[ CAS No. 27912-85-2 ]

Name: 27912-85-2|3-(Benzyloxy)propanoic acid|96%
Brand: Ambeed
SKU: A522087
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Quality Control of [ 27912-85-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 27912-85-2 ]

SDS Specification

Alternatived Products of [ 27912-85-2 ]

Product Details of [ 27912-85-2 ]

CAS No. :	27912-85-2	MDL No. :	MFCD09951713
Formula :	C₁₀H₁₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OZGUGVRKYBSDBN-UHFFFAOYSA-N
M.W :	180.20 g/mol	Pubchem ID :	15608813
Synonyms :

Calculated chemistry of [ 27912-85-2 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.69
TPSA :	46.53 Å²

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) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.77
Log Po/w (XLOGP3) :	1.29
Log Po/w (WLOGP) :	1.53
Log Po/w (MLOGP) :	1.41
Log Po/w (SILICOS-IT) :	1.77
Consensus Log Po/w :	1.55

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.78
Solubility :	2.98 mg/ml ; 0.0165 mol/l
Class :	Very soluble
Log S (Ali) :	-1.87
Solubility :	2.45 mg/ml ; 0.0136 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.72
Solubility :	0.34 mg/ml ; 0.00189 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 27912-85-2 ]

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

Application In Synthesis of [ 27912-85-2 ]

* 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 [ 27912-85-2 ]
Downstream synthetic route of [ 27912-85-2 ]

[ 27912-85-2 ] Synthesis Path-Upstream 1~2

1
[ 95-47-6 ]
[ 27912-85-2 ]
[ 16440-97-4 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1971, p. 1351 - 1362

2
[ 67-56-1 ]
[ 27912-85-2 ]
[ 4126-60-7 ]

Reference： [1] Organic Letters, 2010, vol. 12, # 11, p. 2614 - 2617
[2] Journal of Organic Chemistry, 1962, vol. 27, p. 2742 - 2746

[ 27912-85-2 ] Synthesis Path-Downstream 1~58

1
[ 95-47-6 ]
[ 27912-85-2 ]
[ 16440-97-4 ]

Reference： [1]Bulletin de la Societe Chimique de France,1971,p. 1351 - 1362

2
[ 27912-85-2 ]
[ 4244-66-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With oxalyl dichloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; Cooling with ice;	step one:Under nitrogen protection, 180 g of <strong>[27912-85-2]3-(benzyloxy)propionic acid</strong> was added to the reaction flask.1 L of dichloromethane, 95 g of oxalyl chloride was added dropwise under ice bath, and the reaction was carried out for 3 hours at room temperature.After completion of the reaction, the solvent was distilled under reduced pressure to give 180 g of Intermediate 1.Yield: 90%.
	With thionyl chloride; In N,N-dimethyl-formamide;	1-(2-Benzyloxyethyl)-3-(2-chloroethyl)-2-imidazolidinon, 22a To <strong>[27912-85-2]3-benzyloxypropionic acid</strong> (129.6 g) in ether (310 ml) and N,N-dimethylformamide (4 ml) was added thionyl chloride (155 ml). The solution was refluxed for 2 hours, and solvents and excess thionyl chloride were removed by evaporation in vacuo. Yield 132 g of 3-Benzyloxypropionic acid chloride as an oil.
	With thionyl chloride; In N-methyl-acetamide;	(b) Preparation of 3-benzyloxypropionyl chloride (VIII R1 =H, X=Cl) Thionyl chloride (60 ml) is added dropwise into a 500 ml four-necked flask fitted with a mechanical stirrer, a thermometer, a condenser and a dropping funnel, charged with <strong>[27912-85-2]3-benzyloxypropionic acid</strong> (100 g). Dimethylformamide (two drops) is then added while the temperature is kept at about 20 C. by means of a warm water bath. After stirring at room temperature for 2 hours the excess of thionyl chloride is removed by vacuum distillation and the residue is taken up twice with methylene chloride (two 100 ml portions). By evaporating the methylene chloride under reduced pressure 3-benzyloxypropionyl chloride (108.8 g) is obtained.

