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151-56-4

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151-56-4 Usage

Description

Ethyleneimine is a colourless liquid with an ammonia-like smell or pungent odour. It is highly flammable and reacts with a wide variety of materials. Ethyleneimine is used in polymerisation products, as a monomer for polyethyleneimine and as a comonomer for polymers, for example, with ethylenediamine. Polymerised ethyleneimine is used in paper, textile chemicals, adhesive binders, petroleum, refining chemicals, fuels, lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic chemicals, colloid flocculants, and surfactants. Ethyleneimine readily polymerises, and it behaves like a secondary amine. Ethyleneimine is highly caustic, attacking materials such as cork, rubber, many plastics, metals, and glass except those without carbonate or borax. It polymerises explosively on contact with silver, aluminium, or acid. The activity of ethyleneimine is similar to that of nitrogen and sulphur mustards. Ethyleneimine is used as an intermediate in the production of triethylenemelamine.

Chemical Properties

Different sources of media describe the Chemical Properties of 151-56-4 differently. You can refer to the following data:
1. colourless liquid with an ammonia-like smell
2. Ethyleneimine is a colorless liquid with an ammonia-like smell or pungent odor. It is highly flammable and reacts with a wide variety of materials. Ethyleneimine is used in polymerization products, as a monomer for polyethyleneimin, and as a comonomer for polymers, e.g., with ethylenediamine. Polymerized ethylenimine is used in paper, textile chemicals, adhesive binders, petroleum, refi ning chemicals, fuels, lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic chemicals, colloid fl occulants, and surfactants. Ethyleneimine readily polymerizes, and it behaves like a secondary amine. Ethyleneimine is highly caustic, attacking materials such as cork, rubber, many plastics, metals, and glas except those without carbonate or borax. It polymerizes explosively on contact with silver, aluminum, or acid. The activity of ethyleneimine is similar to that of nitrogen and sulfur mustards. Ethyleneimine is used as an intermediate in the production of triethylenemelamine. Polymerized ethyleneimine is used in paper, textile chemicals, adhesive binders, petroleum, refi ning chemicals, fuels, lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic chemicals, colloid fl occulants, and surfactants
3. Ethyleneimine is a colorless volatile liquid with an ammoniacal odor.
4. The strained three-membered ring structure of ethyleneimine readily undergoes ring-opening reactions, which are catalyzed by acids and occur at moderate temperatures. Ethyleneimine is easily polymerized at elevated temperatures in the presence of catalytic amounts of acid. Reactions with ammonia and primary orsecondary amines in the presence of catalytic amounts of acids yield ethylenediamines; reactions with carboxylic acids yield 2-aminoethyl esters.Ethyleneimine is also a highly reactive secondary amine, and undergoes a large number of reactions under neutral or basic conditions which yield products with the three-membered ring intact. Addition reactions occur with acyl halides, alkyl and substituted alkyl halides, aryl halides, and other halogen-containing compounds. Ethyleneimine forms adducts with aldehydes, ketones, and olefinic compounds (Ham 1978).

Physical properties

Clear, colorless, very flammable liquid with a very strong ammonia odor. Odor threshold concentration is 1.5 ppm (quoted, Amoore and Hautala, 1983).

Uses

Different sources of media describe the Uses of 151-56-4 differently. You can refer to the following data:
1. Ethylenimine is used in the manufacture oftriethylenemelamine and other amines.
2. Ethyleneimine is used to manufacture triethylenemelamine and is used in its polymeric form in paper and textile chemicals, adhesive binders, petroleum-refining chemicals, fuels and lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion-exchange resins, photographic chemicals, colloid flocculants, and surfactants.
3. In the manufacture of triethylenemelamine.

Production Methods

Industrial quantities are made with monoethanolamine via a two-step chemical dehydration process using sulphuric acid and sodium hydroxide, or by reacting 1,2-dichloroethane with ammonia. The U.S. production in 1978 was over 1500 metric tons (Ham 1978).

General Description

A clear colorless liquid with an ammonia-like odor. Flash point 12°F. Less dense than water. Flammable over a wide range of vapor-air concentrations. Vapors irritate the skin, eyes, nose, and throat. May be toxic by prolonged inhalation, skin absorption, or ingestion. Carcinogenic. Vapors heavier than air. May polymerize exothermically if heated or contaminated. If the polymerization takes place inside a container, the container may rupture violently.

Air & Water Reactions

Highly flammable. Soluble in water.

Reactivity Profile

ETHYLENEIMINE vapors are not inhibited and may form polymers in vents or flame arresters, resulting in stopping of the vents. Produces toxic oxides of nitrogen during combustion. Reacts with sodium hypochlorite and other chlorinating agents to give the explosive compound 1-chloroazidine. Decomposes if heated under pressure. or else hazardous polymerization may occur. Incompatible with silver or aluminum, which induce polymerization May polymerize explosively upon contact with acids. Polymerization is catalyzed by carbon dioxide [EPA, 1998].

Hazard

Corrosive, absorbed by skin, causes tumors; exposure should be minimized; a carcinogen. Dangerous fire and explosion hazard, flammable limits in air 3.6–46%. Toxic by skin absorption; possible carcinogen.

