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Product Details of [ 627-42-9 ]

CAS No. :627-42-9 MDL No. :MFCD00000972
Formula : C3H7ClO Boiling Point : -
Linear Structure Formula :- InChI Key :XTIGGAHUZJWQMD-UHFFFAOYSA-N
M.W : 94.54 Pubchem ID :12316
Synonyms :

Calculated chemistry of [ 627-42-9 ]

Physicochemical Properties

Num. heavy atoms : 5
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 22.42
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : Low
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) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 0.67
Log Po/w (WLOGP) : 0.87
Log Po/w (MLOGP) : 0.75
Log Po/w (SILICOS-IT) : 0.9
Consensus Log Po/w : 0.98

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.72
Solubility : 18.2 mg/ml ; 0.192 mol/l
Class : Very soluble
Log S (Ali) : -0.44
Solubility : 34.3 mg/ml ; 0.363 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.34
Solubility : 4.28 mg/ml ; 0.0453 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.88

Safety of [ 627-42-9 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P280 UN#:3271
Hazard Statements:H225-H302+H312+H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 627-42-9 ]

* 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 [ 627-42-9 ]
  • Downstream synthetic route of [ 627-42-9 ]

[ 627-42-9 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 110-85-0 ]
  • [ 627-42-9 ]
  • [ 13484-40-7 ]
  • [ 13484-41-8 ]
YieldReaction ConditionsOperation in experiment
70.1% With hydrogenchloride In methanol; water for 8.5 h; Inert atmosphere Under a nitrogen atmosphere, the reactor 100 ml, piperazine 8.6 g (0.1 mol) g of methanol 10.4 g, was added while stirring 35percent hydrochloric acid 10.4 g (0.1 mol), internal temperature It was referred to as 80 ° C. There, while maintaining the internal temperature below 80 ° C, 2- bromoethanol 8.7g of (0.07 mol) was added dropwise over 0.5 hours, then further continued while stirring for 8 hours in the same temperature conditions, to obtain a reaction solution 36.9g of colorless and transparent. Results The product was analyzed by gas chromatography, is 84.6percent for a yield of N-(2-hydroxyethyl) piperazine, the selectivity, N-(2-hydroxyethyl) piperazine 88.5percent N, N'-bis (2-hydroxyethyl) piperazine, 7.7percent, unknown content was 3.8percent. Along with other examples showing the results of Example 2 in Table 1. Instead of using in Example 2 2-bromoethanol 8.7 g (0.07 mol), 2-methoxyethyl chloride 3.8 g (0.04 mol) reacted in the same manner as in Example 2 except for using It was carried out. Results The product was analyzed by gas chromatography, N-(2-methoxyethyl) piperazine The yield of 70.1percent and the selectivity, N-(2-methoxyethyl) piperazine 83.4percent N, N'- bis (2-methoxy-ethyl) piperazine, and 15.0percent, unknown content was 1.6percent. Along with other examples showing the results of Example 5 shown in Table 1.
Reference: [1] Patent: JP5838628, 2016, B2, . Location in patent: Paragraph 0056; 0059
  • 2
  • [ 110-85-0 ]
  • [ 627-42-9 ]
  • [ 13484-40-7 ]
Reference: [1] J. Appl. Chem. USSR (Engl. Transl.), 1980, vol. 53, # 1, p. 174 - 178[2] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1980, vol. 53, # 1, p. 199 - 203
[3] Patent: JP6070088, 2017, B2, . Location in patent: Paragraph 0056
  • 3
  • [ 77-78-1 ]
  • [ 107-07-3 ]
  • [ 627-42-9 ]
YieldReaction ConditionsOperation in experiment
43% at 120 - 130℃; Calcium carbonate (27.3 g, 273.2 mmol), dimethyl sulfate (23.5 mL, 248.4 mmol), and 2-chloroethanol (16.6 mL, 248.4 mmol) were mixed together in a round bottom flask equippedwith distillation setup. The reaction mixture was heated at 120-130 °C until distillation ceased(overnight). Then the distillate was diluted with ether, washed with 2N NaOH. The aqueouslayer was extracted again with ether, then the combined ether layer was dried (MgSO4), andunderwent normal distillation (fractions collected at vapor temperature 88-90 °C) to get desiredproduct 16 as a colorless liquid. Yield: 10.2 g, 43percent.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 8, p. 1784 - 1788
