Product Name

  • Name

    2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER

  • EINECS
  • CAS No. 198989-07-0
  • Article Data2
  • CAS DataBase
  • Density 1.105 g/cm3
  • Solubility
  • Melting Point 75-77 °C
  • Formula C10H18N2O2
  • Boiling Point 276.372 °C at 760 mmHg
  • Molecular Weight 198.265
  • Flash Point 120.946 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 198989-07-0 (2,5-DIAZA-BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID TERT-BUTYL ESTER)
  • Hazard Symbols
  • Synonyms 2-(tert-Butyloxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane;N-(tert-Butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane;tert-Butyl2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;
  • PSA 41.57000
  • LogP 1.23430

Synthetic route

2,5-diazabicyclo[2.2.1]heptane dihydrobromide

2,5-diazabicyclo[2.2.1]heptane dihydrobromide

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With triethylamine In methanol at -30 - 25℃;200 mg
1'-(5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro-[cyclopropane-1,3'-indoline]-6'-carboxylic acid

1'-(5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro-[cyclopropane-1,3'-indoline]-6'-carboxylic acid

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(1'-(5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro[cyclopropane-1,3-indolin]-6'-ylcarbonyl)-2,5-diazabicyclo-[2.2.1]heptane-2-carboxylate

tert-butyl 5-(1'-(5-(4-acetamidopyridin-2-yl)pyrimidin-2-yl)spiro[cyclopropane-1,3-indolin]-6'-ylcarbonyl)-2,5-diazabicyclo-[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In N,N-dimethyl-formamide at 23℃; for 16h;96.5%
Ethyl 4-bromobenzoate
5798-75-4

Ethyl 4-bromobenzoate

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(4-(ethoxycarbonyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(4-(ethoxycarbonyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 110℃; for 24h;92%
trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl-2-(trifluoroacetyl)-2,5-diazabicyclo[2.2.1]heptane-5-carboxylate

tert-butyl-2-(trifluoroacetyl)-2,5-diazabicyclo[2.2.1]heptane-5-carboxylate

Conditions
ConditionsYield
With triethylamine at 0 - 20℃; for 2.5 - 3.5h;87.2%
2-chloropyridine
109-09-1

2-chloropyridine

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(pyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With methanesulfonato(2-dicyclohexylphosphino-2’,6’-di-i-propoxy-1,1’-biphenyl)(2’-methylamino-1,1‘-biphenyl-2-yl)palladium(II); sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Sealed tube; Inert atmosphere;87%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(5-cyanopyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(5-cyanopyridin-2-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h;85%
3-(5-bromo-2-pyrimidinyl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine
651340-91-9

3-(5-bromo-2-pyrimidinyl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-{2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-{2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With potassium tert-butylate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 60℃;84%
9-ethyl-6,6-dimethyl-8-iodo-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

9-ethyl-6,6-dimethyl-8-iodo-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

C31H34N4O3

C31H34N4O3

Conditions
ConditionsYield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium hexamethyldisilazane In tetrahydrofuran; 1,4-dioxane at 60℃; Inert atmosphere;59%
7-chlorothiazolo[5,4-d]pyrimidin-5-amine
1211527-74-0

7-chlorothiazolo[5,4-d]pyrimidin-5-amine

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(5-aminothiazolo[5,4-d]pyrimidin-7-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
1435954-40-7

tert-butyl 5-(5-aminothiazolo[5,4-d]pyrimidin-7-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 3h;55.5%
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 55℃; for 3h;55.5%
4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

5-(4-nitrophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
877212-94-7

5-(4-nitrophenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
In acetonitrile at 100℃;52%
Stage #1: 4-Fluoronitrobenzene With potassium carbonate In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate In dimethyl sulfoxide at 70℃; for 5h;
[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid
1188374-41-5

[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

5-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester
1232028-17-9

5-{2-[(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetyl}-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.0333333h;
Stage #2: tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate In N,N-dimethyl-formamide at 20℃;		51%
3-bromo-6-chloro-imidazo[1,2-b]pyridazine
13526-66-4

3-bromo-6-chloro-imidazo[1,2-b]pyridazine

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(3-bromoimidazo[1,2-b]pyridazin-6-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
1400874-04-5

tert-butyl 5-(3-bromoimidazo[1,2-b]pyridazin-6-yl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 130℃; for 4h;49%
4-{[(2S,4R)-2-methyl-1-propionyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}benzoic acid

