1972-28-7

Basic information

• Product Name: Diethyl azodicarboxylate
• Synonyms: Diazenedicarboxylic acid, diethyl ester;Diethoxycarbonyldiazene;Diethyl (E)-1,2-diazenedicarboxylate;Diethyl diazodicarboxylate;dlethylazodicarboxylate;Ethyl azodicarboxylate;Formic acid, azodi-, diethyl ester;DIETHYL AZODIFORMATE
• CAS NO: 1972-28-7
• Molecular Formula: C₆H₁₀N₂O₄
• Molecular Weight: 174.15
• EINECS: 217-821-7
• Product Categories: Aromatic Esters;Aliphatics;Inhibitors;Pharmaceutical intermdiate
• Mol File: 1972-28-7.mol

Chemical Properties

• Melting Point: 6°C
• Boiling Point: 106°C (13 mmHg)
• Flash Point: 85°C
• Appearance: Clear orange to orange-red liquid
• Density: 1.106
• Vapor Pressure: 0.589mmHg at 25°C
• Refractive Index: n20/D 1.47
• Storage Temp.: 2-8°C
• Solubility: Miscible with dichloromethane, diethyl ether and toluene.
• Sensitive: Air Sensitive
• Stability: Stable, but may explode if heated under confinement. May be shock sensitive. Decomposes vigorously if heated above 100 C. Incomp
• BRN: 908662
• CAS DataBase Reference: Diethyl azodicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl azodicarboxylate(1972-28-7)
• EPA Substance Registry System: Diethyl azodicarboxylate(1972-28-7)

Safety Data

• Hazard Codes: F,Xn,Xi
• Statements: 5-11-20-36/37/38-48/20-63-65-67-48/20/22-40-20/22-20/21/22-10
• Safety Statements: 26-36/37-62-47-36-35
• RIDADR: UN 3233 4.1
• WGK Germany: 3
• F: 9
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1972-28-7(Hazardous Substances Data)

Usage

Chemical Description

Diethyl azodicarboxylate is a reagent used in organic synthesis to introduce azo groups.

Chemical Description

Diethyl azodicarboxylate is another oxidant used in the preparation of compound 32.

Uses

Diethyl azodicarboxylate is used as a fluorescent CDK inhibitor for the treatment of cancer. It plays a crucial role in modulating cellular processes and inhibiting the growth of cancer cells.
Used in Pharmaceutical Industry:
Diethyl azodicarboxylate is used as a reactant for the preparation of immunostimulants, specifically α-Galactosylceramides. These immunostimulants help enhance the immune response in the body and are used in the development of vaccines and other therapeutic agents.
Used in Biochemical Research:
Diethyl azodicarboxylate is used as a reactant for the preparation of cellotriose and cellotetraose analogues, which serve as transition state mimics for mechanistic studies of cellulases. These analogues help researchers understand the enzymatic processes involved in the breakdown of cellulose, a crucial component in the bioenergy and biofuel industries.
Used in Enzyme Inhibition Studies:
Diethyl azodicarboxylate is used as a reactant for the synthesis of bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase (COMT). These inhibitors are essential in studying the enzyme's role in various biological processes and its potential as a therapeutic target for diseases.
Used in Cannabinoid Research:
Diethyl azodicarboxylate is used as a reactant for the preparation of derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities. These derivatives are crucial in understanding the interactions between cannabinoids and their receptors, which can lead to the development of new therapeutic agents for various conditions.
Used in Organic Synthesis:
Diethyl azodicarboxylate is used as a reactant for the synthesis of Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes. This reaction is an essential step in the development of novel pharmaceutical compounds and other organic molecules with potential applications.
Used in Organic Chemistry:
Diethyl azodicarboxylate is used as a reagent for the annulation of N-protected imines, which are crucial intermediates in the synthesis of various organic compounds, including pharmaceuticals and natural products.
Used in Organic Chemistry:
Diethyl azodicarboxylate is used as a reagent for α-thiocyanation of enolizable ketones with ammonium thiocyanate. This reaction is an important step in the synthesis of various organic compounds with potential applications in the pharmaceutical and chemical industries.
Used in Organic Chemistry:
Diethyl azodicarboxylate is used as a reagent for Diels-Alder reactions, which are fundamental in organic chemistry for the synthesis of complex organic molecules, including pharmaceuticals, natural products, and other specialty chemicals.
General Description:
The DOT Special Approval Submission for Diethyl azodicarboxylate is under review, with an estimated availability in March 2012. As a clear orange to orange-red liquid, it possesses unique chemical properties that make it a versatile reagent and building block in various applications across different industries.

