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472611

Sigma-Aldrich

(1,3-Dioxolan-2-ylmethyl)magnesium bromide solution

0.5 M in THF

Synonym(s):

2-[(Bromomagnesio)methyl]-1,3-dioxolane, Bromo(1,3-dioxolan-2-ylmethyl)magnesium

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About This Item

Empirical Formula (Hill Notation):
C4H7BrMgO2
CAS Number:
Molecular Weight:
191.31
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

Quality Level

concentration

0.5 M in THF

bp

65-67 °C

density

0.938 g/mL at 25 °C

SMILES string

Br[Mg]CC1OCCO1

InChI

1S/C4H7O2.BrH.Mg/c1-4-5-2-3-6-4;;/h4H,1-3H2;1H;/q;;+1/p-1

InChI key

ZDNTZRAFJZERSL-UHFFFAOYSA-M

Application

(1,3-Dioxolan-2-ylmethyl)magnesium bromide is a Grignard reagent that can be used to prepare:
  • 3-[11C]-Propionaldehyde, a key intermediate for the synthesis of radiolabeled compound [11C]SN-38, wherein SN-38 is 7-ethyl-10-hydroxy camptothecin.
  • 1-[(S)-2,2-Dimethyl-(1,3)-dioxolan-4-yl]-4-(1,3-dioxolan2-yl)-2-ol by reacting with D-glyceraldehyde, which is further used to synthesize unsaturated nucleosides.
  • A bicyclo carboxylate intermediate, which is employed in the total synthesis of spirovibsanin A.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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 biodistribution of [11C] SN-38
Apana SM, et al.
Journal of Labelled Compounds & Radiopharmaceuticals, 53(4), 178-182 (2010)
Synthesis, Structure- Activity Relationships, and Drug Resistance of beta-d-3′-Fluoro-2′, 3′-Unsaturated Nucleosides as Anti-HIV Agents
Zhou W, et al.
Journal of Medicinal Chemistry, 47(13), 3399-3408 (2004)
Towards the Total Synthesis of Spirovibsanin A: Total Synthesis of (pm)-5, 14-Bis-epi-spirovibsanin A
Gallen MJ and Williams CM
European Journal of Organic Chemistry, 2008(27), 4697-4705 (2008)

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