Health Hazard

Different sources of media describe the Health Hazard of 151-56-4 differently. You can refer to the following data:
1. 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.
2. Exposures to ethyleneimine cause adverse health effects and poisoning. Ingestion/swallowing, inhalation, or absorption through exposures to skin cause severe irritation, blisters, severe deep burns, and effects of sensitization. Ethyleninime is corrosive to the eye tissue and may cause permanent corneal opacity and conjunctival scarring, severe respiratory tract irritation, and effects of infl ammation in workers. Ethyleneimine is a severe blistering agent, causing third degree chemical burns of the skin. The symptoms of toxicity include, but are not limited to, cough, dizziness, headache, labored breathing, nausea, vomiting, tearing and burning of the eyes, sore throat, nasal secretion, bronchitis, shortness of breath, laryngeal edema, pronounced changes of the trachea and bronchi of lungs. Ethyleneimine with its corrosive effects cause injury to the mucous membranes and acute oral exposure may cause scarring of the esophagus in humans. The onset of symptoms and health effects caused by ethyleneimine depends on exposure concentration.
3. Ethylenimine is a highly poisonous com pound and a severe irritant to the skin, eyes,and mucous membranes. A 20–25% aqueoussolution on contact with the eyes can causecorneal opacity and loss of vision. Skin con tact with the pure liquid or its concentratedsolution can produce severe burns and skinsensitization.Ethylenimine is highly toxic by all routesof exposure. Inhalation of its vapors cancause eye, nose, and throat irritations anddifficulty in breathing. The toxic symptomsnoted from repeated exposures include chestcongestion, delayed lung injury, vomiting,hemorrhage, and kidney damage. An 8-hourexposure to 100 ppm in air proved fatal torabbits. The symptoms from acute oral toxic ity in humans may include nausea, vomiting,dizziness, headache, and pulmonary edema.Chronic toxic effects may result in kidneyand liver damage. The acute oral LD50 valuein rats was 15 mg/kg. Ethylenimine is alsoabsorbed through the skin, exhibiting poi soning effects similar to those of acute oraltoxicity.It exhibited reproductive toxicity in ani mals, indicating paternal effects and specificdevelopmental abnormalities in the centralnervous system, eyes, and ears. Ethylenimineis a mutagen, testing positive in the histi dine reversion–Ames test as well as in thein vitro cytogenetics–human lymphocyte,Drosophila melanogaster–reciprocal translo cation, Saccharomyces cerevisiae gene con version, and other mutagenic tests. Animalstudies show sufficient evidence of carcino genicity. It may cause cancers in the lungsand liver.
4. Ethylenimine is highly toxic by all exposure routes. Airborne exposure causes conjunctivitis, respiratory tract irritation, edema, and albuminuria (Weightman and Hoyle 1964), with possible damage to liver and kidneys; vomiting and other CNS effects may occur at high exposures. Dermal contact to ethylenimineproduces severe irritation, with lesions which are slow to heal. Ethylenimines are also skin sensitizers (Garabrant 1985; Cofield et al 1985). There are no reports which indicate potential reproductive effects or increased risk for cancer in humans exposed to ethylenimine.

Fire Hazard

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, Ethyleneimine 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.

Flammability and Explosibility

Highlyflammable

Chemical Reactivity

Reactivity with Water: Mild reaction, non-hazardous; Reactivity with Common Materials: Contact with silver or aluminum may cause polymerization; Stability During Transport: Stable unless heated under pressure; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Explosive polymerization can occur when in contact with acids; Inhibitor of Polymerization: None used.

Industrial uses

Approximately 50% of ethylenimine produced in the U.S. is polymerized to polyethyleneimine, used as a flocculant in water treatment, and as a wet-strength additive in the textile and paper industries. Polyethylenimine is also used in various adhesives and coatings and to laminate plastic films to paper, other cellulose materials, and metal foils for making cartons in the food industry. The adhesion properties of acrylic latex paints are improved by reaction of acid groups with ethylenimine. Ethylenimines are utilized in the textile industry to improve durability, crease resistance, flame resistance, and dyeing properties. Other uses are found in ion-exchange resin synthesis, in electroplating, as a rocket propellant binder, as a lubricating oil dispersant, and as a hardening agent in the preparation of photographic films. Ethylenimine is used in the manufacture of triethylene melamine, a cancer chemotherapy drug; various ethylenimines are used as insect chemosterilant agents for pest control (Ham 1978).

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Other experimental reproductive effects. Poison by ingestion, skin contact, inhalation, and intraperitoneal routes. Human mutation data reported. A skin, mucous membrane, and severe eye irritant. An allergc sensitizer of skin. Causes opaque cornea, keratoconus, and necrosis of cornea (experimentally). Has been known to cause severe human eye injury. Drinking of carbonated beverages is recommended as an antidote to ths material in stomach. A very dangerous fire and explosion hazard when exposed to heat, flame, or oxidzers. Reacts violently with acids, aluminum chloride + substituted anilines, acetic acid, acetic anhydride, acrolein, acrylic acid, allyl chloride, CS2, Cl2, chlorosulfonic acid, epichlorohydrin, glyoxal, HCl, HF, HNO3, oleum, P-propiolactone, Ag, NaOCl, H2SO4, vinyl acetate. Reacts with chlorinating agents (e.g., sodum hypochlorite solution) to form the explosive 1 chloroaziridine. Reacts with silver or its alloys to form explosive silver derivatives. Dangerous; heat and/or the presence of catalytically active metals or chloride ions can cause a violent exothermic reaction. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Ethyleneimine is used in production of binding agents; formation of plastics; and improving paper strength; in many organic syntheses; as an intermediate and monomer for fuel oil and lubricating refining. The polymerization products, polyethyleneimines, are used as auxiliaries in the paper industry and as flocculation aids in the clarification of effluents. It is also used in the textile industry for increasing wet strength, flame-, water-, shrinkproofing, and stiffening

Carcinogenicity

The carcinogenicity of ethyleneimine was evaluated in two strains of mice, and both gave positive results. Groups of 18 male and 18 female mice of B6C3F1 or B6AKR strains were treated orally (initially by gavage, then in the diet) from age 7 days through 77–78 weeks. The time-weighted average (TWA) dose was about 1.8 mg/kg/day. The incidence of hepatomas and lung adenomas was significantly elevated in both strains and sexes. In B6C3F1 mice, the incidence of hepatomas and pulmonary adenomas was 15/17 and 15/17 in males and 11/15 and 15/15 females, respectively. In the B6AKR strain, hepatomas and adenomas occurred in 9/16 and 12/16 males and in 2/11 and 10/11 females, respectively. In the control groups, hepatomas were 8/79 and 0/87 in male and female B6C3F1 mice and 5/90 and 1/82 in male and female B6AKR mice. The respective incidence of pulmonary adenomas was 5/79, 3/87, 10/90, and 3/82. The incidence of hepatomas and pulmonary adenomas (reported as combined tumors) was significantly (p<0.01) elevated.

