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109-89-7 Usage

Occurrence

Diethylamine occurs in low concentrations in food and other biological materials. Concentrations (in p.p.m.) in fresh products include: spinach (15), apples (3), butterbeans (2.4), shelled peas (0.1), bean salad (1.5) and red cabbage (2.4) (HSDB 1989). Pickled vegetables contain 0-3.2 p.p.m. diethylamine while concentrations (in p.p.m.) in other materials include herring (0-5.2), barley (5.7), hops (3.1), boiled beef (2), tobacco leaf (0.1-35) and cigarette smoke concentrate (0-0.4). Interest in the occurrence of diethylamine in foods arises in part because of its possible formation of a carcinogenic N-nitroso derivative (Neurath et al 1977). Diethylamine has been reported in the exhaust from a gasoline engine (Hampton et al 1982).

Uses

In flotation agents, resins, dyes, resins, pesticides, rubber chemicals, and pharmaceuticals; selective solvent; polymerization and corrosion inhibitors; petroleum chemicals; electroplating; organic synthesis.

Air & Water Reactions

Highly flammable. Soluble in water. Sensitive to heat. May be sensitive to prolonged exposure to air.

Industrial uses

Diethylamine, like many of the other short chain aliphatic amines, has achieved widespread industrial use as an intermediate in the manufacture of a number of commercial products. Among these are included insecticides, pharmaceuticals, textile finishing agents, and corrosion inhibitors (Hawley 1981; Schweizer et al 1978). It is used as a polymerization inhibitor and/or catalyst in the polymer industry and in the manufacture of surfactants and rubber processing accelerators. This amine also is useful as a depilatory agent for animal skins, as a selective solvent for the removal of impurities from oils, fats, and waxes, and as a flotation agent in the petroleum industry (NIOSH/OSHA 1981; HSDB 1989).

Health Hazard

Diethylamine can be harmful if it is inhaled, swallowed, or in contact with skin. Vapors can irritate the eyes and cause irritation of the respiratory tract, leading to coughing and chest pain. Liquid diethylamine can cause severe burns to the eyes and skin. Vision became misty and halos appeared several hours after workmen were exposed to the vapors of amines such as diethylamine (Grant 1986). The edema of the corneal epithelium, which is principally responsible for the disturbances in vision, clears after one or more days, depending on the severity of exposure. Photophobia and discomfort from roughness of the corneal surface also can occur after greater exposure to the amine.

Uses

In the rubber and petroleum industry; in flotation agents; in resins, dyes, pharmaceuticals

storage

Diethylamine should be protected from physical damage. It should be kept stored in a cool, dry, well-ventilated location, away from incompatible chemical substances and away from fi re hazard and smoking areas. The containers should be bonded and grounded for transfer to avoid static sparks. Storage and use areas should be no smoking areas.

Physical properties

Colorless liquid with a fishy, ammonia-like odor. Experimentally determined detection and recognition odor threshold concentrations were 60 μg/m3 (20 ppbv) and 180 μg/m3 (60 ppbv), respectively (Hellman and Small, 1974). Diethylamine is a very strong base in aqueous solution (pKb = 3.0). Its chemistry is governed by the unshared electron pair on the nitrogen, thus it tends to react with acids to form salts.

Reactivity Profile

Diethylamine is a colourless, strongly alkaline, fish odour liquid, and highly inflammable. It has an ammonia-like odour and is completely soluble in water.Causes ignition on contact with cellulose nitrate. Explodes on contact with dicyanofurazan or dicyanofuroxan. Attacks some forms of plastics, rubber and coatings. On burning, diethylamine releases ammonia, carbon monoxide, carbon dioxide, and nitrogen oxides. It is incompatible with several chemical substances such as strong oxidisers, acids, cellulose nitrate, some metals, and dicyanofuroxan. N-nitrosamines, many of which are known to be potent carcinogens, may be formed when diethylamine comes in contact with nitrous acid, nitrates, or atmospheres with high nitrous oxide concentrations.

Environmental fate

Photolytic. Low et al. (1991) reported that the photooxidation of aqueous secondary amine solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions. Chemical/Physical. Diethylamine reacted with NOx in the dark forming diethylnitrosamine. In an outdoor chamber, photooxidation by natural sunlight yielded the following products: diethylnitramine, diethylformamide, diethylacetamide, ethylacetamide, ozone, acetaldehyde, and peroxyacetyl nitrate (Pitts et al., 1978). Reacts with mineral acids forming water-soluble salts (Morrison and Boyd, 1971).

Production Methods

Diethylamine is produced using the three methods also used for the manufacture of ethylamine with very slight modification. The most widely used method is the passing of ammonia and ethanol over a catalyst such as alumina or silica (Schweizer et al 1978). Diethylamine can be separated from the mixture by selective distillations and extractions. This secondary amine can also be produced by the other two methods which involve: 1) passing ammonia, ethanol, and hydrogen over a dehydrogenation catalyst; and 2) passing ammonia and an aldehyde or ketone and hydrogen over a hydrogenation catalyst. U.S. production in 1984 is estimated at 19.7 million pounds (HSDB 1989).

