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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:
180675-22-3
Molecular Weight:
191.31
MDL number:
MFCD01321271
UNSPSC Code:
12352103
PubChem Substance ID:
24870813
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

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

EUH018,EUH019

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

472611-1L:4548173156491
472611-BULK:
472611-VAR:
472611-100ML:4548173156484

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)
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)
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)

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