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[ CAS No. 54497-00-6 ] {[proInfo.proName]}

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Chemical Structure| 54497-00-6
Chemical Structure| 54497-00-6
Structure of 54497-00-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 54497-00-6 ]

CAS No. :54497-00-6 MDL No. :MFCD09744041
Formula : C5H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :SGUYGLMQEOSQTH-UHFFFAOYSA-N
M.W : 118.13 Pubchem ID :100383
Synonyms :

Calculated chemistry of [ 54497-00-6 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.01
TPSA : 46.53 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) : -6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.26
Log Po/w (XLOGP3) : 0.57
Log Po/w (WLOGP) : 0.5
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : 0.19
Consensus Log Po/w : 0.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.67
Solubility : 25.4 mg/ml ; 0.215 mol/l
Class : Very soluble
Log S (Ali) : -1.12
Solubility : 8.96 mg/ml ; 0.0759 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.54
Solubility : 33.8 mg/ml ; 0.286 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 54497-00-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 54497-00-6 ]

* 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 [ 54497-00-6 ]

[ 54497-00-6 ] Synthesis Path-Downstream   1~49

  • 1
  • [ 66502-25-8 ]
  • [ 54497-00-6 ]
  • 2
  • [ 54497-00-6 ]
  • [ 56680-69-4 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; at 80℃; for 3.0h; In a 50 mL single-necked flask, <strong>[54497-00-6]propoxyacetic acid</strong> (2 g) and thionyl chloride (20 mL) were sequentially added.It was heated in an oil bath (80 C) for 3 hours, cooled to room temperature, and excess thionyl chloride was distilled off under reduced pressure.Obtained as a pale yellow oil, the intermediate 2-propoxyacetyl chloride (2.3 g), yield 100%.
94% With thionyl chloride; In dichloromethane; at 0 - 20℃; for 2.0h; General procedure: 2-Alkoxyacetic acid [5A-D: 5A (0.225 g, 2.5 mmol, 0.230 ml), 5B (0.237 g, 2.3 mmol, 0.245 ml), 5C (0.248 g, 2.1 mmol, 0,250 ml) or 5D (0.925 g, 7.0 mmol, 0.930 ml)] was dissolved in dichloromethane (10 mL) in a dry round-bottom flask at 0 C. A solution of thionyl chloride (1.0 equiv.) in dichloromethane (10 mL) was added dropwise at 0 C and the resulted mixture was stirred at 0 C for 1 h and at RT for 1 h. After removal of solvent and other volatiles in vacuum to afford the corresponding 2-alkoxyacetyl chloride 9A-D as colorless oil.
88.3% With thionyl chloride; for 1.0h;Reflux; To 1 mol of <strong>[54497-00-6]2-n-<strong>[54497-00-6]propoxyacetic acid</strong></strong> represented by the formula (II), 180.3 g of thionyl chloride (concentration: 99%, 1.5 mol) was added dropwise, and after the completion of the dropwise addition, the temperature was gradually raised to reflux, and the reaction was kept for 1 hour.Sampling analysis until the content of <strong>[54497-00-6]2-n-<strong>[54497-00-6]propoxyacetic acid</strong></strong> is less than 0.5%,For gas chromatography, the spectrum is shown in Figure 2.The peak at 4.124 min is a crude product of 2-n-propoxyacetyl chloride represented by the formula (III), whereinThe content of the <strong>[54497-00-6]2-n-<strong>[54497-00-6]propoxyacetic acid</strong></strong> propyl ester by-product represented by the formula (IV) was 0.07%.The reaction solution is transferred to a reactor with rectification for purification.Collect -0.09 MPa, 90-95 C distillate product,A purified 2-n-propoxyacetyl chloride represented by the formula (III) is obtained.The weight was 120.6 g and the yield was 88.3%.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 5 - 20℃; for 19.0h; To a solution of <strong>[54497-00-6]propoxyacetic acid</strong> (810 g, 6.7 mol) in methylene chloride (-2 L) with Lambda/,Lambda/-dimethylformamide (7 ml_) chilled in an ice water bath was added dropwise neat oxalyl chloride (665 ml_, 7.6 mol) over -2 hours maintaining an internal temperature < 5C. The reaction mixture was then allowed to warm to ambient temperature. After -17 hours the reaction mixture was reduced in vacuo with the temperature maintained < 200C and vacuum > 50 torr to provide 966 g of the crude acid chloride (-87% pure by 1HNMR). The acid chloride (615 g, 4.5 mol) was dissolved in anhydrous tetrahydrofuran (2 L) and added over -2 hours to a solution of 2,3-diamino-5-bromopyridine (736 g, 3.9 mmol) and triethylamine (455 g, 4.5 mol) in anhydrous tetrahydrofuran (14 L) maintaining a temperature <5C. Additional acid chloride (66 g, 0.5 mol) was added until the reaction was determined to be complete by HPLC. The reaction mixture was filtered, the cake washed with ethyl acetate, and the filtrate concentrated in vacuo. The solvent was removed in vacuo. The crude material was purified by via Biotage column chromatography (eluent = 40% ethyl acetate/hexane to 100% ethyl acetate). Similar fractions were combined, concentrated in vacuo, and the resultant solid triterated with a mixture of ethyl acetate (-200 mL) and hexane (-2 L) to afford 822 g of N-(2- amino-5-bromopyridin-3-yl)-2-propoxyacetamide. H NMR (400 MHz, CHLOROFORM-D) delta ppm 8.10 (bs, 1 H), 8.00 (s, 1 H), 7.80 (s, 1 H), 4.70 (bs, 2H), 4.05 (s, 2H), 3.55 (t, 2H), 1.65 (m, 2H), 0.95 (t, 3H).

