{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-04d6f2c7c1514ea986686e87526ce250","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"5351ea5fb7205cb70273a2e8eeac3630ecaf01e554e2291c8f9958b144bdbd7b","doi":"10.1021/jacs.6b13346","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-361e4a9249924ae7","route_slugs":["ord-04d6f2c7c1514ea986686e87526ce250-b9d2dfdca659"],"reactant_slugs":["ord-compound-b60ac3ca7ac0feb58316"],"product_slugs":["ord-compound-6baa09fa3baa5b87ad60"],"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_341"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"FC1=CC=CC(OC)=C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"456-49-5"}],"amount":{"moles":{"value":0.28,"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":0.007,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"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":0.014,"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":0.28,"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":0.5,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":50,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"FC1=CC(OC)=CC=C1B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"628692-21-7"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":58}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (500 MHz, CDCl3, 23 °C): δ 7.65 (t, J = 7.85 Hz, 1H), 6.69 (dd, J = 8.38, 2.47 Hz, 1H), 6.57 (dd, J = 11.11, 2.08 Hz, 1H), 3.81 (s, 3H), 1.34 (s, 12H).; 13 C NMR (126 MHz, CDCl3, 23 °C): δ 168.68 (d, J = 250.74 Hz), 164.01 (d, J = 11.84 Hz), 137.83 (d, J = 10.54 Hz), 110.05 (d, J = 2.56 Hz), 101.23 (d, J = 28.19 Hz), 83.72, 55.60, 24.94.; 19 F NMR (282 MHz, CDCl3, 23 °C): δ -100.49."}}},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1021/jacs.6b13346"}}},"entities":[{"slug":"ord-compound-b60ac3ca7ac0feb58316","name":"C7H7FO · ORD MFJNOXOAIFNSBX-UHFFFAOYSA-N","smiles":"COc1cccc(F)c1","inchi":"InChI=1S/C7H7FO/c1-9-7-4-2-3-6(8)5-7/h2-5H,1H3","formula":"C7H7FO"},{"slug":"ord-compound-6baa09fa3baa5b87ad60","name":"C13H18BFO3 · ORD PYGFGOBGKWJERN-UHFFFAOYSA-N","smiles":"COc1ccc(B2OC(C)(C)C(C)(C)O2)c(F)c1","inchi":"InChI=1S/C13H18BFO3/c1-12(2)13(3,4)18-14(17-12)10-7-6-9(16-5)8-11(10)15/h6-8H,1-5H3","formula":"C13H18BFO3"}],"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-361e4a9249924ae7","title":"Literature experiment — 10.1021/jacs.6b13346","source_type":"paper","doi":"10.1021/jacs.6b13346","url":"https://doi.org/10.1021/jacs.6b13346","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"]}