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678538

Sigma-Aldrich

(−)-Ipc2B(allyl)borane solution

1 M in pentane

Synonym(s):

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

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25 ML
HUF 125,500.00

HUF 125,500.00

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25 ML
HUF 125,500.00

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

HUF 125,500.00

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optical activity

[α]20/D −35 to ±5°, c = 1

Quality Level

100

concentration

1 M in pentane

bp

35-36 °C

density

0.638 g/mL at 25 °C

storage temp.

−20°C

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

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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.[1][2]

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.[3]

accessory

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Description
Pricing

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-56.2 °F - closed cup

Flash Point(C)

-49 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBL1948
SHBJ6237
SHBH5863
SHBG1511V
SHBD7763V

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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)
Aldrichimica Acta, 25, 23-23 (2002)
Total synthesis of cryptomoscatone F1 through an asymmetric aldol approach
Ramesh, Perla, Atla Raju, and Nitin W. Fadnavis.
Tetrahedron Asymmetry, 26.21, 1251-1255 (2015)
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