  • 3
  • [ 54497-00-6 ]
  • [ 100705-18-8 ]
  • 4
  • [ 6819-41-6 ]
  • [ 79-11-8 ]
  • [ 54497-00-6 ]
  • 5
  • [ 54497-00-6 ]
  • [ 137-07-5 ]
  • 2-propoxymethyl-benzothiazole [ No CAS ]
  • 6
  • [ 54497-00-6 ]
  • [ 31858-85-2 ]
  • [ 32048-66-1 ]
  • 7
  • [ 54497-00-6 ]
  • [ 481-42-5 ]
  • 3-propoxymethylplumbagin [ No CAS ]
  • 8
  • [ 71-23-8 ]
  • [ 79-11-8 ]
  • [ 54497-00-6 ]
  • 11
  • [ 54497-00-6 ]
  • [ 6148-64-7 ]
  • γ-propoxyacetoacetic acid ethyl ester [ No CAS ]
  • 12
  • [ 54497-00-6 ]
  • 4-benzo[1,3]dioxol-5-yl-2-propoxymethyl-4,5-dihydro-3<i>H</i>-pyrrole-3-carboxylic acid ethyl ester [ No CAS ]
  • 13
  • [ 54497-00-6 ]
  • (3S,4R)-4-Benzo[1,3]dioxol-5-yl-2-propoxymethyl-pyrrolidine-3-carboxylic acid ethyl ester [ No CAS ]
  • 14
  • [ 54497-00-6 ]
  • 3-Benzo[1,3]dioxol-5-yl-4-nitro-2-(2-propoxy-acetyl)-butyric acid ethyl ester [ No CAS ]
  • 15
  • [ 54497-00-6 ]
  • trans,trans-2-propoxymethyl-4-(1,3-benzodioxol-5-yl)-1-[[(dibutylamino)carbonyl]methyl]pyrrolidine-3-carboxylate [ No CAS ]
  • 16
  • [ 54497-00-6 ]
  • (2S,3S,4R)-4-Benzo[1,3]dioxol-5-yl-1-dibutylcarbamoylmethyl-2-propoxymethyl-pyrrolidine-3-carboxylic acid ethyl ester [ No CAS ]
  • 17
  • [ 54497-00-6 ]
  • propoxy-acetic acid menthyl ester [ No CAS ]
  • 18
  • [ 54497-00-6 ]
  • [ 106473-81-8 ]
  • 19
  • sodium 2-n-propoxyacetate [ No CAS ]
  • [ 54497-00-6 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In water; for 0.25h; To sodium chloroacetate (843 g, 7.2 mol) in propanol (2.15 kg, 35.8 mol) was added solid sodium hydroxide (357 g, 8.9 mol) at room temperature and heated to 50 0C for -17 hours. Excess propanol was removed in vacuo and the residual solids dissolved water (2.2 L) and cooled in an ice water bath. Concentrated sulfuric acid (483 g) was added in portions over -15 min. The lower aqueous layer was back extracted with ethyl acetate. The combined organic layers were washed with water then brine and reduced in vacuo. The crude acid was taken forward "as is". H NMR (400 MHz, CHLOROFORM-D) delta ppm 10.8 (bs, 1 H), 4.1 (s, 2H), 3.5 (t, 2H), 1.6 (m, 2H), 0.9 (t, 3H).
With hydrogenchloride; In ethyl acetate; The reaction bottle of the obtained product was connected with a condenser and a tail gas absorption device, and the pH value was adjusted with 30% hydrochloric acid, extracted with 400 ml of ethyl acetate each time, extracted three times, and the extracts were combined, and the acetic acid was removed under reduced pressure. The ester was then subjected to gas chromatography, and the spectrum was as shown in Fig. 1. The peak at 5.346 min was 2-n-propoxyacetic acid represented by formula (II).
  • 20
  • lanthanum(III) chloride heptahydrate [ No CAS ]
  • [ 54497-00-6 ]
  • La(C3H7OCH2CO2)3*H2O [ No CAS ]
  • 21
  • [ 54497-00-6 ]
  • [ 1072919-35-7 ]
  • 2-cyclohexyl-6-(N,N-diethylamino)-5-(2-propoxyacetamido)-1H-benzo[d]imidazole [ No CAS ]
  • 22
  • [ 54497-00-6 ]
  • [ 1259926-85-6 ]
  • 2-cyclohexyl-5-(2-propoxyacetamido)-6-(pyrrolidin-1-yl)-1H-benzo[d]imidazole [ No CAS ]