[2] Journal of the American Chemical Society, 1924, vol. 46, p. 2530
[3] Journal of the American Chemical Society, 1924, vol. 46, p. 2530
  • 4
  • [ 109-86-4 ]
  • [ 627-42-9 ]
Reference: [1] Chemische Berichte, 1931, vol. 64, p. 798
[2] Journal of the Chemical Society, 1929, p. 271
[3] Chem. Zentralbl., 1912, vol. 83, # II, p. 1269
[4] Bulletin of the Chemical Society of Japan, 1966, vol. 39, p. 530 - 535
[5] Applied Organometallic Chemistry, 2018, vol. 32, # 4,
  • 5
  • [ 74-85-1 ]
  • [ 627-42-9 ]
  • [ 107-06-2 ]
  • [ 111-44-4 ]
  • [ 110-56-5 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1983, vol. 32, # 3, p. 523 - 525[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 3, p. 582 - 584
  • 6
  • [ 110-71-4 ]
  • [ 123-91-1 ]
  • [ 627-42-9 ]
Reference: [1] Polyhedron, 2011, vol. 30, # 8, p. 1412 - 1419
  • 7
  • [ 110-71-4 ]
  • [ 123-91-1 ]
  • [ 627-42-9 ]
  • [ 107-06-2 ]
Reference: [1] Polyhedron, 2011, vol. 30, # 8, p. 1412 - 1419
  • 8
  • [ 110-71-4 ]
  • [ 1107601-58-0 ]
  • [ 123-91-1 ]
  • [ 627-42-9 ]
Reference: [1] Polyhedron, 2011, vol. 30, # 8, p. 1412 - 1419
  • 9
  • [ 420-37-1 ]
  • [ 107-07-3 ]
  • [ 627-42-9 ]
Reference: [1] Journal of the American Chemical Society, 1978, vol. 100, p. 4242 - 4248
  • 10
  • [ 110-71-4 ]
  • [ 1107601-58-0 ]
  • [ 123-91-1 ]
  • [ 627-42-9 ]
  • [ 107-06-2 ]
Reference: [1] Polyhedron, 2011, vol. 30, # 8, p. 1412 - 1419
  • 11
  • [ 110-71-4 ]
  • [ 74-87-3 ]
  • [ 627-42-9 ]
  • [ 107-06-2 ]
Reference: [1] Dalton Transactions, 2010, vol. 39, # 22, p. 5367 - 5376
  • 12
  • [ 67-56-1 ]
  • [ 74-85-1 ]
  • [ 627-42-9 ]
Reference: [1] Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1958, vol. 31, p. 1880,1882; engl.Ausg.S. 1868, 1870
[2] Journal fuer Praktische Chemie (Leipzig), 1982, vol. 324, # 2, p. 197 - 208
  • 13
  • [ 67-56-1 ]
  • [ 74-85-1 ]
  • [ 627-42-9 ]
  • [ 107-06-2 ]
  • [ 111-44-4 ]
  • [ 110-56-5 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1983, vol. 32, # 3, p. 523 - 525[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1983, # 3, p. 582 - 584
  • 14
  • [ 186581-53-3 ]
  • [ 107-07-3 ]
  • [ 627-42-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1930, vol. 484, p. 17
[2] Justus Liebigs Annalen der Chemie, 1930, vol. 484, p. 17
[3] Journal of Physical Organic Chemistry, 1995, vol. 8, # 2, p. 121 - 126
  • 15
  • [ 15454-33-8 ]
  • [ 627-42-9 ]
Reference: [1] Gazzetta Chimica Italiana, 1897, vol. 27 II, p. 293
  • 16
  • [ 99418-55-0 ]
  • [ 627-42-9 ]
Reference: [1] Chemische Berichte, 1958, vol. 91, p. 1562,1566
  • 17
  • [ 67-56-1 ]
  • [ 473-29-0 ]
  • [ 74-85-1 ]
  • [ 627-42-9 ]
Reference: [1] Zhurnal Obshchei Khimii, 1939, vol. 9, p. 2124[2] Chem. Zentralbl., 1940, vol. 111, # II, p. 199
  • 18
  • [ 74-85-1 ]
  • [ 627-42-9 ]
  • [ 107-06-2 ]
  • [ 107-07-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1982, vol. 324, # 2, p. 197 - 208
  • 19
  • [ 627-42-9 ]
  • [ 123-30-8 ]
  • [ 33311-29-4 ]
YieldReaction ConditionsOperation in experiment
16% With potassium carbonate In N,N-dimethyl-formamide at 80℃; 4-Aminophenol (2.2 g, 19.8 mmol) and potassium carbonate (5.5 g, 39.6 mmol) were dissolved in DMF. To the reaction mixture was added 1 -chloro-2-methoxyethane (2 ml, 21.8 mmol) and the mixture was stirred overnight at 80 0C. The resulting solids were filtered and the filtrate was washed with brine, dried over Na2SO4, concentrated under reduced pressure, and purified by an ISCO system (50 -100 percent EtOAc in hexanes) to afford 538 mg of the desired product (16 percent yield); m/z 168.
Reference: [1] Patent: WO2008/20203, 2008, A1, . Location in patent: Page/Page column 81
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1996 - 2015
  • 20
  • [ 106-41-2 ]
  • [ 627-42-9 ]
  • [ 39255-23-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2004, vol. 52, # 5, p. 577 - 590
  • 21
  • [ 627-42-9 ]
  • [ 139-85-5 ]
  • [ 80407-64-3 ]
YieldReaction ConditionsOperation in experiment