Environmental fate

Photolytic. The vacuum UV photolysis (λ = 147 nm) and γ radiolysis of ethylenimine resulted in the formation of acetylene, methane, ethane, ethylene, hydrogen cyanide, methyl radicals, and hydrogen (Scala and Salomon, 1976). Photolysis of ethylenimine vapor at krypton and xenon lines yielded ethylene, ethane, methane, acetylene, propane, butane, hydrogen, ammonia, and ethyleneimino radicals (Iwasaki et al., 1973). Chemical/Physical. Polymerizes easily (Windholz et al., 1983). Hydrolyzes in water forming ethanolamine (HSDB, 1989). The estimated hydrolysis half-life in water at 25 °C and pH 7 is 154 d (Mabey and Mill, 1978).

Metabolism

When male Dow-Wistar rats were injected intraperitoneally with [14C]-ethylenimine (80mug), approximately half of the dose was excreted in the urine (Wright and Rowe 1967). The major portion of the radioactivity in the urine consisted of unidentified products, although a small amount was excreted unchanged. A small portion, 3-5%, was expired as 14C02, and 1-3% was expired as a volatile, basic material, probably ethylenimine, during 24 h. Significant amounts of radioactivity were accumulated in liver, intestines, cecum, spleen, and kidneys. After 24 h, tissue radioactivity became constant and essentially unavailable for further metabolism. The aziridine ring of drugs is readily cleaved by microsomal enzymes, possibly with intermediate formation of an N-oxide (Oelschlager and Al Shaik 1985).

Shipping

UN1185 Ethyleneimine, stabilized, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquid, Inhalation Hazard Zone A. PGI

Purification Methods

Redistil it in an Ar or N2 atmosphere in a fume hood, and store it over KOH in sealed bottles in a refrigerator. Commercial aziridine has been dried over sodium and distilled from the metal through an efficient column before use [Jackson & Edwards J Am Chem Soc 83 355 1961, Wenker J Am Chem Soc 57 2328 1935]. It is a weaker base than Me2NH (pK2 5 10.87) but is caustic to the skin. It should not be inhaled, causes inflammation of the eyes, nose and throat, and one may become sensitized to it. It is soluble in H2O, has an ammoniacal smell and reacts with CO2. Pure aziridine is comparatively stable but polymerises in the presence of traces of H2O and is occasionally explosive in the presence of acids. CO2 is sufficiently acidic to cause polymerisation (forms linear polymers) which is not free radical promoted. It is stable in the presence of bases. The violet 2:1 Cu complex crystallises from EtOH containing a few drops of aziridine and adding Et2O, and has m 142o(dec). The picrate has m 142o. [O'Rourke et al. J Am Chem Soc 78 2159 1956.] It has also been dried over BaO and has been distilled from sodium under nitrogen. [Allen et al. Org Synth Coll Vol IV 433 1963, Beilstein 20 III/IV 1.] TOXIC.

Toxicity evaluation

Ethyleneimine is an extremely reactive alkylating agent that undergoes ring-opening reactions with cellular nucleophiles.

Incompatibilities

May form explosive mixture with air. Ethyleneimine is a medium strong base. Contact with acids, aqueous acid conditions, oxidizers, aluminum, or carbon dioxide may cause explosive polymerization. Explosive silver derivatives may be formed with silver alloys e.g., silver solder). Self-reactive with heat or atmospheric carbon dioxide. May accumulate static electrical charges, and may cause ignition of its vapors. Attacks rubber, coatings, plastics, and chemically active metals. Ethyleneimine vapors are not inhibited and may form polymers in vents or flame arresters, resulting in stopping of the vents.

Precautions

During use of ethyleninime, students and occupational workers should wear protective equipment, such as gloves, safety glasses, and should have good ventilation. Ethyleninime should be handled as a carcinogen. Ethyleninime vapor/air mixtures are explosive and pose a risk of fi re and explosion on contact with acid(s), oxidants.

Check Digit Verification of cas no

The CAS Registry Mumber 151-56-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 1 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 151-56:
(5*1)+(4*5)+(3*1)+(2*5)+(1*6)=44
44 % 10 = 4
So 151-56-4 is a valid CAS Registry Number.
InChI:InChI=1/C2H3N/c1-2-3/h3H,1H2

151-56-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name aziridine

1.2 Other means of identification

Product number -
Other names Ethylimine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Ethyleneimine is used in polymerization products; as a monomer for polyethyleneimine; as a comonomer for polymers (e.g., with ethylenediamine); and in paper and textile chemicals, adhesives, binders, petroleum refining chemicals, fuels and lubricants, coating resins, varnishes, lacquers, agricultural chemicals, cosmetics, ion exchange resins, photographic chemicals, and surfactants.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:151-56-4 SDS

151-56-4Synthetic route

methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

aniline
62-53-3

aniline

A

ethyleneimine
151-56-4

ethyleneimine

B

(2-Phenylamino-ethyl)-carbamic acid methyl ester
79143-47-8

(2-Phenylamino-ethyl)-carbamic acid methyl ester

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 480h;A n/a
B 98%
1-(phenylaminocarbonyl)aziridine
13279-22-6

