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1972-28-7 Usage

Chemical Description

Different sources of media describe the Chemical Description of 1972-28-7 differently. You can refer to the following data:
1. Diethyl azodicarboxylate is a reagent used in organic synthesis to introduce azo groups.
2. Diethyl azodicarboxylate is another oxidant used in the preparation of compound 32.

Chemical Properties

Clear orange to orange-red liquid

Uses

Different sources of media describe the Uses of 1972-28-7 differently. You can refer to the following data:
1. A fluorescent CDK inhibitor for treatment of cancer
2. Reactant for preparation of:Immunostimulants α-GalactosylceramidesCellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulasesBisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferaseDerivatives of F200 and S383 with cannabinoid CB1 receptor binding activitiesAza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenesReagent for:Annulation of N-protected iminesα-thiocyanation of enolizable ketones with ammonium thiocyanateDiels-Alder reactions

General Description

DOT Special Approval Submission is Under Review. Availability is Estimated as March 2012.

Purification Methods

Dissolve DEAD in toluene, wash it with 10% NaHCO3 till neutral (may require several washes if too much hydrolysis had occurred: check IR for OH bands), then wash with H2O (2x), dry over Na2SO4, filter, evaporate the toluene and distil it through a short Vigreux column (p 11) at as high a vacuum as possible. The main portion boils at 107-111o/15mm. Since it is likely to explode, use an oil bath for heating the still and all operations should be carried -out behind an adequate shield. [Rabjohn Org Synth Coll Vol III 375 1955, see Kauer Org Synth Coll Vol IV 412 1963]. [Beilstein 3 III 233.] It is commercially available as a 40% solution in toluene. This reagent is useful in the Mitsunobu reaction [Mitsunobu Synthesis 1 1981, Gennari et al. J Am Chem Soc 108 6394 1986, Evans et al. J Am Chem Soc 108 6394 1986, Hughes Org React 42 335 1992, Dodge et al. Org Synth 73 110 1996, Hughes Org Prep Proc Int 28 127 1996, Ferguson & Marcelle J Am Chem Soc 128 4576 2006; see also di-tert-butyl azodicarboxylate above and DIAD below]. § A polystyrene supported DEAD version is commercially available with a loading of ~1.2mmol/g.

Check Digit Verification of cas no

The CAS Registry Mumber 1972-28-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,7 and 2 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1972-28:
(6*1)+(5*9)+(4*7)+(3*2)+(2*2)+(1*8)=97
97 % 10 = 7
So 1972-28-7 is a valid CAS Registry Number.
InChI:InChI=1/C6H10N2O4/c1-5(9)11-3-7-8-4-12-6(2)10/h3-4H2,1-2H3/b8-7+

1972-28-7 Well-known Company Product Price

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  • Alfa Aesar

  • (L19348)  Diethyl azodicarboxylate, 97%   

  • 1972-28-7

  • 5g

  • 183.0CNY

  • Detail
  • Alfa Aesar

  • (L19348)  Diethyl azodicarboxylate, 97%   

  • 1972-28-7

  • 25g

  • 573.0CNY

  • Detail
  • Alfa Aesar

  • (L19348)  Diethyl azodicarboxylate, 97%   

  • 1972-28-7

  • 100g

  • 1745.0CNY

  • Detail

1972-28-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Diethyl azodicarboxylate

1.2 Other means of identification

Product number -
Other names (E)-Diethyl diazene-1,2-dicarboxylate

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:1972-28-7 SDS

1972-28-7Synthetic route

2-Benzyloxyethanol
622-08-2

2-Benzyloxyethanol

4-methyl-5-nitrophenol
2042-14-0

4-methyl-5-nitrophenol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With triphenylphosphine95%
diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In dichloromethane for 0.25h; Ambient temperature;88%
With N-Bromosuccinimide In dichloromethane 1.) 0 deg C, 0.5 h, 2.) RT, 1h;86.6%
Stage #1: diethyl hydrazodicarboxylate With chlorine In water; benzene
Stage #2: With sodium carbonate
81%
4,7-Dimethyl-15-oxo-5,6-diphenyl-11,12-diazapentacyclo<8.2.2.14,7.02,9.03,8>pentadeca-5,13-dien-11,12-dicarbonsaeure-diethylester
73240-57-0, 77881-55-1

