ChemicalBook Product Catalog Chemical Reagents Organic reagents Esters Methyl ester compound METHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE

METHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE

Product NameMETHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE
CAS70264-94-7
MFC10H11BrO3
MW259.1
EINECS410-310-1
MOL File70264-94-7.mol

Chemical Properties

Melting point	92-94°C
Boiling point	324.2±32.0 °C(Predicted)
Density	1.432
storage temp.	under inert gas (nitrogen or Argon) at 2-8°C
solubility	Chloroform (Sparingly), Methanol (Slightly)
form	powder to crystal
color	White to Light yellow
InChI	InChI=1S/C10H11BrO3/c1-13-9-5-7(10(12)14-2)3-4-8(9)6-11/h3-5H,6H2,1-2H3
InChIKey	UXSNXOMMJXTFEG-UHFFFAOYSA-N
SMILES	C(OC)(=O)C1=CC=C(CBr)C(OC)=C1
CAS DataBase Reference	70264-94-7(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi,N
Risk Statements	36/37/38-50/53-43-41-38
Safety Statements	26-36/37/39-61-60
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
HazardClass	IRRITANT
PackingGroup	Ⅲ
HS Code	2918999090
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1 Eye Dam. 1 Skin Irrit. 2 Skin Sens. 1

Usage And Synthesis

Preparation

Methyl 4-(bromomethyl)-3-methoxybenzoate is prepared by the following steps:A mixture of methyl 3-methoxy-4-methylbenzoate 37 (5 g, 27.8 mmol), NBS (4.94 g, 27.8 mmol), and benoyl peroxide (0.0008 g, 0.003 mmol) was refluxed in CCl4 (25 ml) for 10 hours. The reaction mixture was allowed to cool and filtered. The residue was washed with CCl4 and the combined filtrate concentrated in vacuo. Purification by column chromatography over silica gel (5-10% EtOAc-pet ether) furnished a colourless solid (7.19 g).Yield : 100%

Uses

Methyl 4-(Bromomethyl)-3-methoxybenzoate is an intermediate used to prepare heteroarylphenyloxoacetyl and heteroarylphenylsulfonyl benzoylpiperazine analogs of BMS 378806 as HIV entry inhibitors. It is also used to synthesize steroid 5α-reductase inhibiting acylpiperidines.

Synthesis

3556-83-0

METHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE

70264-94-7

Step 1: Methyl 4-methyl-3-methoxybenzoate (1.00 g, 5.55 mmol), N-bromosuccinimide (1.09 g, 6.10 mmol) and catalytic amount of 2,2'-azobisisobutyronitrile (AIBN) were mixed in carbon tetrachloride (40 ml) and the reaction was carried out at reflux for 16 hours. After completion of the reaction, the reaction mixture was filtered and the resulting filtrate was washed with brine (25 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give methyl 4-bromomethyl-3-methoxybenzoate (1.4 g, 97% yield).

References

[1] European Journal of Medicinal Chemistry, 1997, vol. 32, # 7-8, p. 547 - 570
[2] Patent: WO2009/55077, 2009, A1. Location in patent: Page/Page column 391-392
[3] Synlett, 2014, vol. 25, # 17, p. 2485 - 2487
[4] Patent: WO2005/105802, 2005, A1. Location in patent: Page/Page column 120-121
[5] Patent: US6391901, 2002, B1

METHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

METHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE Supplier

METHYL 4-(BROMOMETHYL)-3-METHOXYBENZOATE manufacturers

Related Product Information