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N,N,N'-Trimethylethylenediamine, also known as N,N,N'-trimethyl-1,2-ethanediamine, is an organic compound with the chemical formula (CH3)3NCH2CH2NH2. It is a clear colorless liquid synthesized using laser-vaporization supersonic molecular beam and has been studied using pulsed-field ionization zero electron kinetic energy. N,N,N'-TRIMETHYLETHYLENEDIAMINE is characterized by its amine functional groups and is known for its versatile applications in various industries.

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  • 142-25-6 Structure
  • Basic information

    1. Product Name: N,N,N'-TRIMETHYLETHYLENEDIAMINE
    2. Synonyms: 1,2-Diaminoethane, N,N,N'-trimethyl-;2-(Dimethylamino)-N-methylethylamine;Ethylenediamine, N,N,N'-trimethyl-;n,n,n’-trimethyl-2-ethanediamine;N,N,N'-Trimethyl-1,2-ethanediamine;N,N,N'-Trimethyldiaminoethane;N,N,N'-Trimethylethanediamine;Trimethylethylenediamine
    3. CAS NO:142-25-6
    4. Molecular Formula: C5H14N2
    5. Molecular Weight: 102.18
    6. EINECS: 205-529-2
    7. Product Categories: Polyamines;Nitrogen Compounds;Organic Building Blocks
    8. Mol File: 142-25-6.mol
  • Chemical Properties

    1. Melting Point: -30.89°C (estimate)
    2. Boiling Point: 116-118 °C(lit.)
    3. Flash Point: 49 °F
    4. Appearance: Clear colorless/Liquid
    5. Density: 0.786 g/mL at 25 °C(lit.)
    6. Refractive Index: n20/D 1.419(lit.)
    7. Storage Temp.: Flammables area
    8. Solubility: N/A
    9. PKA: 10.34±0.10(Predicted)
    10. BRN: 505989
    11. CAS DataBase Reference: N,N,N'-TRIMETHYLETHYLENEDIAMINE(CAS DataBase Reference)
    12. NIST Chemistry Reference: N,N,N'-TRIMETHYLETHYLENEDIAMINE(142-25-6)
    13. EPA Substance Registry System: N,N,N'-TRIMETHYLETHYLENEDIAMINE(142-25-6)
  • Safety Data

    1. Hazard Codes: F,C
    2. Statements: 11-34-37
    3. Safety Statements: 16-26-36/37/39-45
    4. RIDADR: UN 2733 3/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. F: 34
    8. TSCA: Yes
    9. HazardClass: 3
    10. PackingGroup: II
    11. Hazardous Substances Data: 142-25-6(Hazardous Substances Data)

142-25-6 Usage

Uses

Used in Surfactant Synthesis:
N,N,N'-Trimethylethylenediamine is used as a precursor in the synthesis of a novel gemini surfactant, specifically N,N-dimethyl-N-2-[N'-methyl-N'-(3-sulfopropyl)-alkylammonium]ethyl-1-alkylammonium bromides. These gemini surfactants are known for their enhanced properties compared to traditional surfactants, such as better solubility, lower critical micelle concentration, and improved surface activity.
Used in Pharmaceutical Industry:
N,N,N'-Trimethylethylenediamine is used as an amine component for in-situ formation of alpha-amino alkoxides, which are important intermediates in the synthesis of various pharmaceutical compounds. The compound's reactivity and amine functionality make it a valuable building block for the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
The compound is involved in the synthesis of N,N'-dimethyl-N'-(2-hydroxy-aethyl)-aethylendiamin, which is an important organic compound with various applications in the chemical industry. N,N,N'-Trimethylethylenediamine's versatility as a synthetic building block allows it to be used in the production of a wide range of chemicals, including those used in the manufacturing of dyes, pigments, and other specialty chemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 142-25-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 2 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 142-25:
(5*1)+(4*4)+(3*2)+(2*2)+(1*5)=36
36 % 10 = 6
So 142-25-6 is a valid CAS Registry Number.

