{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-058279c7f35f4dc0ba18c02ccededa40","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"5705f03e516b9dbfef0afb110863c83a062c68ce1e72d282e2369e77d5072af7","doi":"10.1002/anie.201509996","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-815566de10ae9f13","route_slugs":["ord-058279c7f35f4dc0ba18c02ccededa40-530d669f5f3b"],"reactant_slugs":["ord-compound-b8f44a58943279e9b3dc"],"product_slugs":["ord-compound-3978b88cc2ca50e40b5c"],"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_869"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"reagent_5":{"components":[{"identifiers":[{"type":"SMILES","value":"[K].O=C(O)O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"298-14-6"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=C(F)C(F)=C(C(F)=C1F)C(F)(F)F)C(CC)CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1407870-19-2"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"reagent_4":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(O)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"64-19-7"}],"amount":{"moles":{"value":0.02,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N#CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"75-05-8"}],"amount":{"volume":{"value":1.4999925,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"reagent_3":{"components":[{"identifiers":[{"type":"SMILES","value":"N=1C(OC)=CC(OC)=C2C=CC=CC12"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"40335-00-0"}],"amount":{"moles":{"value":0.02,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Pd].O=C(O)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"3375-31-3"}],"amount":{"moles":{"value":0.01,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"[B-](F)(F)(F)F.CC[N+](CC)(CC)CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"429-06-1"}],"amount":{"moles":{"value":0.05,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"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":0.2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"OXYGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":15,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=C(F)C(F)=C(C(F)=C1F)C(F)(F)F)C(CC)C(B2OC(C)(C)C(O2)(C)C)C"},{"type":"CAS_NUMBER","value":"1835284-44-0"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":25}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (400 MHz, CDCl3) δ 8.12 (br s, 1H), 2.54-2.49 (m, 1H), 1.91-1.80 (m, 1H), 1.59-1.50 (m, 1H), 1.48-1.40 (m, 1H), 1.28 (s, 12H), 1.04 (d, J = 7.6 Hz, 3H), 0.98 (t, J = 7.4 Hz, 3H).; 13 C NMR (150 MHz, CDCl3) δ 173.2, 84.1, 51.1, 24.9, 24.6, 24.5, 12.4, 12.3."}}}}}],"provenance":{"doi":"10.1002/anie.201509996"}}},"entities":[{"slug":"ord-compound-b8f44a58943279e9b3dc","name":"C13H12F7NO · ORD VGLQEIXJBXPKJV-UHFFFAOYSA-N","smiles":"CCC(CC)C(=O)Nc1c(F)c(F)c(C(F)(F)F)c(F)c1F","inchi":"InChI=1S/C13H12F7NO/c1-3-5(4-2)12(22)21-11-9(16)7(14)6(13(18,19)20)8(15)10(11)17/h5H,3-4H2,1-2H3,(H,21,22)","formula":"C13H12F7NO"},{"slug":"ord-compound-3978b88cc2ca50e40b5c","name":"C19H23BF7NO3 · ORD HMJMZIMRTJPXGG-UHFFFAOYSA-N","smiles":"CCC(C(=O)Nc1c(F)c(F)c(C(F)(F)F)c(F)c1F)C(C)B1OC(C)(C)C(C)(C)O1","inchi":"InChI=1S/C19H23BF7NO3/c1-7-9(8(2)20-30-17(3,4)18(5,6)31-20)16(29)28-15-13(23)11(21)10(19(25,26)27)12(22)14(15)24/h8-9H,7H2,1-6H3,(H,28,29)","formula":"C19H23BF7NO3"}],"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-815566de10ae9f13","title":"Literature experiment — 10.1002/anie.201509996","source_type":"paper","doi":"10.1002/anie.201509996","url":"https://doi.org/10.1002/anie.201509996","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"]}