51779-32-9

Basic information

• Product Name: Di-tert-butyl iminodicarboxylate
• Synonyms: (BOC)2NH FLUKA;Bis(tert-butoxycarbonyl)amine;IMINODICARBOXYLIC ACID DI-TERT-BUTYL ESTER;LABOTEST-BB LT00233154;DI-T-BUTYL IMINODICARBOXYLATE;DI-TERT-BUTYL IMINODICARBOXYLATE;DI-TERT-BUTYL IMIDODICARBONATE;N-BOC-TERT-BUTYLCARBAMATE
• CAS NO: 51779-32-9
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26
• EINECS: -0
• Product Categories: pharmacetical;Aliphatics;Amination;Synthetic Organic Chemistry
• Mol File: 51779-32-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 114-117 °C(lit.)
• Boiling Point: 273.821 °C at 760 mmHg
• Flash Point: 119.403 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.037 g/cm₃
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.442
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• PKA: 8.25±0.46(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Air & Light Sensitive
• BRN: 1911172
• CAS DataBase Reference: Di-tert-butyl iminodicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Di-tert-butyl iminodicarboxylate(51779-32-9)
• EPA Substance Registry System: Di-tert-butyl iminodicarboxylate(51779-32-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 51779-32-9(Hazardous Substances Data)

Usage

Description

Di-tert-butyl iminodicarboxylate, with the chemical formula [(CH3)3COC(O)]2NH, is an organic compound that exists as a white solid. It is soluble in organic solvents and is known for its role in the synthesis of primary amines from various starting materials.

Uses

Used in Pharmaceutical Synthesis:
Di-tert-butyl iminodicarboxylate is used as a reagent for the preparation of primary amines from alkyl halides. It serves as an alternative to the Gabriel synthesis, offering a different method for the same conversion. Additionally, amines can be prepared from alcohols by dehydration using the Mitsunobu reaction, where the reagent is deprotonated to form the potassium salt, followed by N-alkylation. The Boc protecting groups are then removed under acidic conditions.
Used in Organic Chemistry:
Di-tert-butyl iminodicarboxylate is utilized as a protected amine group in the synthesis of conformationally constrained spirocycles, which are known as CCR1 antagonists. These spirocycles have potential applications in the development of drugs targeting chemokine receptors, which play a role in various immune and inflammatory responses.
Chemical Properties:
Di-tert-butyl iminodicarboxylate is a white to beige crystalline powder, highlighting its solid state and appearance.

InChI:InChI=1/C10H19NO4/c1-9(2,3)14-7(12)11-8(13)15-10(4,5)6/h1-6H3,(H,11,12,13)

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 120-72-9 indole 
• 50624-94-7 oxalic acid tert-butyl ester ethyl ester 
• 78476-42-3 carbonyl isocyanate isothiocyanate 
• 75-65-0 tert-butyl alcohol 
• 77287-34-4 formamide 
• 89004-82-0 potassium bis(tert-butoxycarbonyl)amide 
• 89004-80-8 5-(2-bromoethylidene)-4-t-butoxyfuran-2(5H)-one 
• 92819-78-8 tert-butyl carbazate 
• 35454-04-7 oxalamic Acid Tert-butyl Ester 

Downstream Products

• 115269-99-3 N,N-bis(tert-butoxycarbonyl)allylamine 
• 96308-17-7 Benzyl N,N-di-Boc-glycinate 
• 845658-77-7 di(tert-butyl)-{6-[(4-{3-chloro-4-[(3-fluorobenzyl)oxy]anilino}-5-pyrimidinyl)ethynyl]-2-pyridinyl}methylimidodicarbonate 
• 130400-03-2 C₂₈H₃₃NO₅ 
• 130400-06-5 C₃₉H₅₅NO₆ 
• 894779-66-9 C₁₈H₂₆ClNO₆S 
• 894779-64-7 C₁₉H₂₉NO₅S 
• 146944-34-5 (4-benzylmorpholin-2-ylmethyl)carbamic acid tert-butyl ester 
• 876-03-9 3-(aminomethyl)benzoic acid hydrochloride 
• 52648-79-0 3-amino-butan-2-one 
• 134179-29-6 methyl-3-bromomethyl-5-bis(Boc)aminomethyl-benzoate 
• 198822-96-7 (N(COOC₄H₉)2)Au(P(C₆H₅)3) 
• 1115433-99-2 ethyl (E)-4-[[bis[(1,1-dimethylethoxy)carbonyl]amino]methyl]cinnamate 
• 1092540-88-9 C₃₁H₂₇F₃N₄O₃ 

Relevant articles and documents

Di-tert-butyl Ethynylimidodicarbonate as a General Synthon for the β-Aminoethylation of Organic Electrophiles: Application to the Formal Synthesis of Pyrrolidinoindoline Alkaloids (±)-CPC-1 and (±)-Alline

The reagent di-tert-butyl ethynylimidodicarbonate is demonstrated as a β-aminoethyl anion synthetic equivalent. It can be used to install ethyleneamine groups by exploiting its terminal alkyne reactivity with common organic electrophiles. Reactions exemplified with this terminal ynimide reagent include additions to imines, aldehydes, ketones, pyridinium salts, Michael acceptors, epoxides, and Pd-catalyzed Sonogashira couplings. Subsequent regioselective [3 + 2] cycloadditions of the alkynyl-imides (ynimides) generate N,N-di-Boc imide-functionalized triazole and isoxazole heterocycles. Reduction of the ynimides with Pd-catalyzed hydrogenation generates ethyleneimides with easily removable N,N-di-Boc-carbamate protecting groups, allowing for a flexible ynimide-based approach to ethyleneamine installation. The utility of this two-step aminoethylation strategy was demonstrated in the short formal syntheses of pyrrolidinoindoline alkaloids (±)-CPC-1 and (±)-alline. Analogously, the reagent (N,N,N′)-tri-Boc 2-ethynylhydrazine serves as a β-hydrazinoethyl anion synthetic equivalent.

Synthesis, Properties and Use of Nitridotricarbonic Acid Tri-tert-Butyl Ester

Exhaustive tert-butoxycarbonylation of Boc2NH with Boc2O-DMAP furnishes Boc3N in nearly quantitative yield.This stable compound is susceptible to nucleophiles and affords Boc2NH upon aminolysis.The properties of Boc3N have been exploited in a practical one-pot procedure for the synthesis of Boc2NH from NH4Cl, which is particularly economical in the preparation of Boc215NH.

Synthesis of Analogues of γ-Aminobutyric Acid. Part 11. Unsaturated and Saturated Tetronic Acid Derivatives

5-(2-Aminoethylidene)-4-hydroxyfuran-2(5H)-one (3) and the corresponding reduced 5-(2-aminoethyl) derivative (4) have been synthesised as conformationally restricted analogues of the neurotransmitter GABA.The use of the t-butyl protected reagents bis(t-butoxycarbonyl)amine and 5-ethylidene-4-t-butoxyfuran-2(5H)-one (7b) allowed generation of the required amino compounds under mild acidic deprotection conditions in the final step.