(3aR,7aR)-1,3-bis[(4-bromophenyl)methyl]-2-chloro-2-(prop-2-en-1-yl)-octahydro-1H-1,3,2-benzodiazasilole

• ChemBase ID: 142984
• Molecular Formular: C23H27Br2ClN2Si
• Molecular Mass: 554.82038
• Monoisotopic Mass: 551.99987709
• SMILES: C=CC[Si]1(N([C@@H]2CCCC[C@H]2N1Cc1ccc(cc1)Br)Cc1ccc(cc1)Br)Cl
• Canonical SMILES: C=CC[Si]1(Cl)N(Cc2ccc(cc2)Br)[C@H]2[C@H](N1Cc1ccc(cc1)Br)CCCC2
• InChI: InChI=1S/C23H27Br2ClN2Si/c1-2-15-29(26)27(16-18-7-11-20(24)12-8-18)22-5-3-4-6-23(22)28(29)17-19-9-13-21(25)14-10-19/h2,7-14,22-23H,1,3-6,15-17H2/t22-,23-/m1/s1
• InChIKey: JTYONYYNZDUUGN-DHIUTWEWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,7aR)-1,3-bis[(4-bromophenyl)methyl]-2-chloro-2-(prop-2-en-1-yl)-octahydro-1H-1,3,2-benzodiazasilole
• IUPAC Traditional name: (3aR,7aR)-1,3-bis[(4-bromophenyl)methyl]-2-chloro-2-(prop-2-en-1-yl)-hexahydro-1,3,2-benzodiazasilole
• Synonyms: (3aR,7aR)-2-Allyl-1,3-bis(4-bromobenzyl)-2-chlorooctahydro-1H-benzo[d][1,3,2]diazasilole; (R,R)-1,3-Bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-allyl-1H-1,3,2-benzodiazasilole; (3aR,7aR)-2-烯丙基-1,3-双(4-溴苄基)-2-氯八氢-1H-苯并[d][1,3,2]二氮杂噻咯; (R,R)-1,3-双[(4-溴苯基)甲基]-2-氯八氢-2-烯丙基-1H-1,3,2-苯并二氮杂噻咯

Database IDs

• CAS Number: 546084-25-7
• MDL Number: MFCD10567380
• PubChem SID: 162237210
• PubChem CID: 10415272

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.606098
• LogD (pH = 7.4): 6.4950156
• Log P: 7.1962
• Molar Refractivity: 127.1201 cm^3
• Polarizability: 51.738922 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 95-100 °C
• Flash Point: >110 °C; >230 °F
• Optical Rotation: [α]22/D -53.0°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 3131
• German water hazard class: 1
• Hazard Class: 4.3
• Packing Group: 3
• Risk Statements: 15-34
• Safety Statements: 26-36/37/39-43-45
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H261-H314
• GHS Precautionary statements: P231 + P232-P280-P305 + P351 + P338-P310-P422
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3131 4.3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C23H27Br2ClN2Si

DETAILS

Sigma Aldrich - 704725

Application
An operationally simple regioselective and enantioselective allylation of beta-diketones to provide tertiary carbinols3
Leighton’s Strained Silacycles: Powerful Enantioselective Allylation Reagents
• Enantioselective allylation of aldehydes1,2
Packaging
1, 5 g in glass bottle
Legal Information
U.S. Patent No. 7,534,905