{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-c2b5ef0483ed4d5182be5f4568e9da87","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"9556c99cdc9e72aaae675ca726721eb2f63cb954dc59149b810a6a491c8c7b4e","doi":"10.1021/jacs.7b02232","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-a17f83d783de9635","route_slugs":["ord-c2b5ef0483ed4d5182be5f4568e9da87-108de7687e57"],"reactant_slugs":["phenol"],"product_slugs":["ord-compound-deec121391a0d496c044"],"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_384"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"OC=1C=CC=CC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"108-95-2"}],"amount":{"moles":{"value":1,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]},"reagent_4":{"components":[{"identifiers":[{"type":"SMILES","value":"OC(C)(C)C(O)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"76-09-5"}],"amount":{"moles":{"value":3,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=CC(=CC1)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"108-88-3"}],"amount":{"volume":{"value":2.5,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"reagent_3":{"components":[{"identifiers":[{"type":"SMILES","value":"N(CC)(CC)CC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"121-44-8"}],"amount":{"moles":{"value":1.5,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"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":0.015,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_2":{"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":0.03,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"ClC(Cl)Cl"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"67-66-3"}],"amount":{"volume":{"value":10,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1B(OCC1)B2OCCO2"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"13826-24-9"}],"amount":{"moles":{"value":1.5,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":2,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"OC=1C=CC=CC1B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"269409-97-4"}],"measurements":[{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":65}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"}}}],"provenance":{"doi":"10.1021/jacs.7b02232"}}},"entities":[{"slug":"phenol","name":"Phenol","smiles":"C1=CC=C(C=C1)O","inchi":"InChI=1S/C6H6O/c7-6-4-2-1-3-5-6/h1-5,7H","formula":"C6H6O"},{"slug":"ord-compound-deec121391a0d496c044","name":"C12H17BO3 · ORD VLROJECCXBBKPZ-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2ccccc2O)OC1(C)C","inchi":"InChI=1S/C12H17BO3/c1-11(2)12(3,4)16-13(15-11)9-7-5-6-8-10(9)14/h5-8,14H,1-4H3","formula":"C12H17BO3"}],"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-a17f83d783de9635","title":"Literature experiment — 10.1021/jacs.7b02232","source_type":"paper","doi":"10.1021/jacs.7b02232","url":"https://doi.org/10.1021/jacs.7b02232","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"]}