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870-50-8

Basic Information
CAS No.: 870-50-8
Name: Di-tert-Butyl azodicarboxylate
Molecular Structure:
Molecular Structure of 870-50-8 (Di-tert-Butyl azodicarboxylate)
Formula: C10H18N2O4
Molecular Weight: 230.26
Synonyms: Diazenedicarboxylicacid, bis(1,1-dimethylethyl) ester (9CI);Formic acid, azodi-, di-tert-butylester (7CI,8CI);Azodicarboxylic acid di-tert-butyl ester;Bis(1,1-dimethylethyl)azodicarboxylate;DBAD;1,2-Diazenedicarboxylicacid, 1,2-bis(1,1-dimethylethyl) ester;Di-tert-butyl azodiformate;Di-tert-butyl diazodicarboxylate;NSC 109889;
EINECS: 212-796-9
Density: 1.06 g/cm3
Melting Point: 89-92 °C
Boiling Point: 287.1 °C at 760 mmHg
Flash Point: 107.2 °C
Solubility: insoluble in water
Appearance: yellow crystals or crystalline powder
Hazard Symbols: IrritantXi, FlammableF
Risk Codes: 36/37/38-11
Safety: 26-36-37/39-16
Transport Information:
PSA: 77.32000
LogP: 3.30880
Synthetic route
16466-61-8

1,2-bis(t-butyloxycarbonyl)hydrazine

870-50-8

di-tert-butyl-diazodicarboxylate

Conditions
ConditionsYield
With pyridine; bromine In dichloromethane at 0℃; for 0.25h;100%
With pyridine; bromine In dichloromethane at 0℃; for 1.5h; Inert atmosphere;92%
With pyridine; bromine In dichloromethane at 0℃; for 0.75h;87%
16466-61-8

1,2-bis(t-butyloxycarbonyl)hydrazine

28899-97-0

triphenylbismuth(V) diacetate

870-50-8

di-tert-butyl-diazodicarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 48h;
24424-99-5

di-tert-butyl dicarbonate

870-50-8

di-tert-butyl-diazodicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrazine hydrate / methanol / Inert atmosphere
2: pyridine; bromine / dichloromethane / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: hydrazine hydrate / methanol
2: pyridine; bromine / dichloromethane
View Scheme
Multi-step reaction with 2 steps
1: hydrazine hydrate / methanol / -10 - 20 °C
2: bromine; pyridine / dichloromethane / 0.5 h / 0 °C
View Scheme
24608-52-4

tert-butyl chloroformate

870-50-8

di-tert-butyl-diazodicarboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrazine / ethanol; water / 0.5 h / 10 - 20 °C
2: pyridine; bromine / dichloromethane / 1.5 h / 0 °C / Inert atmosphere
View Scheme
870-50-8

di-tert-butyl-diazodicarboxylate

542-92-7

cyclopenta-1,3-diene

39203-22-0

di-tert-butyl 2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 0℃;100%
In diethyl ether for 48h; Ambient temperature;94%
In dichloromethane Inert atmosphere;89%
In dichloromethane89%
In diethyl ether at 0℃; for 12h;
6165-69-1

Thien-3-ylboronic acid

870-50-8

di-tert-butyl-diazodicarboxylate

di-tert-butyl 1-(thiophen-3-yl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With copper diacetate; 4 A molecular sieve In methanol at 40℃; for 0.666667h;100%
870-50-8

di-tert-butyl-diazodicarboxylate

603-33-8

triphenylbismuthane

65578-58-7

di-tert-butyl 1-phenylhydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With copper diacetate; 1,1,1,3',3',3'-hexafluoro-propanol In acetonitrile at 75℃; for 0.25h;100%
504-60-9

penta-1,3-diene

870-50-8

di-tert-butyl-diazodicarboxylate

1072150-92-5

di-tert-butyl 3-methyl-1,2,3,6-tetrahydropyridazine-1,2-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; Diels-Alder reaction;100%
870-50-8

di-tert-butyl-diazodicarboxylate

7442-52-6, 125117-36-4

methyl 1-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylate

di-tert-butyl 1-(2-(methoxycarbonyl)-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With 3-(3,5-bis(trifluoromethyl)anilino)-4-([(1R,2R)-2-(piperidin-1-yl)cyclohexyl]amino)cyclobut-3-ene-1,2-dione In toluene at -20℃; for 28h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;100%
870-50-8

di-tert-butyl-diazodicarboxylate

84109-76-2

tert-butyl 2-oxocyclopentanecarboxylate

tert-butyl (S)-2-oxo-1-[N,N'-bis(tert-butoxycarbonyl)hydrazino]cyclopentanecarboxylate

