by exposing the oxide support to the vapor of small nitrogen-containing heterocyclic monomers, in contrast to the conventional liquid-phase method, in which the support is dispersed in an organic solution containing monomer species. The aziridine and azetidine monomers are polymerized on the surface of the oxide supports (i.e., silica and alumina), resulting in poly(ethylenimine) or poly(propylenimine) chains attached to the porous solid support. The results suggest that the hybrid materials can be prepared over a wide range of preparation conditions with organic contents comparable to or even higher than those obtained from the standard liquid-phase method. It is demonstrated that supports with more acidity result in the hybrid materials with higher organic content. Interestingly, the resulting supported polyamines have lower molecular weights than the previously reported materials prepared by the liquid-phase method. It is anticipated that the vapor-phase synthesis can be applied for the efficient introduction of polyamines into structural forms of supports such as fibers, membranes, and monoliths, for which the liquid-phase method may be inappropriate or inefficient.

-

Wenker

, p. 2328 (1935)

-

Organocatalyzed cycloaddition of carbon dioxide to aziridines

Wu, Yichen,Liu, Guosheng

, p. 6450 - 6452 (2011)

An efficient and simple process for the fixation of carbon dioxide (CO 2) to aziridine for the synthesis of 2-oxazolidinone by using DBN as catalyst, LiI as an additive under atmospheric pressure was developed. This chemical fixation of CO2 could also be carried out at room temperature with prolonged reaction time.

-

Jadox,Milligen

, p. 278 (1963)

-

The Reactions of NH Radicals with Ethylene and Propene in the Liquid Phase

Kitamura, Takashi,Tsunashima, Shigeru,Sato, Shin

, p. 55 - 59 (1981)

The photolysis of hydrogen azide was studied in liquid ethylene, propene, and the mixture with ethane at the temperature of Dry Ice-methanol.The products observed were aziridine (0.18), ammonia (0.16), and nitrogen (1.0) from the ethylene solution and 2-methylaziridine (0.33), allylamine (0.12), ammonia (0.17), and nitrogen (1.0) from the propene solution.The values in parentheses show the yields relative to that of nitrogen.The relative yields were independent of the concentration of hydrogen azide in the range of 0.8-8*10-2 mol dm-3.The reaction of NH(a1Δ) radicals with olefin consists of three processes: the addition to double bond, the insertion into the C-H bond, and the deactivation to the 3Σ- state.The branching ratios and the relative rate constants of the reactions of NH(a1Δ) radicals with ethylene, propene, and ethane were estimated.

-

Reeves et al.

, p. 3522 (1951)

-

Effect of Distortion on the Hydrolytic Reactivity of Amides. 2. N-Pyramidalization: Decomposition of N-Benzoylaziridines in Aqueous Media

Slebocka-Tilk, H.,Brown, R. S.

, p. 805 - 808 (1987)

The decomposition of para-substituted N-benzoylaziridines (H, OCH3, NO2, Br) in buffered aqueous media is studied at 25 deg C as a function of pH in order to assess the effect of N-pyramidalization on the hydrolytic reactivity of the amide bond.Overall, the reaction shows three dominant terms: OH- and H2O attack on the neutral form and H2O attack on the protonated form of the amide.In base, the exclusive reaction is rate-limiting and irreversible attack of OH- on the C=O unit leading to normal hydrolytic products.This is shown by the first-order dependence on -> from pH 8 to 14 of the hydrolysis rate and by the fact that ca. 50percent 18O-enriched amide recovered from the hydrolysis medium as a function of time shows no 18O loss.Relative to N,N-dimethylbenzamide (kOH-25 deg C = 6.0 * 10-6 M-1 s-1), N-benzoylaziridine is ca. 200 000-fold more susceptible to OH- attack (kOH-25 deg C = 1.1 M-1 s-1).The kOH- terms follow a ?ρ relationship with ρ = 1.68.In acid, the products are not the expected hydrolytic ones of benzoic acid and aziridine.Rather, exclusive ring opening occurs to give p-X-C6H4C(=O)NHCH2CH2OX.In acetate buffers, product analysis by 1H NMR indicates that the ring-opened material consists of alcohol and acetate (X = H and C(=O)CH3).

INFRARED SPECTRUM AND INFRARED-INDUCED CONFORMATIONAL ISOMERIZATION OF 2-BROMOETHYLAMINE IN AN ARGON MATRIX

Nakata, Munetaka,Tasumi, Mitsuo

, p. 1015 - 1016 (1985)

The i.r. spectrum of 2-bromoethylamine was observed in an Ar matrix.At least three conformers coexisted in the matrix.Gauche to trans isomerization around the C-C bond was found to occur in the matrix under i.r. irradiation.