With oxalyl dichloride; N,N-dimethyl-formamide; In hexane; at 0℃; for 1h;

Cool a solution of [27912-85-2]3-benzyloxy-propionic acid (1.66 g, 9.19 mmol) in hexanes (40 mL) to 0C and add oxalyl chloride (3.50 g, 27.6 mmol) dropwise. After the addition is completed, add DMF (2 drops) and stir the resulting mixture for 1 hour. Remove the solvent under reduced pressure and dissolve the crude acid chloride in dry THF (20 mL). In a separate flask, dissolve 2-AMINO-4- (3-TRIFLUOROMETHYL-PYRIDIN-2-YL)-BENZAMIDE (2.35 g, 8. 37 mmol) in dry THF (40 mL) and pyridine (0.727 g, 9.19 mmol) and cool to 0C. Add the solution containing the crude acid chloride dropwise to the second solution. Allow the mixture to warm to room temperature and stir for 1 hour. Add a solution of 10% NaOH (aq) (20 mL) to the mixture and stir the solution for 1 hour. Concentrate the mixture (-20 mL), dilute with water (20 mL), and acidify with conc. HCI. Extract the resulting solution with ETOAC (3 x 50 mL). Wash the combined organic extracts with brine and dry over NA2S04. Remove the solvent under reduced pressure to yield the title compound as a white solid.

Reference： [1]Patent: CN110204522,2019,A .Location in patent: Paragraph 0024; 0025
[2]Recueil des Travaux Chimiques des Pays-Bas,1964,vol. 83,p. 81 - 93
[3]Synthetic Communications,1988,vol. 18,p. 1311 - 1322
[4]Journal of Organic Chemistry,1992,vol. 57,p. 3479 - 3482
[5]Journal of Organic Chemistry,1997,vol. 62,p. 7546 - 7547
[6]Journal of Medicinal Chemistry,1999,vol. 42,p. 706 - 721
[7]Journal of Organic Chemistry,2001,vol. 66,p. 697 - 706
[8]Journal of the American Chemical Society,2001,vol. 123,p. 9681 - 9682
[9]Patent: US5216001,1993,A
[10]Patent: US4576746,1986,A
[11]Chemistry - A European Journal,2008,vol. 14,p. 9240 - 9254
[12]Patent: WO2004/55003,2004,A1 .Location in patent: Page 57-58
[13]Journal of Organic Chemistry,2011,vol. 76,p. 1852 - 1873
[14]Angewandte Chemie - International Edition,2015,vol. 54,p. 15794 - 15798
Angew. Chem.,2015,vol. 127,p. 16020 - 16024,5
[15]Chemistry - A European Journal,2017,vol. 23,p. 13314 - 13318

3
[ 2033-24-1 ]
[ 27912-85-2 ]
[ 145122-40-3 ]

Reference： [1]Canadian Journal of Chemistry,1992,vol. 70,p. 1427 - 1445

4
[ 27912-85-2 ]
[ 110199-16-1 ]
[ 141805-86-9 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 4243 - 4249

5
[ 4126-60-7 ]
[ 27912-85-2 ]

Yield	Reaction Conditions	Operation in experiment
		Sodium metal (249mg, 10. [8MMOL)] was added to benzyl alcohol (30g, [278MMOL)] at room temperature under nitrogen and the reaction was stirred for 30 minutes. Methyl acrylate (25. 9ml, 259mmol) was then added dropwise and the reaction was stirred at room temperature for 18h. After quenching with saturated aqueous ammonium chloride solution [(200ML)] the mixture was extracted with ethyl acetate [(2X300M1)] and the combined organic extracts were washed with brine [(100MOI),] dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was dissolved in ethanol [(300MOI)] and 1M aqueous sodium hydroxide solution [(300ML)] was added dropwise. After 3 hours the ethanol was removed under reduced pressure and the aqueous residue was washed with [DICHLOROMETHANE] [(200ML).] The aqueous phase was then acidified with 2N aqueous hydrochloric acid (150ml), extracted with [DICHLOROMETHANE] [(2X250ML)] and the combined organic extracts were dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was dissolved in 10% aqueous potassium carbonate [SOLUTION (300ML),] washed with diethylether [(300ML)] and the aqueous phase was acidified to pH1 using concentrated hydrochloric acid. The mixture was then extracted with [DICHLOROMETHANE] [(2X300M1)] and the combined organic extracts were dried over magnesium sulphate and concentrated under reduced pressure to provide the title compound (44.4g) as a colourless oil.
	With sodium hydroxide; water; In ethanol; for 3h;	Sodium metal (249 mg, 10.8 mmol) was added to benzyl alcohol (30 g, 278 mmol) at room temperature under nitrogen and the reaction was stirred for 30 minutes. Methyl acrylate (25.9 ml, 259 mmol) was then added dropwise and the reaction was stirred at room temperature for 18 h. After quenching with saturated aqueous ammonium chloride solution (200 ml) the mixture was extracted with ethyl acetate (2×300 ml) and the combined organic extracts were washed with brine (100 ml), dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was dissolved in ethanol (300 ml) and 1 M aqueous sodium hydroxide solution (300 ml) was added dropwise. After 3 hours the ethanol was removed under reduced pressure and the aqueous residue was washed with dichloromethane (200 ml). The aqueous phase was then acidified with 2N aqueous hydrochloric acid (150 ml), extracted with dichloromethane (2×250 ml) and the combined organic extracts were dried over magnesium sulphate and concentrated under reduced pressure. The residual oil was dissolved in 10% aqueous potassium carbonate solution (300 ml), washed with diethylether (300 ml) and the aqueous phase was acidified to pH1 using concentrated hydrochloric acid. The mixture was then extracted with dichloromethane (2×300 ml) and the combined organic extracts were dried over magnesium sulphate and concentrated under reduced pressure to provide the title compound (44.4 g) as a colourless oil. 1H NMR (300 MHz, CDCl3): delta=2.67 (t, 2H), 3.89 (t, 2H), 4.58 (s, 2H), 7.18 (m, 5H).

