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HomeProduct name listtert-Butyl nitrite

tert-Butyl nitrite

  • CAS NO.:540-80-7
  • Empirical Formula: C4H9NO2
  • Molecular Weight: 103.12
  • MDL number: MFCD00002055
  • EINECS: 208-757-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-24 19:19:26
tert-Butyl nitrite Structural

What is tert-Butyl nitrite?

Description

tert-Butyl nitrite is a common reagent used for diazotization, typically for Sandmeyer reactions. Isoamyl nitrite is used for similar purposes.

Chemical properties

clear yellow liquid

The Uses of tert-Butyl nitrite

tert-Butyl nitrite is employed as a reagent for diazotization and nitrosation of alcohols, thiols, amines and cycloalkanes. It plays an important role in photocatalyzed conversion of aryl and heteroarylamines to selenides. It finds application in the preparation of aryl azides from aryl amines. It is also useful for radical multifunctionalization reactions of aliphatic alkenes and source of nitric oxide.

The Uses of tert-Butyl nitrite

tert-Butyl nitrite
To ACN (350 mL) at RT was added CuBr2 (67 g, 300 mmol). The mixture was cooled to 0-5 C and was treated dropwise with t-BuONO (72.5 mL, 535 mmol). The mixture was stirred for 5 min, then was added the SM (35 g, 238 mmol). The reaction was stirred at RT for 2 h. EtOAc (525 mL) was added to the mixture and the reaction was quenched with 10% aq NH4Cl (350 mL) and 2% aq NH3 (175 mL). The layers were separated and the aq layer was extracted with EtOAc. The combined organics were dried and concentrated. The resulting material was purified by silica gel chromatography (eluting with 5% EtOAc/hexane) to provide the product as a yellow solid. [35 g, 70%]

The Uses of tert-Butyl nitrite

Jet propellant.

General Description

tert-Butyl nitrite (TBN) is an efficient NO source. TBN participates in photocatalyzed conversion of aryl- and heteroarylamines to selenides. It also participates in radical multifunctionalization reactions of aliphatic alkenes.

Purification Methods

If it is free from OH bands (IR) then distil it through a 12inch helices packed column under reduced pressure, otherwise wash with aqueous 5% NaHCO3 (effervescence), then H2O, dry (Na2SO4) and fractionate it through a 10 theoretical plates column at ca 10mm pressure. [Allen J Chem Soc 1968 1954, Coe & Doumani J Am Chem Soc 70 1516 1948, UV: Ungnade & Smiley J Org Chem 21 993 1956, IR: Terte Bull Soc Chim Belg 60 240 1951, Beilstein 1 IV 1622.]

Properties of tert-Butyl nitrite

Boiling point: 61-63 °C(lit.)
Density  0.867 g/mL at 25 °C(lit.)
vapor pressure  13.466kPa at 25℃
refractive index  n20/D 1.368(lit.)
Flash point: −10 °F
storage temp.  2-8°C
solubility  alcohol: very soluble(lit.)
form  Liquid
color  Clear yellow
Water Solubility  slightly soluble
Merck  14,1583
BRN  1209339
CAS DataBase Reference 540-80-7(CAS DataBase Reference)
NIST Chemistry Reference (CH3)3CONO(540-80-7)

Safety information for tert-Butyl nitrite

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H225:Flammable liquids
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P233:Keep container tightly closed.
P240:Ground/bond container and receiving equipment.
P241:Use explosion-proof electrical/ventilating/lighting/…/equipment.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

Computed Descriptors for tert-Butyl nitrite

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