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140-28-3 Usage

Chemical Properties

light yellow liquid

Uses

N,N'-Dibenzylethylenediamine is an intermediate of cephalosporin and penicillin.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 3209, 1990 DOI: 10.1021/jo00297a042

Safety Profile

Poison by ingestion,intraperitoneal, and parenteral routes. When heated todecomposition it emits toxic vapors of NOx.

Purification Methods

Dissolve DBED in acid, extract with toluene, basify, extract it with Et2O, dry over solid KOH, evaporate and fractionate it in vacuo. The diacetate crystallises from H2O by addition of EtOH and has m 111o (solubility in H2O is ~25%). The dihydrochloride has m 306-308o (from H2O) and the dipicrate has m 212o(dec) (from H2O). [Frost et al., J Am Chem Soc 71 3842 1949, Beilstein 12 H 1067, 12 III 2304.]

Check Digit Verification of cas no

The CAS Registry Mumber 140-28-3 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 0 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 140-28:
(5*1)+(4*4)+(3*0)+(2*2)+(1*8)=33
33 % 10 = 3
So 140-28-3 is a valid CAS Registry Number.

140-28-3 Well-known Company Product Price

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  • Alfa Aesar

  • (L03540)  N,N'-Dibenzylethylenediamine, 97%   

  • 140-28-3

  • 25g

  • 265.0CNY

  • Detail
  • Alfa Aesar

  • (L03540)  N,N'-Dibenzylethylenediamine, 97%   

  • 140-28-3

  • 100g

  • 736.0CNY

  • Detail
  • Aldrich

  • (D35201)  N,N′-Dibenzylethylenediamine  97%

  • 140-28-3

  • D35201-25G

  • 315.90CNY

  • Detail
  • Aldrich

  • (D35201)  N,N′-Dibenzylethylenediamine  97%

  • 140-28-3

  • D35201-100G

  • 876.33CNY

  • Detail

140-28-3SDS

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 benzathine

1.2 Other means of identification

Product number -
Other names N,N'-DibenzylethylenediaMine

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:140-28-3 SDS

140-28-3Synthetic route

N,N'-bis(benzyliden)ethylendiamine
104-71-2

N,N'-bis(benzyliden)ethylendiamine

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol100%
With sodium tetrahydroborate In ethanol95%
With sodium tetrahydroborate In methanol; dichloromethane88%
N,N'-dibenzoyl-N,N'-dibenzylethylenediamine
82126-37-2

N,N'-dibenzoyl-N,N'-dibenzylethylenediamine

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 0.666667h; Heating;94%
1,2-dibenzyl-1,2-diazetin-3-one
93847-34-8

1,2-dibenzyl-1,2-diazetin-3-one

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With B2H6-THF for 2h; Heating;85%
With diborane In tetrahydrofuran
benzaldehyde
100-52-7

benzaldehyde

ethylenediamine
107-15-3

ethylenediamine

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Stage #1: benzaldehyde; ethylenediamine With sodium sulfate; triethylamine In ethyl acetate at 20℃; for 14h;
Stage #2: With sodium tetrahydroborate In methanol; ethyl acetate for 6h;
70%
Stage #1: benzaldehyde; ethylenediamine
Stage #2: With sodium tetrahydroborate
69%
With sodium tetrahydroborate In methanol at 20℃; Reflux;67.6%
N,N'-ethanediyl-bis-benzamide
644-33-7

N,N'-ethanediyl-bis-benzamide

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating;51%
formic acid
64-18-6

formic acid

N,N'-bis(benzyliden)ethylendiamine
104-71-2

N,N'-bis(benzyliden)ethylendiamine

sodium formate
141-53-7

sodium formate

A

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

B

N-benzylethylenediamine
4152-09-4

N-benzylethylenediamine

N,N'-bis(benzyliden)ethylendiamine
104-71-2

N,N'-bis(benzyliden)ethylendiamine

A

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

B

N-benzylethylenediamine
4152-09-4

N-benzylethylenediamine

Conditions
ConditionsYield
With formic acid
1,2-bis-(benzenesulfonyl-benzyl-amino)-ethane
496039-67-9