4,7-Dimethyl-15-oxo-5,6-diphenyl-11,12-diazapentacyclo<8.2.2.14,7.02,9.03,8>pentadeca-5,13-dien-11,12-dicarbonsaeure-diethylester

A

diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

B

methyl 3',6'-dimethyl[1,1*:2',1
13102-23-3

methyl 3',6'-dimethyl[1,1*:2',1"-terphenyl]-4'-carboxylate

C

4,9-Dimethyl-6,7-diphenyl-5,8-dioxa-13,14-diazahexacyclo<10.2.2.02,11.03,10.04,6.07,9>hexadec-15-en-13,14-dicarbonsaeure-diethylester
86814-76-8

4,9-Dimethyl-6,7-diphenyl-5,8-dioxa-13,14-diazahexacyclo<10.2.2.02,11.03,10.04,6.07,9>hexadec-15-en-13,14-dicarbonsaeure-diethylester

D

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
In diethyl ether; acetone at -25 - -20℃; for 6h; Irradiation;A n/a
B 46%
C 7%
D n/a
4,7-Dimethyl-15-oxo-5,6-diphenyl-11,12-diazapentacyclo<8.2.2.14,7.02,9.03,8>pentadeca-5,13-dien-11,12-dicarbonsaeure-diethylester
73240-57-0, 77881-55-1

4,7-Dimethyl-15-oxo-5,6-diphenyl-11,12-diazapentacyclo<8.2.2.14,7.02,9.03,8>pentadeca-5,13-dien-11,12-dicarbonsaeure-diethylester

A

diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

B

methyl 3',6'-dimethyl[1,1*:2',1
13102-23-3

methyl 3',6'-dimethyl[1,1*:2',1"-terphenyl]-4'-carboxylate

C

4,9-Dimethyl-6,7-diphenyl-5,8-dioxa-13,14-diazahexacyclo<10.2.2.02,11.03,10.04,6.07,9>hexadec-15-en-13,14-dicarbonsaeure-diethylester
86814-76-8

4,9-Dimethyl-6,7-diphenyl-5,8-dioxa-13,14-diazahexacyclo<10.2.2.02,11.03,10.04,6.07,9>hexadec-15-en-13,14-dicarbonsaeure-diethylester

D

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

E

benzene
71-43-2

benzene

Conditions
ConditionsYield
In diethyl ether; acetone at -25 - -20℃; for 6h; Product distribution; Irradiation;A n/a
B 46%
C 7%
D n/a
E n/a
diethyl hydrazinedicarboxylate
5311-96-6

diethyl hydrazinedicarboxylate

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With nitric acid
With water; nitric acid Reagens 4:Aether;
bis-ethoxycarbonylmercurio-hydrazine-N,N'-dicarboxylic acid diethyl ester

bis-ethoxycarbonylmercurio-hydrazine-N,N'-dicarboxylic acid diethyl ester

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With bromine; benzene
diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

benzene
71-43-2

benzene

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With water; chlorine
ethyl azidocarbonate
817-87-8

ethyl azidocarbonate

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
In tetrachloromethane at 25℃; for 100h; Rate constant; Irradiation; other solvents;
mercury salt of hydrazinedicarboxylic acid diethyl ester

mercury salt of hydrazinedicarboxylic acid diethyl ester

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
With iodine
diethyl 3-phenyltriazane-1,2-dicarboxylate
17696-93-4

diethyl 3-phenyltriazane-1,2-dicarboxylate

benzene
71-43-2

benzene

A

[1,4]benzoquinon-[4-(4-amino-anilino)-phenylimine]-phenylimine
108673-54-7

[1,4]benzoquinon-[4-(4-amino-anilino)-phenylimine]-phenylimine

B

aniline
62-53-3

aniline

C

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

D

hydrazodicarboxylic acid ester

hydrazodicarboxylic acid ester

Conditions
ConditionsYield
at 26℃;
at 95℃; Geschwindigkeit;
diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

