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7087-68-5 Usage

Description

N,N-Diisopropylethylamine is also known as Hunig's base and abbreviated as DIPEA or DIEA, It is a sterically hindered amine and an organic compound. The colourless liquid was named as Hung’s base after Siegfried Hunig, a German chemist. It is noteworthy that the compound is commercially available.In organic chemistry, N,N-Diisopropylethylamine is used as a base. Since the nitrogen centre is isolated by an ethyl group and the two isopropyl groups, It can bind to protons. The compound is, therefore, a base similar to 2,2,6,6-tetramethylpiperidine, but a poor nucleophile, a blend of properties that makes it valuable as an organic reagent.

Stability and Reactivity

DIPEA exhibits violent reaction as well as flammability with nitrates, oxidizing agents, and peroxides. It can also react very exothermically and possibility of spitting with halogens and strong acids. In an alkaline environment, the compound is likely to react violently. In addition, the compound can form toxic products such as n-nitrosamines when combined with nitrous acid as well as oxygen, nitrosating agents, and nitrates. Under normal conditions (temperature and pressure), DIPEA is very stable. However, it is soluble in most organic solvents.

Applications

N,N-Diisopropylethylamine is utilized as a base in the palladium(0)catalysed alkoxycarbonylation of both allyl acetates and phosphates. It is used as a neutralizer of the produced phosphoric acid. Notably, the alkyl ester cannot be produced without DIPEA.When combined with boryl triflates, N,N-Diisopropylethylamine is used in the enolate synthesis of ketones for application in directed cross-adol reactions.DIPEA is applied as a proton scavenger in organic synthesis. Since the compound is a sterically hindered amine, it lacks quaternization; therefore, making it a perfect choice of a base for use with extremely reactive alkylating agents. DIPEA is specifically useful as a base in the protection of alcohols as substituted ethers in the field of protecting group chemistry.In the synthesis of peptides, the compound is also used in the coupling of amino acids. The steric nature and basicity of DIPEA during the coupling reaction affects the degree of racemization.

Chemical Properties

Diisopropylethylamine (DIPEA) is a clear, colorless to light yellow liquid, insoluble in water and easily soluble in acetone and other organic solvents.

Uses

N,N-Diisopropylethylamine is used as a base in organic reactions. Used in the preparation of (-)Gambierol a marine polycyclic ether toxin. It is also used in the synthesis of potent inhibitors of human brain memapsin, a key effector in the progression of Alzheimer’s disease.

Application

N,N-Diisopropylethylamine is an important pesticide and pharmaceutical intermediate, which can be used to synthesize anesthetics and herbicides, and can also be used as a sterically hindered amine to participate in various catalytic reactions.

Preparation

N,N-Diisopropylethylamine is used as a non-nucleophilic base in organic synthesis. It is prepared by the alkylation of diisopropylamine with diethyl sulphate. DIPEA can then be purified through distillation from potassium hydroxide if necessary.

General Description

N-Ethyldiisopropylamine (EDIA) reacts with monoactivated Michael acceptors to afford symmetrical sulfones.

Flammability and Explosibility

Highlyflammable

Purification Methods

Distil the amine from ninhydrin, then from KOH [Dryland & Sheppard, J Chem Soc, Faraday Trans 1 125 1986]. It is a strong base and should be stored in the absence of carbon dioxide. [Hünig & Kiessel Chem Ber 91 380, 387 1958, Wotiz et al. J Org Chem 24 1202 1959, Beilstein 4 IV 551.]

Check Digit Verification of cas no

The CAS Registry Mumber 7087-68-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,0,8 and 7 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 7087-68:
(6*7)+(5*0)+(4*8)+(3*7)+(2*6)+(1*8)=115
115 % 10 = 5
So 7087-68-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H19N/c1-6-9(7(2)3)8(4)5/h7-8H,6H2,1-5H3

7087-68-5 Well-known Company Product Price

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  • TCI America

  • (D2937)  N,N-Diisopropylethylamine (ca. 10% in N,N-Dimethylformamide) [for Detection of Primary Amines]  