1,2-bis-(benzenesulfonyl-benzyl-amino)-ethane

A

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

B

N-benzylethylenediamine
4152-09-4

N-benzylethylenediamine

Conditions
ConditionsYield
With hydrogenchloride at 170 - 180℃; im geschlossenen Rohr;
formic acid
64-18-6

formic acid

N-(2-formylaminoethyl)formamide
4938-92-5

N-(2-formylaminoethyl)formamide

benzaldehyde
100-52-7

benzaldehyde

A

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

B

N-benzylethylenediamine
4152-09-4

N-benzylethylenediamine

Conditions
ConditionsYield
auch unter Zusatz von Natriumformiat und Kaliumformiat;
N-(2-formylaminoethyl)formamide
4938-92-5

N-(2-formylaminoethyl)formamide

benzaldehyde
100-52-7

benzaldehyde

A

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

B

N-benzylethylenediamine
4152-09-4

N-benzylethylenediamine

Conditions
ConditionsYield
With formic acid
benzaldehyde
100-52-7

benzaldehyde

ethylenediamine
107-15-3

ethylenediamine

A

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

B

N-benzylethylenediamine
4152-09-4

N-benzylethylenediamine

Conditions
ConditionsYield
With ethanol; sodium
With methanol; nickel at 80 - 100℃; under 58840.6 Torr; Hydrogenation;
N,N'-bis(benzyliden)ethylendiamine
104-71-2

N,N'-bis(benzyliden)ethylendiamine

benzyl chloride
100-44-7

benzyl chloride

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With hexan-1-ol auch mit anderen Schiffschen Basen des Aethylendiamins;
benzyl chloride
100-44-7

benzyl chloride

ethylenediamine
107-15-3

ethylenediamine

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

ethylene dibromide
106-93-4

ethylene dibromide

benzylamine
100-46-9

benzylamine

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

N,N'-dibenzyl-N,N'-1,2-ethanediylbisformamide
10507-25-2

N,N'-dibenzyl-N,N'-1,2-ethanediylbisformamide

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With hydrogenchloride In ethanol Heating;
N,N'-dibenzylethanediamide
3551-78-8

N,N'-dibenzylethanediamide

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 16h; Heating;
N,N'-bis(benzyliden)ethylendiamine
104-71-2

N,N'-bis(benzyliden)ethylendiamine

benzaldehyde
100-52-7

benzaldehyde

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 0℃; for 3h; Yield given;
benzaldehyde
100-52-7

benzaldehyde

ethylenediamine
107-15-3

ethylenediamine

A

1,3-dibenzyl-2-phenylimidazolidine
4597-81-3

1,3-dibenzyl-2-phenylimidazolidine

B

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 0℃; under 760 Torr; for 20h;
1,2-ethanediamine,N,N'-bis(phenylmethylene)

1,2-ethanediamine,N,N'-bis(phenylmethylene)

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 1h;
ethyl 2-(benzylamino)acetate
6436-90-4

ethyl 2-(benzylamino)acetate

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / pyridine / benzene / 0.5 h / 60 - 70 °C
2: 95 percent / aq. NaOH / methanol / 1 h / 0 °C
3: 86 percent / methanol / 35 - 40 °C / Electrolysis
4: 94 percent / HCl / ethanol / 0.67 h / Heating
View Scheme
[benzoyl(benzyl)amino]acetic acid
201405-92-7