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.

InChI:InChI=1/C6H10N2O4/c1-5(9)11-3-7-8-4-12-6(2)10/h3-4H2,1-2H3/b8-7+

Synthetic route

2-Benzyloxyethanol (622-08-2) + 4-methyl-5-nitrophenol (2042-14-0) → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
With triphenylphosphine	95%

diethyl hydrazodicarboxylate (4114-28-7) → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
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) → diethyl hydrazodicarboxylate (4114-28-7) + methyl 3',6'-dimethyl[1,1*:2',1"-terphenyl]-4'-carboxylate (13102-23-3) + 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) + diethylazodicarboxylate (1972-28-7)

Conditions	Yield
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) → diethyl hydrazodicarboxylate (4114-28-7) + methyl 3',6'-dimethyl[1,1*:2',1"-terphenyl]-4'-carboxylate (13102-23-3) + 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) + diethylazodicarboxylate (1972-28-7) + benzene (71-43-2)

Conditions	Yield
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) → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
With nitric acid
With water; nitric acid Reagens 4:Aether;

bis-ethoxycarbonylmercurio-hydrazine-N,N'-dicarboxylic acid diethyl ester → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
With bromine; benzene

diethyl hydrazodicarboxylate (4114-28-7) + benzene (71-43-2) → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
With water; chlorine

ethyl azidocarbonate (817-87-8) → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
In tetrachloromethane at 25℃; for 100h; Rate constant; Irradiation; other solvents;

mercury salt of hydrazinedicarboxylic acid diethyl ester → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
With iodine

diethyl 3-phenyltriazane-1,2-dicarboxylate (17696-93-4) + benzene (71-43-2) → [1,4]benzoquinon-[4-(4-amino-anilino)-phenylimine]-phenylimine (108673-54-7) + aniline (62-53-3) + diethylazodicarboxylate (1972-28-7) + hydrazodicarboxylic acid ester

Conditions	Yield
at 26℃;
at 95℃; Geschwindigkeit;

diethyl hydrazodicarboxylate (4114-28-7) + nitric acid (7697-37-2) → diethylazodicarboxylate (1972-28-7)

diethyl hydrazodicarboxylate (4114-28-7) + water (7732-18-5) + chlorine (7782-50-5) + benzene (71-43-2) → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
Explosionsgefahr !;

diethyl hydrazodicarboxylate (4114-28-7) + nitrogen oxides → diethylazodicarboxylate (1972-28-7)

hydrazine-N,N'-dicarboxylic acid diethyl ester; mercury salt + etheric iodine → diethylazodicarboxylate (1972-28-7)

bromine (7726-95-6) + bis-ethoxycarbonylmercurio-hydrazine-N,N'-dicarboxylic acid diethyl ester + benzene (71-43-2) → ethyl 1-bromoformate (17759-76-1) + diethylazodicarboxylate (1972-28-7) + 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) → diethylazodicarboxylate (1972-28-7)

Conditions	Yield
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) → proline, tetrabutylammonium carboxylate salt + diethylazodicarboxylate (1972-28-7)

Conditions	Yield
In chloroform Equilibrium constant;

cyclopenta-1,3-diene (542-92-7) + diethylazodicarboxylate (1972-28-7) → diethyl 2,3-diazanorbornene-2,3-dicarboxylate (14011-60-0)

Conditions	Yield
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) + diethylazodicarboxylate (1972-28-7) → Diethyl 1-(2-cyclohexen-1-yl)-1,2-hydrazinedicarboxylate (17833-25-9)

Conditions	Yield
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) → diethyl hydrazodicarboxylate (4114-28-7)

