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Merck
CN

678538

(−)-Ipc2B(allyl)borane solution

1 M in pentane

Synonym(s):

(-)-Ipc2B(allyl) solution, (−)-B-Allyldiisopinocampheylborane solution

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About This Item

Linear Formula:
(C10H17)2BCH2CH=CH2
CAS Number:
85116-38-7
Molecular Weight:
326.37
MDL number:
MFCD09038448
UNSPSC Code:
12352002
PubChem Substance ID:
24885432
NACRES:
NA.22

Key Documents

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SMILES string

C[C@H]1[C@@H](C[C@@H]2C[C@H]1C2(C)C)B(CC=C)[C@@H]3C[C@@H]4C[C@H]([C@H]3C)C4(C)C

InChI

1S/C23H39B/c1-8-9-24(20-12-16-10-18(14(20)2)22(16,4)5)21-13-17-11-19(15(21)3)23(17,6)7/h8,14-21H,1,9-13H2,2-7H3/t14-,15-,16+,17+,18-,19-,20-,21-/m1/s1

InChI key

ZIXZBDJFGUIKJS-RLEROFIGSA-N

optical activity

[α]20/D −35 to ±5°, c = 1

concentration

1 M in pentane

bp

35-36 °C

density

0.638 g/mL at 25 °C

storage temp.

−20°C

Quality Level

100

Related Categories

Application

This allylboration reagent is a convenient, salt-free, stable solution of a chiral allyl borane for asymmetric allylation of aldehydes leading to chiral homoallylic alcohols.

Other Notes

Material may become hazy upon cooler storage, this will not affect use
Under refrigerator storage, these salt-free, Ipc2B(allyl) reagents do not show any appreciable decrease in selectivity is observed after several months. They exhibit excellent reactivity and reactions can be performed at 5°C, even in water.

signalword

Danger

Hazard Classifications

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Central nervous system, Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

-56.2 °F - closed cup

flash_point_c

-49 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBL1948
SHBJ6237
SHBH5863
SHBG1511V
SHBD7763V

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Enantio-and diastereoselective synthesis of ?-substituted-?-aminoboronic esters from nitriles
Ramachandran, P. Veeraraghavan, et al.
Tetrahedron Letters, 54.36, 4830-4833 (2013)
Aldrichimica Acta, 25, 23-23 (2002)
Stereoselective Synthesis of 2, 6?Disubstituted Piperidines Using the Iridium?Catalyzed Allylic Cyclization as Configurational Switch: Asymmetric Total Synthesis of (+)?241 D and Related Piperidine Alkaloids.
Gnamm, Christian, et al.
European Journal of Chemistry, 15.9, 2050-2054 (2009)
Total Synthesis and Biological Evaluation of (+)?Neopeltolide and Its Analogues
Fuwa, Haruhiko, et al.
Chemistry?A European Journal , 51.46, 12807-12818 (2009)
Versatile route to 2, 6-dideoxyamino sugars from non-sugar materials: Syntheses of vicenisamine and kedarosamine.
Matsushima, Yoshitaka, et al.
J. Chem. Soc., Perkin Trans., 1.6, 569-577 (2001)
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