  • 7087-68-5

  • 10mL

  • 440.00CNY

  • Detail
  • Alfa Aesar

  • (A11801)  N-Ethyldiisopropylamine, 99%   

  • 7087-68-5

  • 25ml

  • 161.0CNY

  • Detail
  • Alfa Aesar

  • (A11801)  N-Ethyldiisopropylamine, 99%   

  • 7087-68-5

  • 100ml

  • 328.0CNY

  • Detail
  • Alfa Aesar

  • (A11801)  N-Ethyldiisopropylamine, 99%   

  • 7087-68-5

  • 500ml

  • 1055.0CNY

  • Detail
  • Alfa Aesar

  • (A11801)  N-Ethyldiisopropylamine, 99%   

  • 7087-68-5

  • 1000ml

  • 1794.0CNY

  • Detail
  • Alfa Aesar

  • (A11801)  N-Ethyldiisopropylamine, 99%   

  • 7087-68-5

  • 2500ml

  • 3980.0CNY

  • Detail
  • Sigma-Aldrich

  • (03439)  N-Ethyldiisopropylaminesolution  for peptide synthesis, ~2 M in 1-methyl-2-pyrrolidinone

  • 7087-68-5

  • 03439-250ML

  • 967.59CNY

  • Detail

7087-68-5SDS

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 Ethyldiisopropylamine

1.2 Other means of identification

Product number -
Other names N-ethyl-N-propan-2-ylpropan-2-amine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:7087-68-5 SDS

7087-68-5Synthetic route

tetraethylammonium chloride
56-34-8

tetraethylammonium chloride

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With potassium hydroxide In butan-1-ol at 115℃; for 7h; Solvent; Reagent/catalyst; Temperature;97.2%
chloroethane
75-00-3

chloroethane

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With lithium chloride; zinc(II) chloride at 190℃; under 16501.7 Torr; for 10h; Catalytic behavior; Temperature; Pressure; Time; Reagent/catalyst; Autoclave;96.7%
ethanol
64-17-5

ethanol

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With iron(III) oxide; (triphenylphosphine)ruthenium acetate at 78℃; for 24h; Reagent/catalyst; Molecular sieve;92%
With ammonium acetate In aq. phosphate buffer at 34℃; for 10h; pH=8.5; Electrochemical reaction;28%
With Ru(OAc)2(1,1′-bis(diisopropylphosphino)ferrocene)(CO); trifluoroacetic acid at 78℃; for 24h; Inert atmosphere; Schlenk technique;
acetaldehyde
75-07-0

acetaldehyde

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With hydrogen; ZrO2-containing catalyst at 120 - 150℃; under 60006 Torr;80%
Stage #1: acetaldehyde; diisopropylamine With formic acid at 90 - 110℃; for 8.5h;
Stage #2: With hydrogenchloride In water
Stage #3: With sodium hydroxide In water
With hydrogen; 5% Pd(II)/C(eggshell) at 100℃; under 18751.9 Torr; for 9h; Product distribution / selectivity; Autoclave; Inert atmosphere;95.2 %Chromat.
With 5% Pd/C; hydrogen at 120℃; under 18751.9 Torr; for 3h; Autoclave;
ethyl iodide
75-03-6

ethyl iodide

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With butanone
diethyl sulfate
64-67-5

diethyl sulfate

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
at 140℃;
at 140℃;
diisopropylamine
108-18-9

diisopropylamine

methyl iodide
74-88-4

methyl iodide

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

4-Methoxyphenylacetic acid
104-01-8

4-Methoxyphenylacetic acid

1-ethyl-3-(3-dimethylaminopropyl)carbotiimide

1-ethyl-3-(3-dimethylaminopropyl)carbotiimide

N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-amino-β-alanine

N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-amino-β-alanine

N-Trimethylsilylacetamide
13435-12-6

N-Trimethylsilylacetamide

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
In dichloromethane; N,N-dimethyl-formamide
ethyl bromoacetate
105-36-2

ethyl bromoacetate

A

pyrrolidinylacetate ester

pyrrolidinylacetate ester

B

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
In dichloromethane; acetonitrile
vinylsulfomethylpolystyrene resin

vinylsulfomethylpolystyrene resin

n-dioctylamine
1120-48-5

n-dioctylamine

allyl bromide
106-95-6

allyl bromide

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide
acetaldehyde
75-07-0

acetaldehyde

diisopropylamine
108-18-9

diisopropylamine

A

ethanol
64-17-5

ethanol

B

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With hydrogen; 5% Pd(II)/C(eggshell) at 100℃; under 18751.9 Torr; Product distribution / selectivity; Autoclave; Inert atmosphere; Industry scale;A 8.0 %Chromat.
B 81.8 %Chromat.
acetaldehyde
75-07-0

