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Merck
CN

317039

(+)-B-Methoxydiisopinocampheylborane

Synonym(s):

(+)-Diisopinocampheylmethoxyborane

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About This Item

Empirical Formula (Hill Notation):
C21H37BO
CAS Number:
99438-28-5
Molecular Weight:
316.33
UNSPSC Code:
12352001
NACRES:
NA.22
PubChem Substance ID:
24859061
MDL number:
MFCD21332906
Beilstein/REAXYS Number:
6370228

Key Documents

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InChI

1S/C21H37BO/c1-12-16-8-14(20(16,3)4)10-18(12)22(23-7)19-11-15-9-17(13(19)2)21(15,5)6/h12-19H,8-11H2,1-7H3/t12-,13-,14+,15+,16-,17-,18-,19-/m0/s1

SMILES string

COB([C@H]1CC2CC([C@@H]1C)C2(C)C)[C@H]3CC4CC([C@@H]3C)C4(C)C

InChI key

IAQXEQYLQNNXJC-JPDDNCELSA-N

form

solid

Quality Level

100

Related Categories

Application

Both (+)- and (-)-forms are precursors to B-allyldiisopinocampheylborane derivatives, which are subsequently reacted with aldehydes to give homoallylic alcohols and β-amino alcohols of high enantiomeric excess.
Reactant involved in:
  • Oxidative cyclization and alkylation for synthesis of ionomycin
  • Intramolecular conjugate addition for tetrahydropyran synthesis
  • Aldol addition and Suzuki coupling reactions
  • Allylation
  • Synthesis of alkanols

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN0340
SHBP5145
SHBK2417
SHBJ8941
SHBG9199V

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The Journal of Organic Chemistry, 56, 401-401 (1991)
Journal of the Chemical Society. Chemical Communications, 339-339 (1993)
Aldrichimica Acta, 20, 9-9 (1987)

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