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What Is DMAP (4-DMAP)?
DMAP (4-DMAP) (CAS 1122-58-3) is a nucleophilic catalyst with the molecular formula C7H10N2 and molecular weight 122.17 g/mol. [001]
Physical and Chemical Properties
| Property | Value | Source |
|---|---|---|
| CAS Number | 1122-58-3 | |
| Molecular Formula | C7H10N2 | |
| Molecular Weight | 122.17 g/mol |
How It Works
DMAP (4-DMAP) functions as a phase-transfer catalyst (PTC) by shuttling anionic reagents (nucleophiles, bases, oxidizing agents) from the aqueous or solid phase into the organic phase where the substrate resides. The quaternary ammonium cation forms an ion pair with the anionic reagent at the interface, and the lipophilic butyl groups (in TBAB) or cetyl/trimethyl groups (in CTAB) confer sufficient organic solubility to transport the ion pair into the bulk organic phase. Once in the organic phase, the 'naked' anion — free from strong hydration — exhibits dramatically enhanced nucleophilicity/basicity, accelerating the desired transformation by orders of magnitude. After reaction, the catalyst cation returns to the interface to complete the catalytic cycle. Key advantages over stoichiometric methods: lower reaction temperatures, shorter reaction times, and compatibility with aqueous workup. The efficiency depends on the partition coefficient of the ion pair between phases and the extraction constant at the interface.
Key Applications
- Steglich Esterification & Acylation Catalyst: DMAP accelerates acylation by 10,000x via the N-acyl-DMAP pyridinium intermediate — the most reactive acyl transfer species in common use. DCC/DMAP or EDC/DMAP (1.0 eq acid, 1.0-1.2 eq alcohol, 1.1 eq DCC, 0.1 eq DMAP, CH2Cl2, rt, 1-12 h). Enables esterification of sterically hindered secondary and tertiary alcohols at room temperature. [004]
- Silylation & Sulfonylation of Hindered Alcohols: DMAP (5-10 mol%) + Et3N catalyzes TBSCl and TIPSCl protection of sterically hindered secondary alcohols, neopentyl alcohols, and axial alcohols that are unreactive under standard imidazole/DMF conditions. Also essential for tosylation and mesylation of hindered substrates. [004]
- Baylis-Hillman & Morita-Baylis-Hillman Catalyst: DMAP catalyzes the Baylis-Hillman reaction (aldehyde + activated alkene -> alpha-hydroxyalkyl acrylate) with 10-20 mol% loading. DMAP's superior nucleophilicity (vs. DABCO) extends the scope to less activated Michael acceptors including acrylates and acrylamides. [005]
- Polymerization Catalyst: DMAP catalyzes ring-opening polymerization of L-lactide to poly(L-lactic acid) (PLLA). DMAP/benzyl alcohol initiator system produces PLLA with Mn 5,000-50,000 and narrow dispersity. Used for synthesizing biodegradable polymers for biomedical implants and sustainable packaging. [005]
Handling and Storage
- GHS Hazard: H302: Harmful if swallowed, H315: Causes skin irritation, H319: Causes serious eye irritation, H335: May cause respiratory irritation
- Signal Word: Danger
- Pictograms: GHS05, GHS06, GHS07
- Storage: Store at 2-8 °C or as recommended on the Certificate of Analysis. Keep container tightly closed in a cool, dry, well-ventilated area. Protect from moisture and incompatible materials (strong oxidizing agents, acids, bases). For long-term storage, keep under inert gas (N2 or Ar) if the compound is hygroscopic or oxygen-sensitive. Always consult the supplier's Safety Data Sheet (SDS) for lot-specific storage recommendations and shelf-life information.
- PPE: Nitrile gloves, safety goggles with side shields, lab coat, and closed-toe shoes. Work in a well-ventilated fume hood. Use respiratory protection (NIOSH-approved N95 or better) if handling large quantities or if the SDS indicates inhalation hazard. [002]
Always consult the Safety Data Sheet (SDS) from your supplier before handling. SDS documents are lot-specific — different purity grades and formulations may have different hazard classifications. For bulk handling, consult your institution's chemical hygiene plan and perform a job hazard analysis (JHA) before beginning work. Emergency procedures: in case of skin contact, wash immediately with soap and water for at least 15 minutes. For eye contact, rinse cautiously with water for several minutes and remove contact lenses if present. If inhaled, move to fresh air. Seek medical attention if symptoms persist.
