{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-023a74e447fe49c990b8868ee7ea5e9c","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"5690a8d953867466237140bb7145acddcdffe3953bae92934bc84928c640cb9d","doi":"10.1021/ja2097095","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-8872843748e59243","route_slugs":["ord-023a74e447fe49c990b8868ee7ea5e9c-dbab841eabe9"],"reactant_slugs":["ord-compound-c5d07134d9ea3d653818"],"product_slugs":["ord-compound-f7859c08bcce95207623"],"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_948"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"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,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=C(F)C(F)=C(C(F)=C1F)C(F)(F)F)C=2C=CC=CC2"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"80588-64-3"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Pd].O=C(O)C(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"42196-31-6"}],"amount":{"moles":{"value":0.01,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[Na].O=S(=O)(O)C1=CC=C(C=C1)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"657-84-1"}],"amount":{"moles":{"value":0.15,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"[K].O=S(=O)(O)OOS(=O)(=O)O"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"7727-21-1"}],"amount":{"moles":{"value":0.2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"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":"AIR"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=C(F)C(F)=C(C(F)=C1F)C(F)(F)F)C=2C=CC=CC2B3OC(C)(C)C(O3)(C)C"},{"type":"CAS_NUMBER","value":"1352238-53-9"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":54}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (400 MHz, CDCl3) 8.98 (s, 1H), 7.99 (dd, J1 = 5.6 Hz, J2 = 3.2 Hz, 1H), 7.84 (dd, J1 = 5.6 Hz, J2 = 3.6 Hz, 1H), 7.56-7.58 (m, 2H), 1.38 (s, 12H); 13C NMR (100 MHz, CDCl3) 166.13, 137.11, 135.35, 131.40, 130.70, 128.84, 84.99, 24.67; 11B NMR (77 MHz, CDCl3) 12.0;"}}},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1021/ja2097095"}}},"entities":[{"slug":"ord-compound-c5d07134d9ea3d653818","name":"C14H6F7NO · ORD RNPQALWWIIZYLA-UHFFFAOYSA-N","smiles":"O=C(Nc1c(F)c(F)c(C(F)(F)F)c(F)c1F)c1ccccc1","inchi":"InChI=1S/C14H6F7NO/c15-8-7(14(19,20)21)9(16)11(18)12(10(8)17)22-13(23)6-4-2-1-3-5-6/h1-5H,(H,22,23)","formula":"C14H6F7NO"},{"slug":"ord-compound-f7859c08bcce95207623","name":"C20H17BF7NO3 · ORD QMCZFCGKAVWDHJ-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2ccccc2C(=O)Nc2c(F)c(F)c(C(F)(F)F)c(F)c2F)OC1(C)C","inchi":"InChI=1S/C20H17BF7NO3/c1-18(2)19(3,4)32-21(31-18)10-8-6-5-7-9(10)17(30)29-16-14(24)12(22)11(20(26,27)28)13(23)15(16)25/h5-8H,1-4H3,(H,29,30)","formula":"C20H17BF7NO3"}],"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-8872843748e59243","title":"Literature experiment — 10.1021/ja2097095","source_type":"paper","doi":"10.1021/ja2097095","url":"https://doi.org/10.1021/ja2097095","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"]}