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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-(4-ethoxy-phenyl)-3-methyl-hex-4-en-1-one from methyl 4-ethoxybenzoate.
  • 2-(propen-1-yl)chroman-4-ones from chromones.

Signal Word

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

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

-4.0 °F - closed cup

Flash Point(C)

-20 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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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