3,3-Dimethylbutyraldehyde

3,3-Dimethylbutyraldehyde
Names
	Preferred IUPAC name 3,3-Dimethylbutanal
	Other names Neohexanal; 3,3-Dimethylbutyraldehyde; 3-Methylisovaleraldehyde; tert-Butylacetaldehyde;
Identifiers
CAS Number	2987-16-8;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.019.141
PubChem CID	76335;
UNII	CAM6HD7JKI;
CompTox Dashboard (EPA)	DTXSID60183984 ;
	InChI InChI=1S/C6H12O/c1-6(2,3)4-5-7/h5H,4H2,1-3H3 Key: LTNUSYNQZJZUSY-UHFFFAOYSA-N;
	SMILES CC(C)(C)CC=O;
Properties
Chemical formula	C6H12O
Molar mass	100.161 g·mol−1
Appearance	clear fluid
Odor	unpleasant
Density	0.798 g/cm3 (at 25 °C (77 °F))
Melting point	−297.1 °C; −502.9 °F; −24.0 K
Boiling point	−169 to −167 °C; −272 to −269 °F; 104 to 106 K
Solubility in water	7.6 g/L
Hazards
	GHS labelling:
Pictograms
Hazard statements	H225, H315, H319, H335
Precautionary statements	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). Infobox references

3,3-Dimethylbutyraldehyde is a branched saturated aliphatic aldehyde with a 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.^{[citation needed]}

References

^ ^a ^b Sigma-Aldrich Co., 3,3-Dimethylbutyraldehyd. Retrieved on 2020-12-18.
^ 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.

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).

[Sigma-1] Sigma-Aldrich Co., 3,3-Dimethylbutyraldehyd. Retrieved on 2020-12-18.

[prakash-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.

[2]

[1]

Names

Preferred IUPAC name 3,3-Dimethylbutanal
Other names Neohexanal 3,3-Dimethylbutyraldehyde 3-Methylisovaleraldehyde tert-Butylacetaldehyde
Identifiers
CAS Number	2987-16-8
3D model (JSmol)	Interactive image
ECHA InfoCard	100.019.141
PubChem CID	76335
UNII	CAM6HD7JKI
CompTox Dashboard (EPA)	DTXSID60183984
InChI InChI=1S/C6H12O/c1-6(2,3)4-5-7/h5H,4H2,1-3H3 Key: LTNUSYNQZJZUSY-UHFFFAOYSA-N
SMILES CC(C)(C)CC=O
Properties
Chemical formula	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	−297.1 °C; −502.9 °F; −24.0 K
Boiling point	−169 to −167 °C; −272 to −269 °F; 104 to 106 K
Solubility in water	7.6 g/L
Hazards^[1]
GHS labelling:
Pictograms
Hazard statements	H225, H315, H319, H335
Precautionary statements	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). Infobox references