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tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate
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Name

tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate

 EINECS 631-555-2
CAS No. 198904-85-7 Density 1.117 g/cm3
PSA 63.25000 LogP 4.05970
Solubility N/A Melting Point 74-77 °C
Formula C17H21N3O2 Boiling Point N/A
Molecular Weight 299.373 Flash Point N/A
Transport Information N/A Appearance white solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 198904-85-7 (tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate) Hazard Symbols N/A
Synonyms

2-[[4-(2-Pyridinyl)phenyl]methyl]-hydrazinecarboxylic acid 1,1-dimethylethyl ester;

Article Data 16

tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate Synthetic route

198904-84-6

2-[4-(2-pyridinyl)phenyl]methylenehydrazinecarboxylic acid tert-butyl ester

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
With hydrogen; sodium carbonate; triethylamine; 5%-palladium/activated carbon at 40℃; under 760.051 Torr; for 8h;99.76%
With hydrogen; 5%-palladium/activated carbon at 5 - 58℃; under 1520.1 Torr; for 5 - 8h; Nitrogen;99.14%
With hydrogen; palladium on carbon In methanol under 517.162 Torr; for 4h;96.5%
198904-84-6

2-[4-(2-pyridinyl)phenyl]methylenehydrazinecarboxylic acid tert-butyl ester

A

4467-06-5

2-(4-methylphenyl)pyridine

B

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
With hydrogen; triethylamine; 5%-palladium/activated carbon at 40℃; under 760.051 Torr; for 5h;A 0.69%
B 99.17%
With hydrogen; sodium carbonate; 5%-palladium/activated carbon at 40℃; under 760.051 Torr; for 5h;A 0.25%
B 99.16%
With hydrogen; 5%-palladium/activated carbon In methanol at 50℃; under 760.051 Torr; for 5h;A 2.69%
B 97.11%
at 40 - 62℃; under 1520.1 Torr; for 5h; Hydrogen/nitrogen (1/2);A 0.1%
B 97.2%
With hydrogen; 5%-palladium/activated carbon at 5 - 58℃; under 1520.1 Torr; for 5 - 8h; Nitrogen gas;A 2.11%
B 94.41%
857904-11-1

N-(tert-butoxycarbonyl)-N'-[4-(pyridin-2-yl)phenylmethylidene]hydrazine

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
With hydrogen; palladium 10% on activated carbon In methanol for 4h;98%
With hydrogen; palladium 10% on activated carbon In methanol98%
With hydrogen; palladium on activated charcoal In methanol89%
198904-84-6

2-[4-(2-pyridinyl)phenyl]methylenehydrazinecarboxylic acid tert-butyl ester

A

N-(tert-butoxycarbonyl)-N'-[4-5 (pyridin-2-yl)phenylmethylidene]hydrazine

N-(tert-butoxycarbonyl)-N'-[4-5 (pyridin-2-yl)phenylmethylidene]hydrazine

B

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
palladium-carbon In n-heptane; hydrogenA n/a
B 84%
127406-56-8

2-(4-formylphenyl)pyridine

870-46-2

t-butoxycarbonylhydrazine

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
With borane pyridine; acetic acid In methanol at 0 - 20℃; for 2h;78%
109-04-6

2-bromo-pyridine

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) Mg, I2, 2.) <1,3-bis(diphenylphosphino)propane>nickel(II) chloride, diisobutylaluminum hydride, 3.) aq. HCl
2: 93 percent / ethanol / 4 h / Heating
3: 89 percent / H2 / 10percent Pd/C / methanol
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 150 °C / 6750.68 Torr / Sealed tube; Microwave irradiation
2: trimethylsilyl trifluoromethanesulfonate / toluene; isopropyl alcohol / 22 - 50 °C / Microwave irradiation; Sealed tube
3: palladium 10% on activated carbon; sodium formate / ethanol; water / 1.5 h / 57 °C
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 20 h / 76 °C / Inert atmosphere
2: toluene; isopropyl alcohol / 2 h / 80 - 85 °C / Inert atmosphere; Large scale
3: palladium 10% on activated carbon; sodium formate / water; ethanol / 1.5 h / 57 °C
View Scheme
Multi-step reaction with 3 steps
1: palladium diacetate; triphenylphosphine; potassium hydroxide / methanol; tetrahydrofuran / 24 h / 60 °C / Inert atmosphere; Schlenk technique
2: toluene; isopropyl alcohol / 16 h / 20 - 85 °C / Inert atmosphere; Schlenk technique
3: palladium 10% on activated carbon; sodium formate / ethanol; water
View Scheme
127406-56-8