96.4% With tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 105 - 110℃; Inert atmosphere the 121g (leq) ELTA 1200ml and dimethylformamide (DMF) was stirred clear solution; sequentially added 323g (4eq) 2- chloroethyl methyl ether, 944g (8eq) of anhydrous potassium carbonate and 23.6gTetrabutylammonium bromide; purged with nitrogen three times,Under nitrogen, the reaction was heated to 105~110 ° C 13~14h; the filter cake was rinsed DCM until the filtrate was colorless; the combined filtrate was concentrated under reduced pressure to a fraction distilled off; the residue was added DCM, cooled to room temperature , washed with 3Ν K0H, the DCM phase was separated, washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to 45 ° C to give 210g oil ELTB, yield 96.4percent
70% With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 14 h; To a solution of 3,4-dihydroxybenzaldehyde (10 g, 72.5 mmol) (Aldrich) in DMF (200 mL) was added 2-chloroethyl methyl ether (16.5 mL, 181.2 mmol) (Aldrich), potassium carbonate (50 g, 362.3 mmol) and a catalytic amount of potassium iodide (Aldrich).
The reaction mixture was heated at 85° C. for 14 hours.
The reaction mixture was cooled down, diluted with EtOAc and washed with brine.
The organic phase was dried over anhydrous sodium sulfate, evaporated to afford 3,4-bis-(2-methoxy-ethoxy)-benzaldehyde as an oil and was used in the next step without further purification. (Yield 11 g, 70percent).
Reference: [1] Patent: CN105566233, 2016, A, . Location in patent: Paragraph 0015; 0052
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 4, p. 435 - 440
[3] Patent: US2012/184548, 2012, A1, . Location in patent: Page/Page column 23; 24
  • 22
  • [ 627-42-9 ]
  • [ 3943-89-3 ]
  • [ 183322-16-9 ]
YieldReaction ConditionsOperation in experiment
95% at 90 - 95℃; In a dry, clean 500ml reaction flask, 36.4 g was added3,4-dihydroxybenzoate,82.4 g of potassium carbonate,6.0 g of 4-methylaminopyridine,145.6 g of 1-chloro-2-methoxyethane was stirred to a temperature of 90-95 ° C,Reflux insulation, the reaction is completed, cooling down to 20-30 ° C,Add water, stir, place the layer, extract the water layer, combined organic layer, distillation, steaming, cooling cooling. Add isopropyl alcohol and water, filter, filter cake with isopropyl alcohol and water leaching, drying dry product, vacuum drying to obtain 57g products, the yield of 95percent, HPLC purity of 99percent.
87% With potassium <i>tert</i>-butylate; potassium iodide In N,N-dimethyl-formamide at 100℃; for 12 h; A solution of ethyl 3,4-dihydroxybenzoate (1.7 g, 9.3 mmol) was placed in a reaction flask and 8 mL of DMF was added to dissolve it. Potassium tert-butoxide (2.0 g, 17.8 mmol) and potassium iodide (1.0 g, 6.0 mmol), and the temperature was raised to 100 ° C. 2-Chloroethyl methyl ether (3.52 g, 37.2 mmol) was added dropwise and the reaction was continued for 12 h after completion of the dropwise addition. Cooled to room temperature, ice water (200 mL) was added, and extracted three times with ethyl acetate (3 x 200 mL). The organic phase was combined, washed three times with distilled water, three times with saturated brine, dried over anhydrous sodium sulfate overnight, filtered, and the filtrate was evaporated to dryness under reduced pressure to give an oil. The elution system was petroleum ether / ethyl acetate = 1) Ethyl 3,4-bis (2-methoxyethoxy) benzoate.
95 %Chromat. With potassium carbonate In N,N-dimethyl-formamide at 90 - 100℃; for 9 h; [Synthesis Example 1]; (Synthesis of ethyl 3,4-bis(2-methoxyethoxy)benzoate); In a 20 L-volume glass reaction vessel equipped with a stirrer, a thermometer and a reflux condenser, 1,300 g (7.14 moles) of ethyl 3,4-dihydroxybenzoate, 2,324 g (21.4 moles) of 2-chloroethyl methyl ether, 2,958 g (21.4 moles) of potassium carbonate and 6,500 mL of N,N-dimethylformamide were placed. The mixture was allowed to react with each other at 90 to 100°C for 9 hours while stirring. After the reaction was complete, the reaction solution was cooled to room temperature. The reaction solution was then filtered, and washed with 6,500 mL of acetone. The filtrate was concentrated, 3,900 mL of ethyl acetate and 3,900 mL of a saturated aqueous sodium carbonate solution were added to the concentrate. The separated organic layer (ethyl