{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-1139608af0de453f8fc0d7e140ea28b2","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"8c6166fcde1dde4610a4165d9ba6e7c37cacfc18bb53350a853f25e9f4a83531","doi":"10.1021/ja303443m","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-9d66e3417e808cc9","route_slugs":["ord-1139608af0de453f8fc0d7e140ea28b2-436a6e642fbf"],"reactant_slugs":["ord-compound-62164383bf31d8a4b863"],"product_slugs":["ord-compound-ebdb3527f2bcfbc4ce67"],"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_985"},{"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(O)C=C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"54840-15-2"}],"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":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":1.3,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"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":1.5,"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":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC(C)(C)C)NC1=CC=C(O)C=C1B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"1384312-65-5"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":78}}],"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 8.40 (s, 1H), 7.99 (d, 3J= 8.6 Hz, 1H), 7.14 (d, 4J= 2.9 Hz, 1H), 6.90 (dd, 3J= 8.8 Hz, 4J= 2.9 Hz, 1H), 4.70 (s, 1H), 1.49 (s, 9H), 1.33 (s, 12H); 13C NMR (126 MHz, CDCl3 = 77 ppm): δ 153.54, 150.36, 138.23, 121.81, 119.69 (2 C's), 84.21, 79.74, 28.38, 24.81; 11B NMR (96 MHz, CDCl3, BF3·OEt2 = 0 ppm): δ 30.3"}}}}}],"provenance":{"doi":"10.1021/ja303443m"}}},"entities":[{"slug":"ord-compound-62164383bf31d8a4b863","name":"C11H15NO3 · ORD YRQMBQUMJFVZLF-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)Nc1ccc(O)cc1","inchi":"InChI=1S/C11H15NO3/c1-11(2,3)15-10(14)12-8-4-6-9(13)7-5-8/h4-7,13H,1-3H3,(H,12,14)","formula":"C11H15NO3"},{"slug":"ord-compound-ebdb3527f2bcfbc4ce67","name":"C17H26BNO5 · ORD NTRVTYZUMZBMMS-UHFFFAOYSA-N","smiles":"CC(C)(C)OC(=O)Nc1ccc(O)cc1B1OC(C)(C)C(C)(C)O1","inchi":"InChI=1S/C17H26BNO5/c1-15(2,3)22-14(21)19-13-9-8-11(20)10-12(13)18-23-16(4,5)17(6,7)24-18/h8-10,20H,1-7H3,(H,19,21)","formula":"C17H26BNO5"}],"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"]}