3-Iodo-4-methylbenzoic acid Chemical Properties

Melting point:

210-212 °C (lit.)

Boiling point:

278.5°C (rough estimate)

Density 

1.7835 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

form 

Solid

pka

4.02±0.10(Predicted)

color 

Off-White

Sensitive 

Light Sensitive

BRN 

2436216

InChI

InChI=1S/C8H7IO2/c1-5-2-3-6(8(10)11)4-7(5)9/h2-4H,1H3,(H,10,11)

InChIKey

LDDHMKANNXWUAK-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(C)C(I)=C1

CAS DataBase Reference

82998-57-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Iodo-4-methylbenzoic acid Usage And Synthesis

Chemical Properties

beige to brown crystalline powder

Uses

3-Iodo-4-methylbenzoic acid has been used in the preparation of unlabeled N-succinimidyl 4-guanidinomethyl-3-iodobenzoate (SGIMB) and boc-protected derivative of SGIMB (Boc-SGMIB).

Synthesis

The general procedure for the synthesis of 3-iodo-4-methylbenzoic acid from methyl 3-iodo-4-methylbenzoate was as follows: methyl 3-iodo-4-methylbenzoate (3 g, 10.9 mmol, 1 eq.) was dissolved in methanol (30 mL), followed by addition of sodium hydroxide (1.3 g, 32.7 mmol, 3 eq.) and water (15 mL). The reaction mixture was stirred at room temperature for 14 hours. Upon completion of the reaction, the solution was concentrated under reduced pressure and subsequently diluted with the addition of water. The pH of the reaction mixture was adjusted with concentrated hydrochloric acid to 3. The precipitated solid was collected by filtration and dried under reduced pressure to afford the target product 3-iodo-4-methylbenzoic acid in a yield of 2.7 g (96% yield). The 1H NMR (400 MHz, DMSO-d6) data of the product were as follows: δ 2.44 (s, 3H), 7.45 (d, J=8.00 Hz, 1H), 7.85 (d, J=3.18 Hz, 1H), 8.31 (s, 1H).

References

[1] Patent: WO2010/30538, 2010, A2. Location in patent: Page/Page column 197
[2] Patent: WO2011/112186, 2011, A1. Location in patent: Page/Page column 196
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 17, p. 5004 - 5008

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