142-25-6 Well-known Company Product Price

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  • Alfa Aesar

  • (31785)  N,N,N'-Trimethylethylenediamine, 98%   

  • 142-25-6

  • 1g

  • 107.0CNY

  • Detail
  • Alfa Aesar

  • (31785)  N,N,N'-Trimethylethylenediamine, 98%   

  • 142-25-6

  • 5g

  • 414.0CNY

  • Detail
  • Alfa Aesar

  • (31785)  N,N,N'-Trimethylethylenediamine, 98%   

  • 142-25-6

  • 25g

  • 1736.0CNY

  • Detail
  • Aldrich

  • (127124)  N,N,N′-Trimethylethylenediamine  97%

  • 142-25-6

  • 127124-5G

  • 505.44CNY

  • Detail
  • Aldrich

  • (127124)  N,N,N′-Trimethylethylenediamine  97%

  • 142-25-6

  • 127124-25G

  • 2,166.84CNY

  • Detail

142-25-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N,N,N‘-Trimethylethylenediamine

1.2 Other means of identification

Product number -
Other names N1,N1,N2-Trimethylethane-1,2-diamine

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:142-25-6 SDS

142-25-6Synthetic route

(2-chloroethyl)dimethylamine hydrochloride
4584-46-7

(2-chloroethyl)dimethylamine hydrochloride

methylamine
74-89-5

methylamine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
In water for 1h; Ambient temperature;97%
With sodium hydroxide at 25℃;80%
In water for 6h; Heating;60%
4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine
383865-57-4

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine

A

1-(2-Dimethylamino-ethyl)-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-urea

1-(2-Dimethylamino-ethyl)-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-urea

B

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
A 61%
B n/a
3-(N,N-dimethylamino)propylamide
20101-88-6

3-(N,N-dimethylamino)propylamide

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
N,N,N'-trimethyl-N'-phenyl-ethylenediamine
79049-82-4

N,N,N'-trimethyl-N'-phenyl-ethylenediamine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
nitrosieren,mit alkalisch machen und Kochen mit NaHSO3-Loesung;
N-methyl-2-chloroethylamine
32315-92-7

N-methyl-2-chloroethylamine

dimethyl amine
124-40-3

dimethyl amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

2-(dimethylamino)ethyl chloride
107-99-3

2-(dimethylamino)ethyl chloride

methylamine
74-89-5

methylamine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
With water
at 115 - 120℃;
2-(dimethylamino)ethyl chloride
107-99-3

2-(dimethylamino)ethyl chloride

methylamine
74-89-5

methylamine

A

N,N,N',N'',N'''-pentamethyldiethylenetriamine
3030-47-5

N,N,N',N'',N'''-pentamethyldiethylenetriamine

B

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
With water
2-[(2-Dimethylamino-ethyl)-methyl-amino]-2-hydroxy-1-phenyl-ethanone

2-[(2-Dimethylamino-ethyl)-methyl-amino]-2-hydroxy-1-phenyl-ethanone

A

2,2-dihydroxy-1-phenyl-ethanone
1075-06-5

2,2-dihydroxy-1-phenyl-ethanone

B

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
In water at 35℃; Equilibrium constant;
Dimethyl-β-formylaminoethylamine
7249-51-6

Dimethyl-β-formylaminoethylamine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride
(CdI2(N,N,N`-trimethylethylenediamine)
114320-99-9

(CdI2(N,N,N`-trimethylethylenediamine)

A

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

B

cadmium(II) iodide

cadmium(II) iodide

Conditions
ConditionsYield
In neat (no solvent) thermal decompn. by loss of ligand followed by vaporization of metal halide, temp. range 135-300 ° C;
(HgI2(N,N,N`-trimethylethylenediamine)
114321-02-7

(HgI2(N,N,N`-trimethylethylenediamine)

