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407593

Sigma-Aldrich

Methyl 4-bromobenzoate

99%

Synonym(s):

1-Bromo-4-(methoxycarbonyl)benzene, 4-Bromobenzoic acid methyl ester, 4-Methoxycarbonyl-1-bromobenzene, 4-Methoxycarbonylphenyl bromide, Methyl p-bromobenzoate, p-Bromobenzoic acid methyl ester

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About This Item

Linear Formula:
BrC6H4CO2CH3
CAS Number:
Molecular Weight:
215.04
Beilstein:
2045132
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

Assay

99%

form

powder

mp

77-81 °C (lit.)

functional group

bromo
ester

SMILES string

COC(=O)c1ccc(Br)cc1

InChI

1S/C8H7BrO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,1H3

InChI key

CZNGTXVOZOWWKM-UHFFFAOYSA-N

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General description

Methyl 4-bromobenzoate is a para-substituted aryl bromide.[1] Mol­ecules of methyl 4-bromobenzoate are almost planar. The compound is isostructural with methyl 4-iodo­benzoate.[2] The Zeeman effect on the N.Q.R. (nuclear quadrupole resonance) of methyl 4-bromobenzoate on single crystals, has been investigated by the ′geometric method′.[3]

Application

Methyl 4-bromobenzoate may be used in the following syntheses:
  • Three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogs, employed as antifolates.[4]
  • Methyl 4-tri-n-butylstannylbenzoate.[5]
  • Methyl 4-(2-pyridyl)benzoate by cross coupling reaction with lithium 2-pyridyltriolborate.[6]
  • Methyl 4-imidazo[1,2-a]pyridin-3-ylbenzoate by ligand-free Pd(OAc)2 catalyzed reaction with Imidazo[1,2-a]pyridine.[7]
  • Methyl (E)-4-[3-(2-methoxycarbonylvinyl)-thiophen-2-yl]acrylate by reacting with methyl (E)-3-(thiophen-3-y)lacrylate.[1]

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Synthesis of Lithium 2-Pyridyltriolborate and its Cross-Coupling Reaction with Aryl Halides.
Yamamoto Y, et al.
Organic Syntheses, 88, 79-86 (2011)
Synthesis and iodination of methyl 4-tri-n-butylstannylbenzoate, p-(methoxycarbonyl) phenylmercuric chloride and p-(methoxycarbonyl) phenylboronic acid.
Hylarides MD, et al.
Journal of Organometallic Chemistry, 367(3), 259-265 (1989)
Methyl 4-bromobenzoate.
Bolte M and Wissler J.
Acta Crystallographica Section E, Structure Reports Online, 62(3), o1192-o1193 (2006)
Aleem Gangjee et al.
Journal of medicinal chemistry, 47(27), 6893-6901 (2004-12-24)
Bridge homologation of the previously reported classical two-carbon-bridged antifolates, a 5-substituted 2,4-diaminofuro[2,3-d]pyrimidine (1) [which is a 6-regioisomer of LY231514 (Alimta)] and a 6-subsituted 2-amino-4-oxopyrrolo[2,3-d]pyrimidine, afforded the three-carbon-bridged antifolates analogues 4 and 5, with enhanced inhibitory activity against tumor cells in
Phosphine-free palladium-catalyzed direct arylation of imidazo [1,2-a] pyridines with aryl bromides at low catalyst loading.
Fu HY, et al.
The Journal of Organic Chemistry, 77(9), 4473-4478 (2012)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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