Conditions
ConditionsYield
With 3-(3,5-bis(trifluoromethyl)anilino)-4-([(1R,2R)-2-(piperidin-1-yl)cyclohexyl]amino)cyclobut-3-ene-1,2-dione In toluene at 20℃; for 17h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;100%
870-50-8

di-tert-butyl-diazodicarboxylate

4553-07-5

ethyl phenylcyanoacetate

S-ethyl 2-cyano-2-N,N'-di(tert-butoxycarbonyl)hydrazino-phenylacetate

Conditions
ConditionsYield
With 2-[{(1R,2R)-2-(dimethylamino)cyclohexyl}amino]-8-fluoroquinazolin-4(1H)-one In toluene at -78℃; for 3h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;100%
870-50-8

di-tert-butyl-diazodicarboxylate

dibenzyl 2-(buta-3-en-1-yl)malonate

1618700-81-4

2-but-3-enyl-2-(N, N'-di-tert-butoxycarbonylhydrazino)malonic acid di-benzyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;100%
870-50-8

di-tert-butyl-diazodicarboxylate

173541-54-3

dibenzyl 2-allylmalonate

1618700-79-0

2-allyl-2-(N,N’-di-tert-butoxycarbonylhydrazino)malonic acid di-benzyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;100%

di-tert-butyl 2-(but-3-en-1-yl)malonate

870-50-8

di-tert-butyl-diazodicarboxylate

1618700-80-3

2-but-3-enyl-2-(N, N'-di-tert-butoxycarbonylhydrazino)malonic acid di-tert-butyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere;100%
870-50-8

di-tert-butyl-diazodicarboxylate

124-40-3

dimethyl amine

C12H25N3O4

Conditions
ConditionsYield
In acetonitrile at 20℃; for 2h; Inert atmosphere;100%
148-24-3

8-quinolinol

870-50-8

di-tert-butyl-diazodicarboxylate

di-tert-butyl 1-(8-hydroxyquinolin-7-yl)hydrazinyl-1,2-dicarboxylate

Conditions
ConditionsYield
Stage #1: 8-quinolinol With sodium hydride In tetrahydrofuran Inert atmosphere;
Stage #2: di-tert-butyl-diazodicarboxylate In tetrahydrofuran at -5 - 60℃; for 1.5h; Reagent/catalyst; Solvent; Time; Temperature; Inert atmosphere;
99.9%
870-50-8

di-tert-butyl-diazodicarboxylate

87895-02-1

7-methoxy-2,2-dimethyl-4-vinyl-2H-chromene

95334-16-0

3,4-bis(t-butoxycarbonyl)-8-methoxy-5,5-dimethyl-2,3,4,4a-tetrahydro-5H-chromeno<3,4-c>pyridazine

Conditions
ConditionsYield
In dichloromethane for 1h;99%
870-50-8

di-tert-butyl-diazodicarboxylate

156699-37-5

(S)-4-benzyl-3-(5-bromopentanoyl)oxazolidine-2-one

156699-38-6

(4S)-3-<(3S)-N,N'-bis(t-butoxycarbonyl)hexahydropyridazine-3-carboxy>-4-phenylmethyl-2-oxazolidinone

Conditions
ConditionsYield
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide at -78℃;99%
Stage #1: (S)-4-benzyl-3-(5-bromopentanoyl)oxazolidine-2-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.583333h; Inert atmosphere;
Stage #2: di-tert-butyl-diazodicarboxylate In tetrahydrofuran; hexane; dichloromethane at -78℃; for 4h; Inert atmosphere;
Stage #3: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran; hexane; dichloromethane at -78 - 20℃; Inert atmosphere;
63%
Multistep reaction;
With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetra-(n-butyl)ammonium iodide; lithium diisopropyl amide 1.) THF, -78 deg C, 2.) CH2Cl2; Yield given; Multistep reaction;
870-50-8

di-tert-butyl-diazodicarboxylate

542-92-7

cyclopenta-1,3-diene

2,3-diazabicyclo[2.2.1]hept-5-ene-N,N'-di-tert-butyl dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 16h; Diels-Alder reaction;99%
In dichloromethane at 20℃; for 12h;95%
In diethyl ether at 0℃;
870-50-8

di-tert-butyl-diazodicarboxylate

592-46-1

hexa-2,4-diene

1072150-91-4

di-tert-butyl cis-3,6-dimethyl-1,2,3,6-tetrahydropyridazine-1,2-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; Diels-Alder reaction;99%
In tetrachloromethane at -40 - 20℃; for 170h; Diels-Alder reaction;65%

3-ethoxycarbonylpyrrolidin-2,5-dione

870-50-8

di-tert-butyl-diazodicarboxylate

R-(-)-3-ethoxycarbonyl-3-(N,N'-di(tert-butoxycarbonyl)hydrazino)pyrrolidin-2,5-dione