Conditions	Yield
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) + diethylazodicarboxylate (1972-28-7) → dimethylamino-5 ethoxy-7 carboethoxy-9 trioxa-1,4,6diaza-8,9 phospha(V)-5 spiro(4,4)nonene-7,8 (75386-16-2)

Conditions	Yield
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) + diethylazodicarboxylate (1972-28-7) → 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)

Conditions	Yield
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) + diethylazodicarboxylate (1972-28-7) → 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	Yield
In dichloromethane 10 min, 5 deg C, then room t., 24 h;	100%

triphenylphosphine (603-35-0) + diethylazodicarboxylate (1972-28-7) → diethylazodicarboxylate - triphenylphosphine (DEAD-Ph3P) (58477-00-2)

Conditions	Yield
In tetrahydrofuran Mechanism; other phosphine;	100%
In chloroform-d1
In tetrahydrofuran at 0℃; for 1h;

2-benzoylmethyleneimidazolidine (64944-80-5) + diethylazodicarboxylate (1972-28-7) → C17H22N4O5 (112030-72-5)

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

1-phenyl-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one (82100-30-9) + diethylazodicarboxylate (1972-28-7) → C18H24N4O5 (112030-74-7)

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

2-(p-chlorobenzoylmethylene)imidazolidine (107165-82-2) + diethylazodicarboxylate (1972-28-7) → C17H21ClN4O5 (112030-73-6)

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

1-(4-chlorophenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one (107165-83-3) + diethylazodicarboxylate (1972-28-7) → C18H23ClN4O5 (112030-75-8)

Conditions	Yield
In 1,4-dioxane for 48h; Ambient temperature;	100%

1-(4-methoxyphenyl)-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one (107165-84-4) + diethylazodicarboxylate (1972-28-7) → C19H26N4O6 (112030-76-9)

Conditions	Yield
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 + diethylazodicarboxylate (1972-28-7) → 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	Yield
In dichloromethane 10 min, 5 deg C, then room t., 24 h;	100%

1,1-dibenzoylpropane (59875-94-4) + diethylazodicarboxylate (1972-28-7) → diethyl N-(dibenzoylpropyl)hydrazine-N,N-dicarboxylate

Conditions	Yield
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) + diethylazodicarboxylate (1972-28-7) → (2-hydroxy-1-naphthyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

Conditions	Yield
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) + diethylazodicarboxylate (1972-28-7) → (1-hydroxy-4-naphthyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester

Conditions	Yield
With lithium perchlorate; bis(tri-n-butyltin)oxide In diethyl ether at 24.85℃;	100%

(2-methylpyridin-3-yl)methanol (56826-61-0) + diethylazodicarboxylate (1972-28-7) → tert-butyl (3S,4S)-4-[(hydroxyamino)carbonyl]-3-({4-[(2-methyl-3-pyridinyl)methoxy]benzoyl}amino)-1-piperidinecarboxylate trifluoroacetate (362488-31-1)

Conditions	Yield
With ammonium chloride; triphenylphosphine In tetrahydrofuran	100%

d5-ethanol + ethoxyphenylacetate + Methyl 4-hydroxyphenylacetate (14199-15-6) + diethylazodicarboxylate (1972-28-7) → 2-(2-ethoxyphenyl)ethanol (22545-14-8)

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; diethyl ether	100%

2-bromonicotinic acid (35905-85-2) + diethylazodicarboxylate (1972-28-7) → 2-bromonicotinic acid methyl ester (52718-95-3)

Conditions	Yield
With triphenylphosphine In methanol; diethyl ether	100%

Indole-6-carboxylic acid (1670-82-2) + diethylazodicarboxylate (1972-28-7) → 5-methoxycarbonylindole (1011-65-0)

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; methanol; dichloromethane	100%

Succinimide (123-56-8) + 3-t-butyldiphenylsilyloxy-1-(4-hydroxymethyl-1,3-thiazol-2-yl)azetidine (429666-52-4) + diethylazodicarboxylate (1972-28-7) → 3-t-butyldiphenylsilyloxy-1-(4-succinimidomethyl-1,3-thiazol-2-yl)azetidine

