4-Dimethylaminopyridine

4-Dimethylaminopyridine
Names
	IUPAC names N,N-Dimethylpyridin-4-amine; Dimethyl(pyridin-4-yl)azane; Dimethyl(pyridin-4-yl)amine
	Preferred IUPAC name N,N-Dimethylpyridin-4-amine
	Other names 4-(Dimethylamino)pyridine; N,N-Dimethyl-4-aminopyridine; DMAP; 4-Dimethylaminopyridine; 4-(Dimethylamino)azine; N,N-dimethyl-4-aminoazine; 4-(Dimethylamino)azabenzene; N,N-Dimethyl-4-aminoazabenzene
Identifiers
CAS Number	1122-58-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	13646 ;
ECHA InfoCard	100.013.049
PubChem CID	14284;
UNII	PFP1R6P0S8 ;
CompTox Dashboard (EPA)	DTXSID0044369 ;
	InChI InChI=1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3 Key: VHYFNPMBLIVWCW-UHFFFAOYSA-N ; InChI=1/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3 Key: VHYFNPMBLIVWCW-UHFFFAOYAL;
	SMILES n1ccc(N(C)C)cc1;
Properties
Chemical formula	C7H10N2
Molar mass	122.17 g/mol
Appearance	white solid
Melting point	110 to 113 °C (230 to 235 °F; 383 to 386 K)
Boiling point	162 °C (324 °F; 435 K) at 50 mmHg
Acidity (pKa)	9.6 in water, 17.95 (pKa of conjugate acid in acetonitrile)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H310, H315, H319, H335
Precautionary statements	P280, P305+P351+P338, P337+P313
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	deer mice: oral, 450 mg/kg; mice: oral, 350 mg/kg/day; rat: oral, 250 mg/mL; fly: oral, 0.15 mg/mL
Safety data sheet (SDS)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH₃)₂NC₅H₄N. This white solid is of interest because it is more basic than pyridine, owing to the resonance stabilisation from the NMe₂ substituent.

Because of its basicity, DMAP is a useful nucleophilic catalyst for a variety of reactions such as esterifications with anhydrides, the Baylis-Hillman reaction, hydrosilylations, tritylation, the Steglich rearrangement, Staudinger synthesis of β-lactams and many more. Chiral DMAP analogues are used in kinetic resolution experiments of mainly secondary alcohols and Evans auxiliary type amides.^[4]^[5]^[6]

^ Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales". J. Org. Chem. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.
^ ^a ^b ^c Sigma-Aldrich Co., 4-(Dimethylamino)pyridine. Retrieved on 2015-09-03.
^ ^a ^b ^c ^d Nachtergael, Amandine; Coulembier, Olivier; Dubois, Philippe; Helvenstein, Maxime; Duez, Pierre; Blankert, Bertrand; Mespouille, Laetitia (9 February 2015). "Organocatalysis Paradigm Revisited: Are Metal-Free Catalysts Really Harmless?". Biomacromolecules. 16 (2): 507–514. doi:10.1021/bm5015443. PMID 25490408.
^ Donald J Berry; Charles V Digiovanna; Stephanie S Metrick; Ramiah Murugan (2001). "Catalysis by 4-dialkylaminopyridines". Arkivoc: 201–226. Archived from the original on 2007-09-27. Retrieved 2006-11-27.
^ Höfle, G.; Steglich, W.; Vorbrüggen, H. (1978). "4-Dialkylaminopyridines as Highly Active Acylation Catalysts". Angew. Chem. Int. Ed. Engl. 17 (8): 569–583. doi:10.1002/anie.197805691.
^ Ryan P. Wurz (2007). "Chiral Dialkylamine Catalysts in Asymmetric Synthesis". Chem. Rev. 107 (12): 5570–5595. doi:10.1021/cr068370e. PMID 18072804.

[Kaljurand_2005_JOC-1] Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. (2005). "Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales". J. Org. Chem. 70 (3): 1019–1028. doi:10.1021/jo048252w. PMID 15675863.

[sigma-2] Sigma-Aldrich Co., 4-(Dimethylamino)pyridine. Retrieved on 2015-09-03.

[safety-3] Nachtergael, Amandine; Coulembier, Olivier; Dubois, Philippe; Helvenstein, Maxime; Duez, Pierre; Blankert, Bertrand; Mespouille, Laetitia (9 February 2015). "Organocatalysis Paradigm Revisited: Are Metal-Free Catalysts Really Harmless?". Biomacromolecules. 16 (2): 507–514. doi:10.1021/bm5015443. PMID 25490408.

[4] Donald J Berry; Charles V Digiovanna; Stephanie S Metrick; Ramiah Murugan (2001). "Catalysis by 4-dialkylaminopyridines". Arkivoc: 201–226. Archived from the original on 2007-09-27. Retrieved 2006-11-27.

[5] Höfle, G.; Steglich, W.; Vorbrüggen, H. (1978). "4-Dialkylaminopyridines as Highly Active Acylation Catalysts". Angew. Chem. Int. Ed. Engl. 17 (8): 569–583. doi:10.1002/anie.197805691.

[6] Ryan P. Wurz (2007). "Chiral Dialkylamine Catalysts in Asymmetric Synthesis". Chem. Rev. 107 (12): 5570–5595. doi:10.1021/cr068370e. PMID 18072804.

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