{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-19c4d9b183614cef9fce523033f6b00a","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"c6e66e62017772aaf190f62d28566e9211e947cd5f25f78aaa8c4919f94569ee","doi":"10.1039/c2sc20776a","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-78c7181f4410dadf","route_slugs":["ord-19c4d9b183614cef9fce523033f6b00a-ea1a35f04b75","ord-19c4d9b183614cef9fce523033f6b00a-34d047c88437"],"reactant_slugs":["ord-compound-f6778a9414b7182fd2ad"],"product_slugs":["ord-compound-52d1bc79112bc4e2ea21","ord-compound-aaed8a41e3b0461b2222"],"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_680"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OC)C=1C=CC=CC1C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"89-71-4"}],"amount":{"moles":{"value":0.2,"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":0.003,"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":0.006,"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":0.24,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O(C)C(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1634-04-4"}],"amount":{"volume":{"value":0.5,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":25,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"General procedure D was applied to methyl 2-methylbenzoate15h(30 mg, 0.2 mmol). The reaction mixture was allowed to stand for 16hoursgiving a conversion of >99%(GC-MS) and 16hand 17hin a 73:27 mixture (1H NMR spectrum)."},"outcomes":[{"reaction_time":{"value":16,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OC)C1=CC=C(C=C1C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"525362-07-6"}],"measurements":[{"analysis_key":"product_1_NMR_1H","type":"YIELD","percentage":{"value":73}}],"reaction_role":"PRODUCT"},{"identifiers":[{"type":"SMILES","value":"O=C(OC)C1=CC(=CC=C1C)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"478375-39-2"}],"measurements":[{"analysis_key":"product_2_UNKNOWN","type":"YIELD","percentage":{"value":27}}],"reaction_role":"PRODUCT"}],"analyses":{"product_2_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"product_1_NMR_1H":{"type":"NMR_1H","details":"NMR_1H"}}}],"provenance":{"doi":"10.1039/c2sc20776a"}}},"entities":[{"slug":"ord-compound-f6778a9414b7182fd2ad","name":"C9H10O2 · ORD WVWZECQNFWFVFW-UHFFFAOYSA-N","smiles":"COC(=O)c1ccccc1C","inchi":"InChI=1S/C9H10O2/c1-7-5-3-4-6-8(7)9(10)11-2/h3-6H,1-2H3","formula":"C9H10O2"},{"slug":"ord-compound-52d1bc79112bc4e2ea21","name":"C15H21BO4 · ORD GUHFNSOJOCZHQO-UHFFFAOYSA-N","smiles":"COC(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1C","inchi":"InChI=1S/C15H21BO4/c1-10-9-11(7-8-12(10)13(17)18-6)16-19-14(2,3)15(4,5)20-16/h7-9H,1-6H3","formula":"C15H21BO4"},{"slug":"ord-compound-aaed8a41e3b0461b2222","name":"C15H21BO4 · ORD WBHBKJFHYGIUQU-UHFFFAOYSA-N","smiles":"COC(=O)c1cc(B2OC(C)(C)C(C)(C)O2)ccc1C","inchi":"InChI=1S/C15H21BO4/c1-10-7-8-11(9-12(10)13(17)18-6)16-19-14(2,3)15(4,5)20-16/h7-9H,1-6H3","formula":"C15H21BO4"}],"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-78c7181f4410dadf","title":"Literature experiment — 10.1039/c2sc20776a","source_type":"paper","doi":"10.1039/c2sc20776a","url":"https://doi.org/10.1039/c2sc20776a","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"]}