CAS 51779-32-9 Di-tert-butyl Iminodicarboxylate (HCID 279800)

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Basic information

CAS: 51779-32-9
Standard SMILES: CC(C)(C)OC(=O)NC(=O)OC(C)(C)C
InChIKey: XCAQIUOFDMREBA-UHFFFAOYSA-N
Molecular formula: C10H19NO4
Average molar mass: 217.26 g/mol
Monoisotopic mass: 217.13140809

Overview

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Names & identifiers

Preferred name: Di-tert-butyl Iminodicarboxylate
IUPAC: tert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate
English name: Di-tert-butyl iminodicarboxylate
Molecular formula: C10H19NO4
Molecular weight: 217.26

Names & synonyms

Di-tert-butyl IminodicarboxylateImidodicarbonic acid, bis(1,1-dimethylethyl) esterDTXSID70299500RefChem:586105DTXCID70250636672-427-651779-32-9Di-t-butyl iminodicarboxylateDi-tert-butyl-iminodicarboxylateBis(tert-butoxycarbonyl)amineMFCD00043309N-Boc-tert-butylcarbamate

Show more names

(BOC)2NHDBNHDi-Boc Amine(BOC)2NH FLUKAIminodicarboxyL

tert-Butyl iminodicarboxylatedi-tert-butyl imidodicarbonateDi-tert-butyliminodicarboxylatetert-butyl N-[(tert-butoxy)carbonyl]carbamatedi-tert-butyl iminodicarbonatetert-butyl N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate85M4Q7458HIminodicarboxylic Acid Di-tert-butyl Ester

Database identifiers

CAS: 51779-32-9
PubChem CID: 279800
DTXSID: DTXSID70299500
UNII: 85M4Q7458H
EC Number

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 64.6 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 15
Formal charge: 0
Complexity: 221

Physicochemical properties

Melting point: 114 · 114-117 °C(lit.)
Boiling point: 273.8 · 273.8±9.0 °C(Predicted)
Density: 1.037 · 1.037±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Chloroform, Methanol
pka: 8.25 · 8.25±0.46(Predicted)
form: Crystalline Powder
color: White to beige
Water Solubility: Insoluble in water.
Sensitive: Air & Light Sensitive
BRN: 1911172 · 1911172
InChI: InChI=1S/C10H19NO4/c1-9(2,3)14-7(12)11-8(13)15-10(4,5)6/h1-6H3,(H,11,12,13)
InChIKey: XCAQIUOFDMREBA-UHFFFAOYSA-N
SMILES: C(C)(C)(C)OC(=O)NC(=O)OC(C)(C)C
CAS DataBase Reference: 51779 · 51779-32-9(CAS DataBase Reference)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationImidodicarbonic acid, bis(1,1-dimethylethyl) ester: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 29241990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
hazard_note: Irritant
safety_code: 26-37/39
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements

Chemistry & industry

Applications · 2 items

UsesDi-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.

UsesDi-tert-butyl iminodicarboxylate is a protected amine group that is used to prepare conformationally constrained spirocycles as CCR1 antagonists.