{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-07735c61c2ba4303a5458fefe94b7ddd","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"d65b0cbb348bf682a0e3404e106901f52d3e6b4485c012d088b73d7ef248c519","doi":"10.1002/anie.201610041","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-6b3986f4366fa19b","route_slugs":["ord-07735c61c2ba4303a5458fefe94b7ddd-a79062cc6fc7"],"reactant_slugs":["ord-compound-4da63d4da97a8f17618e"],"product_slugs":["ord-compound-581ea91ac6448ad96008"],"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_901"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"S(C1=CC=CC(=C1)CC)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"66794-12-5"}],"amount":{"moles":{"value":0.5,"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"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"1134-35-6"}],"amount":{"moles":{"value":0.03,"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":0.25,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"C=1C=C(C=CC1C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"106-42-3"}],"amount":{"volume":{"value":1.5000015,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]}},"conditions":{"temperature":{"setpoint":{"value":55,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"notes":{"procedure_details":"Yield: A mixture of ortho- and meta-borylated products (103 mg, 74% yield, ortho/meta + para = <0.01); meta-Isomer 5k was obtained by further purification by GPC (93 mg, 67% yield), colorless oil;"},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O1B(OC(C)(C)C1(C)C)C2=CC(SC)=CC(=C2)CC"},{"type":"CAS_NUMBER","value":"2060541-13-9"}],"measurements":[{"analysis_key":"MS of product_1","type":"IDENTITY"},{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":74}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1H NMR (400 MHz, CDCl3) 1.19 (t, 3H), 1.34 (s, 12H), 2.44 (s, 3H), 2.60 (q, J = 7.8 Hz, 2H), 6.93 (d, J = 7.3 Hz, 1H), 6.99 (s, 1H), 7.62 (d, J = 7.3 Hz, 1H); 13C NMR (100 MHz, CDCl3) 15.7, 15.9, 25.1, 29.4, 84.0, 123.6, 123.7, 136.6, 145.4, 148.0; meta-isomer: 1H NMR (400 MHz, CDCl3) 1.21 (t,J = 6.9 Hz, 6.8 Hz, 3H), 1.34 (s, 12H), 2.50 (s, 3H), 2.59 (q, J = 6.9 Hz, 2H), 7.20 (s, 1H), 7.42 (s, 1H), 7.52 (s, 1H); 13C NMR (100 MHz, CDCl3) 15.9, 16.2, 25.0, 29.0, 84.1, 129.5, 130.4, 131.5, 137.9, 144.5"}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 279.1585","data":{"found":{"float_value":279.1585,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201610041"}}},"entities":[{"slug":"ord-compound-4da63d4da97a8f17618e","name":"C9H12S · ORD DSDAKTYVXFUEEM-UHFFFAOYSA-N","smiles":"CCc1cccc(SC)c1","inchi":"InChI=1S/C9H12S/c1-3-8-5-4-6-9(7-8)10-2/h4-7H,3H2,1-2H3","formula":"C9H12S"},{"slug":"ord-compound-581ea91ac6448ad96008","name":"C15H23BO2S · ORD DXFMUBIMBULQSG-UHFFFAOYSA-N","smiles":"CCc1cc(SC)cc(B2OC(C)(C)C(C)(C)O2)c1","inchi":"InChI=1S/C15H23BO2S/c1-7-11-8-12(10-13(9-11)19-6)16-17-14(2,3)15(4,5)18-16/h8-10H,7H2,1-6H3","formula":"C15H23BO2S"}],"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-6b3986f4366fa19b","title":"Literature experiment — 10.1002/anie.201610041","source_type":"paper","doi":"10.1002/anie.201610041","url":"https://doi.org/10.1002/anie.201610041","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"]}