4-(Boc-aminomethyl)pyridine

Base Information

• Chemical Name: 4-(Boc-aminomethyl)pyridine
• CAS No.: 111080-65-0
• Molecular Formula: C11H16 N2 O2
• Molecular Weight: 208.26
• Hs Code.: 29333990
• European Community (EC) Number: 601-040-7
• DSSTox Substance ID: DTXSID00363708
• Wikidata: Q82147455
• Mol file: 111080-65-0.mol

Synonyms:111080-65-0;4-(Boc-aminomethyl)pyridine;N-Boc-4-aminomethylpyridine;tert-Butyl (pyridin-4-ylmethyl)carbamate;4-[(tert-Butoxycarbonylamino)methyl]pyridine;tert-butyl N-(pyridin-4-ylmethyl)carbamate;tert-butyl N-[(pyridin-4-yl)methyl]carbamate;(pyridin-4-ylmethyl)carbamic acid tert-butyl ester;tert-butyl pyridin-4-ylmethylcarbamate;SCHEMBL481947;DTXSID00363708;AMY25008;N-Boc-4-aminomethylpyridine, 96%;MFCD07369734;AKOS009159200;s11724;tert-Butyl(pyridin-4-ylmethyl)carbamate;AS-64532;4-(t-butyloxycarbonylaminomethyl)-pyridine;4-(tert-butyloxycarbonylaminomethyl)pyridin;4-(tert-butyloxycarbonylaminomethyl)pyridine;tert-Butyl [(pyridin-4-yl)methyl]carbamate;4-(tert-butyloxycarbonylaminomethyl) pyridine;B2126;CS-0204397;FT-0687916;EN300-81017;J-002519;J-513653;Carbamic acid,N-(4-pyridinylmethyl)-,1,1-dimethylethyl ester

Chemical Property of 4-(Boc-aminomethyl)pyridine

Chemical Property:

• Vapor Pressure: 5.33E-05mmHg at 25°C
• Melting Point: 80-85 °C(lit.)
• Refractive Index: 1.507
• Boiling Point: 347.6ºC at 760 mmHg
• PKA: 11.44±0.46(Predicted)
• Flash Point: 164ºC
• PSA: 51.22000
• Density: 1.074g/cm3
• LogP: 2.49720
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 208.121177757
• Heavy Atom Count: 15
• Complexity: 205

Purity/Quality:

98%, ^*data from raw suppliers

N-Boc-4-aminomethylpyridine ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCC1=CC=NC=C1
• Uses: N-Boc-4-aminomethylpyridine is an intermediate in the synthesis of SGI-1776-d3 (S282382), and is a Boc derivative of 4-(Aminomethyl)pyridine. 4-(Aminomethyl)pyridine (A618090) is a compound that has derivatives that act as reversible inhibitors of various copper amine oxidases (CAOs).

Technology Process of 4-(Boc-aminomethyl)pyridine

There total 7 articles about 4-(Boc-aminomethyl)pyridine 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: 98.0%

4-(aminomethyl)pyridine (3731-53-1) + di-tert-butyl dicarbonate (24424-99-5) → (pyridin-4-ylmethyl)carbamic acid tert-butyl ester (111080-65-0)

Guidance literature:

With 3a,6a-diphenylglycoluril; In ethanol; at 25 - 30 ℃; for 0.5h;

DOI:10.1016/j.tet.2020.131223

Reference yield: 89.0%

C13H18NO4(1+)*C2H5O4S(1-) + 1,3-dioxoisoindolin-2-yl (tert-butoxycarbonyl)glycinate (91837-43-3) → (pyridin-4-ylmethyl)carbamic acid tert-butyl ester (111080-65-0)

Guidance literature:

C₁₃H₁₈NO₄⁽¹⁺⁾*C₂H₅O₄S^(1-); 1,3-dioxoisoindolin-2-yl (tert-butoxycarbonyl)glycinate; With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; In N,N-dimethyl acetamide; at 25 ℃; for 10h; Inert atmosphere; Irradiation;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 25 ℃; for 0.5h; regioselective reaction;

DOI:10.1039/d2ob00123c

Reference yield: 85.0%

4-(aminomethyl)pyridine (3731-53-1) + N-(tert-butyloxycarbonyl) azide (1070-19-5) → (pyridin-4-ylmethyl)carbamic acid tert-butyl ester (111080-65-0)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 30h; Ambient temperature;

upstream raw materials:

4-(aminomethyl)pyridine

N-(tert-butyloxycarbonyl) azide

di-tert-butyl dicarbonate

pyridine-4-carbonitrile

Downstream raw materials:

tert-butyl 2-hydroxy-2,2-diphenyl-1-(pyridin-4-yl)ethylcarbamate

1-benzyl-4-(((tert-butoxycarbonyl)amino)methyl)pyridin-1-ium bromide

tert-butyl ((1-benzyl-1,2,3,6-tetrahydropyridin-4-yl)methyl)carbamate

C₃₃H₃₇ClN₇O₈S₂⁽¹⁺⁾*I^(1-)

Refernces

• 1、 Elizarov, Arkadij M.,Chiu, Sheng-Hsien,Stoddart, J. Fraser. "An acid-base switchable [2]rotaxane". . p. 9175 - 9181. Retrieved 2002.
• 2、 Yang, Qifei,Olmsted, Courtney,Borhan, Babak. "Absolute stereochemical determination of chiral carboxylic acids". . p. 3423 - 3426. Retrieved 2002.
• 3、 Ingale, Ajit P.,Garad, Dnyaneshwar N.,Ukale, Dattatraya,Thorat, Nitin M.,Shinde, Sandeep V.. "Thiamine hydrochloride as a recyclable organocatalyst for the efficient and chemoselective N-tert-butyloxycarbonylation of amines". supporting information. p. 3791 - 3804. Retrieved 2021/11/04.