Di-tert-butyl Iminodicarboxylate

Base Information

• Chemical Name: Di-tert-butyl Iminodicarboxylate
• CAS No.: 51779-32-9
• Molecular Formula: C10H19NO4
• Molecular Weight: 217.265
• Hs Code.: 29241990
• European Community (EC) Number: 921-192-0,672-427-6
• NSC Number: 131088
• UNII: 85M4Q7458H
• DSSTox Substance ID: DTXSID70299500
• Nikkaji Number: J435.988G
• Wikipedia: Di-tert-butyl-iminodicarboxylate
• Wikidata: Q30715317
• Mol file: 51779-32-9.mol

Synonyms:Di-tert-butyl Iminodicarboxylate;51779-32-9;Di-t-butyl iminodicarboxylate;Di-tert-butyl-iminodicarboxylate;di-tert-butyl imidodicarbonate;tert-Butyl iminodicarboxylate;di-tert-butyl iminodicarbonate;tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate;Imidodicarbonic acid, bis(1,1-dimethylethyl) ester;N-Boc-tert-butylcarbamate;MFCD00043309;85M4Q7458H;di(tert-butyl) imidodicarbonate;UNII-85M4Q7458H;tert-butyl N-[(tert-butoxy)carbonyl]carbamate;NSC 131088;NSC-131088;(Boc)2NH Di-tert-butyl iminodicarboxylate;Iminodicarboxylic Acid Di-tert-butyl Ester;Di-tert-butyliminodicarboxylate;diboc amine;di-boc-amine;bis-Boc amine;Boc2NH;NSC131088;BIS(BOC)AMINE;tert-butyl N-tert-butoxycarbonylcarbamate;di(tert-butoxycarbonyl)amine;HN(BOC)2;Bis(tert-butoxycarbonyl)amine;SCHEMBL101218;di(t-butyl) iminodicarboxylate;di-tert.butyl-iminodicarboxylate;di-tert-butyl imino dicarboxylate;Di-tert-butyl iminodicarboxylate?;DTXSID70299500;BCP31758;CS-D0755;BBL102327;STL556127;AKOS015841493;bis(1,1-dimethylethyl)imidodicarbonate;AB01951;AC-6285;GS-3325;iminodicarboxylic acid di-t-butyl ester;bis(1,1-dimethylethyl) imidodicarbonate;BP-10429;Di-tert-butyl-iminodicarboxylate, >=96%;SY019086;A7621;AM20100269;FT-0627189;I0497;tert-butyl[(tert-butoxy)carbonylamino]formate;(BOC)2NH FLUKA;EN300-112207;(Boc)2-15NH;137052-25-6;IMIDODICARBOXYLIC ACID, DI-TERT-BUTYL ESTER;J-520401;1,3-BIS(1,1-DIMETHYLETHYL) IMIDODICARBONATE;F1905-7211;N-Boc-tert-butylcarbamate, tert-Butyl iminodicarboxylate

Chemical Property of Di-tert-butyl Iminodicarboxylate

Chemical Property:

• Appearance/Colour: white to faint yellow powder
• Vapor Pressure: 0.006mmHg at 25°C
• Melting Point: 114-117 °C
• Refractive Index: 1.442
• Boiling Point: 273.821 °C at 760 mmHg
• PKA: 8.25±0.46(Predicted)
• Flash Point: 119.403 °C
• PSA: 64.63000
• Density: 1.037 g/cm₃
• LogP: 2.83710
• Storage Temp.: 2-8°C
• Sensitive.: Air & Light Sensitive
• Solubility.: Chloroform, Methanol
• Water Solubility.: Insoluble in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 217.13140809
• Heavy Atom Count: 15
• Complexity: 221

Purity/Quality:

99%min ^*data from raw suppliers

Di-tert-butyl Iminodicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(=O)OC(C)(C)C
• Uses: Di-tert-butyl-iminodicarboxylate is an organic compound that can be described with the formula [(CH3)3COC(O)]2NH. It is a white solid that is soluble in organic solvents. The compound is used as a reagent for the preparation of primary amines from alkyl halides. It was popularized as an alternative to the Gabriel synthesis for the same conversion. Amines can also be prepared from alcohols by dehydration using the Mitsunobu reaction. In the usual implementation the reagent is deprotonated to give the potassium salt, which is N-alkylated. The Boc protecting groups are subsequently removed under acidic conditions. Di-tert-butyl iminodicarboxylate is a protected amine group that is used to prepare conformationally constrained spirocycles as CCR1 antagonists.

Technology Process of Di-tert-butyl Iminodicarboxylate

There total 10 articles about Di-tert-butyl Iminodicarboxylate 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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) → iminodicarboxylic acid di-tert-butyl ester (51779-32-9) + nitridotricarbonic acid tri-tert-butyl ester

Guidance literature:

With dmap; ammonium chloride; In acetonitrile; for 23h; Ambient temperature;

Reference yield: 91.0%

N,N,N-tri-tert-butyl iminotricarboxylate → iminodicarboxylic acid di-tert-butyl ester (51779-32-9)

Guidance literature:

With hydrazine hydrate; In methanol; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.joc.0c00781

Reference yield: 79.0%

indole (120-72-9) + C18H29NO8 → iminodicarboxylic acid di-tert-butyl ester (51779-32-9) + (3-Indolmethylen)malonsaeure-diethylester (10184-96-0)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); 2,2-bis[(4S)-4-isopropyloxazolin-2-yl]propane; In 1,4-dioxane; at 20 ℃; for 24h;

DOI:10.1002/cctc.201900575

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

oxalamic Acid Tert-butyl Ester

tert-butyl alcohol

tert-butyl carbazate

Downstream raw materials:

1-<(tert-butoxycarbonyl)amino>-2(E),4(E)-hexadiene

3--1-phenyl-1-propene

N,N-bis(tert-butoxycarbonyl)allylamine

tert-butyl N-(3-bromopropyl)-N-tert-butoxycarbonyl-carbamate

Refernces

• 1、 Tarasenko, Elena A.,Shestakov, Ivan V.,Rybakov, Victor B.,Beletskaya, Irina P.. "Enantioselective Copper(II)/Box-Catalyzed Synthesis of Chiral β3-Tryptophan Derivatives". . p. 3913 - 3918. Retrieved 2019/07/12.
• 2、 Grehn, Leif,Ragnarsson, Ulf. "A Convenient One-Flask Preparation of Di-t-butyl Iminodicarbonate: A Versatile Gabriel Reagent". . p. 275 - 276. Retrieved 2007/10/02.