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Product Details of [ 124-68-5 ]

CAS No. :124-68-5 MDL No. :MFCD00008051
Formula : C4H11NO Boiling Point : -
Linear Structure Formula :OHCH2C(CH3)2NH2 InChI Key :CBTVGIZVANVGBH-UHFFFAOYSA-N
M.W : 89.14 Pubchem ID :11807
Synonyms :

Calculated chemistry of [ 124-68-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 25.25
TPSA : 46.25 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) : -7.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : -0.78
Log Po/w (WLOGP) : -0.28
Log Po/w (MLOGP) : -0.18
Log Po/w (SILICOS-IT) : -0.58
Consensus Log Po/w : -0.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.16
Solubility : 130.0 mg/ml ; 1.46 mol/l
Class : Highly soluble
Log S (Ali) : 0.29
Solubility : 173.0 mg/ml ; 1.94 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.07
Solubility : 75.2 mg/ml ; 0.843 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 124-68-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P273-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P312-P363-P405-P501 UN#:1760
Hazard Statements:H303-H314-H412 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 124-68-5 ]

* 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.

  • Upstream synthesis route of [ 124-68-5 ]
  • Downstream synthetic route of [ 124-68-5 ]

[ 124-68-5 ] Synthesis Path-Upstream   1~33

  • 1
  • [ 201230-82-2 ]
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  • [ 26654-39-7 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 50, p. 12419 - 12423
[2] Tetrahedron Letters, 2007, vol. 48, # 6, p. 929 - 932
[3] Helvetica Chimica Acta, 2007, vol. 90, # 8, p. 1593 - 1598
  • 2
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Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1585 - 1588
[2] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 109, p. 62 - 69
[3] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 109, p. 62 - 69
  • 3
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Reference: [1] Tetrahedron, 1991, vol. 47, # 16-17, p. 2801 - 2820
[2] Journal of the American Chemical Society, 1954, vol. 76, p. 1840,1842
[3] Patent: US5641770, 1997, A,
[4] Patent: US2399118, 1942, ,
  • 4
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  • [ 57-13-6 ]
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YieldReaction ConditionsOperation in experiment
80% at 170 - 220℃; for 2 h; [00121] Preparation of 4,4-dimethyloxazolidin-2-one (DMO) [00122] A mixture of 2-amino-2-methyl-l-propanol (10.0 g, 112 mmole) and urea (13.5 g, 224 mmole) was heated for 1 h at 170-180 °C, for 1 h at 210-220 °C, cold to rt and dissolved in water (50 mL). The solution was extracted with DCM (5 x 50 mL). The combined extracts were dried over Na2S04, filtered and concentrated in vacuo to afford 10.3 g (80percent) of 4,4-dimethyloxazolidin-2-one. lH NMR (CDC13): δ 6.13 (br s, 1H, NH), 4.07 (s, 2H, CH2), 1.32 (s, 6H, 2 CH3) ppm. 13C NMR (CDC13) δ 159.4, 77.1, 55.4, 27.7 ppm.
Reference: [1] Asian Journal of Chemistry, 2011, vol. 23, # 2, p. 929 - 930
[2] Patent: WO2015/68159, 2015, A2, . Location in patent: Paragraph 00121-00122
  • 5
  • [ 541-41-3 ]
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Reference: [1] Chemistry - A European Journal, 2001, vol. 7, # 19, p. 4117 - 4125
  • 6
  • [ 124-38-9 ]
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Reference: [1] RSC Advances, 2014, vol. 4, # 92, p. 50851 - 50857
  • 7
  • [ 96-49-1 ]
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  • [ 26654-39-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2190 - 2196
  • 8
  • [ 1659-31-0 ]
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  • [ 26654-39-7 ]
Reference: [1] Heterocycles, 1986, vol. 24, # 6, p. 1625 - 1630
  • 9
  • [ 124-68-5 ]
  • [ 530-62-1 ]
  • [ 288-32-4 ]
  • [ 26654-39-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 3, p. 481 - 486
  • 10
  • [ 108-24-7 ]
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Reference: [1] Molecules, 2016, vol. 21, # 12,
  • 11
  • [ 201230-82-2 ]
  • [ 75-31-0 ]
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YieldReaction ConditionsOperation in experiment
