{"schemaVersion":1,"kind":"mol2mat-public-reaction-record","experiment":{"reaction_id":"ord-0f930c207abc4c73a4f92506d0df4d13","dataset_id":"ord_dataset-99c23cf435dc42f1af884053bc8b11c7","reaction_class":"Borylation","transformation_sha256":"1b737b408a0878545f770d6c1777c1272f3f2dcde7b7d4f705b972b6ddc5f864","doi":"10.1021/jacs.7b04490","dataset_source_slug":"ord-dataset-99c23cf435dc42f1af884053bc8b11c7","publication_source_slug":"ord-publication-d59685c21407b63d","route_slugs":["ord-0f930c207abc4c73a4f92506d0df4d13-ee0511101668"],"reactant_slugs":["ord-compound-4641c4d9870bc0ee3cb2"],"product_slugs":["ord-compound-970998d56dbf5ce81d47"],"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_409"},{"type":"REACTION_TYPE","details":"borylation","value":"borylation"}],"inputs":{"solvent_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O1CCCC1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"109-99-9"}],"amount":{"volume":{"value":1,"units":"MILLILITER"}},"reaction_role":"SOLVENT"}]},"startingmat_1":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C(OCC)C1=CC(F)=CC=C1Br"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"139911-28-7"}],"amount":{"moles":{"value":0.2,"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":0.003,"units":"MILLIMOLE"}},"reaction_role":"CATALYST"}]},"reagent_1":{"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":0.2,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_2":{"components":[{"identifiers":[{"type":"SMILES","value":"O=C1C=CC=2C=CC=C(C3=CN=C(C=C3)C=4N=CC=CC4)C2N1"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"2098537-91-6"}],"amount":{"moles":{"value":0.007,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]},"reagent_3":{"components":[{"identifiers":[{"type":"SMILES","value":"[K].OC(C)(C)C"},{"type":"CAS_NUMBER","details":"cas number from SURF _cas column","value":"865-47-4"}],"amount":{"moles":{"value":0.009,"units":"MILLIMOLE"}},"reaction_role":"REAGENT"}]}},"conditions":{"temperature":{"setpoint":{"value":80,"units":"CELSIUS"}},"pressure":{"control":{"type":"SEALED"},"atmosphere":{"type":"NITROGEN"}},"stirring":{}},"outcomes":[{"reaction_time":{"value":12,"units":"HOUR"},"products":[{"identifiers":[{"type":"SMILES","value":"O=C(OCC)C1=CC(F)=C(C=C1Br)B2OC(C)(C)C(O2)(C)C"},{"type":"CAS_NUMBER","value":"2098537-76-7"}],"measurements":[{"analysis_key":"NMR of product_1","type":"IDENTITY"},{"analysis_key":"product_1_UNKNOWN","type":"YIELD","percentage":{"value":87}}],"reaction_role":"PRODUCT"}],"analyses":{"product_1_UNKNOWN":{"type":"CUSTOM","details":"UNKNOWN"},"NMR of product_1":{"type":"NMR_1H","data":{"peaks":{"string_value":"1 H NMR (400 MHz, CDCl3): δ7.98 (d, J = 5.6 Hz, 1H), 7.44 (d, J = 8.8 Hz, 1H), 4.40 (q, J = 7.2 Hz, 2H), 1.40 (t, J = 7.2 Hz, 3H), 1.35 (s, 12H).; 13 C NMR (100 MHz, CDCl3): δ166.7, 164.5 (d, J = 80.1 Hz), 142.1 (d, J = 7.8 Hz), 136.2 (d, J = 8.0 Hz), 118.2 (d, J = 27.2 Hz), 115.4 (d, J = 3.5 Hz), 84.6, 62.0, 24.8, 14.1.; 11 B NMR (128 MHz, CDCl3): δ29.0."}}}}}],"provenance":{"doi":"10.1021/jacs.7b04490"}}},"entities":[{"slug":"ord-compound-4641c4d9870bc0ee3cb2","name":"C9H8BrFO2 · ORD ODFAIHQRCRQZGM-UHFFFAOYSA-N","smiles":"CCOC(=O)c1cc(F)ccc1Br","inchi":"InChI=1S/C9H8BrFO2/c1-2-13-9(12)7-5-6(11)3-4-8(7)10/h3-5H,2H2,1H3","formula":"C9H8BrFO2"},{"slug":"ord-compound-970998d56dbf5ce81d47","name":"C15H19BBrFO4 · ORD GTWTUFZYPOZBKG-UHFFFAOYSA-N","smiles":"CCOC(=O)c1cc(F)c(B2OC(C)(C)C(C)(C)O2)cc1Br","inchi":"InChI=1S/C15H19BBrFO4/c1-6-20-13(19)9-7-12(18)10(8-11(9)17)16-21-14(2,3)15(4,5)22-16/h7-8H,6H2,1-5H3","formula":"C15H19BBrFO4"}],"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-d59685c21407b63d","title":"Literature experiment — 10.1021/jacs.7b04490","source_type":"paper","doi":"10.1021/jacs.7b04490","url":"https://doi.org/10.1021/jacs.7b04490","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"]}