1-(phenylaminocarbonyl)aziridine

dimethyl amine
124-40-3

dimethyl amine

A

ethyleneimine
151-56-4

ethyleneimine

B

fenuron
101-42-8

fenuron

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 168h;A n/a
B 94%
piperidine
110-89-4

piperidine

methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

A

ethyleneimine
151-56-4

ethyleneimine

B

(2-Piperidin-1-yl-ethyl)-carbamic acid methyl ester
79143-49-0

(2-Piperidin-1-yl-ethyl)-carbamic acid methyl ester

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 24h;A n/a
B 92%
1-(phenylaminocarbonyl)aziridine
13279-22-6

1-(phenylaminocarbonyl)aziridine

methylamine
74-89-5

methylamine

A

ethyleneimine
151-56-4

ethyleneimine

B

1-methyl-3-phenylurea
1007-36-9

1-methyl-3-phenylurea

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 168h;A n/a
B 92%
methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

A

ethyleneimine
151-56-4

ethyleneimine

B

methyl carbamate
598-55-0

methyl carbamate

Conditions
ConditionsYield
With ammonia In ethanol at 18 - 25℃; for 24h;A n/a
B 90%
ethanolamine
141-43-5

ethanolamine

ethyleneimine
151-56-4

ethyleneimine

Conditions
ConditionsYield
With 1 M DTPP at 60℃; for 48h;90%
With BNTP In dichloromethane at 40℃; for 24h;98 % Chromat.
With potassium hydroxide; sulfuric acid 1.) 80 deg C, overnight; Multistep reaction;
With cesium nitrate; iron nitrate; magnesium nitrate on fluoridated P2O5/SiO2/TiO2 at 370℃; for 8h; Temperature; Reagent/catalyst; Inert atmosphere; chemoselective reaction;
morpholine
110-91-8

morpholine

methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

A

ethyleneimine
151-56-4

ethyleneimine

B

(2-Morpholin-4-yl-ethyl)-carbamic acid methyl ester
79143-50-3

(2-Morpholin-4-yl-ethyl)-carbamic acid methyl ester

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 24h;A n/a
B 88%
1-(phenylaminocarbonyl)aziridine
13279-22-6

1-(phenylaminocarbonyl)aziridine

A

ethyleneimine
151-56-4

ethyleneimine

B

phenyl carbamate
64-10-8

phenyl carbamate

Conditions
ConditionsYield
With ammonia In ethanol at 18 - 25℃; for 168h;A n/a
B 88%
methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

dimethyl amine
124-40-3

dimethyl amine

A

ethyleneimine
151-56-4

ethyleneimine

B

1-methoxycarbonylamino-2-dimethylaminoethane
79143-42-3

1-methoxycarbonylamino-2-dimethylaminoethane

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 24h;A n/a
B 82%
N-(p-toluenesulfonyl)aziridine
3634-89-7

N-(p-toluenesulfonyl)aziridine

ethyleneimine
151-56-4

ethyleneimine

Conditions
ConditionsYield
With carbon dioxide; DBN; lithium iodide In toluene at 90℃; for 5h; Inert atmosphere;82%
methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

A

ethyleneimine
151-56-4

ethyleneimine

B

(2-Aziridin-1-yl-ethyl)-carbamic acid methyl ester
79143-51-4

(2-Aziridin-1-yl-ethyl)-carbamic acid methyl ester

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 24h;A n/a
B 75%
2-chloroethanamine hydrochloride
870-24-6

2-chloroethanamine hydrochloride

ethyleneimine
151-56-4

ethyleneimine

Conditions
ConditionsYield
With sodium hydroxide In water at 50℃; for 2h; Inert atmosphere;75%
With sodium hydroxide In water at 50℃; for 2.5h;74%
With sodium hydroxide at 50℃; under 25 Torr; for 2h;70%
methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

isopropylamine
75-31-0

isopropylamine

A

ethyleneimine
151-56-4

ethyleneimine

B

(2-Isopropylamino-ethyl)-carbamic acid methyl ester
79143-44-5

(2-Isopropylamino-ethyl)-carbamic acid methyl ester

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 24h;A n/a
B 72%
methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

cyclohexylamine
108-91-8

cyclohexylamine

A

ethyleneimine
151-56-4

ethyleneimine

B

(2-Cyclohexylamino-ethyl)-carbamic acid methyl ester
79143-46-7

(2-Cyclohexylamino-ethyl)-carbamic acid methyl ester

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 24h;A n/a
B 63%
sulfuric acid mono-(2-amino-ethyl ester)
926-39-6

sulfuric acid mono-(2-amino-ethyl ester)

ethyleneimine
151-56-4

ethyleneimine

Conditions
ConditionsYield
With sodium hydroxide In water Heating;60%
With sodium hydroxide
With potassium hydroxide
methanol
67-56-1

methanol

ethanolamine
141-43-5

ethanolamine

A

ethyleneimine
151-56-4

ethyleneimine

B

piperazine
110-85-0

piperazine

C

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

1,4-diaza-bicyclo[2.2.2]octane

D

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

(2-hydroxyethyl)(methyl)amine

Conditions
ConditionsYield
With Cs-P-Si mixed-oxide at 300℃; under 750.06 Torr; Title compound not separated from byproducts;A 37 % Chromat.
B n/a
C n/a
D 6%
tetrachloromethane
56-23-5

tetrachloromethane

sulfuric acid mono-(2-amino-ethyl ester)
926-39-6

sulfuric acid mono-(2-amino-ethyl ester)

ethyleneimine
151-56-4

ethyleneimine

2-bromoethylamine hydrobromide
2576-47-8

2-bromoethylamine hydrobromide

ethyleneimine
151-56-4

ethyleneimine

Conditions
ConditionsYield
With water; silver(l) oxide
With potassium hydroxide
With alkaline solution
2-bromoethylamine
107-09-5