93% With tricresyl phosphate; hydrogen; palladium diacetate In diphenylether at 140℃; Autoclave (50 mmol) of palladium acetate and 88 g (250 mmol) of trimethyl phosphite were successively added to a 1000 mL autoclave, and the synthesis gas was fed to a high-pressure autoclave The reactor was pressurized to 3 MPa and the synthesis gas was a mixed gas of H2 and CO in a molar ratio of 1: 1. The stirring was started and the temperature was raised to 140 ° C. When the temperature rose to 140 ° C, the synthesis gas was used to replenish the pressure to 8 MPa and the reaction was started. During the reaction, the synthesis gas pressure was intermittently added so that the reaction pressure was maintained at 7 to 8 MPa. The yield of 2-amino-2-methyl-1-propanol was 93percent after tracing to isopropylamine no longer reacted by gas chromatography.
The reaction mixture was removed, distilled under reduced pressure at 2.5 kPa, and the fraction between 68-72 ° C was collected to give 2-ammoniaMethyl-1-propanol as pure product, 21 g, and the isolated yield was 93percent.
Reference: [1] Patent: CN105418440, 2016, A, . Location in patent: Paragraph 0060; 0061; 0062
  • 12
  • [ 76-39-1 ]
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Reference: [1] Patent: US2673880, 1951, ,
[2] Journal of Organic Chemistry, 1943, vol. 8, p. 11
[3] Patent: US2413153, 1943, ,
[4] Industrial and Engineering Chemistry, 1948, vol. 40, p. 507
[5] Patent: US2139122, 1937, ,
[6] Patent: US2011/224460, 2011, A1, . Location in patent: Page/Page column 5-6
[7] Patent: US2014/121413, 2014, A1, . Location in patent: Paragraph 0024
[8] Patent: CN108178731, 2018, A, . Location in patent: Paragraph 0033; 0035; 0037; 0039; 0041; 0043; 0045; 0046
[9] Patent: US2139122, 1937, ,
  • 13
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Reference: [1] Advanced Synthesis and Catalysis, 2001, vol. 343, # 8, p. 802 - 808
  • 14
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Reference: [1] Synthesis (Germany), 2016, vol. 48, # 6, p. 906 - 916
  • 15
  • [ 32831-43-9 ]
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YieldReaction ConditionsOperation in experiment
103 g With sodium hypochlorite; sodium hydroxide In water at 0 - 70℃; for 0.333333 h; 109 g of sodium hypochlorite and 106 g of sodium hydroxide were weighed and dissolved in 600 g of water. The above solution was dissolved in a temperature of about 0 ° C,The crude product of 2,2-dimethyl-3-hydroxypropionamide was added dropwise with stirring, and the temperature was raised to 70 ° C for 20 min. After the reaction is overThe water was distilled off, and the mixture was purified by filtration to obtain 103 g of 2-amino-2-methyl-1-propanol and 99.2 wtpercent purity.The target product yield was about 86.3percent.The total yield of 2-amino-2-methyl-1-propanol was about 57.4percent.
Reference: [1] Patent: CN107129435, 2017, A, . Location in patent: Paragraph 0034; 0038; 0039; 0044; 0045; 0050; 0051
  • 16
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Reference: [1] Patent: US7271186, 2007, B1, . Location in patent: Page/Page column 33
  • 17
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Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 3121
  • 18
  • [ 76-39-1 ]
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Reference: [1] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 9, p. 3345 - 3353
  • 19
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Reference: [1] Patent: US6353006, 2002, B1, . Location in patent: Page column 138
  • 20
  • [ 62-57-7 ]
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Reference: [1] Monatshefte fuer Chemie, 1953, vol. 84, p. 1097
[2] Chimica Therapeutica, 1969, vol. 4, p. 80 - 88
[3] European Journal of Organic Chemistry, 2008, # 2, p. 350 - 355
[4] Synlett, 2008, # 12, p. 1829 - 1832
  • 21
  • [ 82922-13-2 ]
  • [ 50-00-0 ]
  • [ 75-04-7 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 4, p. 1234 - 1243
  • 22
  • [ 87730-42-5 ]
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Reference: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1993, vol. 32, # 6, p. 641 - 644
  • 23
  • [ 86241-96-5 ]
  • [ 124-68-5 ]
Reference: [1] Russian Journal of Organic Chemistry, 2007, vol. 43, # 7, p. 966 - 969
  • 24
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Reference: [1] Patent: WO2005/115150, 2005, A2, . Location in patent: Page/Page column 76
  • 25
  • [ 22451-34-9 ]
  • [ 114444-46-1 ]
  • [ 124225-44-1 ]
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Reference: [1] Journal of the American Chemical Society, 1990, vol. 112, # 2, p. 779 - 786
  • 26
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 4, p. 1234 - 1243
  • 27
