{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0dc5c76273764473a9c47b34bf982241","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"871eb989560fd547d4d172d0773fb55befb32d19a0162a04ae9b1383515faede","doi":"10.1002/anie.201610041","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-6b3986f4366fa19b","route_slugs":["ord-0dc5c76273764473a9c47b34bf982241-90aa8d4b0885"],"reactant_slugs":["ord-compound-5cc8420176d62ce00a27"],"product_slugs":["ord-compound-b1c5dc35fce4352dc427"],"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_917"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"N#CC1=CC=CC(SC)=C1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"65052-48-4"}],"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":"dtbpy: A mixture of ortho- and meta-borylated products (112 mg, 82% yield, ortho/meta + para = <0.01); meta-Isomer 5s was obtained by further purification of the crude mixture by GPC (67 mg, 60% yield), white solid (mp. 75-77 oC);"},"outcomes":[{"reaction_time":{"value":24,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"N#CC=1C=C(SC)C=C(C1)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"2060541-35-5"}],"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":82}}],"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) 1.37 (s, 12H), 2.47 (s, 3H), 7.34 (s, 1H), 7.35 (d, J = 7.5 Hz, 1H), 7.73-7.75 (d, J = 7.5 Hz, 1H); 13C NMR (100 MHz, CDCl3) 15.7, 25.3,84.9, 115.1, 119.0, 126.3, 126.8, 136.4, 147.6; meta-isomer: 1H NMR (400 MHz, CDCl3) 1.31 (s, 12H), 2.48 (s, 3H), 7.49 (s, 1H), 7.79 (s, 1H), 7.81 (s, 1H); 13C NMR (100 MHz, CDCl3) 15.5, 25.0, 84.8, 112.9, 118.7, 131.1, 134.6, 136.5, 140.4"}}},"MS of product_1":{"type":"HRMS","details":"HRMS Found: 298.1038","data":{"found":{"float_value":298.1038,"description":"Observed m/z"}}}}}],"provenance":{"doi":"10.1002/anie.201610041"}}},"entities":[{"slug":"ord-compound-5cc8420176d62ce00a27","name":"C8H7NS · ORD IHTFSBAUENZVAX-UHFFFAOYSA-N","smiles":"CSc1cccc(C#N)c1","inchi":"InChI=1S/C8H7NS/c1-10-8-4-2-3-7(5-8)6-9/h2-5H,1H3","formula":"C8H7NS"},{"slug":"ord-compound-b1c5dc35fce4352dc427","name":"C14H18BNO2S · ORD OISKEFUGLPBVNA-UHFFFAOYSA-N","smiles":"CSc1cc(C#N)cc(B2OC(C)(C)C(C)(C)O2)c1","inchi":"InChI=1S/C14H18BNO2S/c1-13(2)14(3,4)18-15(17-13)11-6-10(9-16)7-12(8-11)19-5/h6-8H,1-5H3","formula":"C14H18BNO2S"}],"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"]}