Method for synthesizing fluopyram

-

Paragraph 0018; 0033-0036; 0040-0041, (2021/09/26)

The invention provides a method for synthesizing fluopyram, which uses commercially available 2 - bromoethylamine hydrobromide as a starting raw material, generates cyclopropylamine by self nucleophilic substitution reaction under basic conditions, and then reacts with o-trifluorobenzoyl chloride to prepare the key intermediate cyclopropylamine -1 -(2 - (trifluoromethyl) phenyl) methyl ketone. 2,3 -dichloro -5 -trifluoromethylpyridine was reacted with cyclopropylamine -1 -based (2 - (trifluoromethyl) phenyl) methyl ketone after the action of alkyllithium to give fluopyram. 1st-step and 2nd-step reactions are one-pot reaction, the reaction yield is high, the synthesis process is simple, the product purity is high, and the method has huge application value.

METHOD FOR PATHOGENS, MICROORGANISMS, AND PARASITES INACTIVATION

-

Paragraph 0150-0152, (2020/02/16)

The invention provides a method for inactivation or reduction of pathogens, microorganisms or parasites in a sample, media, composition, utility, device, surface or organism by treatment with an alkylating compound of Structure I, followed by elimination or reduction of the residual compound with Structure I by treatment with a neutralizing agent, which eliminates or reduces the toxicity or other undesirable properties of the alkylating compound with Structure I. The neutralizing agent may be present in a treatment solution or be part of a solid-phase agent, and preferably acts by eliminating the alkylating properties of the compound of Structure I.

Barium complexes with crown-ether-functionalised amidinate and iminoanilide ligands for the hydrophosphination of vinylarenes

Le Coz, Erwann,Roueindeji, Hanieh,Roisnel, Thierry,Dorcet, Vincent,Carpentier, Jean-Francois,Sarazin, Yann

supporting information, p. 9173 - 9180 (2019/07/04)

The detailed multistep syntheses of two nitrogen-based sterically congested iminoanilidine and amidine proligands bearing a tethered 15-member aza-ether-crown macrocycle, namely {I^Acrown}H and {Amcrown}H, are reported. These proligands react with [Ba{N(SiMe2H)2}2·(thf)n] to generate the heteroleptic barium complexes [{I^Acrown}BaN(SiMe2H)2] (5) and [{Amcrown}BaN(SiMe2H)2] (6) in high yields. These complexes exhibit high coordination numbers (resp. eight and seven) and are in addition stabilised by mild Ba?H-Si interactions. Unusually for oxophilic elements such as barium, the amidinate ligand in 6 is only η1-coordinated. Complexes 5 and 6 mediate the intermolecular hydrophosphination of styrene with primary (PhPH2) and secondary (HPPh2) phosphines. Their catalytic performance compares favourably with those of other barium precatalysts for these reactions. During the course of the hydrophosphination of styrene with HPPh2 catalysed by 5, the phosphide complex [{I^Acrown}BaPPh2] (7) could be intercepted and crystallographically characterised.

Method for preparing thiotepa

-

Paragraph 0049; 0050, (2018/09/21)

The invention provides a method for preparing thiotepa. The method comprises the following steps: cooling ethylenimine and an organic solvent to a temperature of 15-17 DEG C, dropping an organic solvent of trihalothiophosphorus, dropping an acid-binding agent when the trihalothiophosphorus is dropped to reach a scheduled quantity Y of 49%, maintaining the temperature of 15-17 DEG C, and reacting for 30-45 minutes; filtering, performing reduced pressure distillation on the filtrate to remove the organic solvent so as to obtain the residue, and purifying, so as to obtain the thiotepa. The raw materials and reagent used in the preparation method provided by the invention are cheap and readily available, the produced three wastes are less, and the method is simple in operation, high in yield and suitable for industrial production.