Safety Profile

Moderately toxic by ingestion, inhalation, and skin contact. A skin and severe eye irritant. Exposure to strong vapor can cause severe cough and chest pains. Contact with liquid can damage eyes, possibly permanently; contact with skin causes necrosis and vesciculation. A very dangerous fire hazard when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam, CO2, dry chemical. Explodes on contact with dicyanofurazan. Violent reaction with sulfuric acid. Ignites on contact with cellulose nitrate of sufficiently high surface area. When heated to decomposition it emits toxic fumes of NOx. See also MINES.

Carcinogenicity

No evidence of mutagenicity was seen in Ames bacterial assays.8 Diethylamine has an ammonia-like odor that is detectable at 0.13ppm. The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for diethylamine is 5ppm (15mg/m3) with a short-term excursion limit of 15ppm (45mg/m3) and an A4-not classifiable as a human carcinogen designation; there is a notation for skin absorption.

Uses

Diethylamine is manufactured by heating ethyl chloride and alcoholic ammonia under pressure or by hydrogenation of aziridines in the presence of catalysts. DEA is used as a solvent, as a rubber accelerator, in the organic synthesis of resins, dyes, pesticides, and pharmaceuticals, in electroplating, and as a polymerization inhibitor. Other applications include uses as a corrosion inhibitor. It was reported noneffective as a skin depigmentator.

Description

Diethylamine is a colourless, strongly alkaline, fish odour liquid, and highly inflammable. It has an ammonia-like odour and is completely soluble in water. On burning, diethylamine releases ammonia, carbon monoxide, carbon dioxide, and nitrogen oxides. It is incompatible with several chemical substances such as strong oxidisers, acids, cellulose nitrate, some metals, and dicyanofuroxan. N-nitrosamines, many of which are known to be potent carcinogens, may be formed when diethylamine comes in contact with nitrous acid, nitrates, or atmospheres with high nitrous oxide concentrations. The applications of Diethylamine are numerous. Diethylamine is used in the production of pesticides. It is used in a mixture for the production of DEET which goes into the repellents that are found readily in supermarkets for general use. Diethylamine is also mixed with other chemicals to form Diethylaminoethanole, which is used mainly as a corrosion inhibitor in water treatment facilities as well as production of dyes, rubber, resins, and pharmaceuticals. Diethylamine is also used in manufacture of basic chemicals and pharmaceuticals.

Definition

ChEBI: A secondary aliphatic amine where both N-substituents are ethyl.

General Description

A clear colorless liquid with an ammonia-like odor. Density 5.9 lb / gal. Flash point -15°F. A respiratory irritant. Corrosive to the eyes and skin. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.

Metabolism

Little information is available regarding the metabolism of diethylamine. The amine can be readily absorbed from the respiratory and gastrointestinal tract. It has been reported that following oral administration of diethylamine hydrochloride to humans, much of the amine was recovered in the urine (Beard and Noe 1978). This suggests that it is not readily metabolized and, therefore, may not be a substrate for monoamine oxidase. When administered intraperitoneally to rats, it was moderately inhibitory with respect to liver monoamine oxidase (Valiev 1974). Diethylamine may serve as a precursor for the formation of the reportedly carcinogenic N-nitrosoamines and, indeed, when a diethylamine containing liquid was examined for nitrosation reactions under simulated conditions of the human stomach, N-nitrosodiethylamine was formed (Ziebarth 1985).

Purification Methods

Dry diethylamine with LiAlH4 or KOH pellets. Reflux with, and distil it from, BaO or KOH. Convert it to the p-toluenesulfonamide and crystallise to constant melting point from dry pet ether (b 90-120o), then hydrolyse with HCl, excess NaOH is added, and the amine is passed through a column of activated alumina. Redistil the amine and dry it with activated alumina before use [Swift J Am Chem Soc 64 115 1942]. [Beilstein 4 III 313.] § A polystyrene diethylaminomethyl supported version is commercially available.

Precautions

Occupational workers and users should be very careful during the use and chemical management of diethylamine. Workers should wear impervious protective clothing, including boots, gloves, a laboratory coat, apron or coveralls, as appropriate, to prevent skin contact. The chemical is very hazardous, corrosive, and harmful, and is a very flammable liquid and vapor. Exposures to vapor may cause fl ash fi re. It causes burns and adverse effects to the cardiovascular system. Workers should use chemical safety goggles and a full-face shield to avoid splashing of the chemical substance. An eye-wash fountain and quickdrench facilities in the work area should be maintained by the chemical management unit.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No hazardous reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
InChI:InChI=1/C4H11N/c1-3-5-4-2/h5H,3-4H2,1-2H3/p+1

