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Merck
CN

407593

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:
619-42-1
Molecular Weight:
215.04
Beilstein:
2045132
EC Number:
210-596-6
MDL number:
MFCD00013531
UNSPSC Code:
12352100
PubChem Substance ID:
24865465
NACRES:
NA.22

Key Documents

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Quality Level

100

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. Mol­ecules of methyl 4-bromobenzoate are almost planar. The compound is isostructural with methyl 4-iodo­benzoate. 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′.

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.
  • Methyl 4-tri-n-butylstannylbenzoate.
  • Methyl 4-(2-pyridyl)benzoate by cross coupling reaction with lithium 2-pyridyltriolborate.
  • Methyl 4-imidazo[1,2-a]pyridin-3-ylbenzoate by ligand-free Pd(OAc)2 catalyzed reaction with Imidazo[1,2-a]pyridine.
  • Methyl (E)-4-[3-(2-methoxycarbonylvinyl)-thiophen-2-yl]acrylate by reacting with methyl (E)-3-(thiophen-3-y)lacrylate.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000214829
0000214829
MKCN7257
MKCB7016
MKBL2873V

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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)
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)
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
Methyl 4-bromobenzoate.
Bolte M and Wissler J.
Acta Crystallographica Section E, Structure Reports Online, 62(3), o1192-o1193 (2006)
Zeeman effect on the nuclear quadrupole resonance of 81Br in single crystals of methyl 4-bromobenzoate, 4, 4'-dibromodiphenyl-ether and 4, 4'-dibromodiphenylsulphide at 77 K.
Ambrosetti R, et al.
Molecular Physics, 28(2), 551-558 (1974)
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