{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-03bb8ab8112a4d7a8c80e549cdb4d351","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"008bb5e49b2a906017f6daa390778522ed8df416468be8c63d0c02d4fa513bdd","doi":"10.1002/anie.201509996","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-815566de10ae9f13","route_slugs":["ord-03bb8ab8112a4d7a8c80e549cdb4d351-f5fcf5aca1c4"],"reactant_slugs":["ord-compound-18046dfb732e3491bb8b"],"product_slugs":["ord-compound-9d9b1882a141f04afede"],"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_847"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"reagent_5":{"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"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(NC1=C(F)C(F)=C(C(F)=C1F)C(F)(F)F)C2(C)CCCCC2"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1808952-46-6"}],"amount":{"moles":{"value":0.1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"reagent_4":{"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"}]},"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":"[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"}]},"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":"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"}]},"reagent_1":{"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"}]}},"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)C2(CB3OC(C)(C)C(O3)(C)C)CCCCC2"},{"type":"CAS_NUMBER","value":"1835284-35-9"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":72}}],"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 (600 MHz, CDCl3) δ 8.63 (br s, 1H), 2.17-2.06 (m, 2H), 1.60-1.51 (m, 5H), 1.49-1.44 (m, 2H), 1.40-1.34 (m, 1H), 1.28 (s, 12H), 1.24 (s, 2H).; 13 C NMR (150 MHz, CDCl3) δ 176.0, 84.2, 44.8, 36.5, 25.6, 24.7, 22.8."}}}}}],"provenance":{"doi":"10.1002/anie.201509996"}}},"entities":[{"slug":"ord-compound-18046dfb732e3491bb8b","name":"C15H14F7NO · ORD MRUQICSSUXUZLL-UHFFFAOYSA-N","smiles":"CC1(C(=O)Nc2c(F)c(F)c(C(F)(F)F)c(F)c2F)CCCCC1","inchi":"InChI=1S/C15H14F7NO/c1-14(5-3-2-4-6-14)13(24)23-12-10(18)8(16)7(15(20,21)22)9(17)11(12)19/h2-6H2,1H3,(H,23,24)","formula":"C15H14F7NO"},{"slug":"ord-compound-9d9b1882a141f04afede","name":"C21H25BF7NO3 · ORD XZMHLKDCKNBMLU-UHFFFAOYSA-N","smiles":"CC1(C)OB(CC2(C(=O)Nc3c(F)c(F)c(C(F)(F)F)c(F)c3F)CCCCC2)OC1(C)C","inchi":"InChI=1S/C21H25BF7NO3/c1-18(2)19(3,4)33-22(32-18)10-20(8-6-5-7-9-20)17(31)30-16-14(25)12(23)11(21(27,28)29)13(24)15(16)26/h5-10H2,1-4H3,(H,30,31)","formula":"C21H25BF7NO3"}],"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"]}