109-89-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A11716)  Diethylamine, 99+%    109-89-7 100ml 188.0CNY Detail
Alfa Aesar (A11716)  Diethylamine, 99+%    109-89-7 500ml 219.0CNY Detail
Alfa Aesar (A11716)  Diethylamine, 99+%    109-89-7 2500ml 678.0CNY Detail
Sigma-Aldrich (31730)  Diethylamine  puriss. p.a., ≥99.5% (GC) 109-89-7 31730-250ML 497.25CNY Detail
Sigma-Aldrich (31730)  Diethylamine  puriss. p.a., ≥99.5% (GC) 109-89-7 31730-1L 1,531.53CNY Detail
Aldrich (386456)  Diethylamine  purified by redistillation, 99.5% 109-89-7 386456-100ML 1,695.33CNY Detail

109-89-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Diethylamine

1.2 Other means of identification

Product number -
Other names DEA

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Agricultural chemicals (non-pesticidal),Intermediates,Paint additives and coating additives not described by other categories
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:109-89-7 SDS

109-89-7Synthetic route

1-diethylamino-2,4-dinitronaphthalene
27210-68-0

1-diethylamino-2,4-dinitronaphthalene

ethylamine
75-04-7

ethylamine

A

N-ethyl-2,4-dinitro-1-naphthylamine
27210-67-9

N-ethyl-2,4-dinitro-1-naphthylamine

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In water at 30℃; for 1h;A 100%
B n/a
(N,N-diethylamino)tributyltin
1066-87-1

(N,N-diethylamino)tributyltin

2,5-diethynylthiophene
79109-72-1

2,5-diethynylthiophene

A

2,5-bis[(tributylstannyl)ethynyl]thiophene
166543-55-1

2,5-bis[(tributylstannyl)ethynyl]thiophene

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In neat (no solvent) stoich. amts., stirring (overnight, room temp., dry atmosphere), evapn. (vac.);A 99%
B n/a
phenylphosphonic acid bis(N,N-diethylamide)
4519-35-1

phenylphosphonic acid bis(N,N-diethylamide)

4-methoxy-aniline
104-94-9

4-methoxy-aniline

A

phenyl N,N'-bis(p-methoxyphenyl)phosphorodiamidite
70058-53-6

phenyl N,N'-bis(p-methoxyphenyl)phosphorodiamidite

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
for 12h; Heating;A 26.3%
B 98.5%
N,N'-diethyl-1,2,2,2-tetrafluoropropionamide
392-63-2

N,N'-diethyl-1,2,2,2-tetrafluoropropionamide

A

diethylamine
109-89-7

diethylamine

B

2,3,3,3-Tetrafluoropropanol-1

2,3,3,3-Tetrafluoropropanol-1

Conditions
ConditionsYield
With aluminum (III) chloride; zinc borohydride In methanol at 60℃; for 10h; Reagent/catalyst; Temperature; Solvent;A 95.7%
B 98.1%
trimethylsilyl diethylcarbamate
18279-61-3

trimethylsilyl diethylcarbamate

trimethylsilyl <2-(trimethylsiloxy)ethyl>carbamate
62305-44-6

trimethylsilyl <2-(trimethylsiloxy)ethyl>carbamate

A

N,N'-bis-<β-(trimethylsiloxy)>ethylcarbodiimide
32284-58-5

N,N'-bis-<β-(trimethylsiloxy)>ethylcarbodiimide

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
A 66%
B 98%
4-methoxy-aniline
104-94-9

4-methoxy-aniline

bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

A

N,N'-bis(p-methoxyphenyl)-P-phenylphosphonous diamide
70058-45-6

N,N'-bis(p-methoxyphenyl)-P-phenylphosphonous diamide

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
for 14h; Heating;A 83.7%
B 98%
for 14h; Heating;A 83.7%
B 98%
1-diethylamino-2,4-dinitronaphthalene
27210-68-0

1-diethylamino-2,4-dinitronaphthalene

methylamine
74-89-5

methylamine

A

1-(Methylamino)-2,4-dinitronaphthalene
39139-78-1

1-(Methylamino)-2,4-dinitronaphthalene

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In water at 30℃; for 1h;A 97%
B n/a
bis-(4-hydroxyphenyl)methane
620-92-8

bis-(4-hydroxyphenyl)methane

bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

A

4,4′-methylenedi(benzene-4,1-diyl) bis(N,N-diethyl-P-phenylphosphonamidite)

4,4′-methylenedi(benzene-4,1-diyl) bis(N,N-diethyl-P-phenylphosphonamidite)

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In neat (no solvent) at 115 - 120℃; for 2h;A 97%
B n/a
bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

A

4,4′-(propane-2,2-diyl)di(benzene-4,1-diyl) bis(N,N-diethyl-P-phenylphosphonamidite)
146733-97-3

4,4′-(propane-2,2-diyl)di(benzene-4,1-diyl) bis(N,N-diethyl-P-phenylphosphonamidite)

