Methyl 2-iodobenzoate Chemical Properties

Melting point:

64°C

Boiling point:

149-150 °C/10 mmHg (lit.)

Density 

1.784 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.604(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Ethyl Acetate (Slightly), Methanol

form 

Crystalling or Flaky Powder

color 

White

Water Solubility 

INSOLUBLE

Sensitive 

Light Sensitive

BRN 

2206859

Stability:

Light Sensitive

InChIKey

BXXLTVBTDZXPTN-UHFFFAOYSA-N

CAS DataBase Reference

610-97-9(CAS DataBase Reference)

NIST Chemistry Reference

Methyl-2-iodobenzoate(610-97-9)

EPA Substance Registry System

Benzoic acid, 2-iodo-, methyl ester (610-97-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

3

TSCA 

T

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:Methyl 2-iodobenzoate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl 2-iodobenzoate Usage And Synthesis

Chemical Properties

CLEAR YELLOW LIQUID

Uses

Methyl 2-iodobenzoate may be used in the preparation of:

• N-substituted 4-methylene-3,4-dihydro-1(2H)-isoquinolin-1-ones
• methyl diphenylacetylene-2-carboxylate
• methyl 2-heptynylphenylbenzoate
• (E)-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoic acid methyl ester
• 4-(2-carbomethoxyphenyl)-3-(1-methylethoxy)cyclobut-3-ene-1,2-dione
• 3-(2-carbomethoxyphenyl)-4-methylcyclobuten-3-ene-1,2-dione 2-(ethylene acetal)

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4845, 1971 DOI: 10.1021/ja00748a030

General Description

Methyl 2-iodobenzoate can be prepared from 2-iodobenzoic acid via esterification. It undergoes cobalt-catalyzed cyclization with aldehydes to form phthalide derivatives. The microbial dihydroxylation of methyl 2-iodobenzoate forms a nonracemic iodocyclohexene carboxylate intermediate. This intermediate forms the precursor for preparing kibdelone C.

Synthesis

To a 200 mL methanol solution of 2-iodobenzoic acid (15 g, 60 mmol) was slowly added 8.8 mL of concentrated sulfuric acid dropwise. The reaction mixture was heated to reflux for 16 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated by rotary evaporator to about 20 mL. Subsequently, the concentrate was partitioned between water (appropriate amount) and dichloromethane (appropriate amount). The aqueous phase was further extracted with dichloromethane (2 × 150 mL). The organic layers were combined and washed sequentially with saturated sodium bicarbonate solution (3 × 100 mL) and water (3 × 100 mL). The organic layers were dried over anhydrous sodium sulfate, filtered and the solvent was evaporated to give methyl 2-iodobenzoate (47) as a light yellow oil (15.4 g, 98% yield).The infrared spectrum of methyl 2-iodobenzoate (47) (KBr, νmax, cm?1): 3444, 3057, 2994, 2946, 2894, 2836, 1728, 1579, 1459, 1428, 1290. 1459, 1428, 1290, 1249, 1127, 1100, 1013, 738.

References

[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 17, p. 3213 - 3219
[2] Organometallics, 2013, vol. 32, # 11, p. 3220 - 3226
[3] European Journal of Medicinal Chemistry, 2013, vol. 69, p. 798 - 816
[4] Synthetic Communications, 2017, vol. 47, # 12, p. 1175 - 1184
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 39, p. 11995 - 11999

Methyl 2-iodobenzoate(610-97-9)Related Product Information

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• 4-Aminobenzoic acid
• METHYL THIOPHENE-2-CARBOXYLATE
• 2-Iodobenzoic acid
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