tert-butyl nitrite

• ChemBase ID: 80740
• Molecular Formular: C4H9NO2
• Molecular Mass: 103.11976
• Monoisotopic Mass: 103.06332853
• SMILES: O(N=O)C(C)(C)C
• Canonical SMILES: O=NOC(C)(C)C
• InChI: InChI=1S/C4H9NO2/c1-4(2,3)7-5-6/h1-3H3
• InChIKey: IOGXOCVLYRDXLW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl nitrite
• IUPAC Traditional name: 2-methyl-2-propylnitrit
• Synonyms: 2-Methyl-2-(nitrosooxy)propane; tert-Butyl nitrite; tert-Butyl nitrite; 亚硝酸叔丁酯

Database IDs

• CAS Number: 540-80-7
• EC Number: 208-757-0
• MDL Number: MFCD00002055
• Beilstein Number: 1209339
• Merck Index: 141583
• PubChem SID: 24854101; 162067860; 24852192
• PubChem CID: 10906

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.598058
• LogD (pH = 7.4): 1.598058
• Log P: 1.598058
• Molar Refractivity: 27.0096 cm^3
• Polarizability: 9.895207 Å^3
• Polar Surface Area: 38.66 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 61-63 °C(lit.); 61-63°C; 61-63°C
• Flash Point: -10 °C; 14 °F; -23°C; -23°C(-9°F)
• Density: 0.864 g/mL at 20 °C; 0.867; 0.867 g/mL at 25 °C(lit.)
• Refractive Index: 1.3690; n20/D 1.368; n20/D 1.368(lit.)

Safety Information

• Storage Warning: Highly Flammable/Harmful/Light Sensitive/Keep Cold
• RTECS: RA0802000
• European Hazard Symbols: Flammable (F); X; Harmful (Xn)
• UN Number: 2351; UN2351
• German water hazard class: 1
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-20/22
• Safety Statements: 16-24-46
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H332
• GHS Precautionary statements: P210; P210-P262-P301-P315-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 2351 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (GC); 90%; tech. 90%
• Grade: technical
• Impurities: ≤8% tert-butyl alcohol
• Linear Formula: (CH3)3CONO

DETAILS

Sigma Aldrich - 235385

Application
Reagent used with azidotrimethylsilane for the preparation of aryl azides from aryl amines.1
Other Notes
remainder 2-methyl-2-propanol
Packaging
25, 100 mL in glass bottle

Sigma Aldrich - 20370

Other Notes
Reagent for nitrosations, kinetics1; Clean source of Me3C radicals by near-UV photolysis2
Packaging
100, 500 mL in glass bottle

REFERENCES

• Reagent for non-aqueous nitrosation and diazotization reactions; cf Isopentyl nitrite, L13909, and Isobutyl nitrite, L05259.
• Aromatic amines have been converted in good yields to aryl halides in the presence of the Cu(II) halide: J. Org. Chem., 42, 2426 (1977); 45, 2570 (1980).