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In neat (no solvent) at 115 - 120℃; for 2h;A 97%
B n/a
3-(trimethylsilyl)-1-(trimethylstannyl)propyne
69165-95-3

3-(trimethylsilyl)-1-(trimethylstannyl)propyne

Diethylamino-trimethyl-stannan
1068-74-2

Diethylamino-trimethyl-stannan

A

3-(trimethylsilyl)-1,3-bis(trimethylstannyl)propyne
122691-55-8, 122691-53-6

3-(trimethylsilyl)-1,3-bis(trimethylstannyl)propyne

B

3-(trimethylsilyl)-1,1-bis(trimethylstannyl)propadiene
122691-53-6

3-(trimethylsilyl)-1,1-bis(trimethylstannyl)propadiene

C

(Trimethylsilyl)tris(trimethylstannyl)propadiene
122691-54-7

(Trimethylsilyl)tris(trimethylstannyl)propadiene

D

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In neat (no solvent) heating (180-200°C, 1 h), continuous removal of HNEt2; distn.; elem. anal.; mixt. of propadiene/propyne bis(trimethylastannyl)-derivatives (90:10 %) not separated;A n/a
B n/a
C n/a
D 96%
diethylammonium diethylcarbamate
64882-07-1

diethylammonium diethylcarbamate

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In methanol at 60 - 65℃; for 2h;95%
phenylphosphonic acid bis(N,N-diethylamide)
4519-35-1

phenylphosphonic acid bis(N,N-diethylamide)

aniline
62-53-3

aniline

A

triphenyl phosphite
101-02-0

triphenyl phosphite

B

N,N',N''-triphenylphosphorous triamide
15159-51-0

N,N',N''-triphenylphosphorous triamide

C

phenyl N,N'-diphenylphosphorodiamidite
26350-11-8

phenyl N,N'-diphenylphosphorodiamidite

D

diphenyl phenylphosphoramidite
26350-10-7

diphenyl phenylphosphoramidite

E

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
for 17h; Product distribution; Heating;A n/a
B n/a
C n/a
D n/a
E 94.5%
4-[(diethylamino)methyl]-2,6-bis(1,1-dimethylethyl)phenol
794-53-6

4-[(diethylamino)methyl]-2,6-bis(1,1-dimethylethyl)phenol

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

A

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate
976-56-7

diethyl 4-hydroxy-3,5-di-tert-butylbenzylphosphonate

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
In toluene for 25h; Heating;A 94%
B n/a
bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

4-bromo-aniline
106-40-1

4-bromo-aniline

A

N,N'-bis(p-bromophenyl)-P-phenylphosphonous diamide
70058-46-7

N,N'-bis(p-bromophenyl)-P-phenylphosphonous diamide

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
for 18.5h; Heating;A 68.1%
B 93.6%
1,3-benzothiazol-2-ylhydrazine
615-21-4

1,3-benzothiazol-2-ylhydrazine

bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

A

2-Hydrazono-3-(diethylaminophenylphosphino)-2,3-dihydro-1,3-benzothiazole
131471-58-4

2-Hydrazono-3-(diethylaminophenylphosphino)-2,3-dihydro-1,3-benzothiazole

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
at 110 - 115℃; under 5 - 10 Torr; for 1h;A 92.3%
B n/a
bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

aniline
62-53-3

aniline

A

N,N'-triphenylphosphonous diamide
54459-40-4

N,N'-triphenylphosphonous diamide

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
for 20h; Heating;A 72.2%
B 92.1%
bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

2-Chloroaniline
95-51-2

2-Chloroaniline

A

N,N'-bis(o-chlorophenyl)-P-phenylphosphonous diamide
70058-47-8

N,N'-bis(o-chlorophenyl)-P-phenylphosphonous diamide

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
for 36h; Heating;A 62.4%
B 91.6%
phenylphosphonic acid bis(N,N-diethylamide)
4519-35-1

phenylphosphonic acid bis(N,N-diethylamide)

4-bromo-aniline
106-40-1

4-bromo-aniline

A

triphenyl phosphite
101-02-0

triphenyl phosphite

B

diethylamine
109-89-7

diethylamine

C

diphenyl (p-bromophenyl)phosphoramidite

diphenyl (p-bromophenyl)phosphoramidite

D

phenyl N,N'-bis(p-bromophenyl)phosphorodiamidite

phenyl N,N'-bis(p-bromophenyl)phosphorodiamidite

E

N,N',N''-tris(p-bromophenyl)phosphorous triamide

N,N',N''-tris(p-bromophenyl)phosphorous triamide

Conditions
ConditionsYield
for 22h; Product distribution; Heating;A n/a
B 91.4%
C n/a
D n/a
E n/a
4-Hydroxy-4-methyl-2-pentanone
123-42-2