[benzoyl(benzyl)amino]acetic acid

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 86 percent / methanol / 35 - 40 °C / Electrolysis
2: 94 percent / HCl / ethanol / 0.67 h / Heating
View Scheme
ethyl N-[benzoyl(benzyl)amino]acetate
80326-97-2

ethyl N-[benzoyl(benzyl)amino]acetate

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / aq. NaOH / methanol / 1 h / 0 °C
2: 86 percent / methanol / 35 - 40 °C / Electrolysis
3: 94 percent / HCl / ethanol / 0.67 h / Heating
View Scheme
benzylamine
100-46-9

benzylamine

phenacetimino-ethyl ether-hydrochloride

phenacetimino-ethyl ether-hydrochloride

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / triethylamine / CH2Cl2 / 2 h / 20 °C
2: 89 percent / pyridine / benzene / 0.5 h / 60 - 70 °C
3: 95 percent / aq. NaOH / methanol / 1 h / 0 °C
4: 86 percent / methanol / 35 - 40 °C / Electrolysis
5: 94 percent / HCl / ethanol / 0.67 h / Heating
View Scheme
benzaldehyde
100-52-7

benzaldehyde

SASRIN-maleidobenzoic acid resin

SASRIN-maleidobenzoic acid resin

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 4 h / 20 °C
2: NaBH4 / methanol / 1 h / 20 °C
View Scheme
1,2-dibenzylpyrazolidine-3,5-dione
93847-22-4

1,2-dibenzylpyrazolidine-3,5-dione

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TosN3, NEt3 / acetonitrile
2: 50 percent / H2O / diethyl ether / Irradiation
3: benzene / Heating
4: diborane / tetrahydrofuran
View Scheme
Multi-step reaction with 4 steps
1: 66 percent / triethylamine, toluene-p-sulphonyl azide / acetonitrile / 1.) 0 deg C, 1 h, 2.) RT, 2 h
2: 50 percent / H2O / diethyl ether / 0.75 h / Irradiation
3: 80 percent / toluene / 2 h / Heating
4: 85 percent / diborane-THF complex / 2 h / Heating
View Scheme
1,2-dibenzyl-3-oxo-1,2-diazetidine-4-carboxylic acid
93847-29-1

1,2-dibenzyl-3-oxo-1,2-diazetidine-4-carboxylic acid

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzene / Heating
2: diborane / tetrahydrofuran
View Scheme
Multi-step reaction with 2 steps
1: 80 percent / toluene / 2 h / Heating
2: 85 percent / diborane-THF complex / 2 h / Heating
View Scheme
4-diazo-1,2-dibenzylpyrazolidine-3,5-dione
93847-25-7

4-diazo-1,2-dibenzylpyrazolidine-3,5-dione

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 50 percent / H2O / diethyl ether / Irradiation
2: benzene / Heating
3: diborane / tetrahydrofuran
View Scheme
Multi-step reaction with 3 steps
1: 50 percent / H2O / diethyl ether / 0.75 h / Irradiation
2: 80 percent / toluene / 2 h / Heating
3: 85 percent / diborane-THF complex / 2 h / Heating
View Scheme
ethyl 3-benzylidenecarbazate
16208-36-9

ethyl 3-benzylidenecarbazate

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 95 percent / 40 aq. percent NaOH, trimethylbenzylammonium chloride / benzene / 17 h / Heating
2: 75 percent / H2 / 10 percent Pd-C / ethanol
3: 72 percent / triethylamine / benzene / 3 h
4: NaOEt / ethanol / 20 h / Heating
5: H2O; acetonitrile / 2 h / Heating
6: 66 percent / triethylamine, toluene-p-sulphonyl azide / acetonitrile / 1.) 0 deg C, 1 h, 2.) RT, 2 h
7: 50 percent / H2O / diethyl ether / 0.75 h / Irradiation
8: 80 percent / toluene / 2 h / Heating
9: 85 percent / diborane-THF complex / 2 h / Heating
View Scheme
benzyl bromide
100-39-0