Process route upstream and downstream products

Process route

N,N'-Bis(2-oxo-3-oxazolidin-3-ylcarbonyl)-1,6-hexanediamine
74734-25-1

N,N'-Bis(2-oxo-3-oxazolidin-3-ylcarbonyl)-1,6-hexanediamine

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

dimethylenecyclourethane
497-25-6

dimethylenecyclourethane

Acetonitrile oxide
925-91-7

Acetonitrile oxide

trans-nitrosoethylene
54680-52-3

trans-nitrosoethylene

C<sub>5</sub>H<sub>6</sub>N<sub>2</sub>O<sub>3</sub>*H<sup>(1+)</sup>

C5H6N2O3*H(1+)

2-Oxo-oxazolidine-3-carboxylic acid cyclohexylamide

2-Oxo-oxazolidine-3-carboxylic acid cyclohexylamide

Conditions
Conditions Yield
at 200 - 600 ℃; Product distribution; pyrolysis;
1-(4-methoxy-benzoyl)-aziridine
15269-50-8

1-(4-methoxy-benzoyl)-aziridine

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

sodium anisate
536-45-8

sodium anisate

Conditions
Conditions Yield
With sodium hydroxide; In acetonitrile; at 25 ℃; Rate constant; var. pH (from 13 to neutral);
(S,S)-1,2-bis<2-(methoxymethyl)pyrrolidino>diazene

(S,S)-1,2-bis<2-(methoxymethyl)pyrrolidino>diazene

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

2,3-dihydro-5-methylpyrrol
100791-95-5

2,3-dihydro-5-methylpyrrol

2-methyl-1-pyrrolidine
765-38-8

2-methyl-1-pyrrolidine

prop-1-yne
74-99-7

prop-1-yne

Conditions
Conditions Yield
at 1100 ℃; under 0.08 - 0.4 Torr; Product distribution; other temperatures; also flash-vacuum pyrolysis;
methanol
67-56-1

methanol

ethanolamine
141-43-5

ethanolamine

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

piperazine
110-85-0

piperazine

1,4-diaza-bicyclo[2.2.2]octane
280-57-9,88935-43-7

1,4-diaza-bicyclo[2.2.2]octane

(2-hydroxyethyl)(methyl)amine
109-83-1

(2-hydroxyethyl)(methyl)amine

Conditions
Conditions Yield
With Cs-P-Si mixed-oxide; at 300 ℃; under 750.06 Torr; Title compound not separated from byproducts;
37 % Chromat.
6%
ethylenediamine
107-15-3,85404-18-8

ethylenediamine

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

piperazine
110-85-0

piperazine

1,4-diaza-bicyclo[2.2.2]octane
280-57-9,88935-43-7

1,4-diaza-bicyclo[2.2.2]octane

1,4-pyrazine
290-37-9

1,4-pyrazine

2-Methylpyrazine
109-08-0

2-Methylpyrazine

Conditions
Conditions Yield
With tungsten(VI) oxide; at 380 ℃; Product distribution; Kinetics; Thermodynamic data; var. catalysts, other temp.;
5.2 % Chromat.
2.3 % Chromat.
7.4 % Chromat.
0.6 % Chromat.
2.6 % Chromat.
0.8 % Chromat.
C<sub>12</sub>H<sub>19</sub>Cl<sub>2</sub>N<sub>2</sub>O<sub>2</sub>P

C12H19Cl2N2O2P

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

2-phenylethyl chloride
622-24-2

2-phenylethyl chloride

Conditions
Conditions Yield
In dimethylsulfoxide-d6; at 150 ℃; for 72h; Product distribution; other N-(2-chloroethyl)-2-arylethylphosphoroamidates;
methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

methyl carbamate
598-55-0

methyl carbamate

Conditions
Conditions Yield
With ammonia; In ethanol; at 18 - 25 ℃; for 24h;
90%
1-(phenylaminocarbonyl)aziridine
13279-22-6

1-(phenylaminocarbonyl)aziridine

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

phenyl carbamate
64-10-8

phenyl carbamate

Conditions
Conditions Yield
With ammonia; In ethanol; at 18 - 25 ℃; for 168h;
88%
1-(p-nitrobenzoyl)aziridine
19614-29-0

1-(p-nitrobenzoyl)aziridine

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

sodium 4-nitrobenzoate
3847-57-2

sodium 4-nitrobenzoate

Conditions
Conditions Yield
With sodium hydroxide; In acetonitrile; at 25 ℃; Rate constant; var. pH (from 13 to neutral);
N-benzoylaziridine
7646-66-4

N-benzoylaziridine

ethyleneimine
151-56-4,9002-98-6

ethyleneimine

sodium benzoate
532-32-1

sodium benzoate

Conditions
Conditions Yield
With sodium hydroxide; In acetonitrile; at 25 ℃; Rate constant; var. pH (from 13 to neutral);

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