A

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

B

mercury(II) iodide

mercury(II) iodide

Conditions
ConditionsYield
In neat (no solvent) thermal decompn. by loss of ligand followed by vaporization of metal halide, temp. range 95-180 ° C;
(CdCl2(N,N,N`-trimethylenediamine)2

(CdCl2(N,N,N`-trimethylenediamine)2

A

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

B

cadmium(II) chloride
10108-64-2

cadmium(II) chloride

Conditions
ConditionsYield
In neat (no solvent) thermal decompn. by loss of ligand followed by vaporization of metal halide, temp. range 150-350 ° C;
(CdBr2(N,N,N`-trimethylethylenediamine)2

(CdBr2(N,N,N`-trimethylethylenediamine)2

A

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

B

cadmium(II) bromide

cadmium(II) bromide

Conditions
ConditionsYield
In neat (no solvent) thermal decompn. by loss of ligand followed by vaporization of metal halide, temp. range 140-290 ° C;
(HgCl2(N,N,N`-trimethylethylenediamine)3

(HgCl2(N,N,N`-trimethylethylenediamine)3

A

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

B

mercury dichloride

mercury dichloride

Conditions
ConditionsYield
In neat (no solvent) thermal decompn. by loss of ligand followed by vaporization of metal halide, temp. range 120-170 ° C;
(HgBr2(N,N,N`-trimethylethylenediamine)3

(HgBr2(N,N,N`-trimethylethylenediamine)3

A

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

B

mercury dibromide

mercury dibromide

Conditions
ConditionsYield
In neat (no solvent) thermal decompn. by loss of ligand followed by vaporization of metal halide, temp. range 115-175 ° C;
methanol
67-56-1

methanol

Reaxys ID: 11370757

Reaxys ID: 11370757

ethylenediamine
107-15-3

ethylenediamine

A

N,N,N,N,-tetramethylethylenediamine
110-18-9

N,N,N,N,-tetramethylethylenediamine

B

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

C

N,N-dimethylethylenediamine
108-00-9

N,N-dimethylethylenediamine

D

N-methyl-ethane-1,2-diamine
109-81-9

N-methyl-ethane-1,2-diamine

E

N,N`-dimethylethylenediamine
110-70-3

N,N`-dimethylethylenediamine

Conditions
ConditionsYield
Stage #1: With hydrogen at 200℃; for 3h;
Stage #2: methanol; ethylenediamine With hydrogen at 200℃; under 7500.75 Torr; for 8h; Product distribution / selectivity;
ethylenediamine
107-15-3

ethylenediamine

dimethyl sulfate
77-78-1

dimethyl sulfate

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

Conditions
ConditionsYield
In ethanol Cooling with ice;
N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

N,N,N'-trimethyl-N'-(2-nitrophenyl)-1,2-ethanediamine
371244-16-5

N,N,N'-trimethyl-N'-(2-nitrophenyl)-1,2-ethanediamine

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol at 80℃; for 16h;100%
2-bromo-6-nitro-benzo[d]thiazole
2516-37-2

2-bromo-6-nitro-benzo[d]thiazole

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N,N,N'-trimethyl-N'-(6-nitro-benzothiazol-2-yl)-ethane-1,2-diamine
892840-64-1

N,N,N'-trimethyl-N'-(6-nitro-benzothiazol-2-yl)-ethane-1,2-diamine

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 6h;100%
N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

β-11-O-desacetyl-11-O-propionyl-17-dihydrowortmannin
174304-96-2

β-11-O-desacetyl-11-O-propionyl-17-dihydrowortmannin

propionic acid 4-{[(2-dimethylamino-ethyl)-methyl-amino]-methylene}-6,17-dihydroxy-1-methoxymethyl-10,13-dimethyl-3,7-dioxo-1,3,4,7,10,11,12,13,14,15,16,17-dodecahydro-2-oxa-cyclopenta[a]phenanthren-11-yl ester

propionic acid 4-{[(2-dimethylamino-ethyl)-methyl-amino]-methylene}-6,17-dihydroxy-1-methoxymethyl-10,13-dimethyl-3,7-dioxo-1,3,4,7,10,11,12,13,14,15,16,17-dodecahydro-2-oxa-cyclopenta[a]phenanthren-11-yl ester