4-{[(2S,4R)-2-methyl-1-propionyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}benzoic acid

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(4-{[(2S,4R)-2-methyl-1-propionyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}benzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(4-{[(2S,4R)-2-methyl-1-propionyl-1,2,3,4-tetrahydroquinolin-4-yl]amino}benzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;49%
tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

2,3-dimethylbenzoic acid
603-79-2

2,3-dimethylbenzoic acid

5-(2,3-dimethylbenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

5-(2,3-dimethylbenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 17h;42%
2-Fluoro-4-(trifluoromethyl)benzaldehyde
89763-93-9

2-Fluoro-4-(trifluoromethyl)benzaldehyde

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

t-butyl 5-(2-formyl-5-(trifluoromethyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

t-butyl 5-(2-formyl-5-(trifluoromethyl)phenyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 80℃;34%
para-diiodobenzene
624-38-4

para-diiodobenzene

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

tert-butyl 5-(4-iodophenyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate
1197294-09-9

tert-butyl 5-(4-iodophenyl)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylate

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; 1,1'-bi-2-naphthol In N,N-dimethyl-formamide at 80 - 90℃;33%
3-fluoro-2-methylbenzoic acid
699-90-1

3-fluoro-2-methylbenzoic acid

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

5-(3-fluoro-2-methylbenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

5-(3-fluoro-2-methylbenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 17h;31.62%
2-(3-((7-(3-chloropropoxy)quinazolin-4-yl)amino)-1H-pyrazol-5-yl)-N-(3-fluorophenyl)acetamide
722544-46-9

2-(3-((7-(3-chloropropoxy)quinazolin-4-yl)amino)-1H-pyrazol-5-yl)-N-(3-fluorophenyl)acetamide

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

5-(3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1H-pyrazol-3-yl)amino)quinazolin-7-yl)oxy)propyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

5-(3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1H-pyrazol-3-yl)amino)quinazolin-7-yl)oxy)propyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide at 60℃;29%
1-Bromo-2-chloroethane
107-04-0

1-Bromo-2-chloroethane

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
198989-07-0

tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

5-(2-chloroethyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

5-(2-chloroethyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 20℃; for 17h;24.71%

2,5-Diazabicyclo[2.2.1]heptane-2-carboxylicacid tert-butyl ester Specification

The 2,5-Diazabicyclo[2.2.1]heptane-2-carboxylicacid, 1,1-dimethylethyl ester, with the CAS registry number 198989-07-0, has the systematic name tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate. Its molecular formula is C10H18N2O2 and its molecular weight is 198.26. Moreover, it's also named as N-Boc-2,5-diaza-bicyclo[2.2.1]heptane.

Physical properties about 2,5-Diazabicyclo[2.2.1]heptane-2-carboxylicacid, 1,1-dimethylethyl ester are: (1)ACD/LogP: 0.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.22; (4)ACD/LogD (pH 7.4): -0.55; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 4.38; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 32.78 Å2; (13)Index of Refraction: 1.5; (14)Molar Refractivity: 52.84 cm3; (15)Molar Volume: 179.4 cm3; (16)Polarizability: 20.94×10-24cm3; (17)Surface Tension: 37.3 dyne/cm; (18)Density: 1.104 g/cm3; (19)Flash Point: 120.9 °C; (20)Enthalpy of Vaporization: 51.49 kJ/mol; (21)Boiling Point: 276.4 °C at 760 mmHg; (22)Vapour Pressure: 0.00482 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(C)(C)C)N1CC2NCC1C2
(2)InChI: InChI=1/C10H18N2O2/c1-10(2,3)14-9(13)12-6-7-4-8(12)5-11-7/h7-8,11H,4-6H2,1-3H3
(3)InChIKey: UXAWXZDXVOYLII-UHFFFAOYAY
(4)Std. InChI: InChI=1S/C10H18N2O2/c1-10(2,3)14-9(13)12-6-7-4-8(12)5-11-7/h7-8,11H,4-6H2,1-3H3
(5)Std. InChIKey: UXAWXZDXVOYLII-UHFFFAOYSA-N

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