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3-Chlorophenylmagnesium bromide

0.5 M in THF

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Synonym(s):
(3-Chlorophenyl)magnesium bromide, (m-Chlorophenyl)magnesium bromide, 3-chloro phenyl magnesium bromide, 3-chlorophenyl magnesium bromide, m-chlorophenyl magnesium bromide, Bromo(3-chlorophenyl)magnesium
Empirical Formula (Hill Notation):
C6H4BrClMg
CAS Number:
Molecular Weight:
215.76
MDL number:
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

Quality Level

concentration

0.5 M in THF

bp

65 °C (lit.)

density

0.960 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

Clc1cccc([Mg]Br)c1

InChI

1S/C6H4Cl.BrH.Mg/c7-6-4-2-1-3-5-6;;/h1-2,4-5H;1H;/q;;+1/p-1

InChI key

ZIYRUWPTUPFRQU-UHFFFAOYSA-M

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This Item
429007470260442194
concentration

0.5 M in THF

concentration

0.5 M in THF

concentration

0.5 M in THF

concentration

1.0 M in THF

bp

65 °C (lit.)

bp

65-67 °C

bp

65-67 °C

bp

65-67 °C

density

0.960 g/mL at 25 °C (lit.)

density

0.941 g/mL at 25 °C

density

0.955 g/mL at 25 °C

density

1.013 g/mL at 25 °C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

Application

3-Chlorophenylmagnesium bromide (o-chlorophnylmagnesium bromide) is a Grignard reagent that can be used to synthesize:
  • 2,3-Di(o-chlorophenyl)buta-1,3-dienes by reacting with 1,4-dimethoxy 2-butyne in the presence of a copper(I) salt.
  • 2-Bromo-5-chlorothiophen-3-yl-(3-chlorophenyl)methanol by reacting with 2-bromo-5-chlorothiophene-3-carbaldehyde.
  • 2-(3-Chlorophenyl)-1-phenyl-1H-inden-1-ol from 2- benzoylbenzonitrile as a starting a material.

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

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


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Novel synthesis of 2, 3-diarylbuta-1, 3-dienes from 1, 4-dimethoxybutyne-2
Ishino Y, et al.
Tetrahedron Letters, 21(16), 1527-1528 (1980)
The discovery of 4-1-[({2, 5-dimethyl-4-[4-(trifluoromethyl) benzyl]-3-thienyl}carbonyl) amino] cyclopropyl}benzoic acid (MK-2894), a potent and selective prostaglandin E2 subtype 4 receptor antagonist
Blouin M, et al.
Journal of Medicinal Chemistry, 53(5), 2227-2238 (2010)
Synthesis of 3-substituted 3H-indol-3-ols by the reaction of 2-isocyanophenyl ketones with Grignard reagents
Kobayashi K, et al.
Tetrahedron, 66(40), 7961-7964 (2010)

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