acetaldehyde

diisopropylamine
108-18-9

diisopropylamine

A

N-butyldiisopropylamine
41781-44-6

N-butyldiisopropylamine

B

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With hydrogen; 5% Pd(II)/C(eggshell) at 120℃; under 37503.8 Torr; Product distribution / selectivity; Autoclave; Inert atmosphere; Industry scale;A 6.3 %Chromat.
B 81.1 %Chromat.
diethyl ether
60-29-7

diethyl ether

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With alumina at 360℃; under 760.051 Torr; Temperature; Inert atmosphere; Gas phase; Green chemistry;
tetraethylammonium chloride
56-34-8

tetraethylammonium chloride

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With potassium hydroxide In butan-1-ol at 115℃; for 7h; Solvent; Reagent/catalyst; Temperature;97.2%
chloroethane
75-00-3

chloroethane

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With lithium chloride; zinc(II) chloride at 190℃; under 16501.7 Torr; for 10h; Catalytic behavior; Temperature; Pressure; Time; Reagent/catalyst; Autoclave;96.7%
ethanol
64-17-5

ethanol

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With iron(III) oxide; (triphenylphosphine)ruthenium acetate at 78℃; for 24h; Reagent/catalyst; Molecular sieve;92%
With ammonium acetate In aq. phosphate buffer at 34℃; for 10h; pH=8.5; Electrochemical reaction;28%
With Ru(OAc)2(1,1′-bis(diisopropylphosphino)ferrocene)(CO); trifluoroacetic acid at 78℃; for 24h; Inert atmosphere; Schlenk technique;
acetaldehyde
75-07-0

acetaldehyde

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With hydrogen; ZrO2-containing catalyst at 120 - 150℃; under 60006 Torr;80%
Stage #1: acetaldehyde; diisopropylamine With formic acid at 90 - 110℃; for 8.5h;
Stage #2: With hydrogenchloride In water
Stage #3: With sodium hydroxide In water
With hydrogen; 5% Pd(II)/C(eggshell) at 100℃; under 18751.9 Torr; for 9h; Product distribution / selectivity; Autoclave; Inert atmosphere;95.2 %Chromat.
With 5% Pd/C; hydrogen at 120℃; under 18751.9 Torr; for 3h; Autoclave;
ethyl iodide
75-03-6

ethyl iodide

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With butanone
diethyl sulfate
64-67-5

diethyl sulfate

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
at 140℃;
at 140℃;
diisopropylamine
108-18-9

diisopropylamine

methyl iodide
74-88-4

methyl iodide

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

4-Methoxyphenylacetic acid
104-01-8

4-Methoxyphenylacetic acid

1-ethyl-3-(3-dimethylaminopropyl)carbotiimide

1-ethyl-3-(3-dimethylaminopropyl)carbotiimide

N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-amino-β-alanine

N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-2(S)-amino-β-alanine

N-Trimethylsilylacetamide
13435-12-6

N-Trimethylsilylacetamide

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
In dichloromethane; N,N-dimethyl-formamide
ethyl bromoacetate
105-36-2

ethyl bromoacetate

A

pyrrolidinylacetate ester

pyrrolidinylacetate ester

B

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
In dichloromethane; acetonitrile
vinylsulfomethylpolystyrene resin

vinylsulfomethylpolystyrene resin

n-dioctylamine
1120-48-5

n-dioctylamine

allyl bromide
106-95-6

allyl bromide

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; N,N-dimethyl-formamide
acetaldehyde
75-07-0

acetaldehyde

diisopropylamine
108-18-9

diisopropylamine

A

ethanol
64-17-5

ethanol

B

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With hydrogen; 5% Pd(II)/C(eggshell) at 100℃; under 18751.9 Torr; Product distribution / selectivity; Autoclave; Inert atmosphere; Industry scale;A 8.0 %Chromat.
B 81.8 %Chromat.
acetaldehyde
75-07-0

acetaldehyde

diisopropylamine
108-18-9

diisopropylamine

A

N-butyldiisopropylamine
41781-44-6

N-butyldiisopropylamine

B

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With hydrogen; 5% Pd(II)/C(eggshell) at 120℃; under 37503.8 Torr; Product distribution / selectivity; Autoclave; Inert atmosphere; Industry scale;A 6.3 %Chromat.
B 81.1 %Chromat.
diethyl ether
60-29-7

diethyl ether

diisopropylamine
108-18-9

diisopropylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

Conditions
ConditionsYield
With alumina at 360℃; under 760.051 Torr; Temperature; Inert atmosphere; Gas phase; Green chemistry;
2-(5,8-Dimethoxy-quinolin-4-yl)-phenylamine
114552-24-8

