8.51055

DMAP

4-(Dimethylamino)pyridine Novabiochem^®

• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS05,GHS06,GHS08,GHS09
• Signal Word: Danger
• Hazard Statements: H301 + H331 - H310 - H315 - H318 - H370 - H411
• Precautionary Statements: P262 - P273 - P280 - P301 + P310 - P302 + P352 + P310 - P305 + P351 + P338
• 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