3,3-Dimethylbutyraldehyde

3,3-Dimethylbutyraldehyde
Names
Preferred IUPAC name
3,3-Dimethylbutanal
Other names
  • Neohexanal
  • 3,3-Dimethylbutyraldehyde
  • 3-Methylisovaleraldehyde
  • tert-Butylacetaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.141 Edit this at Wikidata
EC Number
  • 221-054-3
UNII
  • InChI=1S/C6H12O/c1-6(2,3)4-5-7/h5H,4H2,1-3H3
    Key: LTNUSYNQZJZUSY-UHFFFAOYSA-N
  • CC(C)(C)CC=O
Properties
C6H12O
Molar mass 100.161 g·mol−1
Appearance clear fluid[1]
Odor unpleasant
Density 0.798 g/cm3 (at 25 °C (77 °F))
Melting point −24 °C (−11 °F; 249 K)
Boiling point 104 to 106 °C (219 to 223 °F; 377 to 379 K)
7.6 g/L
Hazards[1]
GHS labelling:
GHS02: Flammable GHS07: Exclamation mark
H225, H315, H319, H335
P210, P302+P352, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3,3-Dimethylbutyraldehyde is a branched saturated aliphatic aldehyde with an unpleasant odor that is used in the synthesis of perfumes and neotame.[2]

Synthesis

It can be synthesized from 3,3-dimethyl-1-butanol via a copper catalyzed dehydrogenation.[3]

References

  1. ^ a b Sigma-Aldrich Co., 3,3-Dimethylbutyraldehyd. Retrieved on 2020-12-18.
  2. ^ Prakash, Indra; Bishay, Ihab; Schroeder, Steve (1 December 1999). "Neotame: Synthesis, Stereochemistry and Sweetness". Synthetic Communications. 29 (24): 4461-4467. doi:10.1080/00397919908086610. Retrieved 12 November 2021.
  3. ^ Tanielyan, Setrak K.; Augustine, Robert L. (2012-06-22). "Synthesis of 3,3-Dimethylbutanol and 3,3-Dimethylbutanal, Important Intermediates in the Synthesis of Neotame". Topics in Catalysis. 55 (7–10). Springer Science and Business Media LLC: 625–630. doi:10.1007/s11244-012-9841-z. ISSN 1022-5528.

Other sources

K. Satyavathi, P.B. Raju, K.V. Bupesh, T.N.R. Kiran (2010), "Mini Review. Neotame: High Intensity Low Caloric Sweetener", Asian J. Chem. 7 (22).


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