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499-06-9

Basic Information
CAS No.: 499-06-9
Name: 3,5-Dimethylbenzoic acid
Article Data: 97
Molecular Structure:
Molecular Structure of 499-06-9 (3,5-Dimethylbenzoic acid)
Formula: C9H10O2
Molecular Weight: 150.177
Synonyms: Mesitylenic acid;3, 5-Dimethylbenzoic acid;Benzoic acid, 3,5-dimethyl-;3,5-dimethylbenzoate;Benzoic acid,3,5-dimethyl-;4-09-00-01806 (Beilstein Handbook Reference);
EINECS: 207-876-5
Density: 1.116 g/cm3
Melting Point: 169-171 °C(lit.)
Boiling Point: 277.9 °C at 760 mmHg
Flash Point: 128.2 °C
Solubility: Soluble in methanol. (1 g/10 mL). Slightly soluble in water.
Appearance: white to light yellow crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 37.30000
LogP: 2.00160
Synthetic route
108-67-8

1,3,5-trimethyl-benzene

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; RuIII-Montmorillonite K10 In acetonitrile for 4h; Heating;94%
With 2-Picolinic acid; sodium tetrahydroborate; bismuth(III) oxide; tert.-butylhydroperoxide In pyridine; water; acetic acid at 110℃; for 16h;78%
Stage #1: 1,3,5-trimethyl-benzene With tert.-butylhydroperoxide; sodium hydroxide; tungsten(VI) oxide In water at 80℃; for 10h;
Stage #2: With hydrogenchloride In water
72%
201230-82-2

carbon monoxide

22445-41-6

3,5-dimethylphenyl iodide

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 10h;94%
With 4,4’‐bis(trimethylammoniummethyl)‐2,2’‐bipyridine; bis-triphenylphosphine-palladium(II) chloride; water; sodium carbonate In water at 100℃; under 7600.51 Torr; for 24h; Catalytic behavior; Autoclave;85%

3,5-dihydroxy-triisopropylsilyl benzoate

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With Selectfluor at 150℃; for 0.166667h; Microwave irradiation;93%
With methanol; trimethylsilyl bromide at 20℃; for 4h; chemoselective reaction;90%
124-38-9

carbon dioxide

3,5-dimethylphenyl sulfurofluoridate

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With manganese; bis(triphenylphosphine)nickel(II) chloride; 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 20h; Schlenk technique; Inert atmosphere; Glovebox;92%
1020038-85-0

1-(3,5-dimethylphenyl)butane-1,3-dione

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;89%
5779-95-3

3,5-dimethylbenzaldehyde

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 20 - 75℃; for 20h;87%
With oxygen; dibromobis(pyridine)cobalt(II) In acetic acid at 75℃; Product distribution; Rate constant; other cobalt bromide catalysts, other solvent;
124-38-9

carbon dioxide

22445-41-6

3,5-dimethylphenyl iodide

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With 3,4-benzo-1,1,2,2-tetraethyl-1,2-disilacyclobut-3-ene; cesium fluoride In N,N-dimethyl-formamide at 0 - 20℃; under 760.051 Torr; for 2h;87%
With copper(l) iodide; diethylzinc; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 25℃; under 760.051 Torr;80%
124-38-9

carbon dioxide

556-97-8

1-chloro-3,5-dimethylbenzene

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; tetraethylammonium iodide; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 100℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;84%
124-38-9

carbon dioxide

556-96-7

5-bromo-1,3-xylene

499-06-9

3,5-dimethylbenzoic acid

Conditions
ConditionsYield
With manganese; 2.9-dimethyl-1,10-phenanthroline; lithium acetate; cobalt(II) bromide In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 12h; Inert atmosphere; Schlenk technique;83%
108-67-8

1,3,5-trimethyl-benzene

A

499-06-9

3,5-dimethylbenzoic acid

B

554-95-0

benzene-1,3,5-tricarboxylic acid

Conditions
ConditionsYield
Stage #1: 1,3,5-trimethyl-benzene With C96H72Cr2N8O; C36H24CuN8; 2-hydroxy-6-nitro-1H-isoindole-1,3-dione at 120℃; under 3750.38 Torr; for 3h;
Stage #2: With acetic acid at 180℃; under 7500.75 Torr; for 2.5h;
Stage #3: With acetic acid at 235℃; under 18001.8 Torr; for 1.8h; Reagent/catalyst; Temperature; Pressure; Overall yield = 96.8 %;
A 14.4%
B 82.4%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Mesitylenic acid is an organic compound with the formula C9H10O2. The IUPAC name of this chemical is 3,5-dimethylbenzoic acid. With the CAS registry number 499-06-9, it is also named as Benzoic acid, 3,5-dimethyl-. The product's categories are Carboxylicacid; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts. Besides, it is a white to light yellow crystalline powder, which should be stored in a closed ventilated and dry place. It is used in organic synthesis, also used as an intermediate for pharmaceuticals and pesticides such as tebufenozide, methoxyfenozide.

Physical properties about Mesitylenic acid are: (1)ACD/LogP: 2.82; (2)ACD/LogD (pH 5.5): 1.63; (3)ACD/LogD (pH 7.4): 0.01; (4)ACD/BCF (pH 5.5): 5.33; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 53.14; (7)ACD/KOC (pH 7.4): 1.28; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 26.3 Å2; (12)Index of Refraction: 1.549; (13)Molar Refractivity: 42.83 cm3; (14)Molar Volume: 134.5 cm3; (15)Polarizability: 16.98×10-24cm3; (16)Surface Tension: 43.1 dyne/cm; (17)Density: 1.116 g/cm3; (18)Flash Point: 128.2 °C; (19)Enthalpy of Vaporization: 54.56 kJ/mol; (20)Boiling Point: 277.9 °C at 760 mmHg; (21)Vapour Pressure: 0.00211 mmHg at 25°C.

Preparation: this chemical can be prepared by 1,3,5-trimethyl-benzene. This reaction will need reagent diluted nitric acid.



Uses of Mesitylenic acid: it can be used to produce 3,5-dimethyl-benzoyl chloride. This reaction is a kind of Chlorination. It will need reagent (COCl)2, DMF and solvent CH2Cl2.

When you are using this chemical, please be cautious about it as the following:
Tthis chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)c1cc(cc(c1)C)C
(2)InChI: InChI=1/C9H10O2/c1-6-3-7(2)5-8(4-6)9(10)11/h3-5H,1-2H3,(H,10,11)
(3)InChIKey: UMVOQQDNEYOJOK-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C9H10O2/c1-6-3-7(2)5-8(4-6)9(10)11/h3-5H,1-2H3,(H,10,11)
(5)Std. InChIKey: UMVOQQDNEYOJOK-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 750mg/kg (750mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Medicinal Chemistry. Vol. 11, Pg. 1020, 1968.