2-bromoethylamine

ethyleneimine
151-56-4

ethyleneimine

Conditions
ConditionsYield
With potassium perchlorate In acetic acid at 25℃; Rate constant;
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 17.9℃; Rate constant; Kinetics; Thermodynamic data; var. temp., var. solvents mixtures, var. bases, ΔGa, ΔHa, ΔSa;
With ammonium bromide In water; dimethyl sulfoxide at 60.3℃; Thermodynamic data; other halide, ΔH(excit.), ΔG(excit.), ΔS(excit.);
chloroethylamine
689-98-5

chloroethylamine

ethyleneimine
151-56-4

ethyleneimine

Conditions
ConditionsYield
With water In 1,4-dioxane at 39 - 59℃; Kinetics;
With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 31.4℃; Rate constant; Kinetics; Thermodynamic data; var. temp., var. solvents mixtures, var. bases, ΔGa, ΔHa, ΔSa;
With ammonium chloride In water; dimethyl sulfoxide at 60.3℃; Thermodynamic data; other halide, ΔH(excit.), ΔG(excit.), ΔS(excit.);
3-Fluoropyridine
372-47-4

3-Fluoropyridine

Aziridin-Kation
24151-28-8

Aziridin-Kation

A

ethyleneimine
151-56-4

ethyleneimine

B

2-fluoropyridine-H(1+)
59278-67-0

2-fluoropyridine-H(1+)

Conditions
ConditionsYield
Thermodynamic data;
3-Chloropyridine
626-60-8

3-Chloropyridine

Aziridin-Kation
24151-28-8

Aziridin-Kation

A

ethyleneimine
151-56-4

ethyleneimine

B

3-chloropyridinium
53760-42-2

3-chloropyridinium

Conditions
ConditionsYield
Thermodynamic data;
N-benzoylaziridine
7646-66-4

N-benzoylaziridine

A

ethyleneimine
151-56-4

ethyleneimine

B

sodium benzoate
532-32-1

sodium benzoate

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 25℃; Rate constant; var. pH (from 13 to neutral);
amide P,P-bis (1-aziridinyl) N,N-dimethyl phosphinique
1195-69-3

amide P,P-bis (1-aziridinyl) N,N-dimethyl phosphinique

A

ethyleneimine
151-56-4

ethyleneimine

B

dimethyl amine
124-40-3

dimethyl amine

C

2-(dimethylamino)-3H-1,3,2-oxazaphospholidine-2-oxide

2-(dimethylamino)-3H-1,3,2-oxazaphospholidine-2-oxide

D

C6H16N3O2P

C6H16N3O2P

Conditions
ConditionsYield
In water-d2 Mechanism; other aziridinyl phosphoramides, other products;
1-(p-bromobenzoyl)aziridine
18292-63-2

1-(p-bromobenzoyl)aziridine

A

ethyleneimine
151-56-4

ethyleneimine

B

sodium 4-bromobenzoate
2532-15-2

sodium 4-bromobenzoate

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 25℃; Rate constant; var. pH (from 13 to neutral);
1-(4-methoxy-benzoyl)-aziridine
15269-50-8

1-(4-methoxy-benzoyl)-aziridine

A

ethyleneimine
151-56-4

ethyleneimine

B

sodium anisate
536-45-8

sodium anisate

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 25℃; Rate constant; var. pH (from 13 to neutral);
1-(p-nitrobenzoyl)aziridine
19614-29-0

1-(p-nitrobenzoyl)aziridine

A

ethyleneimine
151-56-4

ethyleneimine

B

sodium 4-nitrobenzoate
3847-57-2

sodium 4-nitrobenzoate

Conditions
ConditionsYield
With sodium hydroxide In acetonitrile at 25℃; Rate constant; var. pH (from 13 to neutral);
ethene
74-85-1

ethene

ethyleneimine
151-56-4

ethyleneimine

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine Mechanism; Irradiation; also with propene; rel. rate constants;
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

A

ethyleneimine
151-56-4

ethyleneimine

B

dimethylenecyclourethane
497-25-6

dimethylenecyclourethane

C

Acetonitrile oxide
925-91-7

Acetonitrile oxide

D

trans-nitrosoethylene
54680-52-3

trans-nitrosoethylene

E

C5H6N2O3*H(1+)

C5H6N2O3*H(1+)

F

2-Oxo-oxazolidine-3-carboxylic acid cyclohexylamide

2-Oxo-oxazolidine-3-carboxylic acid cyclohexylamide

Conditions
ConditionsYield
at 200 - 600℃; Product distribution; pyrolysis;
methyl aziridine-1-carboxylate
671-50-1

methyl aziridine-1-carboxylate

ethylamine
75-04-7

ethylamine

A

ethyleneimine
151-56-4

ethyleneimine

B

methyl N-ethylcarbamate
6135-31-5

methyl N-ethylcarbamate

C

(2-Ethylamino-ethyl)-carbamic acid methyl ester
79143-43-4

(2-Ethylamino-ethyl)-carbamic acid methyl ester

Conditions
ConditionsYield
In ethanol at 18 - 25℃; for 24h;A n/a
B 35 % Chromat.
C 65 % Chromat.
ethyleneimine
151-56-4

ethyleneimine

2-chloro-3,6-diphenyl-3,4-dihydro-1,3,2-oxazophosporin-2-oxide
78993-89-2

2-chloro-3,6-diphenyl-3,4-dihydro-1,3,2-oxazophosporin-2-oxide

2-Aziridin-1-yl-3,6-diphenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide
95886-05-8

2-Aziridin-1-yl-3,6-diphenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide

Conditions
ConditionsYield
In benzene for 0.5h; Ambient temperature;100%
ethyleneimine
151-56-4

ethyleneimine

2-Chloro-6-phenyl-3-p-tolyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide
78993-90-5

