N-(3-Iodopyridin-4-yl)pivalamide

Base Information

• Chemical Name: N-(3-Iodopyridin-4-yl)pivalamide
• CAS No.: 113975-33-0
• Molecular Formula: C₁₀H₁₃IN₂O
• Molecular Weight: 304.131
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID50356049
• Nikkaji Number: J1.077.082C
• Wikidata: Q82135185
• Mol file: 113975-33-0.mol

Synonyms:113975-33-0;N-(3-Iodopyridin-4-yl)pivalamide;N-(3-Iodo-pyridin-4-yl)-2,2-dimethyl-propionamide;N-(3-iodopyridin-4-yl)-2,2-dimethylpropanamide;N-(3-IODO-4-PYRIIDINYL)-2,2-DIMETHYLPROPANAMIDE;3-IODO-4-(2,2,2-TRIMETHYLACETAMIDO)PYRIDINE;N-(3-iodo-4-pyridinyl)-2,2-dimethylpropanamide;PROPANAMIDE, N-(3-IODO-4-PYRIDINYL)-2,2-DIMETHYL-;SCHEMBL3899443;DTXSID50356049;AMY14068;MFCD04971323;AKOS015853819;AB20889;AC-25632;DS-15344;CS-0041086;FT-0677409;N-(3-iodo-4-pyridyl)-2,2-dimethyl-propanamide;A803115;AI-942/42301864;N-(3-Iodo-pyridin-4-yl)-2,2-dimethyl-propionamide, AldrichCPR

Chemical Property of N-(3-Iodopyridin-4-yl)pivalamide

Chemical Property:

• Vapor Pressure: 1.08E-06mmHg at 25°C
• Melting Point: 157.9-158.1°C
• Refractive Index: 1.614
• Boiling Point: 402.6°Cat760mmHg
• Flash Point: 197.3°C
• PSA: 41.99000
• Density: 1.623g/cm³
• LogP: 2.74380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Light Sensitive
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 304.00726
• Heavy Atom Count: 14
• Complexity: 213

Purity/Quality:

98%min ^*data from raw suppliers

N-(3-Iodo-pyridin-4-yl)-2,2-dimethyl-propionamide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of N-(3-Iodopyridin-4-yl)pivalamide

There total 1 articles about N-(3-Iodopyridin-4-yl)pivalamide 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:

4-N-pivaloylaminopyridine (70298-89-4) → 2,2-dimethyl-N-(3-iodo-4-pyridinyl)propanamide (113975-33-0)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodine; Yield given. Multistep reaction; 1.) THF, a) -75 deg C, 15 min, b) -10 deg C, 2 h, 2.) -75 deg C, 2 h;

DOI:10.1021/jo00247a016

Reference yield: 98.0%

2,2-dimethyl-N-(3-iodo-4-pyridinyl)propanamide (113975-33-0) → 3-iodopyridin-4-amine (88511-27-7)

Guidance literature:

With sulfuric acid; for 2h; Heating;

DOI:10.1021/jo0202031

Reference yield:

2,2-dimethyl-N-(3-iodo-4-pyridinyl)propanamide (113975-33-0) → (3-phenylethynyl-pyridin-4-yl)-pyridin-4-yl-carbodiimide

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / aq. sulfuric acid / 2 h / Heating

2: 89 percent / copper(I) iodide; N,N-diisopropylethylamine / Pd(PPh₃)2Cl₂ / dimethylformamide / 12 h / 20 °C

3: triethylamine / p-xylene / 70 °C

4: p-xylene / 50 °C

With copper(l) iodide; sulfuric acid; triethylamine; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In para-xylene; N,N-dimethyl-formamide; 4: aza-Wittig reaction;

DOI:10.1021/jo0202031

upstream raw materials:

4-N-pivaloylaminopyridine

Downstream raw materials:

3-iodopyridin-4-amine

4-amino-3-(2-phenylethynyl)pyridine

C₃₁H₂₃N₂P

2-methyl-1H-pyrrolo[3,2-c]pyridine

Refernces