tert-Butyl (2-formylpyridin-3-yl)carbamate

Base Information

• Chemical Name: tert-Butyl (2-formylpyridin-3-yl)carbamate
• CAS No.: 116026-99-4
• Molecular Formula: C11H14N2O3
• Molecular Weight: 222.244
• Hs Code.: 29339900
• European Community (EC) Number: 802-554-6
• DSSTox Substance ID: DTXSID00448089
• Wikidata: Q72479430
• Mol file: 116026-99-4.mol

Synonyms:116026-99-4;(2-Formyl-pyridin-3-yl)-carbamic acid tert-butyl ester;tert-Butyl (2-formylpyridin-3-yl)carbamate;Tert-butyl N-(2-formylpyridin-3-yl)carbamate;(2-Formyl-pyridin-3-yl)-carbamic acidtert-butyl ester;tert-butyl 2-formylpyridin-3-ylcarbamate;(2-Formylpyridin-3-yl)carbamic acid tert-butyl ester;Carbamic acid, (2-formyl-3-pyridinyl)-, 1,1-dimethylethyl ester;Carbamic acid, N-(2-formyl-3-pyridinyl)-, 1,1-dimethylethyl ester;Boc-3-aminopicolinaldehyde;3-tert-Butyroxcarbonylamine-pyridine-2-carboxaldehyde;SCHEMBL2083740;DTXSID00448089;AHTZIHDCJWVLKK-UHFFFAOYSA-N;AMY19191;MFCD04035594;AKOS015838202;AB16948;3-(Boc-amino)pyridine-2-carboxaldehyde;AS-71994;tert-butyl(2-formylpyridin-3-yl)carbamate;CS-0062512;FT-0677412;EN300-249553;A803552;2-Methyl-2-propanyl (2-formyl-3-pyridinyl)carbamate;Z1505704009;(2-Formyl-pyridin-3-yl)-carbamic acid tert-butyl ester, AldrichCPR

Chemical Property of tert-Butyl (2-formylpyridin-3-yl)carbamate

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 0.002mmHg at 25°C
• Melting Point: 79.4-79.6 °C
• Refractive Index: 1.58
• Boiling Point: 294.957 °C at 760 mmHg
• PKA: 12.42±0.70(Predicted)
• Flash Point: 132.186 °C
• PSA: 68.29000
• Density: 1.212 g/cm³
• LogP: 2.31410
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 222.10044231
• Heavy Atom Count: 16
• Complexity: 260

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl(2-Formylpyridin-3-yl)carbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22-36-43-36/37/38
• Safety Statements: 26-36/37-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=C(N=CC=C1)C=O

Technology Process of tert-Butyl (2-formylpyridin-3-yl)carbamate

There total 8 articles about tert-Butyl (2-formylpyridin-3-yl)carbamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

N-Formylpiperidine (2591-86-8) + (2-bromo-pyridin-3-yl)-carbamic acid tert-butyl ester (116026-98-3) → (2?formyl?pyridin?3?yl)?carbamic acid tert?butyl ester (116026-99-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -78 deg C, 1 h, 2.) -78 deg C to 0 deg C, 0 deg C, 1 h;

DOI:10.1021/jm00119a014

Reference yield: 43.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + (2-bromo-pyridin-3-yl)-carbamic acid tert-butyl ester (116026-98-3) → (2?formyl?pyridin?3?yl)?carbamic acid tert?butyl ester (116026-99-4)

Guidance literature:

(2-bromo-pyridin-3-yl)-carbamic acid tert-butyl ester; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

N,N-dimethyl-formamide; In tetrahydrofuran; at -78 - 0 ℃; for 1h;

Reference yield:

2-bromonicotinic acid (35905-85-2) → (2?formyl?pyridin?3?yl)?carbamic acid tert?butyl ester (116026-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / triethylamine, diphenyl phosphorazidate / 2 h / Heating

2: 90 percent / 1.) n-butyllithium / tetrahydrofuran; hexane / 1.) -78 deg C, 1 h, 2.) -78 deg C to 0 deg C, 0 deg C, 1 h

With n-butyllithium; diphenyl phosphoryl azide; triethylamine; In tetrahydrofuran; hexane;

DOI:10.1021/jm00119a014

upstream raw materials:

N-Formylpiperidine

(2-bromo-pyridin-3-yl)-carbamic acid tert-butyl ester

2-chloro-3-aminopyridine

(E)-2-styrylpyridin-3-amine

Downstream raw materials:

3-aminopyridine-2-carboxaldehyde