2-Chloro-6-phenyl-3-p-tolyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide

2-(1-Aziridinyl)-6-phenyl-3-(p-tolyl)-3,4-dihydro-1,3,2-oxazaphosphorin-2-oxide
95886-04-7

2-(1-Aziridinyl)-6-phenyl-3-(p-tolyl)-3,4-dihydro-1,3,2-oxazaphosphorin-2-oxide

Conditions
ConditionsYield
In benzene for 0.5h; Ambient temperature;100%
ethyleneimine
151-56-4

ethyleneimine

2-Chloro-3-(4-methoxy-phenyl)-6-phenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide
78993-91-6

2-Chloro-3-(4-methoxy-phenyl)-6-phenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide

2-Aziridin-1-yl-3-(4-methoxy-phenyl)-6-phenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide
95886-03-6

2-Aziridin-1-yl-3-(4-methoxy-phenyl)-6-phenyl-3,4-dihydro-[1,3,2]oxazaphosphinine 2-oxide

Conditions
ConditionsYield
In benzene for 0.5h; Ambient temperature;100%
ethyleneimine
151-56-4

ethyleneimine

1-chloroaziridine
10165-13-6

1-chloroaziridine

Conditions
ConditionsYield
With N-chloro-succinimide at 20℃; under 0.1 Torr;99%
With sodium hypochlorite; water at -10℃;
With N-chloro-succinimide under 0.001 Torr; Ambient temperature;
ethyleneimine
151-56-4

ethyleneimine

3-hydroxy-3-methyl-1-cyano-1-butyne
32837-87-9

3-hydroxy-3-methyl-1-cyano-1-butyne

(Z)-4-hydroxy-4-methyl-3-ethyleneimino-2-pentenenitrile

(Z)-4-hydroxy-4-methyl-3-ethyleneimino-2-pentenenitrile

Conditions
ConditionsYield
In chloroform at 10℃; for 2h;99%
ethyleneimine
151-56-4

ethyleneimine

3-chloro-2-phenyl-1-indenone
40920-46-5

3-chloro-2-phenyl-1-indenone

3-aziridino-2-phenyl-1-indenone
94796-57-3

3-aziridino-2-phenyl-1-indenone

Conditions
ConditionsYield
With triethylamine for 0.5h;99%
ethyleneimine
151-56-4

ethyleneimine

3-chloro-2-(4-chlorophenyl)-1-indenone
94796-76-6

3-chloro-2-(4-chlorophenyl)-1-indenone

3-aziridino-2-(4-chlorophenyl)-1-indenone
94796-59-5

3-aziridino-2-(4-chlorophenyl)-1-indenone

Conditions
ConditionsYield
With triethylamine for 0.5h;99%
ethyleneimine
151-56-4

ethyleneimine

3-chloro-2-(4-methoxyphenyl)-1-indenone
94796-75-5

3-chloro-2-(4-methoxyphenyl)-1-indenone

3-aziridino-2-(4-methoxyphenyl)-1-indenone
94796-58-4

3-aziridino-2-(4-methoxyphenyl)-1-indenone

Conditions
ConditionsYield
With triethylamine for 0.5h;99%
ethyleneimine
151-56-4

ethyleneimine

3-chloro-2-(1-naphthyl)-1-indenone
94796-77-7

3-chloro-2-(1-naphthyl)-1-indenone

3-aziridino-2-(1-naphthyl)-1-indenone
94796-60-8

3-aziridino-2-(1-naphthyl)-1-indenone

Conditions
ConditionsYield
With triethylamine for 0.5h;99%
ethyleneimine
151-56-4

ethyleneimine

diethoxyphosphoryldichloroacetaldehyde
84336-27-6

diethoxyphosphoryldichloroacetaldehyde

β-hydroxy-β-ethyleneimino-α,α-dichloroethylphosphonic acid diethyl ester

β-hydroxy-β-ethyleneimino-α,α-dichloroethylphosphonic acid diethyl ester

Conditions
ConditionsYield
In ethanol at 5 - 10℃; for 1h; Addition;99%
ethyleneimine
151-56-4

ethyleneimine

1-{2-[1,3-(oxytetraethylenoxy)-3,5,5-trichloro-cyclotriphosphazatrien-1-yl]-aminoethylamino}anthraquinone
864467-21-0

1-{2-[1,3-(oxytetraethylenoxy)-3,5,5-trichloro-cyclotriphosphazatrien-1-yl]-aminoethylamino}anthraquinone

1-{2-[1,3-(oxytetraethylenoxy)-3,5,5-tri(1-aziridinyl)cyclotriphosphazatrien-1-yl]-aminoethylamino}anthraquinone

1-{2-[1,3-(oxytetraethylenoxy)-3,5,5-tri(1-aziridinyl)cyclotriphosphazatrien-1-yl]-aminoethylamino}anthraquinone

Conditions
ConditionsYield
With sodium hydroxide In benzene at 20℃; for 21.5h;99%
potassium hexafluorophosphate
17084-13-8

