{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0335307c23a84b7ab8ea02c9791ec636","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"ece1c8fb98eaf7766b796904512540a246ae456a58cf859a16616aa63ec35dd8","doi":"10.1021/ja303443m","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-9d66e3417e808cc9","route_slugs":["ord-0335307c23a84b7ab8ea02c9791ec636-c13f421d0ae4"],"reactant_slugs":["ord-compound-3a8313502b65384b1f21"],"product_slugs":["ord-compound-71dd07374ccf341b23f7"],"selection_notes":["Only explicitly marked REACTANT inputs become graph starting points.","Only products with a positive reported numeric YIELD become graph destinations; all reported outcomes remain in raw.","One representative record per exact reactant/product structure set; other conditions are not additional transformations."],"raw":{"identifiers":[{"type":"CUSTOM","details":"rxn_id from SURF table","value":"lit_pub_bo_982"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O(C)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1634-04-4"}],"amount":{"volume":{"value":2,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)NC1=CC=C(Br)C=C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"131818-17-2"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C[OH2+].C[OH2+].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir].[Ir]"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"12148-71-9"}],"amount":{"moles":{"value":0.02,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"73183-34-3"}],"amount":{"moles":{"value":0.75,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C=CC(=CC1C=2N=CC=C(C2)C(C)(C)C)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"72914-19-3"}],"amount":{"moles":{"value":0.04,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":50,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":22,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)NC1=CC=C(Br)C=C1B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"1384312-90-6"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":89}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (500 MHz, CDCl3 = 7.24 ppm): δ 8.60 (bs, 1H), 8.08 (d, 3J= 8.8 Hz, 1H), 7.78 (d, 4J= 2.4 Hz, 1H), 7.47 (dd, 3J= 8.8 Hz, 4J= 2.7 Hz, 1H), 1.50 (s, 9H), 1.34 (s, 12H); 13C NMR (126 MHz, CDCl3 = 77 ppm): δ 152.88, 144.23, 138.35, 135.33, 119.46, 114.27, 84.58, 80.10, 28.31, 24.82; 11B NMR (96 MHz, CDCl3, BF3·OEt2 = 0 ppm): δ 30.6;"}}}}}],"provenance":{"doi":"10.1021/ja303443m"}}},"entities":[{"slug":"ord-compound-3a8313502b65384b1f21","name":"C11H14BrNO2 · ORD VLGPDTPSKUUHKR-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)Nc1ccc(Br)cc1","inchi":"InChI=1S/C11H14BrNO2/c1-11(2,3)15-10(14)13-9-6-4-8(12)5-7-9/h4-7H,1-3H3,(H,13,14)","formula":"C11H14BrNO2"},{"slug":"ord-compound-71dd07374ccf341b23f7","name":"C17H25BBrNO4 · ORD OMPQXBQRXIONDR-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)Nc1ccc(Br)cc1B1OC(C)(C)C(C)(C)O1","inchi":"InChI=1S/C17H25BBrNO4/c1-15(2,3)22-14(21)20-13-9-8-11(19)10-12(13)18-23-16(4,5)17(6,7)24-18/h8-10H,1-7H3,(H,20,21)","formula":"C17H25BBrNO4"}],"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 format (ChemRxiv, 2024, DOI: 10.26434/chemrxiv-2023-nfq7h)","records_in_source":1111,"path":"data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","sha256":"e01a389cac3e6cce5746ef54dbe6b8d3040d764f987b1fc13790f5aeff5598fa","bytes":210626,"repository_url":"https://github.com/open-reaction-database/ord-data/blob/83f971f586f6ad18f358ae4ae99d045e94ed2066/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet","download_url":"https://huggingface.co/datasets/open-reaction-database/ord-data/resolve/93475c46949f9218e1dfb6624096025135db2add/data/99/ord_dataset-99c23cf435dc42f1af884053bc8b11c7.parquet"},"publication":{"slug":"ord-publication-9d66e3417e808cc9","title":"Literature experiment — 10.1021/ja303443m","source_type":"paper","doi":"10.1021/ja303443m","url":"https://doi.org/10.1021/ja303443m","note":"Publication DOI reported by the Open Reaction Database. 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"]}