nitric acid
7697-37-2

nitric acid

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

water
7732-18-5

water

chlorine
7782-50-5

chlorine

benzene
71-43-2

benzene

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
Explosionsgefahr !;
diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

nitrogen oxides

nitrogen oxides

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

hydrazine-N,N'-dicarboxylic acid diethyl ester; mercury salt

hydrazine-N,N'-dicarboxylic acid diethyl ester; mercury salt

etheric iodine

etheric iodine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

bromine
7726-95-6

bromine

bis-ethoxycarbonylmercurio-hydrazine-N,N'-dicarboxylic acid diethyl ester

bis-ethoxycarbonylmercurio-hydrazine-N,N'-dicarboxylic acid diethyl ester

benzene
71-43-2

benzene

A

ethyl 1-bromoformate
17759-76-1

ethyl 1-bromoformate

B

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

C

mercury (II)-bromide

mercury (II)-bromide

(1R,2R,5S,6S)-7,8-Diaza-tricyclo[4.2.2.02,5]deca-3,9-diene-7,8-dicarboxylic acid diethyl ester
24009-91-4, 73285-36-6

(1R,2R,5S,6S)-7,8-Diaza-tricyclo[4.2.2.02,5]deca-3,9-diene-7,8-dicarboxylic acid diethyl ester

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 77 percent / benzene / 48 h / Heating
2: diethyl ether; acetone / 6 h / -25 - -20 °C / Irradiation
View Scheme
C11H18N3O6(1-)*C16H36N(1+)
1316208-44-2

C11H18N3O6(1-)*C16H36N(1+)

A

proline, tetrabutylammonium carboxylate salt

proline, tetrabutylammonium carboxylate salt

B

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Conditions
ConditionsYield
In chloroform Equilibrium constant;
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl 2,3-diazanorbornene-2,3-dicarboxylate
14011-60-0

diethyl 2,3-diazanorbornene-2,3-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 0℃;100%
In diethyl ether at 0℃; for 12h;100%
In diethyl ether; toluene at 20℃; for 21.5h; Reflux;55%
With diethyl ether
cyclohexene
110-83-8

cyclohexene

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

Diethyl 1-(2-cyclohexen-1-yl)-1,2-hydrazinedicarboxylate
17833-25-9

Diethyl 1-(2-cyclohexen-1-yl)-1,2-hydrazinedicarboxylate

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane at -78℃;100%
With tin(IV) chloride In dichloromethane at -60℃; for 0.0833333h;77%
diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl hydrazodicarboxylate
4114-28-7

diethyl hydrazodicarboxylate

Conditions
ConditionsYield
With hydrazine hydrate In toluene; acetonitrile at 20℃; for 0.166667h;100%
With [bis(acetoxy)iodo]benzene; hydrazine hydrate In dichloromethane for 3.5h; Ambient temperature;90%
With tert-Butyl iodide In acetonitrile for 0.166667h; Reflux;90%
[1,3,2]dioxaphospholan-2-yl-dimethyl-amine
7114-39-8

[1,3,2]dioxaphospholan-2-yl-dimethyl-amine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

dimethylamino-5 ethoxy-7 carboethoxy-9 trioxa-1,4,6diaza-8,9 phospha(V)-5 spiro(4,4)nonene-7,8
75386-16-2

dimethylamino-5 ethoxy-7 carboethoxy-9 trioxa-1,4,6diaza-8,9 phospha(V)-5 spiro(4,4)nonene-7,8

Conditions
ConditionsYield
In dichloromethane 10 min, 5 deg C, then room t.,;100%
dimethyl-(4,4,5,5-tetramethyl-[1,3,2]dioxaphospholan-2-yl)-amine
14274-42-1

dimethyl-(4,4,5,5-tetramethyl-[1,3,2]dioxaphospholan-2-yl)-amine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

tetramethyl-2,2,3,3-dimethylamino-5-ethoxy-7 carboethoxy-9 trioxa-1,4,6 diaza-8,9 phospha(V)-5 spiro(4,4)noneme-7,8
75386-17-3

tetramethyl-2,2,3,3-dimethylamino-5-ethoxy-7 carboethoxy-9 trioxa-1,4,6 diaza-8,9 phospha(V)-5 spiro(4,4)noneme-7,8

