{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-07dc922d06514dcda29ba37887e079f1","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"49908a0beff30e41c1c60879297d53a4dffe510040107154b772da9888ebcee9","doi":"10.1021/ja2097095","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-8872843748e59243","route_slugs":["ord-07dc922d06514dcda29ba37887e079f1-e21994359e89"],"reactant_slugs":["ord-compound-b202fc72436300ffdd2b"],"product_slugs":["ord-compound-ba6fc509a632110b8639"],"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_965"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"reagent_2":{"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"}]},"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)C2=CC=CC(=C2)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1300857-04-8"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"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_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(C=CC1=CC=C(C=C1)C(F)(F)F)C=CC2=CC=C(C=C2)C(F)(F)F"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"103836-71-1"}],"amount":{"moles":{"value":0.03,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_4":{"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"}]},"reagent_3":{"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"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"AIR"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=C(F)C(F)=C(C(F)=C1F)C(F)(F)F)C2=CC(=CC=C2B3OC(C)(C)C(O3)(C)C)C"},{"type":"CAS_NUMBER","value":"1352238-55-1"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":82}}],"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 9.29 (s, 1H), 7.85 (s, 1H), 7.76 (d, J= 7.2 Hz, 1H), 7.36 (d, J= 7.6 Hz, 1H), 2.43 (s, 3H), 1.37 (s, 12H).; 13 C NMR 100 MHz, CDCl3 δ 166.41, 141.36, 137.27, 135.86, 132.04, 130.10, 84.95, 24.63, 21.43."}}}}}],"provenance":{"doi":"10.1021/ja2097095"}}},"entities":[{"slug":"ord-compound-b202fc72436300ffdd2b","name":"C15H8F7NO · ORD ZVYDSGJHUBKURU-UHFFFAOYSA-N","smiles":"Cc1cccc(C(=O)Nc2c(F)c(F)c(C(F)(F)F)c(F)c2F)c1","inchi":"InChI=1S/C15H8F7NO/c1-6-3-2-4-7(5-6)14(24)23-13-11(18)9(16)8(15(20,21)22)10(17)12(13)19/h2-5H,1H3,(H,23,24)","formula":"C15H8F7NO"},{"slug":"ord-compound-ba6fc509a632110b8639","name":"C21H19BF7NO3 · ORD ZTMRGEGYBUKPCF-UHFFFAOYSA-N","smiles":"Cc1ccc(B2OC(C)(C)C(C)(C)O2)c(C(=O)Nc2c(F)c(F)c(C(F)(F)F)c(F)c2F)c1","inchi":"InChI=1S/C21H19BF7NO3/c1-9-6-7-11(22-32-19(2,3)20(4,5)33-22)10(8-9)18(31)30-17-15(25)13(23)12(21(27,28)29)14(24)16(17)26/h6-8H,1-5H3,(H,30,31)","formula":"C21H19BF7NO3"}],"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"]}