  • 23
  • [ 54497-00-6 ]
  • 5-amino-2-cyclohexyl-6-(N,N-dimethylamino)-1H-benzo[d]imidazole [ No CAS ]
  • 2-cyclohexyl-6-(N,N-dimethylamino)-5-(2-propoxyacetamido)-1H-benzo[d]imidazole [ No CAS ]
  • 24
  • [ 71-23-8 ]
  • [ 3926-62-3 ]
  • [ 54497-00-6 ]
YieldReaction ConditionsOperation in experiment
76% Sodium (7.00?g, 304?mmol) was dissolved in the corresponding dry alcohol (n-propanol or n-butanol, 300?mL) at 60?C. To the forming solution of sodium alcoholate in the alcohol were added triethylbenzylammonium chloride (0.50?g, 18?mmol) and sodium chloroacetate 4 and the resulted mixture was refluxed for 12?h. After the alcohol was evaporated in vacuum, the residue was dissolved in water (200 ?mL) and 5N HCl was added (to pH?=?2). The solution was extracted with ethyl acetate (3?*?100?mL). The organic phases were unified, washed with brine (50?mL) and dried over Na2SO4. After removal of the solvent by vacuum rotary evaporation, the residue was purified with vacuum distillation to yield 2-propoxyacetic 2C or 2-butoxyacetic acid 2D as colorless oil. 2-Propoxyacetic acid 5C (15.40?g, 130?mmol, 76%): Bp 103?C (9 torr); nD20 1.4231; deltaH (300?MHz, CDCl3) 10.05 (1H, s, COOH), 4.13 (2H, s, CH2COOH), 3.51 (2H, t, J?=?6.6?Hz, CH2O), 1.75-1.54 (2H, m, CH3CH2), 0.94 (3H, t, J?=?7.4?Hz, CH3); deltaC (75?MHz, CDCl3) 175.54, 73.67, 67.70, 22.66, 10.33; nmax (liquid film): 2965, 2939, 2879, 1734, 1430, 1203, 1121, 962, 675?cm-1. Elemental analysis for C5H10O3: required: C 50.84, H 8.53, found C 50.73, H 8.56.
  • 25
  • [ 54497-00-6 ]
  • (±)-2-propoxy-N-(1-phenyletyl)acetamide [ No CAS ]
  • 26
  • [ 54497-00-6 ]
  • (±)-2-propoxy-N-(1-(4-nitrophenyl)ethyl)acetamide [ No CAS ]
  • 27
  • [ 54497-00-6 ]
  • (±)-2-propoxy-N-(1-(4-chlorophenyl)ethyl)acetamide [ No CAS ]
  • 28
  • [ 54497-00-6 ]
  • (±)-2-propoxy-N-(1-(4-bromophenyl)ethyl)acetamide [ No CAS ]
  • 29
  • [ 54497-00-6 ]
  • (±)-2-propoxy-N-(1-phenylpropyl)acetamide [ No CAS ]
  • 30
  • [ 54497-00-6 ]
  • (±)-2-propoxy-N-(1-(3,4-dimethoxyphenyl)ethyl)acetamide [ No CAS ]
  • 31
  • [ 54497-00-6 ]
  • (±)-2-propoxy-N-(4-phenylbutan-2-yl)acetamide [ No CAS ]
  • 32
  • [ 54497-00-6 ]
  • (±)-2-propoxy-N-(1-methoxypropan-2-yl)acetamide [ No CAS ]
  • 33
  • [ 54497-00-6 ]
  • (R)-2-propoxy-N-(1-phenylethyl)acetamide [ No CAS ]
  • 34
  • [ 54497-00-6 ]
  • (R)-2-propoxy-N-(heptan-2-yl)acetamide [ No CAS ]
  • 35
  • [ 54497-00-6 ]
  • (R)-2-propoxy-N-(1-methoxypropan-2-yl)acetamide [ No CAS ]
  • 36
  • [ 54497-00-6 ]
  • (R)-2-propoxy-N-(1-(4-bromophenyl)ethyl)acetamide [ No CAS ]
  • 37
  • [ 54497-00-6 ]
  • (R)-2-propoxy-N-(1-(3,4-dimethoxyphenyl)ethyl)acetamide [ No CAS ]
  • 38
  • [ 54497-00-6 ]
  • [ 67-63-0 ]
