{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-4c9fab8ee46943cda11e836695e3f680","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"7a641f46a530cc4b95b524091b49ceb64e94c04f31c8c0e0eba15a17a1eea5c6","doi":"10.1021/ja0631652","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-3566c7a64f4eff0d","route_slugs":["ord-4c9fab8ee46943cda11e836695e3f680-d8180189ec56"],"reactant_slugs":["ord-compound-d107fd060944dc77a651"],"product_slugs":["ord-compound-74a3cdce7b82d01fb1de"],"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_236"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=CC=2NC(=CC2C1)[Si](C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"116491-57-7"}],"amount":{"moles":{"value":1,"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":0.015,"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":0.03,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"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":2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"CCCCCC"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"110-54-3"}],"amount":{"volume":{"value":3.000003,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":60,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":1,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C2=CC=CC=3C=C(NC32)[Si](C)(C)C"},{"type":"CAS_NUMBER","value":"919119-70-3"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":76}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (CDCl3, 300 MHz): δ 9.25 (br s, 1 H, Ha), 7.79 (d, J= 7.8 Hz, 1 H, Hc/e), 7.67 (d, J = 7.1 Hz, 1 H, Hc/e), 7.13 (dd, J= 7.8, 7.1 Hz, 1 H, Hd), 6.76 (d, J= 2.2 Hz, 1 H, Hb), 1.43 (br s, 12 H, CH3 of BPin), 0.40 (br s, 9 H, CH3 of SiMe3); 13C NMR {1H} (CDCl3, 75 MHz): δ 143.7 (C), 137.9 (C), 129.5 (CH), 127.7 (C), 124.1 (CH), 119.2 (CH), 110.5 (CH), 83.7 (2 C), 24.9 (4 CH3 of BPin), -1.1 (3 CH3 of SiMe3); 11B NMR (CDCl3, 96 MHz): δ 31.4;"}}}}}],"provenance":{"doi":"10.1021/ja0631652"}}},"entities":[{"slug":"ord-compound-d107fd060944dc77a651","name":"C11H15NSi · ORD ISPRGDKNJYQULU-UHFFFAOYSA-N","smiles":"C[Si](C)(C)c1cc2ccccc2[nH]1","inchi":"InChI=1S/C11H15NSi/c1-13(2,3)11-8-9-6-4-5-7-10(9)12-11/h4-8,12H,1-3H3","formula":"C11H15NSi"},{"slug":"ord-compound-74a3cdce7b82d01fb1de","name":"C17H26BNO2Si · ORD DYUKBTITVHRVLS-UHFFFAOYSA-N","smiles":"CC1(C)OB(c2cccc3cc([Si](C)(C)C)[nH]c23)OC1(C)C","inchi":"InChI=1S/C17H26BNO2Si/c1-16(2)17(3,4)21-18(20-16)13-10-8-9-12-11-14(19-15(12)13)22(5,6)7/h8-11,19H,1-7H3","formula":"C17H26BNO2Si"}],"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-3566c7a64f4eff0d","title":"Literature experiment — 10.1021/ja0631652","source_type":"paper","doi":"10.1021/ja0631652","url":"https://doi.org/10.1021/ja0631652","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"]}