potassium hexafluorophosphate

ethyleneimine
151-56-4

ethyleneimine

(C5H5)Fe(CO)3(1+)*CF3SO3(1-)=(C5H5)Fe(CO)3CF3SO3

(C5H5)Fe(CO)3(1+)*CF3SO3(1-)=(C5H5)Fe(CO)3CF3SO3

[C5H5(CO)2Fe(COCH2CH2NH)](1+)*PF6(1-)=[C5H5(CO)2Fe(COCH2CH2NH)]PF6
69532-52-1

[C5H5(CO)2Fe(COCH2CH2NH)](1+)*PF6(1-)=[C5H5(CO)2Fe(COCH2CH2NH)]PF6

Conditions
ConditionsYield
With catalyst: (BrCH2CH2NH3)Br In acetonitrile addn. of aziridine to soln. of complex and bromide via syringe; stirring for 10 min at 25°C under N2; adding an excess of KPF6; stirringfor 5 min; evapn.; washing (Et2O); extg. (CH2Cl29; filtration through MgSO4; reducing volume until crystn. occured; adding Et2O; keeping at -20°C overnight; crystn.; drying in vac.; elem. anal.;99%
With catalyst: (BrCH2CH2CH2NH3)Br In acetonitrile addn. of aziridine to soln. of complex and bromide via syringe; stirring for 10 min at 25°C under N2; adding an excess of KPF6; stirringfor 5 min; evapn.; washing (Et2O); extg. (CH2Cl29; filtration through MgSO4; reducing volume until crystn. occured; adding Et2O; keeping at -20°C overnight; crystn.; drying in vac.; elem. anal.;89%
ethyleneimine
151-56-4

ethyleneimine

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]
12354-84-6, 12354-85-7

bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

[IrCl(Cp(*))(aziridine)2]Cl
1018682-30-8

[IrCl(Cp(*))(aziridine)2]Cl

Conditions
ConditionsYield
In dichloromethane (Ar); 5 equiv. of aziridine added to metal-complex in CH2Cl2; stirred atroom temp. for 2 h; solvent removed in vacuo; purified by stirring in dry n-hexane overnight; decanted; dried in vacuo; elem. anal.;99%
ethyleneimine
151-56-4

ethyleneimine

bis(N,N-diethylamido)-N1-ethyl(bromo)imidophosphate
73954-60-6

bis(N,N-diethylamido)-N1-ethyl(bromo)imidophosphate

2,2-bis(diethylamino)-3-ethyl-1,3,2-diazaphospholidinium bromide

2,2-bis(diethylamino)-3-ethyl-1,3,2-diazaphospholidinium bromide

Conditions
ConditionsYield
In benzene at 10℃;98%
ethyleneimine
151-56-4

ethyleneimine

8-Methoxy-5-quinolinesulfonyl chloride
90429-62-2

8-Methoxy-5-quinolinesulfonyl chloride

N-(8-methoxy-5-quinolylsulfonyl)aziridine
98267-09-5

N-(8-methoxy-5-quinolylsulfonyl)aziridine

Conditions
ConditionsYield
With triethylamine In benzene for 3h; O deg C - 20 deg C;98%
ethyleneimine
151-56-4

ethyleneimine

Acetic acid 4-[(1S,2R)-2-(4-acetoxy-phenyl)-1-chlorocarbonyl-butyl]-phenyl ester
107036-23-7

Acetic acid 4-[(1S,2R)-2-(4-acetoxy-phenyl)-1-chlorocarbonyl-butyl]-phenyl ester

(2R*,3S*)-1-<2,3-bis(4-acetoxyphenyl)-1-pentanoyl>aziridine
107036-26-0

(2R*,3S*)-1-<2,3-bis(4-acetoxyphenyl)-1-pentanoyl>aziridine

Conditions
ConditionsYield
With triethylamine In diethyl ether 1.) -4 deg C, 20 min, 2.) RT, 1 h;98%
ethyleneimine
151-56-4

ethyleneimine

pentapropylphosphorodiamidimidic bromide
73954-61-7

pentapropylphosphorodiamidimidic bromide

2,2-bis(dipropylamino)-3-propyl-1,3,2-diazaphospholidinium bromide

2,2-bis(dipropylamino)-3-propyl-1,3,2-diazaphospholidinium bromide

Conditions
ConditionsYield
In benzene at 10℃;98%
ethyleneimine
151-56-4

ethyleneimine

bis(4-bromophenyl)methanone
3988-03-2

bis(4-bromophenyl)methanone

4,4'-bis(aziridin-1-yl)benzophenone

4,4'-bis(aziridin-1-yl)benzophenone

Conditions
ConditionsYield
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate In toluene at 100℃; for 24h;98%
ethyleneimine
151-56-4

ethyleneimine

geldanamycin

geldanamycin

17-aziridino-17-demethoxy GM

17-aziridino-17-demethoxy GM

Conditions
ConditionsYield
In chloroform for 2h; darkness;98%
ethyleneimine
151-56-4

ethyleneimine

(η5-Cp)Fe(CO)3PF6
38834-26-3

(η5-Cp)Fe(CO)3PF6

[C5H5(CO)2Fe(COCH2CH2NH)](1+)*PF6(1-)=[C5H5(CO)2Fe(COCH2CH2NH)]PF6
69532-52-1

[C5H5(CO)2Fe(COCH2CH2NH)](1+)*PF6(1-)=[C5H5(CO)2Fe(COCH2CH2NH)]PF6

Conditions
ConditionsYield
sodium bromide In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C;98%
With catalyst: (nBu)4N(1+)*Br(1-) or (nBu4)N(1+)*I(1-) In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C;98%
With catalyst: Br(CH2)2NH3(1+)*Br(1-) In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C;98%
With catalyst: Br(CH2)3NH3(1+)*Br(1-) In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C;98%
With catalyst: Et3NH(1+)*Br(1-) In acetonitrile ratio of educts and catalyst: 1:1:1; evapn. in vac. to dryness, extrd. with CH2Cl2, pptd. with ether at -20°C;98%
ethyleneimine
151-56-4

ethyleneimine

(η5-C5H5)(Me)(NO)(PPh3)rhenium(II)

(η5-C5H5)(Me)(NO)(PPh3)rhenium(II)

