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Sigma-Aldrich

DMAP

4-(Dimethylamino)pyridine Novabiochem®

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Synonym(s):
DMAP, 4-Dimethylaminopyridine
Empirical Formula (Hill Notation):
C7H10N2
CAS Number:
1122-58-3
Molecular Weight:
122.17
MDL number:
MFCD00006418
UNSPSC Code:
12352005
EC Index Number:
214-353-5
NACRES:
NA.22

Quality Level

200

product line

Novabiochem®

Assay

≥99.0% (GC)

form

powder

autoignition temp.

420 °C

potency

140 mg/kg LD50, oral (Rat)
90 mg/kg LD50, skin (Rabbit)

reaction suitability

reaction type: Coupling Reactions

manufacturer/tradename

Novabiochem®

pH

11 (20 °C, 60 g/L in H2O)

bp

138-140 °C/24 hPa

mp

110-112 °C

transition temp

flash point 124 °C

bulk density

520 kg/m3

application(s)

peptide synthesis

storage temp.

2-30°C

InChI

1S/C7H10N2/c1-9(2)7-3-5-8-6-4-7/h3-6H,1-2H3/p+1

InChI key

VHYFNPMBLIVWCW-UHFFFAOYSA-O

Related Categories

General description

4-(Dimethylamino)pyridine (DMAP) is a catalyst for esterification and amidation reagents [1,2,3].

Literature references

[1] S. S. Wang, et al. (1981) Int. J. Peptide Protein Res., 18, 459.
[2] J.-P. Gamet, et al. (1984) Tetrahedron, 40, 1995.
[3] K. Takeda, et al. (1991) Synthesis, 1991, 689.

Application

  • Copolymerization of β‐butyrolactones using DMAP as initiator: This research focuses on the use of DMAP in the ring-opening polymerization of β‐butyrolactones, analyzing its efficiency as a catalyst (Palenzuela et al., 2024).
  • Halogen-Bond-Promoted Direct Cross-Coupling: This article details the use of DMAP in a catalytic process for the cross-coupling of alkyl bromides with coumarins, emphasizing its role under light illumination (Guo et al., 2024).
  • Enantiospecific Analysis of Carboxylic Acids: Discusses the superior efficacy of DMAP compared to other catalysts like Et3N in the enantiospecific analysis of carboxylic acids (Mo et al., 2024).

Linkage

Replaces: 01-62-0004

Analysis Note

Colour (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Solubility (1 mmole in 2 ml DMF): clearly soluble
Assay (GC, area%): ≥ 99.0 % (a/a)
Melting range (lower value): ≥ 110 °C
Melting range (upper value): ≤ 113 °C

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 1

Target Organs

Nervous system

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

255.2 °F

Flash Point(C)

124 °C

Certificates of Analysis (COA)

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