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419540

Sigma-Aldrich

1-Propenylmagnesium bromide solution

0.5 M in THF

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About This Item

Linear Formula:
CH3CH=CHMgBr
CAS Number:
14092-04-7
Molecular Weight:
145.28
MDL number:
MFCD00209610
UNSPSC Code:
12352103
PubChem Substance ID:
24866259
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

0.5 M in THF

bp

65 °C

density

0.95 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CC=C[Mg]Br

InChI

1S/C3H5.BrH.Mg/c1-3-2;;/h1,3H,2H3;1H;/q;;+1/p-1

InChI key

HHNLJRLNDSEYOX-UHFFFAOYSA-M

Application

1-Propenylmagnesium bromide solution can be used in the preparation of:
  • Titanocene alkenylidene intermediates in situ from alkenyltitanocene precursors, which then reacts with carbonyl compounds to form the corresponding allenes.[1]
  • 1-(4-ethoxy-phenyl)-3-methyl-hex-4-en-1-one from methyl 4-ethoxybenzoate.[2]
  • 2-(propen-1-yl)chroman-4-ones from chromones.[3]

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH019

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

-4.0 °F - closed cup

flash_point_c

-20 °C - closed cup

ppe

Faceshields, Gloves, Goggles

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Certificates of Analysis (COA)

Lot/Batch Number
SHBK9079
SHBJ9775
SHBJ3447
SHBJ3446
SHBJ1845

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Efficient synthesis of apricoxib, CS-706, a selective cyclooxygenase-2 inhibitor, and evaluation of inhibition of prostaglandin E2 production in inflammatory breast cancer cells.
Mandal P K, et al.
Bioorganic & Medicinal Chemistry Letters, 21(20), 6071-6073 (2011)
Synthesis and antimicrobial activity of 2-alkenylchroman-4-ones, 2-alkenylthiochroman-4-ones and 2-alkenylquinol-4-ones
Hoettecke N, et al.
Bioorganic & Medicinal Chemistry, 16(24), 10319-10325 (2008)
Allenation of carbonyl compounds with alkenyltitanocene derivatives.
Petasis N A and Hu Y H
The Journal of Organic Chemistry, 62(4), 782-783 (1997)

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