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Methyl 2-bromobenzoate

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Name

Methyl 2-bromobenzoate

EINECS 210-241-5
CAS No. 610-94-6 Density 1.498 g/cm3
PSA 26.30000 LogP 2.23570
Solubility insoluble Melting Point 252°C
Formula C8H7BrO2 Boiling Point 241 °C at 760 mmHg
Molecular Weight 215.046 Flash Point 99.6 °C
Transport Information N/A Appearance Colorless or light yellow transparent liquid
Safety 24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 610-94-6 (Methyl 2-bromobenzoate) Hazard Symbols IrritantXi
Synonyms

Benzoicacid, o-bromo-, methyl ester (6CI,7CI,8CI);2-Bromobenzoic acid methyl ester;Methyl o-bromobenzoate;NSC 7318;

Article Data 79

Methyl 2-bromobenzoate Synthetic route

67-56-1

methanol

88-65-3

2-bromobenzoic-acid

610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid Reflux; Inert atmosphere;99%
With sulfuric acid Reflux;99%
With sulfuric acid at 0℃; for 20.25h; Fischer-Speier Esterification; Reflux;96%
67-56-1

methanol

6630-33-7

ortho-bromobenzaldehyde

610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With perchloric acid; sodium percarbonate; vanadia for 1.3h; Cooling;96%
With tert.-butylhydroperoxide; potassium carbonate In water at 60℃; for 6h;87%
With magnesium hydroxide; oxygen at 90℃; under 2250.23 Torr; for 8h;
2142-69-0

2-bromophenyl methyl ketone

A

610-94-6

2-bromobenzoic acid methyl ester

B

1829-37-4

o-bromophenyl acetate

Conditions
ConditionsYield
With hydrogenchloride In chloroform at 20℃; for 12h; Baeyer-Villiger oxidation;A 7%
B 91%
88-65-3

2-bromobenzoic-acid

119-36-8

methyl salicylate

A

610-94-6

2-bromobenzoic acid methyl ester

B

69-72-7

salicylic acid

Conditions
ConditionsYield
Stage #1: 2-bromobenzoic-acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h;
Stage #2: methyl salicylate at 110℃; for 24h;
A 91%
B n/a
67-56-1

methanol

18982-54-2

o-bromobenzyl alcohol

610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With oxygen; potassium carbonate at 60℃; under 750.075 Torr; for 20h;86%
With potassium chloride; dihydrogen peroxide; C5H12CrMo6O25(3-)*3C16H36N(1+) In water at 65℃; for 36h; Schlenk technique;80%
With sodium hypochlorite; tetrabutylammomium bromide In ethyl acetate at 20℃; for 3.51667h;17%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione at 25℃; for 12h; Temperature; chemoselective reaction;24 %Chromat.
67-56-1

methanol

201230-82-2

carbon monoxide

583-53-9

1,2-dibromobenzene

A

610-94-6

2-bromobenzoic acid methyl ester

B

131-11-3

phthalic acid dimethyl ester

C

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 18h; Irradiation;A 4%
B 85%
C 3%
201230-82-2

carbon monoxide

583-53-9

1,2-dibromobenzene

A

610-94-6

2-bromobenzoic acid methyl ester

B

131-11-3

phthalic acid dimethyl ester

C

88-99-3

benzene-1,2-dicarboxylic acid

Conditions
ConditionsYield
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 18h; Irradiation;A 4%
B 85%
C 3%
586-76-5

4-Bromobenzoic acid

107-06-2

1,2-dichloro-ethane

610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With sulfuric acid In methanol84%
75-91-2

tert.-butylhydroperoxide

95-46-5

2-methylphenyl bromide

610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
Stage #1: tert.-butylhydroperoxide; 2-methylphenyl bromide In water; dimethyl sulfoxide
Stage #2: In water; dimethyl sulfoxide at 100℃; for 20h; Sealed tube;
84%
With copper (II)-fluoride In water; dimethyl sulfoxide at 120℃; for 12h; Schlenk technique; Inert atmosphere; Green chemistry;25%
With ultrafine CuO particles dispersed on nitrogen-doped hollow carbon nanospheres In water; dimethyl sulfoxide at 100℃; for 20h; Sealed tube;86 %Chromat.
52711-30-5

1-bromo-2-(methoxymethyl)benzene

610-94-6

2-bromobenzoic acid methyl ester

Conditions
ConditionsYield
With oxygen In water at 25℃; for 12h; Irradiation; Green chemistry;80%
With copper(II) choride dihydrate; oxygen; hydroquinone at 30℃; for 16h; Sealed tube; Irradiation; Green chemistry;41%

Methyl 2-bromobenzoate Specification

The IUPAC name of this chemical is Methyl 2-bromobenzoate. With the CAS registry number 610-94-6 and EINECS registry number 210-241-5, it is also named as Benzoicacid,2-bromo-,methyl ester. In addition, the molecular formula is C8H7BrO2 and the molecular weight is 215.04. It is a kind of clear light yellow liquid and belongs to the classes of Aromatic Esters; Acids & Esters; Bromine Compounds; C8 to C9; Carbonyl Compounds; Esters. And it should be stored in a airtight, cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 2.55; (2)ACD/LogD (pH 5.5): 2.55; (3)ACD/LogD (pH 7.4): 2.55 ; (4)#H bond acceptors: 2; (5)#Freely Rotating Bonds: 2; (6)Polar Surface Area: 26.3 Å2; (7)Index of Refraction: 1.549; (8)Molar Refractivity: 45.71 cm3; (9)Molar Volume: 143.5 cm3; (10)Polarizability: 18.12 ×10-24cm3; (11)Surface Tension: 40.7 dyne/cm; (12)Density: 1.498 g/cm3; (13)Flash Point: 99.6 °C; (14)Enthalpy of Vaporization: 47.79 kJ/mol; (15)Boiling Point: 241 °C at 760 mmHg; (16)Vapour Pressure: 0.0368 mmHg at 25°C.

Preparation of Methyl 2-bromobenzoate: it can be prepared by 2-bromo-benzoic acid and methanol. This reaction will need catalyst sulfuric acid. The yield is about 80%.

Methyl 2-bromobenzoate can be prepared by 2-bromo-benzoic acid and methanol

Uses of Methyl 2-bromobenzoate: it can react with but-3-ynyl-benzene to get 2-(4-phenyl-but-1-ynyl)-benzoic acid methyl ester. This reaction will need reagents trans-bis(triphenylphosphine)palladium(II) chloride, triethylamine and CuI2. The reaction time is 12 hours at reaction temperature of 25 °C. The yield is about 80%.

Methyl 2-bromobenzoate can react with but-3-ynyl-benzene to get 2-(4-phenyl-but-1-ynyl)-benzoic acid methyl ester

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. During using it, you should avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)c1ccccc1Br
(2)InChI: InChI=1/C8H7BrO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,1H3
(3)InChIKey: SWGQITQOBPXVRC-UHFFFAOYAT

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