2-Bromoanisole

Last updated
2-Bromoanisole
2-Bromoanisole.svg
Names
Preferred IUPAC name
1-Bromo-2-methoxybenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.570 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-425-8
PubChem CID
UNII
  • InChI=1S/C7H7BrO/c1-9-7-5-3-2-4-6(7)8/h2-5H,1H3
    Key: HTDQSWDEWGSAMN-UHFFFAOYSA-N
  • COC1=CC=CC=C1Br
Properties
C7H7BrO
Molar mass 187.036 g·mol−1
AppearanceColorless liquid
Melting point 2.5 °C (36.5 °F; 275.6 K)
Boiling point 216 °C (421 °F; 489 K)
Hazards
GHS labelling:
GHS-pictogram-pollu.svg
Warning
H411
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Bromoanisole is an organobromide with the formula BrC6H4OCH3. A colorless liquid, it is one of three isomers of bromoanisole, the others being 3-bromoanisole and 4-bromoanisole. It is a standard coupling partner in metal catalyzed coupling reactions. These reactions include Heck reactions, Buchwald-Hartwig coupling, [1] Suzuki couplings, and Ullmann condensations. [2] The corresponding Grignard reagent readily forms. It is a precursor to o-anisaldehyde. [3] [4]

Related Research Articles

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In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Imine</span> Organic compound or functional group containing a C=N bond

In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.

In chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed acetate esters or simply acetates. Deacetylation is the opposite reaction, the removal of an acetyl group from a chemical compound.

<span class="mw-page-title-main">Anisole</span> Organic compound (CH₃OC₆H₅) also named methoxybenzene

Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. Structurally, it is an ether with a methyl and phenyl group attached. Anisole is a standard reagent of both practical and pedagogical value.

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<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

Grignard reagents or Grignard compounds are chemical compounds with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

<span class="mw-page-title-main">Diglyme</span> Chemical compound

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<span class="mw-page-title-main">4-Bromoanisole</span> Chemical compound

4-Bromoanisole is the organobromine compound with the formula CH3OC6H4Br. It is colorless liquid with a pleasant smell similar to that of anise seed. It is one of three isomers of bromoanisole, the others being 3-bromoanisole and 2-bromoanisole. It is the precursor to many 4-anisyl derivatives.

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<span class="mw-page-title-main">Trimethylsilylacetylene</span> Chemical compound

Trimethylsilylacetylene is the organosilicon compound with the formula (CH3)3SiC2H. A colorless liquid, "tms acetylene", as it is also called, is used as a source of "HC2" in organic synthesis.

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<span class="mw-page-title-main">Diphenylphosphine oxide</span> Chemical compound

Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents.

<span class="mw-page-title-main">Vinyllithium</span> Chemical compound

Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.

<span class="mw-page-title-main">Diethylphosphite</span> Chemical compound

Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.

<span class="mw-page-title-main">Benzophenone imine</span> Chemical compound

Benzophenone imine is an organic compound with the formula of (C6H5)2C=NH. A pale yellow liquid, benzophenone imine is used as a reagent in organic synthesis.

Hydroxymethylation is a chemical reaction that installs the CH2OH group. The transformation can be implemented in many ways and applies to both industrial and biochemical processes.

<span class="mw-page-title-main">Xylylene dibromide</span> Chemical compound

Xylylene dibromide is an organic compound with the formula C6H4(CH2Br)2. It is an off-white solid that, like other benzyl halides, a strong lachrymator. It is a useful reagent owing to the convenient reactivity of the two C-Br bonds. Two other isomers are known, para- and meta-xylylene dibromide.

References

  1. Klapars, Artis; Antilla, Jon C.; Huang, Xiaohua; Buchwald, Stephen L. (2001). "A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and theN-Arylation of Nitrogen Heterocycles". Journal of the American Chemical Society. 123 (31): 7727–7729. doi:10.1021/ja016226z. PMID   11481007.
  2. Buck, Elizabeth; Song, Zhiguo J. (2005). "Preparation of 1-Methoxy-2-(4-Methoxyphenoxy)Benzene". Organic Syntheses. 82: 69. doi:10.15227/orgsyn.082.0069.
  3. Sisti, A. J. (1964). "O-Anisaldehyde". Organic Syntheses. 44: 4. doi:10.15227/orgsyn.044.0004.
  4. Brinkmeyer, R. S.; Collington, E. W.; Meyers, A. I. (1974). "Aldehydes from 4,4-Dimethyl-2-oxazoline and Grignard Reagents: O-Anisaldehyde". Organic Syntheses. 54: 42. doi:10.15227/orgsyn.054.0042.