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; toluene	100%

cyclopenta-1,3-diene (542-92-7) + diethylazodicarboxylate (1972-28-7) → diethyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Conditions	Yield
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) + diethylazodicarboxylate (1972-28-7) → 1,2-bis(ethoxycarbonyl)-3-methyl-5-phenyl-2,3-dihydro-1H-1,2,4-triazole-3-carboxylic acid (1228801-83-9)

Conditions	Yield
In acetonitrile at 20℃; for 11h;	100%

2-Phenylpropanal (34713-70-7) + diethylazodicarboxylate (1972-28-7) → (R)-diethyl 1-(1-oxo-2-phenylpropan-2-yl)hydrazine-1,2-dicarboxylate

Conditions	Yield
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) + diethylazodicarboxylate (1972-28-7) → diethyl 1-(1-(dimethylamino)-3-oxo-3-(2,4-dichlorophenyl)prop-1-en-2-yl)hydrazine-1,2-dicarboxylate

Conditions	Yield
In toluene; acetonitrile at 20℃;	100%

carbon dioxide (124-38-9) + N,N-dimethyl-4-(3-methyl-3-(propylamino)but-1-yn-1-yl)aniline + diethylazodicarboxylate (1972-28-7) → diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(4-(dimethylamino)phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions	Yield
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) + 2-methyl-4-phenyl-N-propylbut-3-yn-2-amine + diethylazodicarboxylate (1972-28-7) → diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions	Yield
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) + C15H21NO + diethylazodicarboxylate (1972-28-7) → diethyl (Z)-1-((4,4-dimethyl-2-oxo-3-propyloxazolidin-5-ylidene)(4-methoxyphenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions	Yield
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) + N-benzyl-2-methyl-4-phenylbut-3-yn-2-amine + diethylazodicarboxylate (1972-28-7) → diethyl (Z)-1-((3-benzyl-4,4-dimethyl-2-oxooxazolidin-5-ylidene)(phenyl)methyl)hydrazine-1,2-dicarboxylate

Conditions	Yield
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) + 2-<2-N-(benzyloxycarbonyl)aminoethoxy>ethanol (145881-74-9) + diethylazodicarboxylate (1972-28-7) → {2-[2-(4-chloro-phenoxy)-ethoxy]-ethyl}-carbamic acid benzyl ester

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; hexane; ethyl acetate	99.8%

Upstream product

• 4114-28-7 diethyl hydrazodicarboxylate 
• 71-43-2 benzene 
• 817-87-8 ethyl azidocarbonate 
• 73240-57-0 4,7-Dimethyl-15-oxo-5,6-diphenyl-11,12-diazapentacyclo<8.2.2.1^4,7.0^2,9.0^3,8>pentadeca-5,13-dien-11,12-dicarbonsaeure-diethylester 
• 17696-93-4 diethyl 3-phenyltriazane-1,2-dicarboxylate 
• 7697-37-2 nitric acid 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 7726-95-6 bromine 
• 24009-91-4 (1R,2R,5S,6S)-7,8-Diaza-tricyclo[4.2.2.0^2,5]deca-3,9-diene-7,8-dicarboxylic acid diethyl ester 
• 622-08-2 2-Benzyloxyethanol 
• 2042-14-0 4-methyl-5-nitrophenol 
• 1316208-44-2 C₁₁H₁₈N₃O₆^(1-)*C₁₆H₃₆N⁽¹⁺⁾ 
• 5311-96-6 diethyl hydrazinedicarboxylate 

