tert-Butyl (3-formylpyridin-4-yl)carbamate

Base Information

• Chemical Name: tert-Butyl (3-formylpyridin-4-yl)carbamate
• CAS No.: 116026-93-8
• Molecular Formula: C11H14N2O3
• Molecular Weight: 222.244
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID40356098
• Wikidata: Q72448421
• Mol file: 116026-93-8.mol

Synonyms:116026-93-8;tert-Butyl (3-formylpyridin-4-yl)carbamate;tert-Butyl 3-formylpyridin-4-ylcarbamate;Tert-butyl N-(3-formylpyridin-4-yl)carbamate;(3-FORMYL-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER;N-BOC-4-AMINO-3-FORMYLPYRIDINE;MFCD01860246;N-Boc-4-amino-3-pyridinecarboxyaldehyde;4-(Boc-amino)nicotinaldehyde;tert-Butyl(3-formylpyridin-4-yl)carbamate;SCHEMBL1197794;DTXSID40356098;UFWCFTNUYXZYKE-UHFFFAOYSA-N;4-(N-Boc-amino)-3-formylpyridine;AKOS015891767;CS-W005685;SB30938;4-(BOC-AMINO)-3-FORMYLPYRIDINE;tert-butyl-3-formylpyridin-4-ylcarbamate;AC-23043;DS-14729;n-boc-4-amino-3-pyridine carboxyaldehyde;SY109071;AM20050687;FT-0658947;EN300-67782;A803550;J-003369;J-524797;Z1083213942;4-[n-(tert-butyloxycarbonyl)amino]-3-pyridinecarboxaldehyde;4-AMINOPYRIDINE-3-CARBOXALDEHYDE, 4-BOC PROTECTED;Carbamic acid, N-(3-formyl-4-pyridinyl)-, 1,1-dimethylethyl ester

Chemical Property of tert-Butyl (3-formylpyridin-4-yl)carbamate

Chemical Property:

• Vapor Pressure: 0.000618mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 310 °C at 760 mmHg
• Flash Point: 141.3 °C
• PSA: 68.29000
• Density: 1.212 g/cm³
• LogP: 2.31410
• XLogP3: 1.4
• 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:

99% ^*data from raw suppliers

tert-Butyl3-Formylpyridin-4-ylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of tert-Butyl (3-formylpyridin-4-yl)carbamate

There total 5 articles about tert-Butyl (3-formylpyridin-4-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: 67.0%

N-(4-pyridyl) t-butyl carbamate (98400-69-2) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4--3-pyridinecarboxaldehyde (116026-93-8)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; pentane; 1.) -78 deg C, 15 min, -20 deg C, 1.5 h, 2.) -15 deg C to room temperature;

DOI:10.1021/jm00119a014

Reference yield: 63.0%

hydrogenchloride (7647-01-0,15364-23-5) + water (7732-18-5) → 4--3-pyridinecarboxaldehyde (116026-93-8)

Guidance literature:

N-(4-pyridyl) t-butyl carbamate; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - -20 ℃; for 1h;

N,N-dimethyl-formamide; In tetrahydrofuran; pentane; at -15 - 20 ℃; for 16h;

hydrogenchloride; water; In tetrahydrofuran; pentane;

Reference yield:

4-aminopyridine (504-24-5) → 4--3-pyridinecarboxaldehyde (116026-93-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / tetrahydrofuran / 1 h / Ambient temperature

2: 67 percent / 1.) tert-butyllithium / tetrahydrofuran; pentane / 1.) -78 deg C, 15 min, -20 deg C, 1.5 h, 2.) -15 deg C to room temperature

With tert.-butyl lithium; In tetrahydrofuran; pentane;

DOI:10.1021/jm00119a014

upstream raw materials:

N-(4-pyridyl) t-butyl carbamate

N,N-dimethyl-formamide

4-aminopyridine

di-tert-butyl dicarbonate

Downstream raw materials:

4-aminonicotinaldehyde

(Z)-methyl 2-(benzyloxycarbonylamino)-3-(4-(tert-butoxycarbonylamino)pyridin-3-yl)acrylate

8-vinyl-[1,6]naphthyridine-2-carboxylic acid 2-isopropoxy-benzylamide

8-bromo-[1,6]naphthyridine-2-carboxylic acid (2-isopropoxybenzylamide)

Refernces

• 1、 -. "SUBSTITUTED AZACHINAZOLINES HAVING AN ANTIVIRAL ACTION". Page/Page column 21. . Retrieved 2008/06/13.
• 2、 Venuti, Michael C.,Stephenson, Robert A.,Alvarez, Robert,Bruno, John J.,Strosberg, Arthur M.. "Inhibitors of Cyclic AMP Phosphodiesterase. 3. Synthesis and Biological Evaluation of Pyrido and Imidazolyl Analogues of 1,2,3,5-Tetrahydro-2-oxoimidazoquinazoline". . p. 2136 - 2145. Retrieved 2007/10/02.