4-Hydroxy-4-methyl-2-pentanone

A

4-methyl-pent-3-en-2-one
141-79-7

4-methyl-pent-3-en-2-one

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
With hexaethylphosphoric triamide at 190℃; further reagent;A 26.8%
B 91.3%
hexaethylphosphoric triamide
2283-11-6

hexaethylphosphoric triamide

A

4-methyl-pent-3-en-2-one
141-79-7

4-methyl-pent-3-en-2-one

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
With 4-Hydroxy-4-methyl-2-pentanone at 190℃;A 26.8%
B 91.3%
O,O'-diethyl thiophosphonate
999-01-9

O,O'-diethyl thiophosphonate

4-[(diethylamino)methyl]-2,6-bis(1,1-dimethylethyl)phenol
794-53-6

4-[(diethylamino)methyl]-2,6-bis(1,1-dimethylethyl)phenol

A

diethylamine
109-89-7

diethylamine

B

3,5-di-tert-butyl-4-hydroxy-O,O-diethylbenzylphosphonate

3,5-di-tert-butyl-4-hydroxy-O,O-diethylbenzylphosphonate

Conditions
ConditionsYield
In toluene for 25h; Heating;A n/a
B 90%
ethylene glycol
107-21-1

ethylene glycol

N,N-tetraethyldiamidothiophosphite S-propyl

N,N-tetraethyldiamidothiophosphite S-propyl

A

1-thiopropane
107-03-9

1-thiopropane

B

1,4,6,9-tetraoxa-5λ5-phosphaspiro[4,4]nonane
3646-10-4, 54515-09-2, 673460-28-1

1,4,6,9-tetraoxa-5λ5-phosphaspiro[4,4]nonane

C

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
at 120 - 130℃; for 1h;A n/a
B 90%
C n/a
at 120 - 130℃; for 1h; Product distribution;A n/a
B 90%
C n/a
1-Bicyclo[2.2.1]hept-5-en-2-yl-butane-1,2-dione
74895-71-9

1-Bicyclo[2.2.1]hept-5-en-2-yl-butane-1,2-dione

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

A

(Z)-1-Bicyclo[2.2.1]hept-5-en-2-yl-2-trimethylsilanyloxy-but-2-en-1-one
74895-77-5

(Z)-1-Bicyclo[2.2.1]hept-5-en-2-yl-2-trimethylsilanyloxy-but-2-en-1-one

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 30 - 40℃; for 18h;A 90%
B n/a
1-(3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-butane-1,2-dione
74895-74-2

1-(3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-butane-1,2-dione

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

A

(Z)-1-(3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-2-trimethylsilanyloxy-but-2-en-1-one
74895-80-0

(Z)-1-(3-Methyl-bicyclo[2.2.1]hept-5-en-2-yl)-2-trimethylsilanyloxy-but-2-en-1-one

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 30 - 40℃; for 18h;A 90%
B n/a
carbon monoxide
201230-82-2

carbon monoxide

benzenenesulfenyl dimethylamine
6667-19-2

benzenenesulfenyl dimethylamine

A

N,N'-diethylurea
623-76-7

N,N'-diethylurea

B

N,N,N',N'-tetraethyloxamide
14288-05-2

N,N,N',N'-tetraethyloxamide

C

diethylamine
109-89-7

diethylamine

D

diethylthiocarbamic acid S-phenyl ester

diethylthiocarbamic acid S-phenyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In pyridine at 80℃; under 14701.2 Torr; for 10h; Carbonylation;A n/a
B 1.4 % Spectr.
C 3 % Spectr.
D 90%
2-hydrazino-6-methylbenzothiazole
20174-69-0

2-hydrazino-6-methylbenzothiazole

bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

A

C18H23N4PS
131471-59-5

C18H23N4PS

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
at 110 - 115℃; under 5 - 10 Torr; for 1h;A 89.7%
B n/a
N-ethyl-N-hydroxy-ethanamine
3710-84-7

N-ethyl-N-hydroxy-ethanamine

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
With carbon monoxide; hexarhodium hexadecacarbonyl In 2-ethoxy-ethanol; water at 40℃; under 12160 Torr; for 5h;89%
With N,N,N'N'-tetramethyl-1,3-propanediamine; carbon monoxide; water; hexarhodium hexadecacarbonyl In 2-ethoxy-ethanol at 40℃; under 6080 Torr; for 5h;93 % Chromat.
With N,N,N'N'-tetramethyl-1,3-propanediamine; carbon monoxide; water; hexarhodium hexadecacarbonyl In 2-ethoxy-ethanol at 40℃; under 6080 Torr; for 5h; Product distribution; Mechanism; (CH3)2NC3H6NH-substituted polystyrene instead of TMPDA; analogous reaction of other hydroxylamines;93 % Chromat.
(2-hydroxyethyl)urea
2078-71-9