Downstream Products

• 10465-81-3 1,1'-(Azodicarbonyl)dipiperidin 
• 54660-01-4 (N-methyl-anilinomethyl)-hydrazine-N,N'-dicarboxylic acid diethyl ester 
• 298-12-4 Glyoxilic acid 
• 116838-28-9 2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide 
• 14011-60-0 diethyl 2,3-diazanorbornene-2,3-dicarboxylate 
• 2621-79-6 ethyl N-methyl-N-phenylcarbamate 
• 622-37-7 Phenyl azide 
• 5579-27-1 1,4-dimethyl-1,4-diphenyl-2-tetrazine 
• 687-48-9 ethyl N,N-dimethylcarbamate 
• 7249-39-0 diethyl 4,5-dimethyl-1,2,3,6-tetrahydro-1,2-pyridazincarboxylate 
• 17696-93-4 diethyl 3-phenyltriazane-1,2-dicarboxylate 
• 5311-96-6 diethyl hydrazinedicarboxylate 
• 106-51-4 p-benzoquinone 
• 16396-49-9 N-benzyl-N'-(ethoxycarbonyl)ethoxycarbohydrazide 

Relevant articles and documents

Synthesis and neuroprotective properties of isosteric analogs of nicotine

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.

Kinetic profiling of prolinate-catalyzed α-amination of aldehydes

Deconvolution of the role of off-cycle species from the desired catalytic cycle leads to an optimized protocol for the prolinate-catalyzed amination of aldehydes. The scope of complex reaction networks will be greatly broadened by understanding ancillary rate processes that influence the productive catalytic pathway.

METHOD FOR PRODUCING AZO COMPOUNDS

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 nitrite compounds, bromine compounds and a solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

METHOD FOR PRODUCING AZO COMPOUNDS

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

METHOD FOR PRODUCING AZO COMPOUNDS

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 groups of 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 vanadium or cerium compounds, and a solvent. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

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

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.

PROCESSES FOR THE PREPARATION OF HIGHLY PURE PRUCALOPRIDE SUCCINATE AND ITS INTERMEDIATES

Provided herein are purification processes for the preparation of highly pure prucalopride succinate salt. Provided also herein are improved, commercially viable and industrially advantageous processes for the preparation of Prucalopride and its intermediate compounds, for example, methyl 4-acetylamino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylate and alkyl 4-[[(4-amino-5-chloro-2,3-dihydro-7-benzofuranyl)carbonyl]-amino]-1-piperidinecarboxylate.

Method of manufacturing Azodicarboxylic acid diester compd. (by machine translation)

PROBLEM TO BE SOLVED: To provide a manufacturing method in which an azodicarboxylate diester compound can be efficiently obtained in a high yield and which is industrially advantageous.SOLUTION: There is provided a manufacturing method for azodicarboxylate diester compound including: a process (a) of obtaining a 1,2-hydrazine dicarboxylate diester compound through reaction between hydrazine and a halocarbonate ester; and a process (b) of obtaining an azodicarboxylate diester compound represented by general formula (2) (where A represents a hydrocarbon or a hydrocarbon which may have an ether bond) by oxidizing the 1,2-hydrazine dicarboxylate diester compound obtained in the process (a), the 1,2-hydrazine dicarboxylate diester compound being neither isolated nor refined.

Cu-Catalyzed Aerobic Oxidation of Di-tert-butyl Hydrazodicarboxylate to Di-tert-butyl Azodicarboxylate and Its Application on Dehydrogenation of 1,2,3,4-Tetrahydroquinolines under Mild Conditions

A new class of co-catalytic system was developed with homogeneous CuI and di-tert-butyl azodicarboxylate for aerobic dehydrogenation of 1,2,3,4-tetrahydroquinolines under mild conditions. The developed co-catalytic system is consisting of di-tert-butyl azodicarboxylate-mediated dehydrogenation of 1,2,3,4-tetrahydroquinoline and aerobic oxidative regeneration of di-tert-butyl azodicarboxylate from di-tert-butyl hydrazodicarboxylate using molecular oxygen as a terminal oxidant. A variety of quinolines were efficiently synthesized by the developed Cu and di-tert-butyl azodicarboxylate co-catalytic system.

Macroporous polystyrene-supported (diacetoxyiodo)benzene: An efficient heterogeneous oxidizing reagent

A heterogeneous, cross-linked macroporous polystyrene-supported (diacetoxyiodo) benzene reagent has been prepared. This reagent is completely insoluble in all solvents and has a rigid pore structure that allows it to function without the need for swelling. Its utility in a variety of oxidation reactions has been demonstrated. Georg Thieme Verlag Stuttgart.