  • [ 115-11-7 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1969, vol. 311, p. 15 - 35
  • 28
  • [ 116221-74-0 ]
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Reference: [1] Gazzetta Chimica Italiana, 1993, vol. 123, # 10, p. 549 - 552
  • 29
  • [ 67-66-3 ]
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  • [ 67-64-1 ]
  • [ 90032-83-0 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10632 - 10641
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 31, p. 8878 - 8883[3] Angew. Chem., 2016, vol. 128, # 31, p. 9024 - 9029,6
[4] Advanced Synthesis and Catalysis, 2011, vol. 353, # 11-12, p. 2093 - 2110
  • 30
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  • [ 67-64-1 ]
  • [ 90032-83-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 52, p. 15840 - 15844[2] Angew. Chem., 2015, vol. 127, # 52, p. 16066 - 16070,5
  • 31
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YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 20℃; for 2.83333 h; (3a)
(2-Hydroxy-1,1-dimethylethyl)carbamic acid t-butyl ester
230.4 ml of di-t-butyl dicarbonate (1.00 mol) was added to a solution of 98.05 g of 2-amino-2-methyl-1-propanol (1.10 mol) and 154 ml of triethylamine (1.10 mol) in methylene chloride (500 ml) at room temperature over 20 minutes, and the mixture was stirred at room temperature for 2.5 hours.
The reaction mixture was concentrated under reduced pressure and diluted with a 10percent citric acid aqueous solution, followed by extraction with ethyl acetate.
Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate.
After filtration, the solvent was evaporated under reduced pressure to obtain 189.25 g of the crude title compound (yield: quant.).
Colorless solid.
1H NMR spectrum (CDCl3, 400 MHz), δ: 4.64 (br s, 1H), 4.01 (br s, 1H), 3.59 (d, 2H, J = 6.3 Hz), 1.43 (s, 9H), 1.25 (s, 6H).
99% With iron(III) trifluoromethanesulfonate In neat (no solvent) at 20℃; for 0.0666667 h; Green chemistry General procedure: Fe(OTf)3 (1 molpercent) was added to a magnetically stirred mixture of anamine (1 mmol) and Boc2O (1 mmol) at room temperature. The mixturewas stirred until completion of the reaction (TLC), then diluted withEtOAc and washed with water. The organic layer was dried overanhydrous MgSO4, then the solvent was distillated off under vacuum toyield the highly pure N‑Boc derivatives
98% at 0 - 20℃; for 2 h; Di-tert-butyl dicarbonate (21.82 g, 100.00 mmol) was added in portions to a solution of 2- amino-2-methylpropan-i-ol (8.91 g, 100.0 mmol) in DCM (270 ml) at 0 °C. The reaction was stirred at room temperature for 2 hours, then was washed with 2N HC1 (100 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to give tert-butyl (1-hydroxy- 2-methylpropan-2-yl)carbamate (18.56 g, 98 percent) as a white solid. ‘H NMR (400 MHz,CDC13, 27 °C) 1.25 (6H, s), 1.43 (9H, s), 3.58 (2H, d), 4.67 (1H, s).
97% With triethylamine In dichloromethane at 22 - 25℃; for 4 h; 2-Amino-2-methyl-l-propanol (5 g, 56.1 mmol), (Boc)20 (13.46 g, 61.7 mmol) and triethyl amine (6.24 g, 61.7 mmol) were dissolved in 50 mL of dichloromethane. The reaction mixture was stirred for 4 h at 22 to 25 °C. Above mixture was washed with water (25 mL x 2), dried over anhydrous sodium sulfate and concentrated under vacuum to get tert-buty] (1- hydroxy-2-methylpropan-2-yl)carbamate (10.3 g, 97percent yield).
90% With 1,3-disulfonic acid imidazolium hydrogen sulfate In neat (no solvent) at 20℃; for 0.0333333 h; Green chemistry General procedure: Amine (1 mmol) was added to the mixture of (Boc)2O (1 mmol) and DSIMHS (6.5 mg, ~ 0.02 mmol) with constant stirring at room temperature under solvent-free conditions. After completion of the reaction (monitored by TLC),   ethyl acetate (3 × 5 mL) was added to the reaction mixture and the catalyst was decanted and washed with ethyl acetate (2 × 5 mL) and dried. The product was purified by column chromatography, using   ethyl acetate–petroleum ether (2:8) eluent.
75.36% With triethylamine In dichloromethane at 0 - 20℃; for 1 h; To a solution of compound 1 (10.00 g, 112.18 mmol, 1.00 Eq) in DCM (200 mL) was added Et3N (23.00 g, 227.30 mmol, 2.03 Eq). The mixture was cooled to 0° C. and Boc2O (38.40 g, 175.95 mmol, 1.57 Eq) was added, the mixture was stirred at 20° C. for 1 hr. The mixture was diluted with EA and washed with water. The organic phase was concentrated in vacuo. The residue was purified by silica gel chromatography (Petroleum ether/Ethyl acetate=15/1) to afford compound 2 (16.00 g, 84.54 mmol, 75.36percent yield) as white solid.