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

(C5H5)Re(NO)(P(C6H5)3)(C2H4NH)(1+)*CF3SO3(1-)={(C5H5)Re(NO)(P(C6H5)3)(C2H4NH)}{CF3SO3}

(C5H5)Re(NO)(P(C6H5)3)(C2H4NH)(1+)*CF3SO3(1-)={(C5H5)Re(NO)(P(C6H5)3)(C2H4NH)}{CF3SO3}

Conditions
ConditionsYield
In toluene (Schlenk flask); soln. of Re-complex is cooled to -45°C (CH3CN/CO2), CF3SO3H is added dropwise, after 5 min cyclic amine is added and the cold bath is removed; after 60 min hexane is added with stirring, filtrate is washed with hexane and dried under vacuum, elem. anal.;98%
ethyleneimine
151-56-4

ethyleneimine

zinc(II) chloride
7646-85-7

zinc(II) chloride

(aziridine)2ZnCl2
27184-23-2

(aziridine)2ZnCl2

Conditions
ConditionsYield
In dichloromethane anhydrous metal chloride suspd. in dry CH2Cl2; 5 equiv. of aziridine added; stirred overnight at 21°C; filtered off; solvent removed in vacuo; purified by stirring in dry n-hexane overnight at ambient temp.; n-hexane phase removed by decantation; dried in vacuo; elem. anal.;98%
In not given (Ar); mole ratio ZnCl2:ethylenimine = 1:2; soln. of ethylenimine added dropwise to a soln. of ZnCl2 with stirring and cooling to -20°C; stirred for 3-4 h; ppt. sepd.; washed (cold soln.); dried (vac.); elem. anal.;
ethyleneimine
151-56-4

ethyleneimine

palladium dichloride

palladium dichloride

trans-[bis(aziridine)dichloridopalladium(II)]
92344-36-0, 21654-58-0

trans-[bis(aziridine)dichloridopalladium(II)]

Conditions
ConditionsYield
In dichloromethane anhydrous metal chloride suspd. in dry CH2Cl2; 2 equiv. of aziridine added; stirred overnight at 21°C; filtered off; solvent removed in vacuo; purified by stirring in dry n-hexane overnight at ambient temp.; n-hexane phase removed by decantation; dried in vacuo; elem. anal.;98%
ethyleneimine
151-56-4

ethyleneimine

2,3-dimethoxybenzoic acid
1521-38-6

2,3-dimethoxybenzoic acid

C11H13NO3

C11H13NO3

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 0 - 20℃; for 2h; Temperature;97.5%
ethyleneimine
151-56-4

ethyleneimine

pentabutylphosphorodiamidimic bromide
81675-82-3

pentabutylphosphorodiamidimic bromide

2,2-bis(dibutylamino)-3-butyl-1,3,2-diazaphospholidinium bromide

2,2-bis(dibutylamino)-3-butyl-1,3,2-diazaphospholidinium bromide

Conditions
ConditionsYield
In benzene at 10℃;97%
ethyleneimine
151-56-4

ethyleneimine

amino(1-aziridinyl)bis(diethylamino)phosphonium chloride

amino(1-aziridinyl)bis(diethylamino)phosphonium chloride

C12H31N5P(1+)*Cl(1-)

C12H31N5P(1+)*Cl(1-)

Conditions
ConditionsYield
at 20℃; for 1h;97%
ethyleneimine
151-56-4

ethyleneimine

4-(bis-methylsulfanyl-methylene)-2-phenyl-5-p-tolyl-2,4-dihydro-pyrazol-3-one
59848-50-9

4-(bis-methylsulfanyl-methylene)-2-phenyl-5-p-tolyl-2,4-dihydro-pyrazol-3-one

4-<(N-aziridinomethylthio)methylene>-3-(p-methylphenyl)-5-oxo-1-phenyl-Δ2-pyrazoline
61254-28-2

4-<(N-aziridinomethylthio)methylene>-3-(p-methylphenyl)-5-oxo-1-phenyl-Δ2-pyrazoline

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃; for 3h;97%
ethyleneimine
151-56-4

ethyleneimine

cis-bromoamminebis(1,2-diaminoethane)cobalt(III) bromide monohydrate

cis-bromoamminebis(1,2-diaminoethane)cobalt(III) bromide monohydrate

cis-{Co(en)2(aziridine)(NH3)}Br3*EtOH

cis-{Co(en)2(aziridine)(NH3)}Br3*EtOH

Conditions
ConditionsYield
With C2H5OH In neat (no solvent) careful addn. of aziridine to solid cis-(Co(NH3)(en)2Br)Br2*H2O under stirring and cooling in a dry ice/acetone bath in N2 atm.; stirring at room temp. for 6 h; pptn. by slow addn. of ethanol and diethyl ether;; filtration; washing with ether; drying in vac. over P2O5; elem. anal.;;97%
ethyleneimine
151-56-4

ethyleneimine

{Pt(CF3)(P(C6H5)3)2(NCC2H5)}(1+)*BF4(1-)={Pt(CF3)(P(C6H5)3)2(NCC2H5)}BF4

{Pt(CF3)(P(C6H5)3)2(NCC2H5)}(1+)*BF4(1-)={Pt(CF3)(P(C6H5)3)2(NCC2H5)}BF4

{Pt(CF3)(P(C6H5)3)2(NHCH2CH2)}(1+)*BF4(1-)={Pt(CF3)(P(C6H5)3)2(NHCH2CH2)}BF4

{Pt(CF3)(P(C6H5)3)2(NHCH2CH2)}(1+)*BF4(1-)={Pt(CF3)(P(C6H5)3)2(NHCH2CH2)}BF4

Conditions
ConditionsYield
In tetrahydrofuran reaction under N2: a suspn. of Pt-complex in THF is treated with aziridine at 0°C, removing the ice-bath, warming to room temp., stirring for 5 h; reaction is controlled by IR-spectroscopy, filtn., vac. drying, elem. anal.;97%

151-56-4Relevant articles and documents

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.

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.

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.

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.

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.

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).

Method for synthesizing fluopyram

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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.

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.