Conditions
ConditionsYield
Stage #1: 3-ethoxycarbonylpyrrolidin-2,5-dione With lanthanum(III) isopropoxide; N,N-dimethyl acetamide In chloroform at 0 - 20℃; Inert atmosphere;
Stage #2: di-tert-butyl-diazodicarboxylate With air In chloroform at 0℃; for 1.5h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
99%
With (R)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide; lanthanum(III) nitrate hexahydrate; D-valine t-butyl ester In ethyl acetate at -40℃; for 24h; Diels amination; optical yield given as %ee;99 %Spectr.
Stage #1: 3-ethoxycarbonylpyrrolidin-2,5-dione With (R)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide; lanthanum(III) nitrate hexahydrate; D-valine t-butyl ester In ethyl acetate at 0℃; for 1h; Inert atmosphere; Large scale;
Stage #2: di-tert-butyl-diazodicarboxylate In ethyl acetate at 0 - 5℃; for 1h; Reagent/catalyst; Inert atmosphere; Large scale; enantioselective reaction;
n/a
1109280-48-9

1,3-di(tert-butoxycarbonyl)succinimide

870-50-8

di-tert-butyl-diazodicarboxylate

C24H39N3O10

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; Br(1-)*C46H38F12P(1+) In toluene at -20℃; for 40h; optical yield given as %ee; enantioselective reaction;99%
870-50-8

di-tert-butyl-diazodicarboxylate

84109-76-2

tert-butyl 2-oxocyclopentanecarboxylate

C20H34N2O7

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; Br(1-)*C46H38F12P(1+) In toluene at -40℃; for 16h; optical yield given as %ee; enantioselective reaction;99%
870-50-8

di-tert-butyl-diazodicarboxylate

375349-06-7

tert-butyl 2,3-dihydro-1-oxo-1H-indene-2-carboxylate

1068504-73-3

C24H34N2O7

Conditions
ConditionsYield
With Br(1-)*C42H42P(1+); potassium carbonate In toluene at 0℃; for 0.5h;99%
870-50-8

di-tert-butyl-diazodicarboxylate

375349-06-7

tert-butyl 2,3-dihydro-1-oxo-1H-indene-2-carboxylate

C24H34N2O7

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; Br(1-)*C46H38F12P(1+) In toluene at -20℃; for 14h; optical yield given as %ee; enantioselective reaction;99%
3036-66-6

1-methoxybuta-1,3-diene

870-50-8

di-tert-butyl-diazodicarboxylate

252984-42-2

di-tert-butyl 3-methoxy-1,2,3,6-tetrahydropyridazine-1,2-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h; Diels-Alder reaction;99%
870-50-8

di-tert-butyl-diazodicarboxylate

916600-70-9

2,2,2-trifluoroethyl α-methyl α-cyanoacetate

1180556-64-2

C16H24F3N3O6

Conditions
ConditionsYield
With 9-O-benzyl-6'-hydroxycinchonidine In toluene at -60℃; optical yield given as %ee; enantioselective reaction;99%
1109280-48-9

1,3-di(tert-butoxycarbonyl)succinimide

870-50-8

di-tert-butyl-diazodicarboxylate

C24H39N3O10

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; Br(1-)*C46H38F12P(1+) In toluene at -20℃; for 40h; optical yield given as %ee;99%
870-50-8

di-tert-butyl-diazodicarboxylate

84109-76-2

tert-butyl 2-oxocyclopentanecarboxylate

C20H34N2O7

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; Br(1-)*C46H38F12P(1+) In toluene at -40℃; for 16h; optical yield given as %ee;99%
870-50-8

di-tert-butyl-diazodicarboxylate

375349-06-7

tert-butyl 2,3-dihydro-1-oxo-1H-indene-2-carboxylate

(S)-di-tert-butyl 1-(2-(tert-butoxycarbonyl)-1-oxo-2,3-dihydro-1H-inden-2-yl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; Br(1-)*C46H38F12P(1+) In toluene at -20℃; for 14h; optical yield given as %ee;99%
870-50-8

di-tert-butyl-diazodicarboxylate

1190830-35-3

methyl 3-amino-2-(4-fluorophenyl)-3-oxopropanoate

1190830-46-6

(R)-di-tert-butyl 1-(1-amino-2-(4-fluorophenyl)-3-methoxy-1,3-dioxopropan-2-yl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
Stage #1: methyl 3-amino-2-(4-fluorophenyl)-3-oxopropanoate With (R)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide; lanthanum(III) nitrate hexahydrate; D-valine t-butyl ester In ethyl acetate at 0 - 20℃;
Stage #2: di-tert-butyl-diazodicarboxylate In ethyl acetate at 0℃; for 14h; optical yield given as %ee; enantioselective reaction;
99%
With (R)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide; lanthanum(III) nitrate hexahydrate; D-valine t-butyl ester; triethylamine In ethyl acetate at 23℃; for 10h; Kinetics; Reagent/catalyst; Concentration; Temperature; optical yield given as %ee; enantioselective reaction;> 99 %Spectr.
1190830-38-6

