MilliporeSigma
All Photos(5)

107700

Sigma-Aldrich

4-(Dimethylamino)pyridine

ReagentPlus®, ≥99%

Sign Into View Organizational & Contract Pricing

Select a Size

Synonym(s):
N,N-Dimethylpyridin-4-amine, DMAP
Empirical Formula (Hill Notation):
C7H10N2
CAS Number:
Molecular Weight:
122.17
Beilstein:
110354
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

product line

ReagentPlus®

Assay

≥99%

form

chips
crystalline powder
flakes

mp

108-110 °C (lit.)

solubility

H2O: 50 mg/mL

storage temp.

room temp

SMILES string

CN(C)c1ccncc1

InChI

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

InChI key

VHYFNPMBLIVWCW-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
PHR2925394058.20499
form

chips, crystalline powder, flakes

form

solid

form

crystals, pellets

form

solid

mp

108-110 °C (lit.)

mp

108-110 °C (lit.)

mp

108-110 °C (lit.), 111-114 °C

mp

110-112 °C

solubility

H2O: 50 mg/mL

solubility

-

solubility

methanol: 0.1 g/mL, clear, colorless to almost colorless

solubility

60 g/L

storage temp.

room temp

storage temp.

2-8°C

storage temp.

-

storage temp.

2-30°C

Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

General description

4-(Dimethylamino)pyridine (DMAP) is a highly versatile nucleophilic catalyst for acylation reactions and esterifications. It is also employed in various organic transformations like Baylis-Hillman reaction, Dakin-West reaction, protection of amines, C-acylations, silylations, applications in natural products chemistry, and many others.

Application

4-(Dimethylamino)pyridine can be used as a catalyst:
  • To synthesize 3,5-disubstituted 2,6-dicyanoaniline by reacting malononitrile, aldehydes, and β-nitroolefins.
  • For the acylation of alcohols with acid anhydrides under auxiliary base- and solvent-free conditions to synthesize corresponding esters.
  • In Baylis-Hillman reaction to form carbon-carbon bond by the coupling of an activated alkene with an aldehyde or ketone.
A highly efficient catalyst for acylation reactions

Legal Information

ReagentPlus 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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Customers Also Viewed

Akira Iida et al.
Organic letters, 8(23), 5215-5218 (2006-11-03)
[Structure: see text] A powerful Ti-crossed Claisen condensation between ketene silyl acetals (KSAs) and acid chlorides was successfully performed to give alpha-monoalkylated esters and thermodynamically unfavorable (less accessible) alpha,alpha-dialkylated beta-keto esters in good yield (46 examples; 41-98% yield). A closely
A M van Wijk et al.
Analytical and bioanalytical chemistry, 400(5), 1375-1385 (2011-03-30)
A generic LC-MS/MS method was developed for the analysis of potentially genotoxic alkyl halides. A broad selection of alkyl halides were derivatized using 4-dimethylaminopyridine in acetonitrile. The reaction conditions for derivatization, i.e., solvent, reaction time, temperature and concentration of alkyl
Capture and visualization of hydrogen sulfide by a fluorescent probe.
Chunrong Liu et al.
Angewandte Chemie (International ed. in English), 50(44), 10327-10329 (2011-09-08)
Min Suk Shim et al.
Journal of controlled release : official journal of the Controlled Release Society, 133(3), 206-213 (2008-11-11)
To maximize therapeutic effects, targeted delivery of nucleic acids (e.g., DNA and RNA) in their appropriate intracellular targets is highly desirable. In this study, primary amines of a model polymeric nonviral carrier, polyethylenimine (PEI), at two molecular weights (0.8 and
Hangxiang Wang et al.
Journal of the American Chemical Society, 133(31), 12220-12228 (2011-07-19)
Catalysts hold promise as tools for chemical protein modification. However, the application of catalysts or catalyst-mediated reactions to proteins has only recently begun to be addressed, mainly in in vitro systems. By radically improving the affinity-guided DMAP (4-dimethylaminopyridine) (AGD) catalysts

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service