1,6-Bis(tert-butoxycarbonylamino)hexane

Base Information

• Chemical Name: 1,6-Bis(tert-butoxycarbonylamino)hexane
• CAS No.: 16644-54-5
• Molecular Formula: C16H32N2O4
• Molecular Weight: 316.441
• DSSTox Substance ID: DTXSID20383024
• Nikkaji Number: J1.407.547J
• Wikidata: Q82174569
• Mol file: 16644-54-5.mol

Synonyms:1,6-BIS(TERT-BUTOXYCARBONYLAMINO)HEXANE;16644-54-5;Tert-butyl N-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexyl]carbamate;Di-tert-butyl hexane-1,6-diyldicarbamate;starbld0018861;Hexamethylenedi-carbamic Acid Di-tert-butyl Ester;SCHEMBL343419;DTXSID20383024;AKOS027447338;FT-0663211;Hexane-1,6-diylbis(carbamic acid tert-butyl) ester;J-010285

Chemical Property of 1,6-Bis(tert-butoxycarbonylamino)hexane

Chemical Property:

• PSA: 83.64000
• LogP: 4.00500
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 316.23620751
• Heavy Atom Count: 22
• Complexity: 309

Purity/Quality:

97% ^*data from raw suppliers

1,6-Bis(tert-butoxycarbonylamino)hexane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCCCCNC(=O)OC(C)(C)C
• Uses: Protected 1,6-Diaminohexane.

Technology Process of 1,6-Bis(tert-butoxycarbonylamino)hexane

There total 8 articles about 1,6-Bis(tert-butoxycarbonylamino)hexane 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: 100.0%

1,6-Hexanediamine (124-09-4) + di-tert-butyl dicarbonate (24424-99-5) → N,N'-bis(tert-butoxycarbonyl)-1,6-hexanediamine (16644-54-5)

Guidance literature:

1,6-Hexanediamine; With triethylamine; at 20 ℃; for 0.5h; Inert atmosphere;

di-tert-butyl dicarbonate; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201103434

Reference yield: 85.0%

3-bromopropylamine tert-butylcarbamate (83948-53-2) → N,N'-bis(tert-butoxycarbonyl)-1,6-hexanediamine (16644-54-5)

Guidance literature:

With triethanolamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; [Ni(2,2′:6′,2''-terpyridine)(pyridine)(CH₃CN)₂](PF₆)₂; In acetonitrile; at 23 - 28 ℃; for 12h; Inert atmosphere; Sealed tube; Irradiation;

DOI:10.1021/acs.joc.6b02830

Reference yield: 79.0%

bromobenzene (108-86-1,52753-63-6) + 3-bromopropylamine tert-butylcarbamate (83948-53-2) → biphenyl (92-52-4,1594-86-1) + N,N'-bis(tert-butoxycarbonyl)-1,6-hexanediamine (16644-54-5) + propylcarbamic acid tert-butyl ester (105678-25-9) + N-tert-butoxycarbonyloxy-3-phenylpropylamine (147410-39-7) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-Dimethoxy-2,2'-bipyridin; NiI₂*3.5H₂O; sodium iodide; zinc; at 20 - 60 ℃; for 20h; chemoselective reaction;

DOI:10.1021/ja301769r

upstream raw materials:

tert-butyl alcohol

Hexamethylene diisocyanate

1,6-Hexanediamine

N-(tert-butyloxycarbonyl) azide

Downstream raw materials:

N,N'-dimethyl-1,6-hexanediamine

N,N'-dibenzyl-N,N'-di-Boc-1,6-diaminohexane

N,N'-dibenzylhexane-1,6-diammonium chloride

tert-butyl N-(6-aminohexyl)carbamate

Refernces

• 1、 -. "CHEMICAL BLOWING AGENT AND THERMALLY EXPANDABLE THERMOPLASTIC COMPOSITION". Page/Page column 30. . Retrieved 2016/07/05.
• 2、 Shirini, Farhad,Jolodar, Omid Goli,Seddighi, Mohadeseh,Borujeni, Hojatollah Takbiri. "Preparation, characterization and application of succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the N-Boc protection of amines". . p. 19790 - 19798. Retrieved 2015/03/18.