acetate layer) was washed twice with 3,900 mL of a saturated aqueous sodium chloride solution to obtain a solution mixture containing ethyl 3,4-bis(2-methoxyethoxy)benzoate. The solution mixture was analyzed (according to an absolute quantitative method) by a high performance liquid chromatography. It was confirmed that 2,023 g of ethyl 3,4-bis(2-methoxyethoxy)benzoate was produced (reaction yield: 95percent). After 3,939 mL of acetic acid was added to the solution mixture, the mixture was concentrated under reduced pressure to distill ethyl acetate off. Thus, an acetic acid solution of ethyl 3,4-bis(2-methoxyethoxy)benzoate was obtained.
Reference: [1] Patent: CN106892821, 2017, A, . Location in patent: Paragraph 0029; 0030
[2] Patent: CN104725327, 2017, B, . Location in patent: Paragraph 0069-0071
[3] Molecules, 2006, vol. 11, # 4, p. 286 - 297
[4] Patent: EP1650196, 2006, A1, . Location in patent: Page/Page column 6
  • 23
  • [ 269410-08-4 ]
  • [ 627-42-9 ]
  • [ 847818-71-7 ]
YieldReaction ConditionsOperation in experiment
100% With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5 h; Microwave irradiation 4-( 4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1H-pyrazole (1 00 mg, 0.52mmol), 1-chloro-2-methoxyethane (0.056 mL, 0.62 mmol) and cesium carbonate (252mg, 0.73 mmol) in DMF (1 mL) were heated in microwave reactor at 160 °C for 30 min.The reaction mixture was concentrated under reduced pressure and purified by silica gelchromatography (ISCO, hexanes/ethyl acetate 0-100percent over 15 min) to isolate CompoundB162a (130 mg, 100percent yield). HPLC: RT = 1.0 min (LCMS Method M). MS (ES): m/z= 253.0 [M+H( 1H NMR (500MHz, CHLOROFORM-d) 8 8.04 (s, 1H), 7.83 (d,J=18.4 Hz, 1H), 4.37 (t, J=5.2 Hz, 1H), 3.78 (t, J=5.2 Hz, 1H), 3.38-3.31 (m, 2H), 2.98(s, 3H), 2.90 (s, 3H), 1.34 (s, 6H), 1.26 (s, 3H).
72% With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5 h; microwave irradiation 2-Chloroethyl methyl ether (0.050 ml, 0.63 mmol) was added to a stirred solution of 4- (4,4,5, 5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-pyrazole (5.0 g, 25.77 mmol) and cesium carbonate (12.59 g, 38.65 mmol) in DMF (27 ml). The mixture was stirred at 160 °C for 30 min. under microwave irradiation and then the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; MeOH in DCM 2/98). The desired fractions were collected and evaporated in vacuo to yield intermediate 67 (4.6 g, 72percent) as a pale yellow oil.
72% With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5 h; Microwave irradiation Example A67
1-(2-Methoxy-ethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
2-Chloroethyl methyl ether (0.050 ml, 0.63 mmol) was added to a stirred solution of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (5.0 g, 25.77 mmol) and cesium carbonate (12.59 g, 38.65 mmol) in DMF (27 ml).
The mixture was stirred at 160° C. for 30 min. under microwave irradiation and then the solvent was evaporated in vacuo.
The crude product was purified by flash column chromatography (silica; MeOH in DCM 2/98).
The desired fractions were collected and evaporated in vacuo to yield intermediate 67 (4.6 g, 72percent) as a pale yellow oil.
Reference: [1] Patent: WO2014/15088, 2014, A1, . Location in patent: Paragraph 00223
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4196 - 4212
[3] Patent: WO2011/110545, 2011, A1, . Location in patent: Page/Page column 95-96
[4] Patent: US2012/329792, 2012, A1, . Location in patent: Page/Page column 46
  • 24
  • [ 2075-46-9 ]
  • [ 627-42-9 ]
  • [ 948570-75-0 ]
YieldReaction ConditionsOperation in experiment
49.5% With potassium carbonate In acetonitrile for 18 h; Reflux 4-Nitropyrazole (2.0 g, 17.68 mmol),The solution obtained by dissolving 2-chloroethyl methyl ether (2.01 g, 21.26 mmol) and potassium carbonate (4.88 g, 35.31 mmol) in 40 mL of acetonitrile was refluxed for 18 h.Spin dry,A silica gel column (PE/EA = 4:1) gave 1.5 g of a pale yellow solid.Yield: 49.5percent.
Reference: [1] Patent: CN104583195, 2018, B, . Location in patent: Paragraph 0633; 0634; 0635; 0636; 0637
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