2-isocyano-2-methylpropane

• ChemBase ID: 129762
• Molecular Formular: C5H9N
• Molecular Mass: 83.13166
• Monoisotopic Mass: 83.07349929
• SMILES: CC(C)(C)[N+]#[C-]
• Canonical SMILES: CC([N+]#[C-])(C)C
• InChI: InChI=1S/C5H9N/c1-5(2,3)6-4/h1-3H3
• InChIKey: FAGLEPBREOXSAC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-isocyano-2-methylpropane
• IUPAC Traditional name: tert-butyl isocyanide
• Synonyms: tert-Butyl isocyanide; t-BuNC; propanC; 2-isocyano-2-methyl; Tert-Butyl isocyanide; 叔丁基异氰酸酯; 叔丁基异腈

Database IDs

• CAS Number: 7188-38-7
• EC Number: 230-553-5
• MDL Number: MFCD00000002
• Beilstein Number: 1903156
• PubChem SID: 24855763; 162224051; 24851976
• PubChem CID: 23577
• Chemspider ID: 22045
• Wikipedia Title: Tert-Butyl_isocyanide

CALCULATED PROPERTIES

• Acid pKa: 16.183996
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -0.90444934
• LogD (pH = 7.4): -0.90444934
• Log P: -0.90444934
• Molar Refractivity: 35.3172 cm^3
• Polarizability: 10.279807 Å^3
• Polar Surface Area: 4.36 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: N/A in water
• Apperance: Colorless liquid
• Melting Point: ? °C
• Boiling Point: 90-92°C; 91 °C; 91 °C(lit.)
• Flash Point: -2 °C; -2°C(28°F); 28.4 °F
• Density: 0.735; 0.735 g/cm3, liquid; 0.735 g/mL at 25 °C(lit.)
• Refractive Index: 1.3755; n20/D 1.376; n20/D 1.376(lit.)

Safety Information

• RTECS: EQ7102500
• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: 1993; UN1992
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-23
• Safety Statements: 16-45; 9-20-36-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H330
• GHS Precautionary statements: P210-P260-P284-P310; P210-P303+P361+P353-P304+P340-P320-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Linear Formula: (CH3)3CNC

DETAILS

Sigma Aldrich - 260630

Packaging
1, 5 g in ampule
Application
Forms complexes with metals. Inserts into metal-carbon bonds to form iminoacyls.1 Used in the synthesis of isoxazolines2 and to trap 2-cyclopropylidene-1,3-diones.3

Sigma Aldrich - 20074

Other Notes
Reaction with organometallic reagents, a review1; Cyanation of acetals2

REFERENCES

• Useful intermediate in multicomponent reactions. For example, forms a reactive 1 : 1 adduct with acetylenic esters, e.g. Dimethyl acetylenedicarboxylate, A11437, which can be trapped with strong C-H acids, such as 4-Hydroxy-6-methyl-2-pyrone, L11457:
  
• In the presence of a free-radical initiator, can be used in a tin-free procedure for alkyl radical reactions: Angew. Chem. Int. Ed., 43, 3598 (2004).