407593

Sigma-Aldrich

Methyl 4-bromobenzoate

99%

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

Quality Level

assay

99%

mp

77-81 °C (lit.)

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 furo2,3-dpyrimidine and 6-substituted pyrrolo2,3-dpyrimidine analogs, employed as antifolates.
  • Methyl 4-tri-n-butylstannylbenzoate.
  • Methyl 4-(2-pyridyl)benzoate by cross coupling reaction with lithium 2-pyridyltriolborate.
  • Methyl 4-imidazo1,2-apyridin-3-ylbenzoate by ligand-free Pd(OAc)2 catalyzed reaction with Imidazo1,2-apyridine.
  • Methyl (E)-4-3-(2-methoxycarbonylvinyl)-thiophen-2-ylacrylate by reacting with methyl (E)-3-(thiophen-3-y)lacrylate.

Packaging

10 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

Xi

Risk Statement

36/37/38

Safety Statement

26

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
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)
Methyl 4-bromobenzoate.
Bolte M and Wissler J.
Acta Crystallographica Section E, Structure Reports Online, 62(3), o1192-o1193 (2006)
Palladium-acetate catalyst for regioselective direct arylation at C2 of 3-furanyl or 3-thiophenyl acrylates with inhibition of Heck type reaction.
Chen L, et al.
Tetrahedron, 69(22), 4381-4388 (2013)
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...

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