{"product_id":"dmap-1122-58-3","title":"4-Dimethylaminopyridine (DMAP) | CAS 1122-58-3 | ≥99%","description":"\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e  \u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: 700; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eTechnical Specifications\u003c\/h3\u003e\n\u003c\/div\u003e\n\u003ctable style=\"width: 100%; border-collapse: collapse; font-size: 0.95em; border: 1px solid #e4e8f0; border-top: none; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif;\"\u003e\u003ctbody\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eCAS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e1122-58-3\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eEC \/ EINECS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e214-353-5\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMDL Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eMFCD00006418\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eRTECS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eUS9230000\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eSMILES\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eCN(C)C1=CC=NC=C1\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eInChI\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eInChI=1S\/C7H10N2\/c1-9(2)7-3-5-8-6-4-7\/h3-6H,1-2H3\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eInChIKey\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eVHYFNPMBLIVWCW-UHFFFAOYSA-N\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePubChem CID\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e14284\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMolecular Formula\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eC₇H₁₀N₂\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMolecular Weight\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e122.17 g\/mol\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMelting Point\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e108–112 °C (lit.)\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eSolubility\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e~50 mg\/mL in water (25 °C); soluble in methanol, DCM, chloroform, acetone, ethyl acetate\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eLog P\u003csub\u003eow\u003c\/sub\u003e\n\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e1.34 (n-octanol\/water; ECHA registration dossier)\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePurity\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e≥99.0%\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePhysical Form\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eOff-white crystalline powder\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eHS Code\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e2933.39\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eCountry of Origin\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eFinland\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eShelf Life\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eRetest period: 36 months from date of manufacture.\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eStorage Conditions\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eStore in a cool, dry place in a tightly sealed container\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003c\/tbody\u003e\u003c\/table\u003e\n\u003c\/div\u003e\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e  \u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: 700; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eProduct Description \u0026amp; Scientific Applications\u003c\/h3\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"padding: 16px 20px; border: 1px solid #e4e8f0; border-top: none; font-family: Georgia, 'Times New Roman', serif; font-size: 0.95em; line-height: 1.65; color: #333;\"\u003e\n\u003cp\u003e\u003cstrong\u003e4-(Dimethylamino)pyridine (DMAP)\u003c\/strong\u003e is one of the most effective nucleophilic acylation catalysts in synthetic chemistry. Lone-pair donation from the 4-dimethylamino substituent stabilises positive charge in the N-acylpyridinium intermediate, making the pyridine nitrogen far more nucleophilic and basic than pyridine itself; in a representative benzoylation benchmark, DMAP gives approximately 10⁴-fold rate enhancement over both pyridine and triethylamine. The catalytic cycle in standard alcohol acylation proceeds through nucleophilic attack of DMAP on the acyl donor (anhydride, mixed anhydride, acid chloride, carbodiimide-activated carboxylic acid, or carbonate) to form an N-acylpyridinium \/ carboxylate ion pair, in which the counter-anion assists deprotonation of the incoming alcohol. The result is a system that efficiently transfers acyl, carbonate, carbamoyl, sulfonyl, and selected silyl groups to weakly nucleophilic or sterically encumbered substrates under mild, near-neutral conditions where pyridine alone is ineffective.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eSteglich esterification\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eDMAP is the catalytic component that makes the DCC-mediated Steglich procedure effective for ester formation. A carboxylic acid is first activated as the O-acylisourea by dicyclohexylcarbodiimide; DMAP then rapidly intercepts this intermediate to form a reactive N-acylpyridinium salt. This interception suppresses the principal failure mode of carbodiimide esterification — 1,3-acyl migration of the O-acylisourea to the unreactive N-acylurea — and enables high-yield esterification of hindered, acid-sensitive, or epimerisation-prone substrates with secondary and tertiary alcohols under mild conditions. The same activation mode underpins the routine use of DCC\/DMAP in fragment couplings during complex-molecule and natural-product total synthesis, particularly where strongly acidic, strongly basic, or high-temperature esterification conditions are excluded.