Regulatory & Compliance
Chemical Inventories: DMAP (4-DMAP) (CAS 1122-58-3) is listed on major chemical inventories including the TSCA (Toxic Substances Control Act) inventory in the United States, EINECS (European Inventory of Existing Commercial Chemical Substances) in the EU, and similar inventories in Japan (ENCS), China (IECSC), Korea (KECL), and Australia (AICS). The specific regulatory status of CAS 1122-58-3 should be verified with the appropriate national authority before importing into any jurisdiction, as inventory listing status can change with regulatory updates and new chemical assessments.
GHS Classification: Refer to the Handling and Storage section above for the Globally Harmonized System hazard classification. The GHS classification is harmonized across most jurisdictions, but specific national implementations (EU CLP Regulation, US OSHA HazCom 2012, China GB 30000 series) may have additional requirements.
Transport Information: Verify the proper shipping name, UN number, hazard class, and packing group with your supplier before shipping. Transport regulations (IATA/ICAO for air, IMDG for sea, ADR/RID for road/rail in Europe, 49 CFR for US ground) may impose quantity limits, packaging requirements, and documentation obligations. Some compounds may be classified as dangerous goods requiring specialized handling and certified packaging.
Export Control: DMAP (4-DMAP) is a standard research and industrial chemical. However, always verify that no specific export control regulations apply to your destination country. Certain chemical categories (precursors, dual-use chemicals) may require export licenses under the Chemical Weapons Convention (CWC), Australia Group guidelines, or national export control laws. Contact your local trade compliance office for the most current regulatory guidance.
[004] [002]
Frequently Asked Questions
What is the CAS number of DMAP (4-DMAP)?
The CAS Registry Number is 1122-58-3. Always specify the CAS number when ordering to ensure correct compound identification regardless of naming conventions. [001]
What is the molecular weight of DMAP (4-DMAP)?
The molecular weight is 122.17 g/mol based on the molecular formula C7H10N2. Use this value to calculate molar equivalents, determine reaction stoichiometry, and prepare solutions of known concentration. [001]
What is DMAP (4-DMAP) used for?
DMAP (4-DMAP) is used for: Steglich Esterification & Acylation Catalyst (DMAP accelerates acylation by 10,000x via the N-acyl-DMAP pyridinium intermediat...); Silylation & Sulfonylation of Hindered Alcohols (DMAP (5-10 mol%) + Et3N catalyzes TBSCl and TIPSCl protection of sterically hind...); Baylis-Hillman & Morita-Baylis-Hillman Catalyst (DMAP catalyzes the Baylis-Hillman reaction (aldehyde + activated alkene -> alpha...). For detailed protocols, see the Key Applications section above. [002]
How should DMAP (4-DMAP) be stored?
Store at 2-8 °C or as recommended on the Certificate of Analysis. Keep container tightly closed in a cool, dry, well-ventilated area. Protect from moisture and incompatible materials (strong oxidizing agents, acids, bases). For long-term storage, keep under inert gas (N2 or Ar) if the compound is hygroscopic or oxygen-sensitive. Always consult the supplier's Safety Data Sheet (SDS) for lot-specific storage recommendations and shelf-life information.. Always consult the Safety Data Sheet (SDS) from your specific supplier for the most accurate storage recommendations. [002]
Where can I buy DMAP (4-DMAP)?
DMAP (4-DMAP) (CAS 1122-58-3) is available from CoreyChem. For bulk pricing, custom packaging, and a certificate of analysis, submit an inquiry to our sales team with your CAS number, required quantity, and desired purity. [003]
Where to Buy
DMAP (4-DMAP) is available in the CoreyChem catalog.
[View DMAP (4-DMAP) (CAS 1122-58-3) on CoreyChem →](https://careerchemical.com/product/1122-58-3) [003]
To request a quote, check bulk availability, or inquire about custom packaging for DMAP (4-DMAP), contact our sales team at [email protected] or submit an inquiry through our website. We respond to all inquiries within one business day with pricing and availability information tailored to your specific requirements.
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References & Sources
https://www.tcichemicals.com/US/en/search/?text=1122-58-3
https://pubchem.ncbi.nlm.nih.gov/compound/1122-58-3
https://pubchem.ncbi.nlm.nih.gov/compound/1122-58-3#section=Use-and-Manufacturing