(2-hydroxyethyl)urea

N,N-diethyl-1,1,1-trimethylsilanamine
996-50-9

N,N-diethyl-1,1,1-trimethylsilanamine

A

diethylamine
109-89-7

diethylamine

B

N-<2-(trimethylsiloxy)ethyl>-N'-(trimethylsilyl)urea
75226-87-8

N-<2-(trimethylsiloxy)ethyl>-N'-(trimethylsilyl)urea

Conditions
ConditionsYield
With ammonium sulfate at 120℃; for 1h;A 82%
B 89%
bis(diethylamino)phenylphosphine
1636-14-2

bis(diethylamino)phenylphosphine

(4-chloro-1,3-benzothiazol-2-yl)hydrazine
51769-38-1

(4-chloro-1,3-benzothiazol-2-yl)hydrazine

A

C17H20ClN4PS
131471-60-8

C17H20ClN4PS

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
at 110 - 115℃; under 5 - 10 Torr; for 1h;A 88.5%
B n/a
1-butanethiol
109-79-5

1-butanethiol

dibutyl diethylphosphoramidodithioite
52416-06-5

dibutyl diethylphosphoramidodithioite

A

merphos
150-50-5

merphos

B

diethylamine
109-89-7

diethylamine

Conditions
ConditionsYield
for 0.5h; Ambient temperature;A 88%
B 77%
1,3-propanesultone
1120-71-4

1,3-propanesultone

diethylamine
109-89-7

diethylamine

3-(diethylamino)propane-1-sulfonic acid
1116-85-4

3-(diethylamino)propane-1-sulfonic acid

Conditions
ConditionsYield
In dichloromethane at 10℃; for 1h; Product distribution / selectivity;100%
In dichloromethane Inert atmosphere;53%
4-chloro-benzoyl chloride
122-01-0

4-chloro-benzoyl chloride

diethylamine
109-89-7

diethylamine

4-chloro-N,N-diethyl-benzamide
7461-38-3

4-chloro-N,N-diethyl-benzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 6h;100%
With sodium carbonate In tert-butyl methyl ether; water at 15 - 25℃; for 1h; Schotten-Baumann Reaction; Inert atmosphere;98.7%
In toluene at 50℃;90%
methyl vinyl ketone
78-94-4

methyl vinyl ketone

diethylamine
109-89-7

diethylamine

4-(diethylamino)butan-2-one
3299-38-5

4-(diethylamino)butan-2-one

Conditions
ConditionsYield
With copper diacetate In water at 20℃; for 12h; aza-Michael addition;100%
copper diacetate In water at 20℃; for 15h; aza-type Michael addition;100%
at 0℃; Inert atmosphere;99%
2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

diethylamine
109-89-7

diethylamine

2-bromo-N,N-diethylbenzamide
76041-86-6

2-bromo-N,N-diethylbenzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;100%
In dichloromethane at 0 - 20℃; Schlenk technique;99%
In dichloromethane at 0 - 20℃; for 0.5h;95%
formaldehyd
50-00-0

formaldehyd

4-acetaminophenol
103-90-2

4-acetaminophenol

diethylamine
109-89-7

diethylamine

N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide
121-78-8

N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide

Conditions
ConditionsYield
In ethanol at 80℃; for 1.5h; Microwave irradiation;100%
In ethanol for 12h; Heating;80%
In ethanol at 80℃; for 1h; Microwave irradiation;77%
Nonanoyl chloride
764-85-2

Nonanoyl chloride

diethylamine
109-89-7

diethylamine

N,N-diethyl nonanamide
10385-09-8

N,N-diethyl nonanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;100%
With diethyl ether; triethylamine
With benzene
fumaryl dichloride
627-63-4

fumaryl dichloride

diethylamine
109-89-7

diethylamine

N1,N1,N4,N4-tetraethylfumaramide
111328-65-5, 138895-86-0, 37511-04-9

N1,N1,N4,N4-tetraethylfumaramide

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃; Inert atmosphere;100%
With diethyl ether
diethylamine
109-89-7

diethylamine

acrylonitrile
107-13-1

acrylonitrile

3-diethylaminopropionitrile
5351-04-2

3-diethylaminopropionitrile

Conditions
ConditionsYield
With copper diacetate In water at 20℃; for 12h; aza-Michael addition;100%
iron(III) chloride In water at 20℃; for 15h; aza-type Michael addition;100%
1-butyl-3-methylimidazolium Tetrafluoroborate In water at 20℃; for 7h; aza-Michael reaction;97%
diethylamine
109-89-7

diethylamine

butyryl chloride
141-75-3

butyryl chloride

N,N-diethyl-butyramide
1114-76-7

N,N-diethyl-butyramide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
With benzene
With diethyl ether
In benzene
With sodium carbonate In benzene at 0 - 5℃;
diethylamine
109-89-7

diethylamine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2-Chloro-N,N-diethylacetamide
2315-36-8