Conditions
ConditionsYield
In dichloromethane Product distribution; 10 min, 5 deg C, then room t; reactions of phosphites and cyclis aminophosphites;100%
In dichloromethane 10 min, 5 deg C, then room t.,;100%
2-dimethylamino-1,3,2-benzodioxaphosphole
18389-60-1

2-dimethylamino-1,3,2-benzodioxaphosphole

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

O-phenylene-2,3 dimethylamino-5 ethoxy-7 carboethoxy-9 trioxa-1,4,6 diaza-8,9 phospha(V)-5 spiro(4,4)nonene-7,8

O-phenylene-2,3 dimethylamino-5 ethoxy-7 carboethoxy-9 trioxa-1,4,6 diaza-8,9 phospha(V)-5 spiro(4,4)nonene-7,8

Conditions
ConditionsYield
In dichloromethane 10 min, 5 deg C, then room t., 24 h;100%
triphenylphosphine
603-35-0

triphenylphosphine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethylazodicarboxylate - triphenylphosphine (DEAD-Ph3P)
58477-00-2

diethylazodicarboxylate - triphenylphosphine (DEAD-Ph3P)

Conditions
ConditionsYield
In tetrahydrofuran Mechanism; other phosphine;100%
In chloroform-d1
In tetrahydrofuran at 0℃; for 1h;
2-benzoylmethyleneimidazolidine
64944-80-5

2-benzoylmethyleneimidazolidine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

C17H22N4O5
112030-72-5

C17H22N4O5

Conditions
ConditionsYield
In 1,4-dioxane for 48h; Ambient temperature;100%
1-phenyl-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one
82100-30-9

1-phenyl-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

C18H24N4O5
112030-74-7

C18H24N4O5

Conditions
ConditionsYield
In 1,4-dioxane for 48h; Ambient temperature;100%
2-(p-chlorobenzoylmethylene)imidazolidine
107165-82-2

2-(p-chlorobenzoylmethylene)imidazolidine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

C17H21ClN4O5
112030-73-6

C17H21ClN4O5

Conditions
ConditionsYield
In 1,4-dioxane for 48h; Ambient temperature;100%
1-(4-chlorophenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one
107165-83-3

1-(4-chlorophenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

C18H23ClN4O5
112030-75-8

C18H23ClN4O5

Conditions
ConditionsYield
In 1,4-dioxane for 48h; Ambient temperature;100%
1-(4-methoxyphenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one
107165-84-4

1-(4-methoxyphenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

C19H26N4O6
112030-76-9

C19H26N4O6

Conditions
ConditionsYield
In 1,4-dioxane for 48h; Ambient temperature;100%
((2S,4R,5S)-3,4-Dimethyl-5-phenyl-[1,3,2]oxazaphospholidin-2-yl)-dimethyl-amine

((2S,4R,5S)-3,4-Dimethyl-5-phenyl-[1,3,2]oxazaphospholidin-2-yl)-dimethyl-amine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

dimethyl-1,2-phenyl-3 dimethylamino-5 ethoxy-7 carboethoxy-9 dioxa-4,6-triaza-1,8,9 phospha(V)-5 spiro(4,4)nonene-7,8

dimethyl-1,2-phenyl-3 dimethylamino-5 ethoxy-7 carboethoxy-9 dioxa-4,6-triaza-1,8,9 phospha(V)-5 spiro(4,4)nonene-7,8

Conditions
ConditionsYield
In dichloromethane 10 min, 5 deg C, then room t., 24 h;100%
1,1-dibenzoylpropane
59875-94-4

