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610-97-9

Basic Information
CAS No.: 610-97-9
Name: Methyl 2-iodobenzoate
Article Data: 86
Molecular Structure:
Molecular Structure of 610-97-9 (Methyl 2-iodobenzoate)
Formula: C8H7IO2
Molecular Weight: 262.047
Synonyms: Benzoicacid, o-iodo-, methyl ester (6CI,7CI,8CI);2-Iodobenzoic acid methyl ester;Methyl o-iodobenzoate;NSC 34638;
EINECS: 210-243-6
Density: 1.753 g/cm3
Melting Point: 64 °C
Boiling Point: 258.8 °C at 760 mmHg
Flash Point: 110.3 °C
Solubility: insoluble in water
Appearance: clear yellow liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36-24/25
PSA: 26.30000
LogP: 2.07780
Synthetic route
67-56-1

methanol

88-67-5

2-Iodobenzoic acid

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
With sulfuric acid Reflux;100%
With sulfuric acid for 3h; Reflux;99%
With sulfuric acid at 80℃; for 2.5h; Inert atmosphere;99%
67-56-1

methanol

609-67-6

2-Iodobenzoyl chloride

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
With sulfuric acid Reflux;98%
With sodium hydroxide
With oxalyl dichloride In dichloromethane for 0.5h; Inert atmosphere;
With triethylamine at 0 - 20℃; for 2h;
With triethylamine at 0 - 20℃; for 0.5h;0.42 g
88-67-5

2-Iodobenzoic acid

74-88-4

methyl iodide

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
With potassium carbonate In acetone98%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;96%
Stage #1: 2-Iodobenzoic acid With caesium carbonate In N,N-dimethyl-formamide
Stage #2: methyl iodide In N,N-dimethyl-formamide at 50℃; for 1h;
95%
693232-15-4

2-(methoxycarbonyl)phenylzinc iodide

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.166667h; Substitution;96%
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.166667h;48%
431-47-0

trifluoroacetic acid-methyl ester

32730-83-9

1-(2-iodophenyl)pentan-1-one

A

360-34-9

1,1,1-trifluoro-2-hexanone

B

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
Stage #1: trifluoroacetic acid-methyl ester With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 1-(2-iodophenyl)pentan-1-one In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; Schlenk technique;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃; for 0.25h; Inert atmosphere; Schlenk technique;
A n/a
B 96%
134-20-3

2-carbomethoxyaniline

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
Stage #1: 2-carbomethoxyaniline With sulfuric acid; sodium nitrite In water at 0 - 7℃; Inert atmosphere;
Stage #2: With sulfuric acid; sodium hydrogensulfite; potassium iodide In water at -5 - 80℃; for 1.58333h; Inert atmosphere;
93%
Stage #1: 2-carbomethoxyaniline With sulfuric acid; sodium nitrite
Stage #2: With potassium iodide
Stage #1: 2-carbomethoxyaniline With toluene-4-sulfonic acid In acetonitrile at 20℃; for 0.166667h;
Stage #2: With potassium iodide; sodium nitrite In water; acetonitrile at 0 - 20℃;
723259-89-0

2-iodo-N-(quinolin-8-yl)benzamide

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 110℃; for 36h; Sealed tube;93%
93-58-3

benzoic acid methyl ester

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
Stage #1: benzoic acid methyl ester With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; cadmium(II) chloride-N,N,N',N'-tetramethylethylenediamine In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere; chemoselective reaction;
89%
Stage #1: benzoic acid methyl ester With (2,2,6,6-tetramethylpiperidido)2Ag(CN)Li2 In tetrahydrofuran at -40℃; for 2h;
Stage #2: With iodine In tetrahydrofuran at 20℃; for 3h; Reagent/catalyst; chemoselective reaction;
86%
With N-iodo-succinimide; silver hexafluoroantimonate; trifluorormethanesulfonic acid; nickel diacetate In 1,2-dichloro-ethane at 80℃; for 12h; regioselective reaction;77%
Stage #1: benzoic acid methyl ester With cadmium(II) chloride-N,N,N',N'-tetramethylethylenediamine; 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at 20℃; for 2h; Inert atmosphere;
Stage #2: With iodine In tetrahydrofuran; hexane Inert atmosphere; regioselective reaction;
62%
With 2,2,6,6-tetramethylpiperidinyl-lithium; iodine; di-tert-butylzinc 1.) THF, RT, 2.) THF, RT; Yield given; Multistep reaction;
353-42-4

boron trifluoride dimethyl etherate

88-67-5

2-Iodobenzoic acid

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
at 120℃; for 4h; Reflux;89%
88-67-5

2-Iodobenzoic acid

616-38-6

carbonic acid dimethyl ester

610-97-9

o-iodo-methyl-benzoic acid

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 16h; Inert atmosphere; Green chemistry;88%
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  • Benzoicacid, 2-iodo-, methyl ester

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    610-97-9

    Benzoicacid, 2-iodo-, methyl ester

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Specification

The IUPAC name of this product is methyl 2-iodobenzoate. With the CAS registry number 610-97-9, it is also named as Benzoic acid, 2-iodo-, methyl ester; AI3-11097; NSC 34638. The product's categories are aromatic esters, acids & esters, iodine compounds, carbonyl compounds and esters.  

The Methyl 2-iodobenzoate is clear yellow liquid which is sensitive to light. This chemical must be stored in tightly sealed containers in a cool place. It is irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing. 

The Methyl 2-iodobenzoate is a starting material for the preparation of iodosobenzoate, useful oxidants (such as 2-Iodoxybenzoic acid) which performs the synthesis of carbonyl compounds from primary/secondary alcohols and unsaturated carbonyl compounds from carbonyl compounds.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.74; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.74; (4)ACD/LogD (pH 7.4): 2.74; (5)ACD/BCF (pH 5.5): 70.9; (6)ACD/BCF (pH 7.4): 70.9; (7)ACD/KOC (pH 5.5): 735; (8)ACD/KOC (pH 7.4): 735; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.597; (13)Molar Refractivity: 50.93 cm3; (14)Molar Volume: 149.3 cm3; (15)Polarizability: 20.19×10-24 cm3; (16)Surface Tension: 45.3 dyne/cm; (17)Enthalpy of Vaporization: 49.64 kJ/mol; (18)Vapour Pressure: 0.0134 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Exact Mass: 261.949072; (21)MonoIsotopic Mass: 261.949072; (22)Topological Polar Surface Area: 26.3; (23)Heavy Atom Count: 11.

People can use the following data to convert to the molecule structure. SMILES: O=C(OC)c1ccccc1I; InChI: InChI=1/C8H7IO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,1H3; InChIKey: BXXLTVBTDZXPTN-UHFFFAOYAN. Methyl 2-iodobenzoate has many suppliers, such as BenzChem Co., Ltd., Changzhou Ilhang Fine Chemical Co., Ltd. and Changzhou Xixialong International Co., Ltd..