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[ CAS No. 603-80-5 ] {[proInfo.proName]}

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Chemical Structure| 603-80-5
Chemical Structure| 603-80-5
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Product Details of [ 603-80-5 ]

CAS No. :603-80-5 MDL No. :MFCD00671541
Formula : C8H8O3 Boiling Point : No data available
Linear Structure Formula :- InChI Key :RIERSGULWXEJKL-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :252023
Synonyms :

Calculated chemistry of [ 603-80-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 40.39
TPSA : 57.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.78
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.4
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.19
Consensus Log Po/w : 1.23

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.04
Solubility : 1.39 mg/ml ; 0.0091 mol/l
Class : Soluble
Log S (Ali) : -2.27
Solubility : 0.809 mg/ml ; 0.00532 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.57
Solubility : 4.13 mg/ml ; 0.0272 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.01

Safety of [ 603-80-5 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 603-80-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 603-80-5 ]

[ 603-80-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 603-80-5 ]
  • [ 108-24-7 ]
  • [ 168899-58-9 ]
YieldReaction ConditionsOperation in experiment
99.28% In einem Planschliffbecher werden 320,0 g Wasser und 120,0 g Natronlauge (w = 30 %) 80,0 g 3-Hydroxy-2-methylbenzoesäure (Gehalt 97,78 %) vermengt. Dabei stellt sich ein pH von 6,9 ein. Die klare Lösung wird auf 0C abgekühlt und durch Zudosieren von Natronlauge (w = 30 %) auf pH = 9 eingestellt. Jetzt werden bei 0 - 5C Acetanhydrid und Natronlauge simultan so eindosiert, dass der pH-Wert im Bereich von 8,8 - 9,2 bleibt. Es werden in 2,5 h 112,6 g Acetanhydrid und 172,25 g Natronlauge (w = 30 %) zudosiert. Danach wird 1,5 h nachgerührt. In einem zweiten Planschliffbecher werden 150,0 g Wasser vorgelegt und auf 0C abgekühlt. Hierzu dosiert man simultan das Reaktionsgemisch des ersten Bechers und Salzsäure (w = 37 %) bei maximal 5C so ein, dass ein pH von 3,8 - 4,2 eingehalten wird. Dabei fällt das Produkt als weißer Niederschlag aus. Durch Nachdosieren von Salzsäure (w = 37 %) wird der pH auf eingestellt. Das Produkt wird abgesaugt und mit 500,0 g Wasser nachgewaschen. Der Niederschlag wird im Vakuumtrockenschrank 16 h bei 60C getrocknet. Man erhält 172,6 g 3-Acetoxy-2-methylbenzoesäure (Gehalt 99,9 %). Das entspricht 99,28 % d.Th.
  • 2
  • [ 603-80-5 ]
  • [ 108-24-7 ]
  • [ 64-19-7 ]
  • [ 168899-58-9 ]
YieldReaction ConditionsOperation in experiment
87.6% sulfuric acid; at 20 - 44℃; for 2h; Acetic acid (8750 mL), 3-hydroxy-2-methylbenzoic acid (3500 g), and sulfuric acid (70 mL) were charged into a 22 liter reactor. The reactor contents were stirred to give a homogeneous mixture. The mixture exothermed to 36 C. Acetic anhydride (2390 mL) was added to the mixture in the 22 L reactor. An exotherm warmed the reactor contents from 36 to 44 C. The reaction mixture was stirred at ambient temperature for two hours (reactor contents allowed to cool slowly). The reaction was tested for complete conversion of the starting material by TLC. The reaction mixture was generally a tan slurry at the completion of the reaction. Purified water (17500 mL) was added to a 50 L extractor, and the reaction mixture from the 22 L reactor was added to this water. The 22 L reactor was rinsed into the 50 L extractor with purified water (3500 mL). The reaction mixture was vacuum filtered, washing the reactor and filter cake with purified water (3500 mL). The wet filter cake was transferred to a 50 L extractor, and purified water (14000 mL) was added, with stirring, to obtain a homogeneous slurry. The reslurried mixture was vacuum filtered, and the reactor and filter cake were rinsed with purified water (3500 mL). The filter cake was pulled as dry as possible and then transferred to drying pans. The product was dried in a vacuum oven at 60 - 80 C and ≥28 mm Hg for 12 - 72 hours. Theoretical yield: 4466 g. Actual weight produced: 3910 g (87.6%). HPLC assay: 89.4% or 87.7%. Purification was achieved as