2-(5,8-Dimethoxy-quinolin-4-yl)-phenylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

N-[2-(5,8-Dimethoxy-quinolin-4-yl)-phenyl]-2,2,2-trifluoro-acetamide
114552-23-7

N-[2-(5,8-Dimethoxy-quinolin-4-yl)-phenyl]-2,2,2-trifluoro-acetamide

Conditions
ConditionsYield
at 0℃; for 0.5h;100%
N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

phenylacetylene
536-74-3

phenylacetylene

4-(1-methyl-2,4-dioxo-6-(2-phenylethynyl)-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzoic acid
451473-18-0

4-(1-methyl-2,4-dioxo-6-(2-phenylethynyl)-1,4-dihydro-2H-quinazolin-3-ylmethyl)-benzoic acid

Conditions
ConditionsYield
CuI; dichlorobis(triphenylphosphine)palladium[II]100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

4-iodophenylalanine tert-butyl ester

4-iodophenylalanine tert-butyl ester

N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester
217326-89-1

N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester

Conditions
ConditionsYield
In dichloromethane100%
concentrated H2 SO4

concentrated H2 SO4

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

4-iodophenylalanine tert-butyl ester

4-iodophenylalanine tert-butyl ester

A

(S)-2'-methoxybiphenylalanine t-butyl Ester Hydrochloride

(S)-2'-methoxybiphenylalanine t-butyl Ester Hydrochloride

B

N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester
217326-89-1

N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In dichloromethane; diethylene glycol dimethyl ether; ethyl acetateA 100%
B n/a
1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid

1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid

O-allylhydroxylamine hydrochloride
38945-21-0

O-allylhydroxylamine hydrochloride

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide

1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide

Conditions
ConditionsYield
With benzotriazol-1-ol In dichloromethane100%
ditertbutyldicarbonate

ditertbutyldicarbonate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

4-iodophenylalanine tert-butyl ester

4-iodophenylalanine tert-butyl ester

N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester
217326-89-1

N-[(1,1-dimethylethoxy)carbonyl]-4-iodo-L-phenylalanine 1,1-dimethylethyl ester

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane100%
3-bromo-7-chloro-5-(2-chlorophenyl)pyrazolo[1,5-a]pyrimidine
672323-76-1

3-bromo-7-chloro-5-(2-chlorophenyl)pyrazolo[1,5-a]pyrimidine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

tert-butyl 4-(aminomethyl)piperidine-1-carboxylate
144222-22-0

tert-butyl 4-(aminomethyl)piperidine-1-carboxylate

4-{[3-BROMO-5-(2-CHLOROPHENYL)PYRAZOLO[1,5-a]PYRIMIDIN-7-YLAMINO]METHYL}PIPERIDINE-1-CARBOXYLIC ACID tert-BUTYL ESTER
672316-65-3

4-{[3-BROMO-5-(2-CHLOROPHENYL)PYRAZOLO[1,5-a]PYRIMIDIN-7-YLAMINO]METHYL}PIPERIDINE-1-CARBOXYLIC ACID tert-BUTYL ESTER

Conditions
ConditionsYield
In 1,4-dioxane100%
2-ethyl-4,5-dihydrooxazole
10431-98-8

2-ethyl-4,5-dihydrooxazole

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

M-PEOZ-OH 2000

M-PEOZ-OH 2000

Conditions
ConditionsYield
Stage #1: 2-ethyl-4,5-dihydrooxazole; methyl trifluoromethanesulfonate In chlorobenzene at 20 - 110℃; for 0.666667h;
Stage #2: N-ethyl-N,N-diisopropylamine In chlorobenzene at 0 - 50℃; for 18h;
100%
sodium hydroxide
1310-73-2