Reference： [1]Synthetic Communications,1988,vol. 18,p. 1311 - 1322
[2]Journal of Organic Chemistry,1992,vol. 57,p. 4243 - 4249
[3]Patent: WO2004/31156,2004,A1 .Location in patent: Page 30
[4]Patent: US2005/54707,2005,A1 .Location in patent: Page/Page column 12

6
[ 67-56-1 ]
[ 27912-85-2 ]
[ 4126-60-7 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 2614 - 2617
[2]Journal of Organic Chemistry,1962,vol. 27,p. 2742 - 2746

7
[ 292638-85-8 ]
[ 100-51-6 ]
[ 27912-85-2 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 9681 - 9682

8
[ 27912-85-2 ]
[ 71-36-3 ]
[ 257956-62-0 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 191 - 198

9
[ 940877-17-8 ]
[ 27912-85-2 ]
[ 940877-21-4 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1951 - 1954

10
[ 850534-46-2 ]
[ 27912-85-2 ]
[ 940876-99-3 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1951 - 1954

11
[ 27912-85-2 ]
[ 940877-01-0 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1951 - 1954

12
[ 27912-85-2 ]
(6R)-2-(2-benzyloxyethyl)-2-methoxy-4-methylene-6-phenethyl-tetrahydropyran [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1951 - 1954

13
[ 27912-85-2 ]
[ 940877-22-5 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1951 - 1954

14
[ 27912-85-2 ]
{2-[(2S)-6-(2-benzyloxy-ethyl)-6-methoxy-4-methylene-tetrahydropyran-2-yl]ethoxy}-tert-butyl-diphenylsilane [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1951 - 1954

15
[ 100-44-7 ]
sodium-compound of acetoacetanilide [ No CAS ]
[ 27912-85-2 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1951 - 1954

16
[ 27912-85-2 ]
[ 372161-02-9 ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 9681 - 9682

17
[ 27912-85-2 ]
3-benzyloxy-thiopropionic acid S-tert-butyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 697 - 706

18
[ 27912-85-2 ]
[ 326596-68-3 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 697 - 706

19
[ 27912-85-2 ]
2-benzyloxymethyl-5-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-4-phenylselanylhexanethioic acid S-tert-butyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 697 - 706

20
[ 27912-85-2 ]
2-benzyloxymethyl-5-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-6-phenyl-4-phenylselanylhexanethioic acid S-tert-butyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 697 - 706

21
[ 27912-85-2 ]
3-benzyloxy-1-butoxy-propan-1-ol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 191 - 198

22
[ 27912-85-2 ]
1-butoxy-3-benzyloxypropyl acetate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 191 - 198

23
[ 27912-85-2 ]
[ 223679-68-3 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 706 - 721

24
[ 27912-85-2 ]
[ 223679-77-4 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 706 - 721

25
[ 27912-85-2 ]
[ 223679-05-8 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 706 - 721

26
[ 27912-85-2 ]
[ 1027601-95-1 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 706 - 721

27
[ 27912-85-2 ]
[ 197389-28-9 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7546 - 7547

28
[ 27912-85-2 ]
[ 1027940-69-7 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7546 - 7547

29
[ 27912-85-2 ]
(4R,5S)-3-((R)-3-Benzyloxy-2-fluoro-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7546 - 7547

30
[ 27912-85-2 ]
(S)-3-Benzyloxy-2-fluoro-propionaldehyde [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7546 - 7547

31
[ 27912-85-2 ]
(R)-3-Benzyloxy-2-fluoro-propionaldehyde [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 7546 - 7547

32
[ 6328-48-9 ]
[ 27912-85-2 ]