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eYamaguchi macrolactonisation and mixed-anhydride esterification\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eIn the Yamaguchi protocol, the carboxylic acid is converted to a mixed anhydride with 2,4,6-trichlorobenzoyl chloride and tertiary amine base, then activated by DMAP for ester formation. In the classical mechanistic picture, DMAP attacks preferentially at the less hindered aliphatic acyl carbonyl of the mixed anhydride, generating the productive N-acylpyridinium intermediate while the bulky trichlorobenzoyl fragment functions as an activating auxiliary rather than the product acyl group. Mechanistic studies also indicate that in situ formation of symmetrical aliphatic anhydrides can participate, which explains why the transformation remains highly regioselective despite the mixed-anhydride manifold. Under high-dilution macrolactonisation conditions, this acyl-transfer chemistry enables intramolecular closure of seco-acids with suppressed oligomerisation, making DMAP central to medium- and large-ring lactone synthesis and hindered intermolecular esterification.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eProtecting-group installation\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eDMAP is the standard catalyst for acetylation and benzoylation of alcohols with anhydrides or acid chlorides, and for Boc protection of less nucleophilic or hindered nitrogen substrates — anilines, sulfonamides, indoles, and hindered secondary amines — with Boc₂O where the uncatalysed reaction is sluggish. It is also commonly used as an auxiliary catalyst in tosylation and mesylation of hindered alcohols with TsCl \/ MsCl, and in demanding silyl-protection workflows where Et₃N or imidazole alone are insufficient. In multifunctional substrates such as polyols, carbohydrates, nucleosides, and peptide intermediates, careful stoichiometry control with DMAP can favour acylation at the less hindered hydroxyl, although regioselectivity remains substrate-dependent. A real caveat is over-functionalisation: Boc₂O\/DMAP chemistry can generate di-Boc or N,N-bis-Boc products from amines and symmetrical dialkyl carbonates from aliphatic alcohols via carbonic–carbonic anhydride intermediates. Controlled acyl-donor equivalents, reaction time, and catalytic DMAP loading are therefore part of method design.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eRing-opening polymerisation of cyclic esters\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eDMAP is one of the foundational organocatalysts for living ring-opening polymerisation (ROP) of lactide. In representative bulk L-lactide systems using benzyl alcohol as initiator, DMAP functions as a transesterification catalyst and can deliver predictable degrees of polymerisation up to ~60 with dispersities below 1.2 under high-temperature bulk conditions; related lower-temperature bulk protocols are valid but show condition-dependent control. Mechanistic work shows that lactide ROP should not simply be mapped onto the ordinary acylpyridinium pathway of anhydride acylation. Instead, DMAP is best treated as a bifunctional catalyst in which the pyridine basic centre and an acidic ortho-CH cooperate in alcohol activation and cyclic-ester carbonyl organisation, making alcohol\/base activation more favourable than direct nucleophilic acylpyridinium formation. Related DMAP and aminopyridine organocatalyst platforms are used across lactide, lactone, carbonate, and O-carboxyanhydride polymerisation research where metal-free polyester or polycarbonate synthesis is required.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eOther Applications\u003c\/strong\u003e\u003c\/p\u003e\n\u003cul\u003e\n\u003cli\u003eSteglich-modified Dakin–West acylation chemistry for conversion of amino-acid derivatives to α-acylamino methyl ketones under mild conditions.\u003c\/li\u003e\n\u003cli\u003eSubstrate-specific Morita–Baylis–Hillman annulation of salicylaldehydes with acrylonitrile to 3-cyano-2H-chromenes, where DMAP can outperform DABCO in that defined substrate class.\u003c\/li\u003e\n\u003cli\u003eAsymmetric acyl transfer with chiral or planar-chiral DMAP analogues for kinetic resolution of secondary alcohols and amines.\u003c\/li\u003e\n\u003cli\u003eReference nucleophile and Lewis-base catalyst in Mayr-scale reactivity benchmarking and quantitative acyl-transfer kinetic studies.                                                    \u003c\/li\u003e\n\u003c\/ul\u003e\n\u003cp\u003e\u003cstrong\u003eFurther Reading\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eFor guidance on selecting between carbodiimides, aminium\/uronium salts, phosphonium salts, and other reagent classes for amide and peptide bond formation, see NorrChemica's Lab Journal guide: \u003ca href=\"https:\/\/www.norrchemica.com\/blogs\/lab-journal\/choosing-a-coupling-reagent-for-amide-and-peptide-bond-formation\"\u003eChoosing a Coupling Reagent for Amide and Peptide Bond Formation\u003c\/a\u003e.\u003c\/p\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e  \u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: 700; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eShipping Destinations\u003c\/h3\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"border: 1px solid #e4e8f0; border-top: none; padding: 12px 16px; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.95em;\"\u003e\u003cul style=\"margin: 0; padding: 0; list-style: none;\"\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eEU \u0026amp; UK only: 3–7 business days.\u003c\/li\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eClassified as dangerous goods — shipping restrictions apply outside the EU\/UK.\u003c\/li\u003e\n\u003c\/ul\u003e\u003c\/div\u003e\n\u003c\/div\u003e","brand":"NorrChemica™","offers":[{"title":"25 g","offer_id":52239556968785,"sku":"NOR-1122583-25g","price":30.0,"currency_code":"EUR","in_stock":true},{"title":"50 g","offer_id":52239557001553,"sku":"NOR-1122583-50g","price":43.0,"currency_code":"EUR","in_stock":true},{"title":"100 g","offer_id":52239385198929,"sku":"NOR-1122583-100g","price":69.0,"currency_code":"EUR","in_stock":true},{"title":"250 g","offer_id":52239385231697,"sku":"NOR-1122583-250g","price":125.0,"currency_code":"EUR","in_stock":true},{"title":"500 g","offer_id":52239557034321,"sku":"NOR-1122583-500g","price":196.0,"currency_code":"EUR","in_stock":true},{"title":"1 kg","offer_id":52239557067089,"sku":"NOR-1122583-1kg","price":349.0,"currency_code":"EUR","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0954\/6357\/1793\/files\/DMAP_NORRCHEMICA.png?v=1781395080","url":"https:\/\/www.norrchemica.com\/products\/dmap-1122-58-3","provider":"NorrChemica","version":"1.0","type":"link"}