sodium hydroxide

(+/-)-1-[9-benzyl-3,9-diazabicyclo[4.2.1]non-9-yl]-propane-1-one

(+/-)-1-[9-benzyl-3,9-diazabicyclo[4.2.1]non-9-yl]-propane-1-one

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

9-benzyl-3,9-diazabicyclo[4.2.1]nonane

9-benzyl-3,9-diazabicyclo[4.2.1]nonane

Conditions
ConditionsYield
Stage #1: (+/-)-1-[9-benzyl-3,9-diazabicyclo[4.2.1]non-9-yl]-propane-1-one; N-ethyl-N,N-diisopropylamine With propionic acid In tetrahydrofuran for 1h;
Stage #2: sodium hydroxide In diethyl ether
100%
disodium (11-(3-carboxypropyl)-2,2,10,10-tetramethyl-1-(3-sulfonatopropyl)-2,3,4,8,9,10-hexahydro-1H-dipyrido[3,2-b:2',3'-i]phenoxazine-11-ium-4,8-diyl)dimethanesulfonate

disodium (11-(3-carboxypropyl)-2,2,10,10-tetramethyl-1-(3-sulfonatopropyl)-2,3,4,8,9,10-hexahydro-1H-dipyrido[3,2-b:2',3'-i]phenoxazine-11-ium-4,8-diyl)dimethanesulfonate

O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate
105832-38-0

O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

2C8H19N*C35H44N4O14S3

2C8H19N*C35H44N4O14S3

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;100%
C11H13ClN4
1228231-19-3

C11H13ClN4

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

1-(7-methyl-6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]inden-10-yl)-azetidine-3-carboxylic acid diisopropylethylamine salt
1228231-28-4

1-(7-methyl-6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]inden-10-yl)-azetidine-3-carboxylic acid diisopropylethylamine salt

Conditions
ConditionsYield
In ethanol at 75℃; for 4h;100%
(6S,7S)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxylic acid
791834-68-9

(6S,7S)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxylic acid

O-benzylhydroxylamine hydrochloride

O-benzylhydroxylamine hydrochloride

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

(6S,7S)-N-(benzyloxy)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxamide

(6S,7S)-N-(benzyloxy)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxamide

Conditions
ConditionsYield
Stage #1: (6S,7S)-6-((4-phenylpiperazin-1-yl)carbonyl)-5-azaspiro(2,5)octane-7-carboxylic acid; O-benzylhydroxylamine hydrochloride With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 3h;
100%
C66H52N6O8

C66H52N6O8

zinc diacetate
557-34-6

zinc diacetate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

C66H49N6O8Zn(1-)*H(1+)*C8H19N

C66H49N6O8Zn(1-)*H(1+)*C8H19N

Conditions
ConditionsYield
In chloroform-d1; d(4)-methanol at 20℃;100%
α-methyl-ω-aminopoly(ethylene glycol)

α-methyl-ω-aminopoly(ethylene glycol)

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

A

N-ethyldiisopropylamine hydrobromide

N-ethyldiisopropylamine hydrobromide

B

α-methyl-ω-(2-bromoacetamido)poly(ethylene glycol)

α-methyl-ω-(2-bromoacetamido)poly(ethylene glycol)

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 18h;A n/a
B 100%
N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

2,2,2,2-Tetrafluor-1,3-dihydro-4,6-bis(trifluormethyl)-1,3,5,2λ5-triazaphosphinin

2,2,2,2-Tetrafluor-1,3-dihydro-4,6-bis(trifluormethyl)-1,3,5,2λ5-triazaphosphinin

2,2,2,2-Tetrafluor-1,3-dihydro-4,6-bis(trifluormethyl)-1,3,5,2λ5-triazaphosphininethyl-diisopropylaminaddukt

2,2,2,2-Tetrafluor-1,3-dihydro-4,6-bis(trifluormethyl)-1,3,5,2λ5-triazaphosphininethyl-diisopropylaminaddukt

Conditions
ConditionsYield
In tetrahydrofuran at -20℃;99%
N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

N2-Z-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithine
250215-21-5

N2-Z-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithyl-N5-acetyl-N5-O-acetyl-L-ornithine

N2-Z-N5-acetyl-N5-hydroxyl-L-ornithyl-N5-acetyl-N5-hydroxyl-L-ornithyl-N5-acetyl-N5-hydroxyl-L-ornithine, DIPEA salt

N2-Z-N5-acetyl-N5-hydroxyl-L-ornithyl-N5-acetyl-N5-hydroxyl-L-ornithyl-N5-acetyl-N5-hydroxyl-L-ornithine, DIPEA salt

Conditions
ConditionsYield
In methanol at 20℃; for 12h; Deacetylation;99%
4-(4'-trifluoromethyl-biphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid
486436-98-0

4-(4'-trifluoromethyl-biphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid

