Synthesis of tert-Butyl nitrite

Preparation of tert-Butyl nitrite

Alternative Names: Tert-Butyl nitrite; 540-80-7; T-Butyl nitrite; Tert-butylnitrite; 1,1-Dimethylethyl nitrite; nitrous acid, t-butyl ester;

Preparation of tert-Butyl nitrite

Preparation of tert-Butyl nitrite

To the 500 ml flask fitted with a thermometer, a stirrer and a dropping funnel, 74 g of tert-butyl alcohol and a solution of 76 g sodium nitrite dissolved in 440 m of water are placed. The mixture is cooled to 0 °C and with stirring from the dropping funnel 90 ml of concentrated hydrochloric acid are added so that the solution temperature did not rise above 5 °C. When all hydrochloric acid has been added the solution is transferred to a separatory funnel and washed with 400 ml of water. The aqueous layer is discarded and the organic phase is washed with 5% sodium bicarbonate (3 X 50 ml), then with water (3 x 50 ml), dried with calcium chloride and distilled by collecting fraction boiling at 62-64 °C. Yield 62 g (60%), boiling point 63 °C. tert-Butyl nitrite is a yellow mobile liquid, readily soluble in organic solvents.

J. Am. Chem. Soc, 70, 1516-1519, (1948)

IUPAC Name

tert-butyl nitrite

InChI

InChI=1S/C4H9NO2/c1-4(2,3)7-5-6/h1-3H3

InChI Key

IOGXOCVLYRDXLW-UHFFFAOYSA-N

Canonical SMILES

CC(C)(C)ON=O

Depositor-Supplied Synonyms

tert-Butyl nitrite, 540-80-7, t-Butyl nitrite, tert-butylnitrite, 1,1-Dimethylethyl nitrite, NITROUS ACID, t-BUTYL ESTER, (CH3)3CONO, Nitrous Acid tert-Butyl Ester, CCRIS 2098, alpha,alpha-Dimethylethyl nitrite, IOGXOCVLYRDXLW-UHFFFAOYSA-N, EINECS 208-757-0, SBB007659, Nitrous acid, 1,1-dimethylethyl ester, BRN 1209339, t-butylnitrite, t-Butyinitrite, t-butyl-nitrite, tert.butylnitrite, tertbutyl nitrite, Tert-buty nitrite, tert butyl nitrite, tert-butyl-nitrite, tert.-butylnitrite, tert.-butyl nitrite, tertiary butyl nitrite, Tertiary-butyl nitrite, (tert-butyl)nitrosooxy, 2-methyl-2-propylnitrit, 2-methyl2-propyl nitrite, ACMC-1AZ9M, 2-methyl-2-propyl nitrite, AC1L1W7B, SCHEMBL27393, KSC269O4T, UNII-4780H7U8LU, 2-methyl-2-nitrosooxy-propane, 235385_ALDRICH, 2-Methyl-2-(nitrosooxy)propane, 20370_FLUKA, CTK1G9749, IOGXOCVLYRDXLW-UHFFFAOYSA-, EBD5877, MolPort-002-317-356, 4780H7U8LU, ACN-S002405, ACT08292, ANW-31948, ZINC03861664, .alpha.,.alpha.-Dimethylethyl nitrite, AKOS000121071, RP18809, RTC-064032, TRA0000122, AN-45744, CJ-10963, KB-61399, LS-96767, OR010879, SC-15268, TC-064032, FT-0632348, N0357, Nitrous acid, 1,1-dimethylethyl ester (9CI), 28090-EP2270011A1, 28090-EP2295411A1, 28090-EP2298767A1, 28090-EP2301918A1, 28090-EP2305769A2, 28090-EP2308833A2, 28090-EP2311815A1, 28090-EP2314588A1, 28090-EP2374788A1, 49758-EP2269993A1, 49758-EP2284157A1, 49758-EP2284159A1, 49758-EP2292228A1, 49758-EP2295411A1, 49758-EP2308833A2, 49758-EP2311825A1, 4-01-00-01622 (Beilstein Handbook Reference), A829951, I14-5867, 3B3-020416, InChI=1/C4H9NO2/c1-4(2,3)7-5-6/h1-3H3, 1,2-Dimercaptoethane; Dithioethyleneglycol; Ethylene mercaptan

Removed Synonyms

CID10906

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