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[ CAS No. 73401-74-8 ] {[proInfo.proName]}

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Chemical Structure| 73401-74-8
Chemical Structure| 73401-74-8
Structure of 73401-74-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 73401-74-8 ]

CAS No. :73401-74-8 MDL No. :MFCD00065692
Formula : C9H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :FWZBPBKAANKOJQ-UHFFFAOYSA-N
M.W : 166.17 Pubchem ID :3283498
Synonyms :

Calculated chemistry of [ 73401-74-8 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.11
TPSA : 57.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : 0.61
Log Po/w (WLOGP) : 0.65
Log Po/w (MLOGP) : 1.1
Log Po/w (SILICOS-IT) : 1.4
Consensus Log Po/w : 1.01

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.43
Solubility : 6.22 mg/ml ; 0.0374 mol/l
Class : Very soluble
Log S (Ali) : -1.39
Solubility : 6.73 mg/ml ; 0.0405 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.0
Solubility : 1.67 mg/ml ; 0.0101 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 73401-74-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 73401-74-8 ]

* 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.

  • Upstream synthesis route of [ 73401-74-8 ]
  • Downstream synthetic route of [ 73401-74-8 ]

[ 73401-74-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 73401-74-8 ]
  • [ 34841-47-9 ]
YieldReaction ConditionsOperation in experiment
59% With manganese(IV) oxide In chloroform at 50℃; for 18 h; Example 87; Stage 1 - Preparation of (4-formylphenyl)acetic acid; To [4-(hydroxymethyl)phenyl]acetic acid (3g, 18mmol) in CHCI3 (5OmL) under N2 was added manganese dioxide (7.7g, 90mmol) and the reaction mixture was stirred at 500C for 18h. The crude was filtered through a pad of celite, washed with DCM (5OmL) and concentrated under reduced pressure to give the desired product (1.76g, 59percent). 1H NMR (300MHz, Cf6-DMSO) δ: 12.49 (1 H, br s), 9.99 (1 H1 s), 7.89-7.84 (2H, m), 7.50 (2H, d, J=7.9Hz), 3.72 (2H1 s).
Reference: [1] Patent: WO2008/40934, 2008, A1, . Location in patent: Page/Page column 72-73
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 11, p. 1990 - 1995
[3] Chemical Communications, 2017, vol. 53, # 65, p. 9159 - 9162
  • 2
  • [ 13737-36-5 ]
  • [ 73401-74-8 ]
YieldReaction ConditionsOperation in experiment
71.9% With sodium hydroxide In water at 18 - 25℃; Large scale 2-(4-(Hydroxymethyl)phenyl)acetic acid (C)
To a solution of NaOH (1.61 kg, 40.2 mol, 4 eq) in water (90 L) was added B (2.3 kg, 10.0 mol, 1 eq) and the resulting mixture was stirred at RT overnight. TLC analysis indicated consumption of B.
The reaction mixture was then carefully acidified with concentrated H2SO4 (1.0 L) to pH˜2.
Then, solid NaCl (25 kg) was added to the mixture followed by extraction with EtOAc (33 L*3).
The combined organic phase was washed with brine, dried over Na2SO4, and concentrated until a significant amount of solid precipitated.
The resulting suspension was kept at ˜4-6° C. overnight to allow for further crystallization.
The solid product was then collected by filtration.
The filter cake was washed with petroleum ether (2 L*2) to yield the title compound (1.2 kg, yield: 71.9percent). HPLC purity: 97.8percent (220 nm); 1H NMR (300 MHz, DMSO-d6) δ 12.27 (s, 1H), 7.26-7.12 (m, 4H), 5.14 (s, 1H), 4.47 (s, 2H), 3.53 (s, 2H).
71.9% With sodium hydroxide In water at 20℃; Large scale To a solution of NaOH (1.61 kg, 40.2 mol, 4 eq) in water (90 L) was added B (2.3 kg, 10.0 mol, 1 eq) and the resulting mixture was stirred at RT overnight. TLC analysis indicated consumption of B. The reaction mixture was then carefully acidified with concentrated H2SO4 (1.0 L) to pH ~2. Then, solid NaCl (25 kg) was added to the mixture followed by extraction with EtOAc (33 L x 3). The combined organic phase was washed with brine, dried over Na2S04, and concentrated until a significant amount of solid precipitated. The resulting suspension was kept at ~4-6°C overnight to allow for further crystallization. The solid product was then collected by filtration. The filter cake was washed with petroleum ether (2 L x 2) to yield the title compound (1.2 kg, yield: 71.9percent). HPLC purity: 97.8percent (220 nm); 1H NMR (300 MHz, OMSO-d6) δ 12.27 (s, 1H), 7.26-7.12 (m, 4H), 5.14 (s, 1H), 4.47 (s, 2H), 3.53 (s, 2H).
55% With sodium hydroxide; sodium chloride; sodium acetate In water 44(i)
4-Hydroxymethylphenylacetic acid
A solution of 9.00 g (39.3 mmol) of p-bromomethylphenylacetic acid, 3.14 g (78.6 mmol) of sodium hydroxide and 3.54 g (43.2 mmol) of sodium acetate in 40 ml of water was stirred for 4 hours at 100° C.
At the end of this time, it was cooled to room temperature and then acidified with 2N aqueous hydrochloric acid.
It was then extracted with ethyl acetate.
The extract was washed with a saturated aqueous solution of sodium chloride.
The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure.
The resulting residue was recrystallized from a mixture of ethyl acetate and methylene chloride to give 3.60 g (yield 55percent) of the title compound, melting at 136°-137° C.
Infrared Absorption Spectrum (KBr) νmax cm-1: 3304, 1703, 1520, 1421, 1408, 1360, 1288, 1234, 1200, 1188, 1009.
33 g for 2 h; Reflux Compound 2 (50 g) was added to 200 ml of water,Stir and heat to reflux for 2 hours,Anti-strain clarification,Then cool to room temperatureThe ice bath cooled to about 2 degrees,A white solid precipitated and was filtered. The cake was washed twice with water to give a white solid.The white solid was dried at 50[deg.] C. for 10 hours to yield about 33 g of compound 3.

Reference: [1] Patent: US9643927, 2017, B1, . Location in patent: Page/Page column 33;34
[2] Patent: WO2017/86941, 2017, A1, . Location in patent: Paragraph 00105
[3] Patent: US5534529, 1996, A,
[4] Patent: CN107434780, 2017, A, . Location in patent: Paragraph 0055; 0059-0061
  • 3
  • [ 622-47-9 ]
  • [ 73401-74-8 ]
Reference: [1] Patent: US9643927, 2017, B1,
[2] Patent: WO2017/86941, 2017, A1,
[3] Patent: CN107434780, 2017, A,
  • 4
  • [ 73401-74-8 ]
  • [ 75-36-5 ]
  • [ 96524-70-8 ]
Reference: [1] Patent: US2014/161736, 2014, A1, . Location in patent: Page/Page column
  • 5
  • [ 73401-74-8 ]
  • [ 96524-70-8 ]
Reference: [1] Patent: WO2013/149997, 2013, A1,
[2] Patent: WO2014/86924, 2014, A1,
[3] Patent: WO2007/106016, 2007, A1,
  • 6
  • [ 73401-74-8 ]
  • [ 1429651-50-2 ]
Reference: [1] Patent: WO2013/52110, 2013, A1,
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