4-(pyrimidin-4-yl-carbonylamino)-benzylamine
486437-37-0

4-(pyrimidin-4-yl-carbonylamino)-benzylamine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

N-[4-(pyrimidin-4-yl-carbonylamino)-phenylmethyl]-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid amide
486435-54-5

N-[4-(pyrimidin-4-yl-carbonylamino)-phenylmethyl]-4-(4'-trifluoromethylbiphenyl-2-carbonylamino)-1-methyl-pyrrole-2-carboxylic acid amide

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N-methyl-acetamide99%
(RS)-2-amino-2-methyl-1-[N-(2-methoxybenzyl)amino]-3-(1H-indol-3-yl)propane

(RS)-2-amino-2-methyl-1-[N-(2-methoxybenzyl)amino]-3-(1H-indol-3-yl)propane

4-nitrophenol acetate
830-03-5

4-nitrophenol acetate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

1-(2-methoxybenzyl)-2,4-dimethyl-4-(1H-indol-3-ylmethyl)-2-imidazoline
176249-60-8

1-(2-methoxybenzyl)-2,4-dimethyl-4-(1H-indol-3-ylmethyl)-2-imidazoline

Conditions
ConditionsYield
In tetrahydrofuran; ethyl acetate99%
pyridin-2-yl (1,1,1-trifluoro-2-methylpropan-2-yl) carbonate
630424-75-8

pyridin-2-yl (1,1,1-trifluoro-2-methylpropan-2-yl) carbonate

methyl tert-leucinate
3850-31-5

methyl tert-leucinate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

(S)-3,3-Dimethyl-2-(2,2,2-trifluoro-1,1-dimethyl-ethoxycarbonylamino)-butyric acid methyl ester
1028801-63-9

(S)-3,3-Dimethyl-2-(2,2,2-trifluoro-1,1-dimethyl-ethoxycarbonylamino)-butyric acid methyl ester

Conditions
ConditionsYield
With sodium hydroxide In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran99%
ammonium chloride

ammonium chloride

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

2,4-Dihydroxybenzaldehyde
95-01-2

2,4-Dihydroxybenzaldehyde

ethyl chloromethyl ether
3188-13-4

ethyl chloromethyl ether

2,4-bis(ethoxymethoxy)benzaldehyde
128837-29-6

2,4-bis(ethoxymethoxy)benzaldehyde

Conditions
ConditionsYield
In N,N-dimethyl-formamide99%
1,5-dioxaspiro[5.5]undecane-2,4-dione
1658-27-1

1,5-dioxaspiro[5.5]undecane-2,4-dione

pentafluoronitrobenzen
880-78-4

pentafluoronitrobenzen

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

C15H11F4NO6*C8H19N

C15H11F4NO6*C8H19N

Conditions
ConditionsYield
In acetonitrile at 30℃; for 0.333333h;99%
N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

N-ethyl-N-isopropylpropan-2-amine oxide

N-ethyl-N-isopropylpropan-2-amine oxide

Conditions
ConditionsYield
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide; acetonitrile In tert-butyl alcohol at 20℃; for 18h; Green chemistry; chemoselective reaction;98%
With 2,2,6,6-tetramethylpiperidin-1-oxoammonium chloride Ambient temperature;
With sodium hydroxide; dihydrogen peroxide; N-tosylimidazole In methanol for 1.5h;
With C19H16FeN4O5(1-); dihydrogen peroxide at 20℃; for 2h; pH=10; aq. buffer;40.2 %Chromat.
With dihydrogen peroxide In water at 0 - 30℃;
pyrrolidine
123-75-1

pyrrolidine

4-bromo-2-methylbenzoic acid
68837-59-2

4-bromo-2-methylbenzoic acid

O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate
125700-67-6

O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

(4-bromo-2-methylphenyl)(pyrrolidin-1-yl)methanone
276678-35-4

(4-bromo-2-methylphenyl)(pyrrolidin-1-yl)methanone

Conditions
ConditionsYield
In tetrahydrofuran; water98%
2-[4-(N-benzyl-methylamino)-3-nitro-phenyl]-2-methyl-3-amino-1-pyrrolidino-propan-1-one

2-[4-(N-benzyl-methylamino)-3-nitro-phenyl]-2-methyl-3-amino-1-pyrrolidino-propan-1-one