ethyl 3-amino-2-(4-nitrophenyl)-3-oxopropanoate

870-50-8

di-tert-butyl-diazodicarboxylate

1190830-49-9

(R)-di-tert-butyl 1-(1-amino-3-ethoxy-2-(4-nitrophenyl)-1,3-dioxopropan-2-yl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
Stage #1: ethyl 3-amino-2-(4-nitrophenyl)-3-oxopropanoate With (R)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide; lanthanum(III) nitrate hexahydrate; D-valine t-butyl ester In ethyl acetate at 0 - 20℃;
Stage #2: di-tert-butyl-diazodicarboxylate In ethyl acetate at 0℃; for 10h; optical yield given as %ee; enantioselective reaction;
99%
870-50-8

di-tert-butyl-diazodicarboxylate

1190830-41-1

ethyl 3-amino-2-(naphthalen-2-yl)-3-oxopropanoate

1190830-52-4

(R)-di-tert-butyl 1-(1-amino-3-ethoxy-2-(naphthalen-2-yl)-1,3-dioxopropan-2-yl)hydrazine-1,2-dicarboxylate

Conditions
ConditionsYield
Stage #1: ethyl 3-amino-2-(naphthalen-2-yl)-3-oxopropanoate With (R)-N-(2-hydroxyphenyl)-2-(2-hydroxybenzoylamino)-3-methylbutylamide; lanthanum(III) nitrate hexahydrate; D-valine t-butyl ester In ethyl acetate at 0 - 20℃;
Stage #2: di-tert-butyl-diazodicarboxylate In ethyl acetate at 0℃; for 18h; optical yield given as %ee; enantioselective reaction;
99%
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    Di-tert-Butyl azodicarboxylate

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    Di-tert-Butyl azodicarboxylate CAS NO.870-50-8

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  • Di-Tert-Butyl Azodicarboxylate

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    870-50-8

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    870-50-8

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    870-50-8

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    870-50-8

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    870-50-8

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    870-50-8

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  • CAS NO.:870-50-8

  • Casno:

    870-50-8

    CAS NO.:870-50-8

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    870-50-8

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Chemistry

The Molecular formula of Di-tert-Butyl azodicarboxylate(870-50-8): C10H18N2O4
The Molecular Weight of Di-tert-Butyl azodicarboxylate(870-50-8): 230.26
The Molecular Structure of Di-tert-Butyl azodicarboxylate(870-50-8): 
EINECS: 212-796-9
Melting point: 89-92 °C(lit.)
Boiling Point: 287.1 °C at 760 mmHg 
Flash Point: 107.2 °C 
Index of Refraction: 1.459 
Molar Refractivity: 59.17 cm
Molar Volume: 216.1 cm3 
Polarizability: 23.45×10-24 cm
Surface Tension: 32 dyne/cm 
Density: 1.06 g/cm3 
Enthalpy of Vaporization: 52.63 kJ/mol 
Vapour Pressure: 0.00253 mmHg at 25°C 
Storage temp.: 2-8°C
Water Solubility: Insoluble
Sensitive: Light Sensitive
BRN: 1911434
IUPAC Name: tert-butyl N-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate
Synonyms: Azodicarboxylic acid di-tert-butyl ester;DI-T-BUTYL AZODICARBOXYLATE;Di-tert-butyl azodicarboxylate 98%;Di-tert-butyl Azodicarboxylate (20% in Toluene);DI-TERT-BUTYL AZODICARBOXYLATE;Di-tert-B-butyl azodicarboxylate, 98%;1,2-Bis(tert-butoxycarbonyl)diazene;Di-Tert-ButylAzodicarboxylate(Dbad);

Safety Profile

The Hazard Codes of Di-tert-Butyl azodicarboxylate(870-50-8):   Xi,  F
Hazard Note: Irritant
The Hazard Codes of Di-tert-Butyl azodicarboxylate(870-50-8):
11:  Highly Flammable 
36/37/38:  Irritating to eyes, respiratory system and skin 
The Hazard Codes of Di-tert-Butyl azodicarboxylate(870-50-8):
16:  Keep away from sources of ignition - No smoking 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
37/39:  Wear suitable gloves and eye/face protection 
RIDADR: 1325
WGK Germany: 3