benzyl bromide

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 95 percent / 40 aq. percent NaOH, trimethylbenzylammonium chloride / benzene / 17 h / Heating
2: 75 percent / H2 / 10 percent Pd-C / ethanol
3: 72 percent / triethylamine / benzene / 3 h
4: NaOEt / ethanol / 20 h / Heating
5: H2O; acetonitrile / 2 h / Heating
6: 66 percent / triethylamine, toluene-p-sulphonyl azide / acetonitrile / 1.) 0 deg C, 1 h, 2.) RT, 2 h
7: 50 percent / H2O / diethyl ether / 0.75 h / Irradiation
8: 80 percent / toluene / 2 h / Heating
9: 85 percent / diborane-THF complex / 2 h / Heating
View Scheme
2,3-dibromopropionic acid ethyl ester
3674-13-3

2,3-dibromopropionic acid ethyl ester

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

ethyl 1,4-dibenzylpiperazin-2-carboxylate
72351-59-8

ethyl 1,4-dibenzylpiperazin-2-carboxylate

Conditions
ConditionsYield
With triethylamine In toluene at 40 - 80℃; for 3h;100%
With triethylamine In toluene at 80 - 95℃; for 3h;94%
With triethylamine In toluene at 80℃; for 3h;93%
Divinyl sulfone
77-77-0

Divinyl sulfone

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

4,7-dibenzyl-1-thia-4,7-diazacyclononane 1,1-dioxide

4,7-dibenzyl-1-thia-4,7-diazacyclononane 1,1-dioxide

Conditions
ConditionsYield
In water; isopropyl alcohol for 1h; aza-Michael addition; Heating;100%
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

N,N'-(benzyl)-N,N'-[(tert-butoxycarbonyl)methyl]ethylenediamine
1171249-41-4

N,N'-(benzyl)-N,N'-[(tert-butoxycarbonyl)methyl]ethylenediamine

Conditions
ConditionsYield
Stage #1: N,N'-Dibenzylethylenediamine With potassium carbonate In acetonitrile for 1h; Reflux;
Stage #2: bromoacetic acid tert-butyl ester In acetonitrile for 24h; Reflux;
100%
With potassium carbonate In acetonitrile for 24h; Reflux;100%
Stage #1: N,N'-Dibenzylethylenediamine With sodium carbonate In acetonitrile at 20℃; for 0.5h;
Stage #2: bromoacetic acid tert-butyl ester In acetonitrile at 90℃;
95%
With sodium carbonate In acetonitrile at 60℃;93%
pyridine-2-carbaldehyde
1121-60-4

pyridine-2-carbaldehyde

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

2-(1,3-dibenzyl-imidazolidin-2-yl)-pyridine
693243-72-0

2-(1,3-dibenzyl-imidazolidin-2-yl)-pyridine

Conditions
ConditionsYield
In water at 20℃; for 3h;99%
thiophene-2-carbaldehyde
98-03-3

thiophene-2-carbaldehyde

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,3-dibenzyl-2-thiophen-2-yl-imidazolidine
311788-17-7

1,3-dibenzyl-2-thiophen-2-yl-imidazolidine

Conditions
ConditionsYield
In water at 20℃; for 3h;99%
In ethanol; water at 80℃; for 3h;50%
In ethanol; water at 20℃;50%
N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

N,N'-Dibenzyl-N,N'-dinitroso-1,2-diaminoethane
69239-61-8

N,N'-Dibenzyl-N,N'-dinitroso-1,2-diaminoethane

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite for 20h; Heating;98%
With hydrogenchloride; sodium nitrite In water94%
O,O'-di(α-bromo-α-phenylacetyl)-L-tartaric acid diisopropyl ester
1417715-03-7

O,O'-di(α-bromo-α-phenylacetyl)-L-tartaric acid diisopropyl ester

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

A

(S)-1,4-dibenzyl-3-phenylpiperazin-2-one
1327310-96-2

(S)-1,4-dibenzyl-3-phenylpiperazin-2-one

B

(R)-1,4-dibenzyl-3-phenylpiperazin-2-one
1327310-54-2

(R)-1,4-dibenzyl-3-phenylpiperazin-2-one

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 12h; enantioselective reaction;A 98%
B n/a
3-methylbenzene-1,2-diol
488-17-5