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

2-[4-(N-benzyl-methylamino)-3-nitro-phenyl]-2-methyl-3-tert.butyloxycarbonylamino-1-pyrrolidino-propan-1-one
345957-94-0

2-[4-(N-benzyl-methylamino)-3-nitro-phenyl]-2-methyl-3-tert.butyloxycarbonylamino-1-pyrrolidino-propan-1-one

Conditions
ConditionsYield
In 1,4-dioxane98%
5-Iodo-thiophene-2-carboxylic acid
60166-85-0

5-Iodo-thiophene-2-carboxylic acid

hydrochloric acid salt of (S)-3-amino-2-(2,4,6,-trimethyl-benzyloxycarbonylamino)-propionic acid tert-butyl ester

hydrochloric acid salt of (S)-3-amino-2-(2,4,6,-trimethyl-benzyloxycarbonylamino)-propionic acid tert-butyl ester

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

(S)-3-[(5-Iodo-thiophene-2-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

(S)-3-[(5-Iodo-thiophene-2-carbonyl)-amino]-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid tert-butyl ester

Conditions
ConditionsYield
With sodium hydrogencarbonate; citric acid In N,N-dimethyl-formamide98%
(-)-2,3,7,8-tetrahydro-2,2,3,3,7,7,8,8-octamethyl-N(1),N(9)-(2,2,2',2'-tetramethyl-1,1'-({(1S,2S)-cyclohexan-1,2-diyl}dinitrilo)bis{propyl})-11H-dipyrrin-1,9-diimine

(-)-2,3,7,8-tetrahydro-2,2,3,3,7,7,8,8-octamethyl-N(1),N(9)-(2,2,2',2'-tetramethyl-1,1'-({(1S,2S)-cyclohexan-1,2-diyl}dinitrilo)bis{propyl})-11H-dipyrrin-1,9-diimine

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

cobalt(II) chloride
7646-79-9

cobalt(II) chloride

(+)-dibromo(2,3,7,8-tetrahydro-2,2,3,3,7,7,8,8-octamethyl-N(1),N(9)-(2,2,2',2'-tetramethyl-1,1'-({(1S,2S)-cyclohexan-1,2-diyl}dinitrilo)bis{propyl})-11H-dipyrrin-1,9-diiminato(1-))cobalt(III)

(+)-dibromo(2,3,7,8-tetrahydro-2,2,3,3,7,7,8,8-octamethyl-N(1),N(9)-(2,2,2',2'-tetramethyl-1,1'-({(1S,2S)-cyclohexan-1,2-diyl}dinitrilo)bis{propyl})-11H-dipyrrin-1,9-diiminato(1-))cobalt(III)

Conditions
ConditionsYield
With iodine; potassium bromide In dichloromethane; acetonitrile addn. of CoCl2 in MeCN to soln. of org. ligand and EtN(i-Pr)2 in CH2Cl2, stirring at room temp. overnight, evapn., dissolving residue in CH2Cl2 and aq. satd. soln. of KBr with stirring, addn. of I2 in CH2Cl2; extn. of aq. phase (CH2Cl2), washing (satd. KBr soln., H2O), filtration (silica gel, CH2Cl2/MeOH 100:3), drying in vac. at room temp.;98%
Bis(p-nitrophenyl) phosphate
645-15-8

Bis(p-nitrophenyl) phosphate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

N-ethyl-N-isopropylpropan-2-aminium bis(4-nitrophenyl) phosphate

N-ethyl-N-isopropylpropan-2-aminium bis(4-nitrophenyl) phosphate

Conditions
ConditionsYield
In toluene at 20℃; for 2h;98%
tert-butyl (23-((bis(benzyloxy)phosphoryl)oxy)-11-oxo-3,6,9,15,18,21-hexaoxa-12-azatricosyl)carbamate

tert-butyl (23-((bis(benzyloxy)phosphoryl)oxy)-11-oxo-3,6,9,15,18,21-hexaoxa-12-azatricosyl)carbamate

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

2,2-dimethyl-4,16-dioxo-3,8,11,14,20,23,26-heptaoxa-5,17-diazaoctacosan-28-yl phosphate di diisopropylaethylamonium salt

2,2-dimethyl-4,16-dioxo-3,8,11,14,20,23,26-heptaoxa-5,17-diazaoctacosan-28-yl phosphate di diisopropylaethylamonium salt