follows. The crude 3-acetoxy-2-methylbenzoic acid (3910 g from above) and ethyl acetate (16.0 L) were charged to a 50 L reactor. The reactor contents were heated to reflux (77 C) until all solids went into solution. The reactor contents were cooled to < 70 C. Hexanes (19.5 L) were added to the reactor. The reactor contents were again heated to reflux (69 C), and then the mixture was cooled to <10 C for 1 hour. The cooled slurry from this step was vacuum filtered, and the reactor was rinsed with cold mother liquors. The filter cake was pulled as dry as possible and then transferred to drying pans. The product was dried in a vacuum oven at 60 - 70 C and ≥28 mm Hg for 12 - 72 hours. Theoretical yield: 3910 g. Actual weight produced: 3128 g (80%). This procedure improves the HPLC UV apparent purity from 89 - 92% to >98%. The single largest impurity drops from 4 - 6% to <1%. The isolated product is a tan solid. 1H NMR δ 8.0 (d, 1H), 7.3 (overlapping m, 2H), 2.5 (s, 3H), 2.3 (s, 3H).
  • 3
  • [ 603-80-5 ]
  • [ 168899-58-9 ]
YieldReaction ConditionsOperation in experiment
90.0% With hydrogenchloride; sodium hydroxide; In water; acetic anhydride; 3-Acetoxy-2-methylbenzoic acid 60.9 g (0.40 mol) of 3-hydroxy-2-methylbenzoic acid are introduced into 500 ml of 2N sodium hydroxide solution (1.00 mol) with stirring and the solution formed in the course of this is cooled to 5 C. 61.3 g (0.60 mol) of acetic anhydride are added to the cooled solution. The reaction mixture is cooled here such that the temperature does not exceed 8 C. The reaction mixture is then acidified with 88 ml of 37% hydrochloric acid. The precipitated product is filtered off, washed three times with 50 ml of water and dried in vacuo. 69.9 g of 3-acetoxy-2-methylbenzoic acid are obtained. This corresponds to a yield of 90.0% of theory. Melting point 147-148 C.
31% With sulfuric acid; acetic anhydride; In water; EXAMPLE 81 3-(Acetyl)hydroxy-2-methylbenzoic acid To a heterogeneous solution of 3.06 g (30 mmol) of acetic anhydride and 1.53 g (10 mmol) of 3-hydroxy-2-methylbenzoic acid was added one drop of concentrated sulfuric acid. The mixture was heated with a heat gun for 2 min. and then poured into 14 mL of cold water. The resulting precipitate was collected by vacuum filtration, washed twice with water and dried overnight in a vacuum oven. Recrystallization from 20% ethyl acetate/hexane (7 mL) gave 595 mg of a white solid, which is 3-(Acetyl)hydroxy-2-methyl benzoic acid. Yield: 31% IR (CHCl3): 3700-2300 (br), 1765, 1698, 1460, 1404, 1372, 1299, 1273, 1172, 1081, 1041, 1012, 933, 913, 865, 823 cm-1. MS (FD): m/e 194 (M+, 100).
31% With sulfuric acid; acetic anhydride; In water; EXAMPLE 81 3-(Acetyl)hydroxy-2-methylbenzoic acid STR69 To a heterogeneous solution of 3.06 g (30 mmol) of acetic anhydride and 1.53 g (10 mmol) of 3-hydroxy-2-methylbenzoic acid was added one drop of concentrated sulfuric acid. The mixture was heated with a heat gun for 2 min. and then poured into 14 mL of cold water. The resulting precipitate was collected by vacuum filtration, washed twice with water and dried overnight in a vacuum oven. Recrystallization from 20% ethyl acetate/hexane (7 mL) gave 595 mg of a white solid, which is 3-(Acetyl)hydroxy-2-methyl benzoic acid. Yield: 31% IR (CHCl3): 3700-2300 (br), 1765, 1698, 1460, 1404, 1372, 1299, 1273, 1172, 1081, 1041, 1012, 933, 913, 865, 823 cm-1. MS (FD): m/e 194 (M+, 100).
31% With sulfuric acid; acetic anhydride; In water; EXAMPLE 81 3-(Acetyl)hydroxy-2-methylbenzoic acid STR71 To a heterogeneous solution of 3.06 g (30 mmol) of acetic anhydride and 1.53 g (10 mmol) of 3-hydroxy-2-methylbenzoic acid was added one drop of concentrated sulfuric acid. The mixture was heated with a heat gun for 2 min. and then poured into 14 mL of cold water. The resulting precipitate was collected by vacuum filtration, washed twice with water and dried overnight in a vacuum oven. Recrystallization from 20% ethyl acetate/hexane (7 mL) gave 595 mg of a white solid, which is 3-(Acetyl)hydroxy-2-methyl benzoic acid. Yield: 31% IR (CHCl3): 3700-2300 (br), 1765, 1698, 1460, 1404, 1372, 1299, 1273, 1172, 1081, 1041, 1012, 933, 913, 865, 823 cm-1. MS (FD): m/e 194 (M+, 100).

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