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
3-acetylbenzene-1-sulfonyl chloride
73035-16-2

3-acetylbenzene-1-sulfonyl chloride

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

3-acetyl-N-[2-(dimethylamino)ethyl]-N-methylbenzenesulfonamide
1186422-04-7

3-acetyl-N-[2-(dimethylamino)ethyl]-N-methylbenzenesulfonamide

Conditions
ConditionsYield
In tetrahydrofuran for 18h;100%
Pentafluoropyridine
700-16-3

Pentafluoropyridine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

C10H13F4N3
1193367-04-2

C10H13F4N3

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; regioselective reaction;100%
Decyl-oxiran
2855-19-8

Decyl-oxiran

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

2,5-dimethyl-7-hydroxy-2,5-diazaheptadecane
1233939-61-1

2,5-dimethyl-7-hydroxy-2,5-diazaheptadecane

Conditions
ConditionsYield
In ethanol at 20℃; for 120h;100%
N- (4-fluoro-2-methoxy-5-nitrophenyl)-4-(1H-indol-3-yl)pyrimidin-2-amine
1421372-34-0

N- (4-fluoro-2-methoxy-5-nitrophenyl)-4-(1H-indol-3-yl)pyrimidin-2-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(4-(1H-indol-3-yl)pyrimidin-2-yl)-N4-(2-(dimethylamino)ethyl)-2-methoxy-N4-methyl-5-nitrobenzene-1,4-diamine
1421373-32-1

N1-(4-(1H-indol-3-yl)pyrimidin-2-yl)-N4-(2-(dimethylamino)ethyl)-2-methoxy-N4-methyl-5-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 120℃; for 0.5h; Microwave irradiation; Inert atmosphere;100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 140℃; for 0.5h; Microwave irradiation;80%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 140℃; for 0.5h; Inert atmosphere; Microwave irradiation;80%
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 140℃; for 1h;73.1%
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 140℃; for 2.5h;0.36 g
N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1,N1,N2-trimethyl-N2-[2-(phenylsulfonyl)ethyl]-1,2-ethanediamine
1496553-60-6

N1,N1,N2-trimethyl-N2-[2-(phenylsulfonyl)ethyl]-1,2-ethanediamine

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
methyl 2-amino-4-bromo-6-fluoro-3-nitro-benzoate
1160683-38-4

methyl 2-amino-4-bromo-6-fluoro-3-nitro-benzoate

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

methyl 2-amino-4-bromo-6-[(2-dimethylaminoethyl)methylamino]-3-nitrobenzoate

methyl 2-amino-4-bromo-6-[(2-dimethylaminoethyl)methylamino]-3-nitrobenzoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at -45℃; for 2h; Inert atmosphere;100%
4-fluoro-2-methoxy-5-nitro-phenylamine
1075705-01-9

4-fluoro-2-methoxy-5-nitro-phenylamine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-dimethylaminoethyl)-5-methoxy-N1-methyl-2-nitro-1,4-phenylenediamine

N1-(2-dimethylaminoethyl)-5-methoxy-N1-methyl-2-nitro-1,4-phenylenediamine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 48h; Inert atmosphere;100%
With potassium carbonate In acetonitrile at 85℃; for 12h;79.2%
With potassium carbonate In acetonitrile at 80℃; Inert atmosphere;62.5%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(naphthalen-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(naphthalen-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(6-(naphthalen-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(6-(naphthalen-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
6-(3-(dimethylamino)phenyl)-N-(4-fluoro-2-methoxy-5-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