1,1-dibenzoylpropane

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl N-(dibenzoylpropyl)hydrazine-N,N-dicarboxylate

diethyl N-(dibenzoylpropyl)hydrazine-N,N-dicarboxylate

Conditions
ConditionsYield
With triphenylphosphine In acetonitrile for 24h; Michael addition; Heating;100%
triphenylphosphine In acetonitrile at 25℃; for 24h;100%
tris(triphenylphosphine)ruthenium(II) chloride In acetonitrile for 24h; Product distribution; Further Variations:; Catalysts; Reaction partners; Temperatures; reflux, in dark;83%
β-naphthol
135-19-3

β-naphthol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

(2-hydroxy-1-naphthyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

(2-hydroxy-1-naphthyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With lithium perchlorate; bis(tri-n-butyltin)oxide In diethyl ether at 24.85℃;100%
With 1,3,4-triphenyl-1,2,4-triazolium hexafluorophosphate; potassium tert-butylate In chloroform at 20℃; for 4h; Inert atmosphere;75%
α-naphthol
90-15-3

α-naphthol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

(1-hydroxy-4-naphthyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

(1-hydroxy-4-naphthyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With lithium perchlorate; bis(tri-n-butyltin)oxide In diethyl ether at 24.85℃;100%
(2-methylpyridin-3-yl)methanol
56826-61-0

(2-methylpyridin-3-yl)methanol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

tert-butyl (3S,4S)-4-[(hydroxyamino)carbonyl]-3-({4-[(2-methyl-3-pyridinyl)methoxy]benzoyl}amino)-1-piperidinecarboxylate trifluoroacetate
362488-31-1

tert-butyl (3S,4S)-4-[(hydroxyamino)carbonyl]-3-({4-[(2-methyl-3-pyridinyl)methoxy]benzoyl}amino)-1-piperidinecarboxylate trifluoroacetate

Conditions
ConditionsYield
With ammonium chloride; triphenylphosphine In tetrahydrofuran100%
d5-ethanol

d5-ethanol

ethoxyphenylacetate

ethoxyphenylacetate

Methyl 4-hydroxyphenylacetate
14199-15-6

Methyl 4-hydroxyphenylacetate

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

2-(2-ethoxyphenyl)ethanol
22545-14-8

2-(2-ethoxyphenyl)ethanol

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; diethyl ether100%
2-bromonicotinic acid
35905-85-2

2-bromonicotinic acid

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

2-bromonicotinic acid methyl ester
52718-95-3

2-bromonicotinic acid methyl ester

Conditions
ConditionsYield
With triphenylphosphine In methanol; diethyl ether100%
Indole-6-carboxylic acid
1670-82-2

Indole-6-carboxylic acid

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

5-methoxycarbonylindole
1011-65-0

5-methoxycarbonylindole

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; methanol; dichloromethane100%
Succinimide
123-56-8

Succinimide

3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine
429666-52-4

3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

3-t-butyldiphenylsilyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine

3-t-butyldiphenylsilyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; toluene100%
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

diethyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; Diels-Alder reaction;100%
In dichloromethane at 20℃; Diels-Alder reaction;100%
In diethyl ether at 0℃;100%
2-phenyl-4-methyl-4H-oxazolin-5-one
51127-13-0, 71963-72-9, 87480-74-8, 13302-43-7

2-phenyl-4-methyl-4H-oxazolin-5-one

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

1,2-bis(ethoxycarbonyl)-3-methyl-5-phenyl-2,3-dihydro-1H-1,2,4-triazole-3-carboxylic acid
1228801-83-9

1,2-bis(ethoxycarbonyl)-3-methyl-5-phenyl-2,3-dihydro-1H-1,2,4-triazole-3-carboxylic acid

Conditions
ConditionsYield
In acetonitrile at 20℃; for 11h;100%
2-Phenylpropanal
34713-70-7

2-Phenylpropanal

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

(R)-diethyl 1-(1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate

(R)-diethyl 1-(1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With (S)-4-(tert-butoxy)-2-methyl-4-oxobutanoic acid In tetrahydrofuran at 0℃; for 24h; enantioselective reaction;100%
With (S)-N-((1R,2R)-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)cyclohexyl)pyrrolidine-2-carboxamide; salicylic acid In dichloromethane at 0℃; for 23h; optical yield given as %ee; enantioselective reaction;96%
With trifluoroacetic acid; (1R,2R)-N-1',8'-naphthaloyl-1,2-diaminocyclohexane In 1,2-dichloro-ethane at 25℃; for 5h; enantioselective reaction;96%
1-(2,4-dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one
137235-13-3