3-methylbenzene-1,2-diol

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,4-dibenzyl-5-methyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione
1418195-31-9

1,4-dibenzyl-5-methyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione

Conditions
ConditionsYield
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction;98%
In aq. phosphate buffer at 20℃; pH=7; Electrochemical reaction;93.2%
diphenylsilane
775-12-2

diphenylsilane

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

C28H28N2Si

C28H28N2Si

Conditions
ConditionsYield
With C14H38BaSi4*3C4H8O In benzene at 60℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;98%
benzaldehyde
100-52-7

benzaldehyde

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,3-dibenzyl-2-phenylimidazolidine
4597-81-3

1,3-dibenzyl-2-phenylimidazolidine

Conditions
ConditionsYield
In water for 3h;97%
In water at 20℃; for 3h;91%
In benzene85%
trifluoroacetic acid
76-05-1

trifluoroacetic acid

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1-bromo-3-propanol
627-18-9

1-bromo-3-propanol

C22H32N2O2*2C2HF3O2

C22H32N2O2*2C2HF3O2

Conditions
ConditionsYield
Stage #1: N,N'-Dibenzylethylenediamine; 1-bromo-3-propanol With N-ethyl-N,N-diisopropylamine In acetonitrile for 12h; Heating;
Stage #2: trifluoroacetic acid In water; acetonitrile
97%
acetic acid
64-19-7

acetic acid

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

N,N'-dibenzylethylenediamine diacetate
122-75-8

N,N'-dibenzylethylenediamine diacetate

Conditions
ConditionsYield
In ethyl acetate at 5 - 60℃; for 1h;96.91%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,3-dibenzyl-2-(2-chloro-phenyl)-imidazolidine
307338-79-0

1,3-dibenzyl-2-(2-chloro-phenyl)-imidazolidine

Conditions
ConditionsYield
In water at 20℃; for 3h;96%
1,4-dioxane-2,6-dione
4480-83-5

1,4-dioxane-2,6-dione

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

[(Benzyl-{2-[benzyl-(2-carboxymethoxy-acetyl)-amino]-ethyl}-carbamoyl)-methoxy]-acetic acid
123845-15-8

[(Benzyl-{2-[benzyl-(2-carboxymethoxy-acetyl)-amino]-ethyl}-carbamoyl)-methoxy]-acetic acid

Conditions
ConditionsYield
In benzene96%
In tetrahydrofuran at 50℃; for 12h;96%
With triethylamine In benzene for 4h; Heating;
formaldehyd
50-00-0

formaldehyd

2,4-di-tert-Butylphenol
96-76-4

2,4-di-tert-Butylphenol

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

N,N'-dibenzyl-N,N'-bis[(3,5-di-t-butyl-2-hydroxyphenyl)methylene]-1,2-diaminoethane
423719-59-9

N,N'-dibenzyl-N,N'-bis[(3,5-di-t-butyl-2-hydroxyphenyl)methylene]-1,2-diaminoethane

Conditions
ConditionsYield
In methanol Mannich condensation; Heating;96%
In methanol; water Reflux;90.1%
In ethanol at 90℃;25%
In water Mannich reaction;
2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,3-dibenzyl-2-(2,4-dichloro-phenyl)-imidazolidine
303098-32-0