Conditions
ConditionsYield
Stage #1: tert-butyl (23-((bis(benzyloxy)phosphoryl)oxy)-11-oxo-3,6,9,15,18,21-hexaoxa-12-azatricosyl)carbamate With palladium 10% on activated carbon; hydrogen In methanol for 1.5h; Inert atmosphere;
Stage #2: N-ethyl-N,N-diisopropylamine Inert atmosphere;
98%
4-((5-azidopentyl)oxy)benzonitrile

4-((5-azidopentyl)oxy)benzonitrile

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

2-(4-iodophenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile
298212-99-4

2-(4-iodophenyl)-1,8a-dihydroazulene-1,1-dicarbonitrile

1,1-dicyano-2-(4-(1-(5-(4-cyanophenoxy)pentyl)-1H-1,2,3-triazol-4-yl)phenyl)-1,8a-dihydroazulene

1,1-dicyano-2-(4-(1-(5-(4-cyanophenoxy)pentyl)-1H-1,2,3-triazol-4-yl)phenyl)-1,8a-dihydroazulene

Conditions
ConditionsYield
With copper(l) iodide In toluene at 20℃; for 48h;98%
1,5-dioxaspiro[5.5]undecane-2,4-dione
1658-27-1

1,5-dioxaspiro[5.5]undecane-2,4-dione

2,3,4-trifluoronitrobenzene
771-69-7

2,3,4-trifluoronitrobenzene

N-ethyl-N,N-diisopropylamine
7087-68-5

N-ethyl-N,N-diisopropylamine

C15H13F2NO6*C8H19N

C15H13F2NO6*C8H19N

Conditions
ConditionsYield
In acetonitrile at 45℃; for 20h;98%

7087-68-5Relevant articles and documents

Method for preventing catalyst ZnCl2 from caking in diisopropylethylamine production

-

Paragraph 0036-0072, (2020/08/09)

The invention discloses a method for preventing catalyst ZnCl2 from caking in diisopropylethylamine production, which takes diisopropylamine and chloroethane as raw materials, and comprises the following steps: adding ZnCl2 serving as a catalyst into the raw materials, and adding an anti-caking agent to form a reaction system; reacting the reaction system for 5-10 hours at the reaction temperatureof 150-190 DEG C and under the reaction pressure of 1.5-2.2 MPa; and carrying out alkali dissolution on the obtained reaction liquid, separating out a water phase, and carrying out atmospheric distillation on an organic phase to obtain the N,N-diisopropylethylamine serving as a product. According to the method disclosed by the invention, the catalyst is prevented from caking in the reaction, andthe product yield is high.

Electroactivated alkylation of amines with alcohols: Via both direct and indirect borrowing hydrogen mechanisms

Appiagyei, Benjamin,Bhatia, Souful,Keeney, Gabriela L.,Dolmetsch, Troy,Jackson, James E.

supporting information, p. 860 - 869 (2020/02/21)

A green, efficient N-alkylation of amines with simple alcohols has been achieved in aqueous solution via an electrochemical version of the so-called "borrowing hydrogen methodology". Catalyzed by Ru on activated carbon cloth (Ru/ACC), the reaction works well with methanol, and with primary and secondary alcohols. Alkylation can be accomplished by either of two different electrocatalytic processes: (1) in an undivided cell, alcohol (present in excess) is oxidized at the Ru/ACC anode; the aldehyde or ketone product condenses with the amine; and the resulting imine is reduced at an ACC cathode, combining with protons released by the oxidation. This process consumes stoichiometric quantities of current. (2) In a membrane-divided cell, the current-activated Ru/ACC cathode effects direct C-H activation of the alcohol; the resulting carbonyl species, either free or still surface-adsorbed, condenses with amine to form imine and is reduced as in (1). These alcohol activation processes can alkylate primary and secondary aliphatic amines, as well as ammonia itself at 25-70 °C and ambient pressure.

METHOD FOR PRODUCING N-ETHYL-DIISOPROPYLAMINE

-

Paragraph 0078-0079, (2017/01/26)

A process for preparing N-ethyldiisopropylamine by reacting acetaldehyde with diisopropylamine and hydrogen at elevated temperature and under pressure in the presence of a heterogeneous hydrogenation catalyst, the catalyst being a supported transition metal catalyst comprising Pd and/or Pt as catalytically active metal, wherein the diisopropylamine used has a purity of 58% to 94% by weight and impurities as follows: 3% to 20% by weight of water, 3% to 20% by weight of isopropanol, 0% to 2% by weight of others.

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