1-(2,4-dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl 1-(1-(dimethylamino)-3-oxo-3-(2,4-dichlorophenyl)prop-1-en-2-yl)hydrazine-1,2-dicarboxylate

diethyl 1-(1-(dimethylamino)-3-oxo-3-(2,4-dichlorophenyl)prop-1-en-2-yl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
In toluene; acetonitrile at 20℃;100%
carbon dioxide
124-38-9

carbon dioxide

N,N-dimethyl-4-(3-methyl-3-(propylamino)but-1-yn-1-yl)aniline

N,N-dimethyl-4-(3-methyl-3-(propylamino)but-1-yn-1-yl)aniline

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(4-(dimethylamino)phenyl)methyl)hydrazine-1,2-dicarboxylate

diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(4-(dimethylamino)phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -40℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; stereoselective reaction;100%
carbon dioxide
124-38-9

carbon dioxide

2-methyl-4-phenyl-N-propylbut-3-yn-2-amine

2-methyl-4-phenyl-N-propylbut-3-yn-2-amine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(phenyl)methyl)hydrazine-1,2-dicarboxylate

diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -40℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; stereoselective reaction;100%
carbon dioxide
124-38-9

carbon dioxide

C15H21NO

C15H21NO

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(4-methoxyphenyl)methyl)hydrazine-1,2-dicarboxylate

diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(4-methoxyphenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -40℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; stereoselective reaction;100%
carbon dioxide
124-38-9

carbon dioxide

N-benzyl-2-methyl-4-phenylbut-3-yn-2-amine

N-benzyl-2-methyl-4-phenylbut-3-yn-2-amine

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

diethyl (Z)-1-((3-benzyl-4,4-dimethyl-2-oxooxazolidin-5-ylidene)(phenyl)methyl)hydrazine-1,2-dicarboxylate

diethyl (Z)-1-((3-benzyl-4,4-dimethyl-2-oxooxazolidin-5-ylidene)(phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With silver(I) acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at -40℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; stereoselective reaction;100%
4-chloro-phenol
106-48-9

4-chloro-phenol

2-<2-N-(benzyloxycarbonyl)aminoethoxy>ethanol
145881-74-9

2-<2-N-(benzyloxycarbonyl)aminoethoxy>ethanol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

{2-[2-(4-chloro-phenoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester

{2-[2-(4-chloro-phenoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; hexane; ethyl acetate99.8%

1972-28-7Relevant articles and documents

-

Buechi et al.

, p. 37,39, 40 (1962)

-

Synthesis and neuroprotective properties of isosteric analogs of nicotine

Matveeva,Podrugina,Morozkin,Tkachenko,Zefirov

, p. 1149 - 1153 (2000)

A method has been developed for the synthesis of isosteric analogs of nicotine involving ethers of S(-)-1-2-pyrrolidinemethanol and S(-)-1-2-pyrrolidineethanol based on the Mitsunobu reaction. The results of testing the synthesized compounds as calcium channel blockers are presented.

-

Reynolds,Hauser

, p. Warnungsbeilage (1958)

-

METHOD FOR PRODUCING AZO COMPOUNDS

-

Paragraph 0050; 0051, (2018/08/22)

PROBLEM TO BE SOLVED: To provide a method that can produce azo compounds at good yields by making oxygen or an oxygen-containing gas act on hydrazo compounds when oxidatively dehydrogenating them. SOLUTION: Azo compounds are produced by making oxygen or an oxygen-containing gas act on hydrazo compounds in the presence of at least one compound selected from the group consisting of vanadium and cerium compounds, the oxidation reaction to be performed without using a solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light

M?rz,Chudoba,Kohout,Cibulka

supporting information, p. 1970 - 1975 (2017/03/11)

The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.

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