1,3-dibenzyl-2-(2,4-dichloro-phenyl)-imidazolidine

Conditions
ConditionsYield
In water at 80℃; for 3h;96%
cis-1,4-bis(acetyloxy)but-2-ene
25260-60-0

cis-1,4-bis(acetyloxy)but-2-ene

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

racemic-1,4-Dibenzyl-2-vinylpiperazine
126544-40-9

racemic-1,4-Dibenzyl-2-vinylpiperazine

Conditions
ConditionsYield
Stage #1: cis-1,4-bis(acetyloxy)but-2-ene; N,N'-Dibenzylethylenediamine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triisopropyl phosphite In tetrahydrofuran for 18.25h;
Stage #2: With sodium hydroxide In diethyl ether; water pH=14;
96%
With triphenylphosphine; dichloro bis(acetonitrile) palladium(II) In benzene Heating;67%
Stage #1: cis-1,4-bis(acetyloxy)but-2-ene; N,N'-Dibenzylethylenediamine In tetrahydrofuran for 18.25h;
Stage #2: With sodium hydroxide In diethyl ether; water pH=14;
formaldehyd
50-00-0

formaldehyd

Nitroethane
79-24-3

Nitroethane

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,4-dibenzyl-6-methyl-6-nitroperhydro-1,4-diazepine
492437-19-1

1,4-dibenzyl-6-methyl-6-nitroperhydro-1,4-diazepine

Conditions
ConditionsYield
Stage #1: formaldehyd; N,N'-Dibenzylethylenediamine In ethanol for 4h; Reflux;
Stage #2: Nitroethane In ethanol for 16h; Inert atmosphere; Reflux;
96%
Stage #1: formaldehyd; N,N'-Dibenzylethylenediamine In ethanol for 2h; Reflux; Inert atmosphere;
Stage #2: Nitroethane In ethanol Reflux; Inert atmosphere;
78%
3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione
1418195-30-8

1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione

Conditions
ConditionsYield
In aq. phosphate buffer at 20℃; pH=7; Electrochemical reaction;95.5%
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction;
succinic acid anhydride
108-30-5

succinic acid anhydride

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

C24H28N2O6
1311508-39-0

C24H28N2O6

Conditions
ConditionsYield
In dichloromethane at 20℃;95%
In N,N-dimethyl-formamide at 20℃; for 12h;84.7%
benzene-1,2-diol
120-80-9

benzene-1,2-diol

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione
1418195-30-8

1,4-dibenzyl-1,2,3,4-tetrahydroquinoxaline-6,7-dione

Conditions
ConditionsYield
In aq. phosphate buffer at 20℃; pH=7; Mechanism; pH-value; Electrochemical reaction;94.8%
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction;
4-acetaminophenol
103-90-2

4-acetaminophenol

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

N-(1,4,6,9-tetrabenzyl-10-oxo-1H,2H,3H,4H,5H,6H,7H,8H,9H-pyrazino[2,3-g]quinoxalin-5-ylidene)acetamide

N-(1,4,6,9-tetrabenzyl-10-oxo-1H,2H,3H,4H,5H,6H,7H,8H,9H-pyrazino[2,3-g]quinoxalin-5-ylidene)acetamide

Conditions
ConditionsYield
In water at 25℃; Electrochemical reaction; Green chemistry;94.3%
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,3-dibenzyl-2-(2-methoxy-phenyl)-imidazolidine

1,3-dibenzyl-2-(2-methoxy-phenyl)-imidazolidine

Conditions
ConditionsYield
In water at 20℃; for 3h;94%
(E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid
28010-23-3

(E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

N,N'-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-N,N'-dibenzylethylenediamine

N,N'-bis[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-N,N'-dibenzylethylenediamine

Conditions
ConditionsYield
94%
formaldehyd
50-00-0

formaldehyd

β-naphthol
135-19-3

β-naphthol

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,1′-[N,N′-dibenzylethane-1,2-diylbis(azanediyl)bis(methylene)]di(naphthalen-2-ol)

1,1′-[N,N′-dibenzylethane-1,2-diylbis(azanediyl)bis(methylene)]di(naphthalen-2-ol)

Conditions
ConditionsYield
Stage #1: formaldehyd; N,N'-Dibenzylethylenediamine In methanol at 20℃; for 0.333333h;
Stage #2: β-naphthol In methanol for 2h;
93%
1,1-dimethyl-2-oxoethyl diphenylphosphinodithioate

