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transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lit_pub_bo_277"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"N1=CC=CC2=CC=CC(N)=C12"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"578-66-5"}],"amount":{"moles":{"value":0.03,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1CCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-99-9"}],"amount":{"volume":{"value":2.5,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=CC=1C=CC=CC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas 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product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz, CDCl3): δ 10.54 (s, 1H), 7.95 (d, J = 6.8 Hz, 1H), 7.85 (d, J = 6.8 Hz, 1H), 7.54-7.61 (m, 3H), 1.39 (s, 12H). 13C NMR (100 MHz, CDCl3): δ 194.8, 141.4, 135.6, 133.1, 130.9, 128.0, 84.6, 25.0. 11B NMR (128 MHz, CDCl3): δ 33.5."}}}}}],"provenance":{"doi":"10.1021/jacs.5b11683"}}},"entities":[{"slug":"benzaldehyde","name":"Benzaldehyde","smiles":"C1=CC=C(C=C1)C=O","inchi":"InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H","formula":"C7H6O"},{"slug":"ord-compound-1ab8be221383d6507421","name":"C13H17BO3 · ORD SLJMPQLPRHIAOM-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2ccccc2C=O)OC1(C)C","inchi":"InChI=1S/C13H17BO3/c1-12(2)13(3,4)17-14(16-12)11-8-6-5-7-10(11)9-15/h5-9H,1-4H3","formula":"C13H17BO3"}],"dataset":{"dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","name":"Borylation dataset from Roche","description":"Borylation reactions which were extracted from the literature by Roche scientists and published in the SURF 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Experimental record data adapted under CC BY-SA 4.0; https://creativecommons.org/licenses/by-sa/4.0/"},"license":"CC-BY-SA-4.0","license_url":"https://creativecommons.org/licenses/by-sa/4.0/","attribution":"Open Reaction Database contributors and the cited original publications","changes":["Bounded selection across datasets and publications","Deduplicated exact transformations across conditions","Canonicalized molecular structures using RDKit; calculated identifiers, formulae and molecular weights","Explicitly incomplete directed branches for all recorded reactants and positively measured products","Removed submitter account and contact fields from provenance; retained scientific input and outcome fields"]}