2-Chloro-N,N-diethylacetamide

Conditions
ConditionsYield
In dichloromethane; water at 5℃; Temperature; Solvent;100%
With triethylamine In dichloromethane at 0℃;99%
With triethylamine In 1,2-dichloro-ethane at 10 - 20℃; for 3h; Cooling with ice;95%
formaldehyd
50-00-0

formaldehyd

diethylamine
109-89-7

diethylamine

phenylacetylene
536-74-3

phenylacetylene

diethyl-(3-phenyl-prop-2-ynyl)-amine
22396-72-1

diethyl-(3-phenyl-prop-2-ynyl)-amine

Conditions
ConditionsYield
With copper dichloride at 80℃; under 150.015 Torr; for 3h; Mannich reaction;100%
With silver nitrate at 105℃; for 0.133333h; microwave irradiation;99%
copper(l) iodide In water; dimethyl sulfoxide at 30℃; for 10h;98%
diethylamine
109-89-7

diethylamine

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

N,N-diethyl-2,4-dinitroaniline
837-64-9

N,N-diethyl-2,4-dinitroaniline

Conditions
ConditionsYield
In ethanol; water at 60℃; for 6h;100%
In acetonitrile at 25℃; for 2h; Solvent;85%
With ethanol
With sodium carbonate In acetone for 5h; Substitution; Heating;
In acetonitrile at 25℃; Kinetics; Solvent;
diethylamine
109-89-7

diethylamine

hydrocinnamic acid chloride
645-45-4

hydrocinnamic acid chloride

N,N-diethyl-3-phenylpropanamide
18859-19-3

N,N-diethyl-3-phenylpropanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;96%
diethylamine
109-89-7

diethylamine

ethyl acrylate
140-88-5

ethyl acrylate

ethyl 3-(diethylamino)propionate
5515-83-3

ethyl 3-(diethylamino)propionate

Conditions
ConditionsYield
With copper diacetate In water at 20℃; for 12h; aza-Michael addition;100%
iron(III) chloride In dichloromethane at 25℃; for 42h; Product distribution; various catalysts and further amines with various Michael acceptors;96%
iron(III) chloride In dichloromethane at 25℃; for 42h;96%
diethylamine
109-89-7

diethylamine

diethylphosphoramidous dichloride
1069-08-5

diethylphosphoramidous dichloride

Conditions
ConditionsYield
With phosphorus trichloride In diethyl ether at -78 - 20℃; for 2h;100%
With phosphorus trichloride In diethyl ether at -78 - 20℃; Inert atmosphere;100%
With phosphorus trichloride In diethyl ether at -78 - 20℃; for 2h;100%
diethylamine
109-89-7

diethylamine

N-Nitrosodiethylamine
55-18-5

N-Nitrosodiethylamine

Conditions
ConditionsYield
With [NO(1+)*18-crown-6*H(NO3)2(1-)] In dichloromethane at 20℃; for 0.0833333h;100%
With magnesium hydrogen sulfate; silica gel; sodium nitrite In dichloromethane at 20℃; for 1h; Nitrosation;98%
With aluminium trichloride; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.5h; Nitrosation;98%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

diethylamine
109-89-7

diethylamine

N,N-diethyl-3-oxobutanamide
2235-46-3

N,N-diethyl-3-oxobutanamide

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; Inert atmosphere;100%
In tetrahydrofuran at 0℃; for 0.0833333h; Inert atmosphere;100%
With triethylamine In methanol; toluene at 0℃; for 2h;95%
diethylamine
109-89-7

diethylamine

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

dimethyl (2E)-2-(diethylamino)but-2-enedioate
996-85-0

dimethyl (2E)-2-(diethylamino)but-2-enedioate

Conditions
ConditionsYield
In water at 20℃; for 2h; Michael-type addition;100%
In diethyl ether
4-butanolide
96-48-0

4-butanolide

diethylamine
109-89-7

diethylamine

N,N-Diethyl-4-hydroxy-butyramide
86452-59-7

N,N-Diethyl-4-hydroxy-butyramide

Conditions
ConditionsYield
In acetonitrile at 30℃; under 6750540 Torr; for 96h;100%
Stage #1: diethylamine With diisobutylaluminium hydride In tetrahydrofuran; toluene
Stage #2: 4-butanolide In tetrahydrofuran at 45℃; for 2h;
72%
carbon monoxide
201230-82-2

carbon monoxide

benzyl bromide
100-39-0

benzyl bromide

diethylamine
109-89-7

diethylamine

S-benzyl N,N-diethylthiolcarbamate
30085-50-8

S-benzyl N,N-diethylthiolcarbamate

Conditions
ConditionsYield
With sulfur; selenium In tetrahydrofuran 1.) 30 deg C; 2.) rt.;100%
With n-butyllithium; sulfur 1.) THF/hexane, from -78 deg C to -20 deg C; 2.) - 78 deg C; 3.) 20 deg C, 1 atm, 2 h; Yield given. Multistep reaction;
Yield given. Multistep reaction;
7-chloro-1,3-dimethyl-6-azalumazine
54632-27-8