6-(3-(dimethylamino)phenyl)-N-(4-fluoro-2-methoxy-5-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(3-(dimethylamino)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(3-(dimethylamino)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
6-(4-(dimethylamino)phenyl)-N-(4-fluoro-2-methoxy-5-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

6-(4-(dimethylamino)phenyl)-N-(4-fluoro-2-methoxy-5-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(4-(dimethylamino)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(4-(dimethylamino)phenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(3-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(3-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(3-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(3-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
N3-(4-fluoro-2-methoxy-5-nitrophenyl)-N6-(3-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1Hindazole-3,6-diamine

N3-(4-fluoro-2-methoxy-5-nitrophenyl)-N6-(3-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1Hindazole-3,6-diamine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N3-(4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)-N6-(3-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3,6-diamine

N3-(4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)-N6-(3-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-3,6-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-5-(naphthalen-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-5-(naphthalen-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(5-(naphthalen-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(5-(naphthalen-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-5-(naphthalen-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-5-(naphthalen-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(5-(naphthalen-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(5-(naphthalen-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-N4-(5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-N4-(5-(4-fluorophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;100%
(2-((5-fluoro-2-((4-fluoro-2-methoxy-5-nitrophenyl)amino)pyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide

(2-((5-fluoro-2-((4-fluoro-2-methoxy-5-nitrophenyl)amino)pyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

(2-((2-((4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide

(2-((2-((4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxy-5-nitrophenyl)amino)-5-fluoropyrimidin-4-yl)amino)phenyl)dimethylphosphine oxide

Conditions
ConditionsYield
In 1,4-dioxane at 100℃; for 2h;100%
N-(6-chloro-2-isopropyloxy-5-nitropyridin-3-yl)acetamide

N-(6-chloro-2-isopropyloxy-5-nitropyridin-3-yl)acetamide

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N-{6-{[2-(dimethylamino)ethyl](methyl)amino}-2-isopropyloxy-5-nitropyridin-3-yl}acetamide

N-{6-{[2-(dimethylamino)ethyl](methyl)amino}-2-isopropyloxy-5-nitropyridin-3-yl}acetamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃;100%
3-fluoro-4-nitrobenzoic acid
403-21-4

3-fluoro-4-nitrobenzoic acid

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

3-((2-(dimethylamino)ethyl)(methyl)amino)-4-nitrobenzoic acid

3-((2-(dimethylamino)ethyl)(methyl)amino)-4-nitrobenzoic acid

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃;100%
With caesium carbonate In acetonitrile at 20℃; for 10h;
2-chloro-4-fluorobenzaldehyde
84194-36-5

2-chloro-4-fluorobenzaldehyde

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

2-chloro-4-{[2-(dimethylamino)ethyl](methyl)amino}benzaldehyde

2-chloro-4-{[2-(dimethylamino)ethyl](methyl)amino}benzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 5.25h;100%
2-Amino-6-bromopyridine
19798-81-3

2-Amino-6-bromopyridine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N2-(2-(dimethylamino)ethyl)-N2-methylpyridine-2,6-diamine

N2-(2-(dimethylamino)ethyl)-N2-methylpyridine-2,6-diamine

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 200℃; for 0.333333h; Microwave irradiation;100%
N-(4-fluoro-2-methoxy-5-nitro-phenyl)acetamide

N-(4-fluoro-2-methoxy-5-nitro-phenyl)acetamide

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

C14H22N4O4

C14H22N4O4

Conditions
ConditionsYield
With sodium carbonate In ethanol at 80℃; for 1.5h; Inert atmosphere;99.87%
(4-fluoro-2-methoxy-5-nitrophenyl)carbamic acid tert-butyl ester

(4-fluoro-2-methoxy-5-nitrophenyl)carbamic acid tert-butyl ester

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N-(t-butoxycarbonyl)-4-((N,1-(2-(N,N-dimethylamino)ethyl)-N,1-methyl)amino)-2-methoxy-5-nitroanilide