75.36% With triethylamine In dichloromethane at 0 - 20℃; for 0.5 h; To a solution of compound 1 (10.00 g, 112.18 mmol, 1.00 Eq) in DCM (200 mL) was added Et3N (23.00 g, 227.30 mmol, 2.03 Eq). The mixture was cooled to 0° C. and Boc2O (38.40 g, 175.95 mmol, 1.57 Eq) was added, the mixture was stirred at 20° C. for 1 hr. The mixture was diluted with EA and washed with water. The organic phase was concentrated in vacuo. The residue was purified by silica gel chromatography (Petroleum ether/Ethyl acetate=15/1) to afford compound 2 (16.00 g, 84.54 mmol, 75.36percent yield) as white solid.
68% at 20℃; Example 4
(tert-Butoxy)-N-(1-hydroxy-2-methylpropyl)carboxamide (4)
Following the general procedure for the N-Boc-protection of ω-amino-2,2-dimethylalcohols of Description 2, 1.783 g (20.0 mmol) of 2-amino-2-methyl-1-propanol was reacted with 3.274 g (15.0 mmol) of di-tert-butyl-dicarbonate in a mixture of 20 mL of a saturated aqueous solution of sodium bicarbonate (NaHCO3) and 40 mL of acetonitrile to provide 1.937 g (68percent yield) of the title compound (4) as a colorless solid of sufficient purity to be used in subsequent steps without further isolation and purification. 1H NMR (400 MHz, CDCl3): δ=1.26 (s, 6H), 1.44 (s, 9H), 3.59 (d, J=6.0 Hz, 2H), 4.00-4.20 (br. m, 1H), 4.64-4.72 (br. m, 1H) ppm. MS (ESI) m/z 212.92 (M+Na)+.
53% at 25℃; for 1 h; 2-Amino-2-methyl-propan-1-ol (53 g, 0.59 mol) and di-tert-butyl dicarbonate (65.0 g, 0.297 mol) were combined in H2O (500 mL) and stirred at 25 °C for 1 h. The reaction mixture was extracted with CHCl3 (2 x 250 mL). The organics were dried and concentrated to a white amorphous solid which was recrystallized from hot hexanes to afford desired material (30 g, 53percent) as a white solid: 13C NMR (CD3OD, 100 MHz) δ 157.76, 80.135, 70.095, 54.992, 29.247, 24.695.
750 g With sodium hydrogencarbonate; sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 18 h; Intermediate 12: tert-butyl (l-hydroxy-2-meth lpropan-2-yl)carbamate - Preparation 2
To a solution of 2-amino-2-methylpropan-l-ol (500 g, 5.61 mol, Alfa) in THF (3.0 L) and water (1.0 L) was added Na2C03 (10.11 g, 95 mmol) and sodium bicarbonate (10.37 g, 123 mmol) and stirring continued at 0 QC. di-ferf-Butyl dicarbonate (1.56 L, 6.7 mol) was added. The reaction mixture was stirred at RT for 18 h. The THF layer was separated and the aqueous layer extracted with ethyl acetate (1.5 L). The combined organic layers were washed with brine solution (2 x 2 L), were dried over anhydrous Na2S04 and then concentrated under reduced pressure to afford crude title compound. The crude material was dissolved in petroleum ether (750 mL) and cooled to -50 °C. The resulting solid was filtered and washed with petroleum ether to give the title compound (750 g) as a white solid. (0250) *H NMR (400 MHz, DMSO-d6) δ: 6.08 (1H, s), 4.67 (1H, t), 3.29 (2H, s), 1.37 (9H, s), 1.13 (6H, s).

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Reference: [1] Patent: WO2004/838, 2003, A1, . Location in patent: Page 71-72
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Chemical Structure| 1185-53-1

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2-Amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride

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Chemical Structure| 27646-80-6

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2-Methyl-2-(methylamino)propan-1-ol

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Chemical Structure| 534-03-2

[ 534-03-2 ]

2-Aminopropane-1,3-diol

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Chemical Structure| 1305208-37-0

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(3-Aminooxetan-3-yl)methanol

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Amines

Chemical Structure| 77-86-1

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2-Amino-2-(hydroxymethyl)propane-1,3-diol

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Chemical Structure| 1185-53-1

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2-Amino-2-(hydroxymethyl)propane-1,3-diol hydrochloride

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2-Methyl-2-(methylamino)propan-1-ol

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Chemical Structure| 534-03-2

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2-Aminopropane-1,3-diol

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