7-chloro-1,3-dimethyl-6-azalumazine

diethylamine
109-89-7

diethylamine

7-(diethylamino)-1,3-dimethyl-6-azalumazine
111934-38-4

7-(diethylamino)-1,3-dimethyl-6-azalumazine

Conditions
ConditionsYield
In dichloromethane for 2.5h;100%
formaldehyd
50-00-0

formaldehyd

N-(3-sec-Butyl-4-hydroxy-phenyl)-acetamide
13780-89-7

N-(3-sec-Butyl-4-hydroxy-phenyl)-acetamide

diethylamine
109-89-7

diethylamine

N-(3-sec-Butyl-5-diethylaminomethyl-4-hydroxy-phenyl)-acetamide
107244-66-6

N-(3-sec-Butyl-5-diethylaminomethyl-4-hydroxy-phenyl)-acetamide

Conditions
ConditionsYield
In ethanol for 48h; Heating;100%
formaldehyd
50-00-0

formaldehyd

N-(6-Hydroxy-2',5'-dimethoxy-biphenyl-3-yl)-acetamide
101712-35-0

N-(6-Hydroxy-2',5'-dimethoxy-biphenyl-3-yl)-acetamide

diethylamine
109-89-7

diethylamine

N-(5-Diethylaminomethyl-6-hydroxy-2',5'-dimethoxy-biphenyl-3-yl)-acetamide
101712-53-2

N-(5-Diethylaminomethyl-6-hydroxy-2',5'-dimethoxy-biphenyl-3-yl)-acetamide

Conditions
ConditionsYield
In ethanol; water Heating;100%
formaldehyd
50-00-0

formaldehyd

N-(6-Hydroxy-2'-trifluoromethyl-biphenyl-3-yl)-acetamide
79290-53-2

N-(6-Hydroxy-2'-trifluoromethyl-biphenyl-3-yl)-acetamide

diethylamine
109-89-7

diethylamine

N-(5-Diethylaminomethyl-6-hydroxy-2'-trifluoromethyl-biphenyl-3-yl)-acetamide
79290-47-4

N-(5-Diethylaminomethyl-6-hydroxy-2'-trifluoromethyl-biphenyl-3-yl)-acetamide

Conditions
ConditionsYield
In ethanol; water Heating;100%
formaldehyd
50-00-0

formaldehyd

3a,3b,4,4a,7a,8,8b-octahydro-4,8-ethenopyrrolo<3',4':3,4>cyclobut<1,2-f>isoindole-1,3,5,7<2H,6H>tetrone
10403-51-7

3a,3b,4,4a,7a,8,8b-octahydro-4,8-ethenopyrrolo<3',4':3,4>cyclobut<1,2-f>isoindole-1,3,5,7<2H,6H>tetrone

diethylamine
109-89-7

diethylamine

C24H34N4O4
96488-35-6

C24H34N4O4

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide at 70℃; for 6h;100%
ethylene glycol diacrylate
2274-11-5

ethylene glycol diacrylate

diethylamine
109-89-7

diethylamine

1,10-bis-diethylamino-4,7-dioxa-3,8-dioxodecane
81166-07-6

1,10-bis-diethylamino-4,7-dioxa-3,8-dioxodecane

Conditions
ConditionsYield
In diethyl ether for 18h; Ambient temperature;100%
Diethylamino-(chlormethyl)-chlorphosphin
22606-71-9

Diethylamino-(chlormethyl)-chlorphosphin

diethylamine
109-89-7

diethylamine

P-(Chloromethyl)-N,N,N',N'-tetraethylphosphonous diamide
100548-25-2

P-(Chloromethyl)-N,N,N',N'-tetraethylphosphonous diamide

Conditions
ConditionsYield
In diethyl ether100%
o-formylbenzonitrile
7468-67-9

o-formylbenzonitrile

diethylamine
109-89-7

diethylamine

3-Diethylamino-2,3-dihydro-isoindol-1-one
93679-82-4

3-Diethylamino-2,3-dihydro-isoindol-1-one

Conditions
ConditionsYield
at 40℃; for 1h;100%
(E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one
59938-06-6

(E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one

diethylamine
109-89-7

diethylamine

β-(N,N-diethylamino)vinyltrifluoromethylketone
34648-03-8

β-(N,N-diethylamino)vinyltrifluoromethylketone

Conditions
ConditionsYield
In acetonitrile Ambient temperature;100%
In cyclohexane at 19.9℃; Rate constant; other solvents; ΔG(excit.), ΔH(excit.), ΔS(excit.);
In cyclohexane at 19.9℃; Yield given;
4-bromo-4-methyl-1-phenyl-pent-1-yn-3-one
87064-07-1

4-bromo-4-methyl-1-phenyl-pent-1-yn-3-one

diethylamine
109-89-7

diethylamine

(Z)-4-Bromo-1-diethylamino-4-methyl-1-phenyl-pent-1-en-3-one
87064-08-2

(Z)-4-Bromo-1-diethylamino-4-methyl-1-phenyl-pent-1-en-3-one

Conditions
ConditionsYield
In hexane Ambient temperature;100%

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