2-(4-formylphenyl)pyridine

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / ethanol / 4 h / Heating
2: 89 percent / H2 / 10percent Pd/C / methanol
View Scheme
Multi-step reaction with 2 steps
1: toluene; isopropyl alcohol / 2 h / 80 - 85 °C / Inert atmosphere; Large scale
2: palladium 10% on activated carbon; sodium formate / water; ethanol / 1.5 h / 57 °C
View Scheme
Multi-step reaction with 2 steps
1: toluene; isopropyl alcohol / 16 h / 20 - 85 °C / Inert atmosphere; Schlenk technique
2: palladium 10% on activated carbon; sodium formate / ethanol; water
View Scheme
24856-58-4

1,1-dimethoxy-1-(4-bromophenyl)methane

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) Mg, I2, 2.) <1,3-bis(diphenylphosphino)propane>nickel(II) chloride, diisobutylaluminum hydride, 3.) aq. HCl
2: 93 percent / ethanol / 4 h / Heating
3: 89 percent / H2 / 10percent Pd/C / methanol
View Scheme
87199-17-5

4-formylphenylboronic acid,

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 150 °C / 6750.68 Torr / Sealed tube; Microwave irradiation
2: trimethylsilyl trifluoromethanesulfonate / toluene; isopropyl alcohol / 22 - 50 °C / Microwave irradiation; Sealed tube
3: palladium 10% on activated carbon; sodium formate / ethanol; water / 1.5 h / 57 °C
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol / 20 h / 76 °C / Inert atmosphere
2: toluene; isopropyl alcohol / 2 h / 80 - 85 °C / Inert atmosphere; Large scale
3: palladium 10% on activated carbon; sodium formate / water; ethanol / 1.5 h / 57 °C
View Scheme
Multi-step reaction with 3 steps
1: palladium diacetate; triphenylphosphine; potassium hydroxide / methanol; tetrahydrofuran / 24 h / 60 °C / Inert atmosphere; Schlenk technique
2: toluene; isopropyl alcohol / 16 h / 20 - 85 °C / Inert atmosphere; Schlenk technique
3: palladium 10% on activated carbon; sodium formate / ethanol; water
View Scheme
98760-08-8

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

198904-85-7

N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridine-2-yl)benzyl]hydrazine

198904-86-8

1-[4-(pyridine-2-yl)phenyl]-5(S)-2,5-bis[(tert-butyloxycarbonyl)amino]-4(S)-hydroxy-6-phenyl-2-azahexane

Conditions
ConditionsYield
In isopropyl alcohol for 24h; Inert atmosphere; Reflux; Large scale;85.4%
In isopropyl alcohol Heating / reflux;75%
In isopropyl alcohol for 16h; Heating;69%

tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate Chemical Properties

Product Name: Tert-butyl N-[(4-pyridin-2-ylphenyl)methylamino]carbamate (CAS NO.198904-85-7)

Molecular Formula: C17H21N3O2
Molecular Weight: 299.37g/mol
Mol File: 198904-85-7.mol
Appearance: White Solid
Density: 1.117 g/cm3
Surface Tension: 43.027 dyne/cm
XLogP3-AA: 2.8
H-Bond Donor: 2
H-Bond Acceptor: 4
Structure Descriptors of Tert-butyl N-[(4-pyridin-2-ylphenyl)methylamino]carbamate (CAS NO.198904-85-7):
  IUPAC Name: tert-butyl N-[(4-pyridin-2-ylphenyl)methylamino]carbamate
  Canonical SMILES: CC(C)(C)OC(=O)NNCC1=CC=C(C=C1)C2=CC=CC=N2
  InChI: InChI=1S/C17H21N3O2/c1-17(2,3)22-16(21)20-19-12-13-7-9-14(10-8-13)15-6-4-5-11-18-15/h4-11,19H,12H2,1-3H3,(H,20,21) 
  InChIKey: GIMJTKJSKPENNG-UHFFFAOYSA-N
Product Categories: API intermediates; Aromatics Compounds; Aromatics; Heterocycles 

tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate Specification

 Tert-butyl N-[(4-pyridin-2-ylphenyl)methylamino]carbamate , its CAS NO. is 198904-85-7, the synonyms are N-1-(tert-butoxycarbonyl)-N-2-[4-(pyridin-2-yl)benzyl]hydrazine ; tert-butyl 2-[4-(pyridin-2-yl)benzyl]hydrazinecarboxylate . 

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