1,1-dimethyl-2-oxoethyl diphenylphosphinodithioate

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1-(1,3-dibenzyl-1,3-diazolidin-5-yl)-1-methylethyldiphenylphosphinodithioate

1-(1,3-dibenzyl-1,3-diazolidin-5-yl)-1-methylethyldiphenylphosphinodithioate

Conditions
ConditionsYield
In benzene at 50℃; for 5h; Molecular sieve;93%
In benzene at 50℃; for 5h; Molecular sieve;93%
3-methocycatechol
934-00-9

3-methocycatechol

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,4-dibenzyl-5-methoxy-1,2,3,4-tetrahydroquinoxaline-6,7-dione
1418195-32-0

1,4-dibenzyl-5-methoxy-1,2,3,4-tetrahydroquinoxaline-6,7-dione

Conditions
ConditionsYield
In aq. phosphate buffer at 20℃; pH=7; Electrochemical reaction;92.6%
In aq. phosphate buffer; acetonitrile at 25℃; for 20h; pH=7.0; Reagent/catalyst; Electrochemical reaction;66%
perfluorobenzaldehyde
653-37-2

perfluorobenzaldehyde

N,N'-Dibenzylethylenediamine
140-28-3

N,N'-Dibenzylethylenediamine

1,3-dibenzyl-2-pentafluorophenyl-imidazolidine
693243-77-5

1,3-dibenzyl-2-pentafluorophenyl-imidazolidine

Conditions
ConditionsYield
In water at 20℃; for 3h;92%

140-28-3Relevant articles and documents

Synthesis of heterobinuclear Cu(Ⅱ)-Ni(Ⅱ) complex: Structure, CT-DNA interaction, hydrolytic function and antibacterial studies

Ding, Peipei,Wang, Yang,Kou, Huizhi,Li, Jianfen,Shi, Baoxian

, p. 836 - 843 (2019)

A new benzyls pendant-armed macrobicyclic heterbinuclear Cu(Ⅱ)-Ni(Ⅱ) complex has been obtained by template-directed synthesis and characterized by elemental analysis, IR spectra, electrospray mass spectra, and single crystal X-ray diffraction. The complex was bridged by two phenolic oxygens and an acetate radical, with the Cu(Ⅱ)-Ni(Ⅱ) distance of 2.9292(8) ?. The hydrolytic function, CT-DNA binding and antibacterial properties were also studied. The initial rate values for the hydrolysis of 4-nitophenylphosphate to 4-nitrophenolate by the Cu(Ⅱ)-Ni(Ⅱ) complex was 1.33 × 10?5 s?1, and 104 times faster than that the spontaneous hydrolysis of the phosphate monoester. The complex shows a better binding property to CT-DNA and the intrinsic binding constant is 1.29 × 105 M?1. The Stern-Volmer constant is 1.25 × 105 M?1. The viscosity increased obviously with the increase of complex concentration, the results showed that the complex bind to DNA through intercalation mode, which was in accordance with the absorption and emission spectral studies. The antibacterial activities against E.coli was also investigated using the Gentamycinas reference system.

A combination risk assessment of paracetamol: Electrochemical oxidation behavior and cytotoxic effect evaluation of paracetamol in the presence of: N 1, N 2-dibenzylethane-1,2-diamine

Dowlati, Bahram,Othman, Mohamed Rozali,Ahmad, Azizan,Safaei, Elham

, p. 5121 - 5127 (2016)