N-(t-butoxycarbonyl)-4-((N,1-(2-(N,N-dimethylamino)ethyl)-N,1-methyl)amino)-2-methoxy-5-nitroanilide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 60℃; for 2h;99%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 45℃; for 2h; Inert atmosphere;98%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 60℃; for 2h;92%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-2-nitro-N4-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)benzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-2-nitro-N4-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)benzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;99%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(naphthalen-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(naphthalen-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(6-(naphthalen-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(6-(naphthalen-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;99%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(isoquinolin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(isoquinolin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(isoquinolin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-N4-(6-(isoquinolin-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-5-methoxy-N1-methyl-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;99%
N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(1-methyl-1H-indol-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N-(4-fluoro-2-methoxy-5-nitrophenyl)-6-(1-methyl-1H-indol-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-amine

N,N',N'-trimethylenediamine
142-25-6

N,N',N'-trimethylenediamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(6-(1-methyl-1H-indol-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

N1-(2-(dimethylamino)ethyl)-5-methoxy-N1-methyl-N4-(6-(1-methyl-1H-indol-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-2-nitrobenzene-1,4-diamine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 90℃; for 0.666667h; Microwave irradiation;99%

142-25-6Relevant articles and documents

Multi-ammonia dithio-formic acid sulfite derivative and preparation method and application thereof

-

Paragraph 0111-0118, (2017/07/07)

The invention provides a multi-ammonia dithio-formic acid sulfite derivative which has a structure as shown in a formula (I). The invention further provides a method for preparing the derivative and application of the derivative as a reducing agent - chain transfer agent to the aspect of free radical polymerization reaction. A preparation method is simple, reaction conditions are mild, and the multi-ammonia dithio-formic acid sulfite derivative has very good application effects and application values in the free radical polymerization reaction triggered in an oxidation-reduction system.

A complete series of 6-deoxy-monosubstituted tetraalkylammonium derivatives of α-, β-, and γ-cyclodextrin with 1, 2, and 3 permanent positive charges

Popr, Martin,Hybelbauerova, Simona,Jindrich, Jindrich

supporting information, p. 1390 - 1396 (2014/07/22)

An efficient synthetic route toward the preparation of a complete series of monosubstituted tetraalkylammonium cyclodextrin (CD) derivatives is presented. Monotosylation of native CDs (α-, β-, γ-) at position 6 gave the starting material. Reaction of monotosylate (mono-Ts-CD) with 45% aqueous trimethylamine gave CDs substituted with one cationic functional group in a single step. Derivatives equipped with a substituent containing two cationic sites separated by an ethylene or a propylene linker were prepared by reacting mono-Ts-CD with neat N,N,N'-trimethylethane-1,2-diamine or N,N,N'- trimethylpropane-1,3-diamine and subsequent methylation by CH3I in good yields. Finally, analogues bearing a moiety with three tetraalkylammonium sites were synthesized by reacting mono-Ts-CD with bis(3-aminopropyl)amine and subsequent methylation. The majority of the presented reactions are very straightforward with a simple work-up, which avoids the need of chromatographic separation. Thus, these reactions are suitable for the multigram-scale production of monosubstituted cationic CDs. 2014 Popr et al;.

METHOD FOR PRODUCING N-MONOALKYL-SUBSTITUTED ALKYLENE AMINE

-

Page/Page column 8, (2010/02/11)

PROBLEM TO BE SOLVED: To provide a method for producing an N-monoalkyl-substituted alkylene amine especially useful for uses such as medicine intermediates, agrochemical intermediates, urethane resin-foaming catalysts, surfactants and the like among alkyl-substituted alkylene amine compounds from an alcohol and an alkylene amine as raw materials. SOLUTION: This method for producing the N-monoalkyl-substituted alkylene amine is characterized by reacting the alkylene amine with a ≥2C alkyl alcohol in the presence of a copper-containing oxide catalyst system. The N-monoalkyl-substituted alkylenamine is produced in high conversion and in N-monoalkylation selectivity.

SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS

-

, (2008/06/13)

The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed

Tetracyclic benzimidazole derivatives and combinatorial libraries thereof

-

, (2008/06/13)

The present invention relates to novel tetracyclic benzimidazole derivative compounds of the following formula: wherein R1to R10have the meanings described in here. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing tetracyclic benzimidazole derivative compounds.

Benzothiazole derivatives with activity as adenosine receptor ligands

-

, (2008/06/13)

The present invention relates to substituted benzothiazole derivitives and to their pharmaceutically acceptable salts useful for the treatment of diseases related to the adenosine receptor.

2-aminopyridine derivatives and combinatorial libraries thereof

-

, (2008/06/13)

The present invention relates to novel 2-aminopyridine derivative compounds of the following formula: wherein R1to R5have the meanings provided herein. The invention further relates to combinatorial libraries containing two or more such compounds, as well as methods of preparing 2-aminopyridine derivative compounds.

Antineoplastic heteronapthoquinones

-

, (2008/06/13)

This invention relates to a naphthoquinone derivatives, to processes and to intermediates for preparing these derivatives, to pharmaceutical composition and to the use of these derivatives as antitumor agents in mammals.

Synthesis, characterization, and biological evaluation of a novel class of N-(arylethyl)-N-alkyl-2-(1-pyrrolidinyl)ethylamines: Structural requirements and binding affinity at the σ receptor

De Costa,Radesca,Di Paolo,Bowen

, p. 38 - 47 (2007/10/02)

By synthesizing and testing a part-structure, N-[2-(3,4- dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamine (3), derived from our previously reported high affinity σ receptor ligands (1S,2R)-(-)-N-[2- (3,4-dichlorophenyl)-ethyl]-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine [(-)- 2] and (+)-2, we have identified a novel class of superpotent (subnanomolar affinity) σ ligands specific for the σ receptor labeled by [3H]-(+)-3-PPP. When 3 was tested for its capacity to displace [3H]-(+)-3-PPP from guinea pig brain membranes, it exhibited a K(i) of 0.34 nM, which is better than either of its parent compounds (-)-2 (K(i) = 1.3 nM) and (+)-2 (K(i) = 6.0 nM). Other compounds related to 3 such as N-[2-(3,4-dichlorophenyl)ethyl]-N- methyl-2-(1-homopiperidinyl)ethylamine (19) exhibited K(i) = 0.17 nM ([3H]- (+)-3-PPP). The determinants for high σ receptor affinity of 3 were examined by manipulation of this structure in a number of different ways. The high efficacy of these compounds for the σ receptor, their relative chemical simplicity and ease of synthesis, and their high degree of selectivity identifies N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1- pyrrolidinyl)ethylamine (3) and related compounds as a highly promising base for determination of the functional role of σ receptors as well as the development of novel therapeutic agents.

1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-α,α-diarylpyrrolidine, piperidine and homopiperidineacetamides and acetonitriles

-

, (2008/06/13)

Novel 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-α,α-diaryl-pyrrolidine, piperidine and homopiperidineacetamides and acetonitriles having the formula: STR1 wherein; n is zero, one or two; X is oxygen or sulfur; Z is STR2 p is 0 to 5 inclusive with the proviso that when Z is STR3 p is at least one; Y is aminocarbonyl or cyano; Ar1 and Ar2 are 2, 3 or 4-pyrido, phenyl or substituted phenyl; R is hydrogen or loweralkyl; R1, R2 and R3 are hydrogen, cycloalkyl, loweralkyl, phenyl, substituted phenyl, phenylloweralkyl, and R2 and R3 taken with the adjacent nitrogen may form a heterocyclic residue, and diastereoisomers when possible and pharmaceutical salts; and the method and pharmaceutical compositions for treating cardiac arrhythmias therewith are disclosed.

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