Neopentylamine

Neopentylamine
Names
	IUPAC name 2,2-dimethylpropan-1-amine
Identifiers
CAS Number	5813-64-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	72173;
ECHA InfoCard	100.024.890
EC Number	227-378-1;
PubChem CID	79882;
UNII	988C7435J3;
CompTox Dashboard (EPA)	DTXSID4022232 ;
	InChI InChI=1S/C5H13N/c1-5(2,3)4-6/h4,6H2,1-3H3 Key: XDIAMRVROCPPBK-UHFFFAOYSA-N;
	SMILES CC(C)(C)CN;
Properties
Chemical formula	C5H13N
Molar mass	87.166 g·mol−1
Appearance	colorless liquid
Density	0.74 g/cm3
Melting point	−70 °C (−94 °F; 203 K)
Boiling point	80–82 °C (176–180 °F; 353–355 K)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant, Flammable, Corrosive
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H314
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P370+P378, P403+P235, P405, P501
Flash point	-13
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). (what is ?) Infobox references

Neopentylamine is an organic compound with the molecular formula (CH₃)₃CCH₂NH₂. It is a colorless liquid. The molecule is the primary amine derivative of neopentane, (CH₃)₄C.

Like most alkyl amines, it degrades slowly in air.^[1]

Synthesis

Neopentylamine is prepared by the reaction of neopentyl alcohol with ammonia in the presence of a hydrogenation catalyst.^[2]

Use

It is a common building block.^[3] For example, some experimental drugs incorporate this amine.^[4]^[5]

References

^ "Neopentylamine 5813-64-9 | Tokyo Chemical Industry UK Ltd". www.tcichemicals.com. Retrieved 2021-03-01.
^ US 4495369, Werner, Friedrich; Blank, Heinz U. & Gramm, Gunther et al., "Process for the preparation of neopentylamine", published 1985-01-22, issued 1981-09-22, assigned to Bayer AG
^ "Neopentylamine Safety Data Sheet". Fisher Scientific. Retrieved March 1, 2021.
^ Biamonte, Marco A.; Shi, Jiandong; Hong, Kevin; Hurst, David C.; Zhang, Lin; Fan, Junhua; Busch, David J.; Karjian, Patricia L.; Maldonado, Angelica A.; Sensintaffar, John L.; Yang, Yong-Ching; Kamal, Adeela; Lough, Rachel E.; Lundgren, Karen; Burrows, Francis J.; Timony, Gregg A.; Boehm, Marcus F.; Kasibhatla, Srinivas R. (2006). "Orally Active Purine-Based Inhibitors of the Heat Shock Protein 90". Journal of Medicinal Chemistry. 49 (2): 817–828. doi:10.1021/jm0503087. PMID 16420067.
^ Fraser, Robert R.; Mansour, Tarek S. (1984). "Acidity measurements with lithiated amines: Steric reduction and electronic enhancement of acidity". The Journal of Organic Chemistry. 49 (18): 3442–3443. doi:10.1021/jo00192a059.

[1] "Neopentylamine 5813-64-9 | Tokyo Chemical Industry UK Ltd". www.tcichemicals.com. Retrieved 2021-03-01.

[2] US 4495369, Werner, Friedrich; Blank, Heinz U. & Gramm, Gunther et al., "Process for the preparation of neopentylamine", published 1985-01-22, issued 1981-09-22, assigned to Bayer AG

[3] "Neopentylamine Safety Data Sheet". Fisher Scientific. Retrieved March 1, 2021.

[4] Biamonte, Marco A.; Shi, Jiandong; Hong, Kevin; Hurst, David C.; Zhang, Lin; Fan, Junhua; Busch, David J.; Karjian, Patricia L.; Maldonado, Angelica A.; Sensintaffar, John L.; Yang, Yong-Ching; Kamal, Adeela; Lough, Rachel E.; Lundgren, Karen; Burrows, Francis J.; Timony, Gregg A.; Boehm, Marcus F.; Kasibhatla, Srinivas R. (2006). "Orally Active Purine-Based Inhibitors of the Heat Shock Protein 90". Journal of Medicinal Chemistry. 49 (2): 817–828. doi:10.1021/jm0503087. PMID 16420067.

[5] Fraser, Robert R.; Mansour, Tarek S. (1984). "Acidity measurements with lithiated amines: Steric reduction and electronic enhancement of acidity". The Journal of Organic Chemistry. 49 (18): 3442–3443. doi:10.1021/jo00192a059.

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