{"product_id":"products-2-chloropyridine-3-boronic-acid-cas-381248-04-0","title":"2-Chloropyridine-3-boronic Acid | CAS 381248-04-0 | ≥98%","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;\"\u003e381248-04-0\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;\"\u003eEC \/ EINECS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e624-435-6\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;\"\u003eMFCD03094997\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;\"\u003eB(C1=C(N=CC=C1)Cl)(O)O\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\/C5H5BClNO2\/c7-5-4(6(9)10)2-1-3-8-5\/h1-3,9-10H\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;\"\u003eVRDAOVQZVXYRNH-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;\"\u003e2762704\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;\"\u003eC₅H₅BClNO₂\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;\"\u003e157.36 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;\"\u003e160 °C\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;\"\u003eSoluble in methanol, ethanol, DMSO, DMF, and dilute aqueous alkali; sparingly soluble in water at neutral pH\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≥98%. May contain varying amounts of the corresponding boronic acid anhydrides\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;\"\u003eWhite to off-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;\"\u003e2931.90\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\u003e2-Chloropyridine-3-boronic acid\u003c\/strong\u003e ((2-chloropyridin-3-yl)boronic acid) is an electron-deficient heteroaryl boronic acid bearing boron at the pyridine 3-position and chlorine at the adjacent 2-position. The two handles are orthogonal in reactivity, which is what the reagent is for.\u003c\/p\u003e\n\u003cp\u003eMay contain small amounts of the cyclic anhydride tris(2-chloropyridin-3-yl)boroxine. Under aqueous or basic coupling conditions the two forms re-equilibrate and the impact on yield is minor.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003ePosition and stability:\u003c\/strong\u003e boron at C-3 sits two bonds from the ring nitrogen, outside the arrangement that destabilises the 2-pyridyl isomer. 3- and 4-pyridylboronic acids survive heating under strongly basic conditions with a half-life over a week at pH 12 and 70 °C, whereas the 2-pyridyl isomer degrades in tens of seconds at neutral pH. The compound therefore couples directly without MIDA or trifluoroborate masking. As with other N-heteroaryl boronic acids, the Lewis-basic nitrogen can coordinate palladium and slow turnover, and bulky electron-rich biarylphosphines are the standard remedy on demanding substrates. The basic ring nitrogen is also protonated under acidic work-up, which complicates isolation.\u003c\/p\u003e\n\u003cp\u003e\u003cstrong\u003eApplications and Reactions\u003c\/strong\u003e\u003c\/p\u003e\n\u003cul\u003e\n\u003cli\u003e\n\u003cstrong\u003eSuzuki–Miyaura cross-coupling:\u003c\/strong\u003e installs the 2-chloropyridin-3-yl group onto aryl, heteroaryl and vinyl halides under Pd(PPh₃)₄ or Pd(dppf)Cl₂ with K₂CO₃ in aqueous dioxane. C–Cl bonds are less reactive than C–Br under palladium catalysis, so the boron couples in preference to the ring chloride.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eSequential functionalisation:\u003c\/strong\u003e the surviving 2-chloro substituent is a competent electrophile for palladium-catalysed amination, and 2-chloropyridines couple with primary and secondary amines under Buchwald–Hartwig conditions. Coupling at boron followed by amination at C-2 gives 2,3-disubstituted pyridines from a single reagent. Uncatalysed nucleophilic aromatic substitution is not a substitute here: 2-halopyridines without an additional electron-withdrawing group are poor SNAr substrates with amines.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eMedicinal-chemistry building block:\u003c\/strong\u003e the 3-pyridyl group is among the most common nitrogen heterocycles in approved drugs and a frequent phenyl bioisostere, raising aqueous solubility and adding a hydrogen-bond acceptor. The retained chloride allows late-stage diversification at C-2.\u003c\/li\u003e\n\u003cli\u003e\n\u003cstrong\u003eBoron surrogates:\u003c\/strong\u003e for demanding or iterative couplings the C-3 boron is also used as its pinacol ester, MIDA boronate or potassium trifluoroborate.\u003c\/li\u003e\n\u003c\/ul\u003e\n\u003cp\u003e\u003cstrong\u003eFurther Reading\u003c\/strong\u003e\u003c\/p\u003e\n\u003cp\u003eFor boronic acids, boronic esters, organotrifluoroborates, protodeboronation, boroxine content, and Suzuki–Miyaura reagent selection, see NorrChemica's Lab Journal guide: \u003ca href=\"https:\/\/www.norrchemica.com\/blogs\/lab-journal\/boron-reagent-selection-suzuki-miyaura-coupling\"\u003eChoosing Your Boron Source for Suzuki–Miyaura Coupling\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: Priority delivery, 2–5 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\u003eUnited States (DDP): 3–7 business days, duties and taxes prepaid.\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\u003eEFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.\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\u003eWorldwide: 7–14 business days, selected locations.\u003c\/li\u003e\n\u003c\/ul\u003e\u003c\/div\u003e\n\u003c\/div\u003e","brand":"NorrChemica™","offers":[{"title":"1 g","offer_id":53672692941137,"sku":"NOR-381248040-1g","price":29.2,"currency_code":"EUR","in_stock":true},{"title":"2 g","offer_id":53672692973905,"sku":"NOR-381248040-2g","price":43.2,"currency_code":"EUR","in_stock":true},{"title":"5 g","offer_id":53672693006673,"sku":"NOR-381248040-5g","price":57.2,"currency_code":"EUR","in_stock":true},{"title":"10 g","offer_id":53672693039441,"sku":"NOR-381248040-10g","price":94.2,"currency_code":"EUR","in_stock":true},{"title":"25 g","offer_id":53672693072209,"sku":"NOR-381248040-25g","price":179.2,"currency_code":"EUR","in_stock":true},{"title":"50 g","offer_id":54511296086353,"sku":"NOR-381248040-50g","price":309.9,"currency_code":"EUR","in_stock":true},{"title":"100 g","offer_id":54511296119121,"sku":"NOR-381248040-100g","price":589.9,"currency_code":"EUR","in_stock":true},{"title":"250 g","offer_id":54511296151889,"sku":"NOR-381248040-250g","price":1429.0,"currency_code":"EUR","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0954\/6357\/1793\/files\/NorrChemica_2-Chloropyridine-3-boronic_Acid_v2.png?v=1782773193","url":"https:\/\/www.norrchemica.com\/products\/products-2-chloropyridine-3-boronic-acid-cas-381248-04-0","provider":"NorrChemica","version":"1.0","type":"link"}