The cytotoxic effect of paracetamol in the presence of a diamine derivative was evaluated in liver cells. In this study, hydropyrazinoquinoxalinylidene-acetamide (HPQA), as an agent that is toxic to the liver, was synthesized in an electrochemical cell as a simulated body environment by an electrooxidation reaction. A direct electron transfer (DET) mechanism occurred during the process on the surface of the carbon anode. The electrochemical oxidation of paracetamol was studied using cyclic voltammetry and controlled-potential coulometry (CPC) techniques. The product was characterized by FT-IR, 1H NMR, 13C NMR and ESI-MS2 after purification. The cytotoxicity of the final compound was evaluated using an MTT assay on the CCL-13 liver cell line. The results indicate that the presence of amine derivatives leads to an increase in the toxic effects of paracetamol in the human body. The cell viability at a concentration of 500 μg mL-1 was 78% for paracetamol, whereas the viability of liver cells in the presence of the product was 18% at 168 μg mL-1. A cycloaddition mechanism was suggested according to the overall results that were obtained.

Platinum Assisted Tandem P–C Bond Cleavage and P–N Bond Formation in Amide Functionalized Bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o: Synthesis, Mechanistic, and Catalytic Studies

Balakrishna, Maravanji S.,Kunchur, Harish S.

supporting information, (2022/01/19)

The reactions of amide functionalized bisphosphine o-Ph2PC6H4C(O)N(H)C6H4PPh2-o (1) with platinum salts are described. Treatment of 1 with [Pt(COD)Cl2] yielded a chelate complex, [PtCl2{o-Ph2PC6H4C(O)N(H)C6H4PPh2-o}κ2-P,P] (2), which on subsequent treatment with LiHMDS formed a novel 1,2-azaphospholene-phosphine complex [Pt(C6H5)Cl{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (3) involving a tandem P–C bond cleavage and P–N bond formation. The same complex 3 on passing dry HCl gas afforded the dichloro complex [PtCl2{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (5). Complex 2 upon refluxing in toluene or treatment of 1 with [Pt(COD)Cl2] in the presence of a base at room temperature resulted in the pincer complex [PtCl{o-Ph2PC6H4C(O)N(C6H4PPh2-o)}κ3-P,N,P] (4). Reaction of 1 with [Pt(COD)ClMe] at room temperature also afforded the pincer complex [PtMe{o-Ph2PC6H4C(O)N(C6H4PPh2-o)}κ3-P,N,P] (6). Mechanistic studies on 1,2-azaphospholene formation showed the reductive elimination of LiCl to form a phosphonium salt that readily adds one of the P–C bonds oxidatively to the in situ generated Pt0 species to form a chelate complex 3. The analogous palladium complex [PdCl2{o-C6H4{C(O)N(o-PPh2(C6H4))P(Ph)}}κ2-P,P] (7) showed excellent catalytic activity toward N-alkylation of amines with alcohols with a very low catalyst loading (0.05 mol %), and the methodology is very efficient toward the gram-scale synthesis of many N-alkylated amines.

A new macrocyclic heterobinuclear Cu(II)-Zn(II) complex: synthesis, crystal structure, phosphate hydrolysis, and DNA binding studies

Kou, Huizhi,Wang, Yang,Ding, Peipei,Li, Jianfen,Shi, Baoxian

, p. 1683 - 1696 (2019/05/22)

A new macrocyclic heterobinuclear Cu(II)-Zn(II) complex was synthesized and characterized by elemental analysis, FT-IR, ES-MS, and single-crystal X-ray diffraction. Five-coordinate geometry for the new complex is proposed. The copper…zinc distance bridged by two phenolic oxygens and a acetate ligand is 2.9508 ?. The phosphate ester hydrolysis activity and the DNA binding ability of the complex were studied. The results showed that the present complex has an efficient catalytic activity of phosphoester bond cleavage. The catalytic rate constant kcat for the hydrolysis of 4-nitrophenyl phosphate disodium salt hexahydrate (pNPP) by the synthesized complex is 2.69 × 10?4 s?1 and 105 times faster than the spontaneous hydrolysis of the phosphate monoester. The complex shows a good binding ability to calf thymus (CT-DNA) and the corresponding binding constant is 1.9 × 105 M?1. The linear Stern-Volmer quenching constant obtained by the fluorescent spectroscopic is 6.3 × 104 M?1.

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