  • isopropyl 2-propoxyacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With toluene-4-sulfonic acid; for 12.0h;Reflux; The corresponding 2-alkoxyacetic acid [2-propoxy- 5C (2.00 g, 16.9 mmol), 2-butoxyacetic acid 5D (2.24 g, 16.9 mmol)] and p-toluenesulfonic acid (0.05 equiv., 0.155 g, 0.845 mmol) were dissolved in 2-propanol (30 mL) and refluxed for 12h. After evaporation of 2-propanol from the reaction mixture, the desired isopropyl ester (2C or 2D) was obtained by vacuum distillation. Isopropyl 2-propoxyacetate 2C (1.73 g, 10.8 mmol, 64%): Bp 60C (8 torr); nD20 1.4068; deltaH (300MHz, CDCl3) 5.09 (1H, hept, J=6.2Hz, MeCHMe), 4.03 (2H, s, CH2COO), 3.48 (2H, t, J=6.7Hz, CH2Et), 1.73-1.56 (2H, m, CH2Me), 1.26 (6H, d, J=6.3Hz, MeCHMe), 0.94 (3H, t, J=7.4Hz, CH2CH3); dC (75MHz, CDCl3) 170.38, 73.68, 68.69, 68.53, 22.97, 22.00, 10.61; nmax (liquid film): 2979, 2938, 2878, 1749, 1730, 1466, 1375, 1277, 1205, 1127, 1104, 957, 931, 726, 584, 411cm-1. Elemental analysis for C8H16O3: required: C 59.98, H 10.07, found C 60.03, H 9.98.
  • 39
  • [ 54497-00-6 ]
  • C22H14Cl2O5 [ No CAS ]
  • C32H32O11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In acetonitrile; at 20℃; for 24.0h;Molecular sieve; Darkness; General procedure: Fluorescein bis(chloromethyl ether) (30.0 mg, 69.9 mumol, 1.0 eq), (2-methylthio)acetic acid (29.7 mg, 279.6 mumol, 4.0 eq), and Cs2CO3 (91.1 mg, 279.6 mumol, 4.0 eq) were dissolved in dry CH3CN (1 ml). Molecular sieves (100 mg) were added, and the reaction was covered in foil and allowed to stir for 24 h at ambient temperature. The reaction mixture was adsorbed onto celite and purified via column chromatography.
  • 40
  • [ 54497-00-6 ]
  • N-2-[7-(6-methoxypyridin-3-yl)-2-oxo-1-(2-propoxyethyl)-1,2-dihydropyrido[2,3-b]pyrazin-3-yl]-N',N'-dimethylglycinamide [ No CAS ]
  • 41
  • [ 54497-00-6 ]
  • [ 915381-35-0 ]
  • 42
  • [ 54497-00-6 ]
  • [ 915381-34-9 ]
  • 43
  • [ 54497-00-6 ]
  • [ 915381-36-1 ]
  • 44
  • [ 54497-00-6 ]
  • [ 915381-37-2 ]
  • 45
  • [ 54497-00-6 ]
  • C18H19ClN4O3 [ No CAS ]
  • 46
  • [ 54497-00-6 ]
  • [ 445-03-4 ]
  • [ 68836-61-3 ]
YieldReaction ConditionsOperation in experiment
85.5% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 12h; 2-Amino-5-chlorobenzotrifluoride (5 g) and <strong>[54497-00-6]propoxyacetic acid</strong> (4.53 g, 1.5 eq) were dissolved in DMF (30 mL).DIPEA (6.6 g, 2 eq), HATU (14.6 g, 1.5 eq) was added sequentially, and the mixture was stirred at room temperature for 12 hours.The reaction was monitored by TLC. After the reaction was completed, water (50 mL) and ethyl acetate (50 mL) were added, and the organic phase was shaken and extracted again 2-3 times.The organic phases were combined and concentrated under reduced pressure.(Petroleum ether: ethyl acetate = 10:1) purifiedN-(n-propoxymethylformyl)-4-chloro-alpha,alpha,alpha-trifluorotoluidine (6.5 g), yield 85.5%.
  • 47
  • [ 54497-00-6 ]
  • (Z)-4-chloro-α,α,α-trifluoro-N-(1-amino-2-propoxyethylidene)oxotoluidine [ No CAS ]
  • (E)-4-chloro-α,α,α-trifluoro-N-(1-amino-2-propoxyethylidene)oxotoluidine [ No CAS ]
  • 48
  • [ 54497-00-6 ]
  • (E)-N-(4-chloro-2-(trifluoromethyl)phenyl)-2-propoxyacetyl chloride [ No CAS ]
  • 49
  • [ 54497-00-6 ]
  • [ 68836-61-3 ]
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