{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-007e4516c96b4fe39eecc394269f1434","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"56bc4da6f42530d393ea57aebeb0dd45123a6e9f4934de012df3adaab2af48d8","doi":"10.1021/ja500712z","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-f8bddb7db1a1b53f","route_slugs":["ord-007e4516c96b4fe39eecc394269f1434-02ce5b65f33b"],"reactant_slugs":["ord-compound-8f05d42a692a08fe3a2a"],"product_slugs":["ord-compound-2b80c6a04c1eaaca696d"],"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_96"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"catalyst_1":{"components":[{"identifiers":[{"type":"SMILES","value":"[CH2-][Co+]12N3=C(C(=N1C1CCCCC1)C)C=CC=C3C(=N2C1CCCCC1)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1234351-63-3"}],"amount":{"moles":{"value":0.03905,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1BOC(C)(C)C1(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"25015-63-8"}],"amount":{"moles":{"value":0.781,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=CC2=C(C1)C=CN2C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"603-76-9"}],"amount":{"moles":{"value":0.781,"units":"MILLIMOLE"}},"reaction_role":"REACTANT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C2=CC=3C=CC=CC3N2C"},{"type":"CAS_NUMBER","value":"596819-10-2"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_GC","type":"YIELD","percentage":{"value":59}}],"reaction_role":"PRODUCT"}],"analyses":{"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (chloroform-d, 23°C): δ 7.64 (d, Δν1/2 = 8.05 Hz, 1H), 7.07-7.35 (m, 5H), 3.95 (s, 3H), 1.35 (s, 12H). {1H}13C NMR (chloroform-d, 23°C): δ 140.23, 127.94, 123.27, 121.67, 119.39, 114.36, 109.78, 83.77, 32.30, 24.91."}}},"product_1_GC":{"type":"GC","details":"GC"}}}],"provenance":{"doi":"10.1021/ja500712z"}}},"entities":[{"slug":"ord-compound-8f05d42a692a08fe3a2a","name":"C9H9N · ORD BLRHMMGNCXNXJL-UHFFFAOYSA-N","smiles":"Cn1ccc2ccccc21","inchi":"InChI=1S/C9H9N/c1-10-7-6-8-4-2-3-5-9(8)10/h2-7H,1H3","formula":"C9H9N"},{"slug":"ord-compound-2b80c6a04c1eaaca696d","name":"C15H20BNO2 · ORD KMLZZUZKSQWHKC-UHFFFAOYSA-N","smiles":"Cn1c(B2OC(C)(C)C(C)(C)O2)cc2ccccc21","inchi":"InChI=1S/C15H20BNO2/c1-14(2)15(3,4)19-16(18-14)13-10-11-8-6-7-9-12(11)17(13)5/h6-10H,1-5H3","formula":"C15H20BNO2"}],"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-f8bddb7db1a1b53f","title":"Literature experiment — 10.1021/ja500712z","source_type":"paper","doi":"10.1021/ja500712z","url":"https://doi.org/10.1021/ja500712z","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"]}