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[ CAS No. 109-83-1 ] {[proInfo.proName]}

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Chemical Structure| 109-83-1
Chemical Structure| 109-83-1
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Product Details of [ 109-83-1 ]

CAS No. :109-83-1 MDL No. :MFCD00002839
Formula : C3H9NO Boiling Point : -
Linear Structure Formula :HNCH3(CH2CH2OH) InChI Key :OPKOKAMJFNKNAS-UHFFFAOYSA-N
M.W : 75.11 Pubchem ID :8016
Synonyms :

Safety of [ 109-83-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P260-P264-P270-P271-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P314-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501 UN#:2735
Hazard Statements:H227-H302+H312-H314-H335-H373-H402 Packing Group:
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Application In Synthesis of [ 109-83-1 ]

* 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 [ 109-83-1 ]
  • Downstream synthetic route of [ 109-83-1 ]

[ 109-83-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 109-83-1 ]
  • [ 131543-46-9 ]
  • [ 18424-96-9 ]
Reference: [1] Patent: US5066804, 1991, A,
[2] Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 188 - 199
  • 2
  • [ 109-83-1 ]
  • [ 131543-46-9 ]
  • [ 18424-96-9 ]
  • [ 67992-27-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1978, vol. <II>, p. 83 - 88
  • 3
  • [ 109-83-1 ]
  • [ 4535-90-4 ]
YieldReaction ConditionsOperation in experiment
96% With thionyl chloride In dichloromethane EXAMPLE 2
N-Methyl-N-(2-chloroethyl)amine, hydrochloride salt
Hydrogen chloride was bubbled into a stirred solution of 2-(methylamino)ethanol (10 g, 133 mmol) in CH2 Cl2 (25 ml) until the mixture turned wet litmus paper red.
The mixture was cooled to 0° C., and thionyl chloride (15.82 g, 133 mmol) was added dropwise.
The mixture was allowed to stir overnight at room temperature.
The solvent was removed under reduced pressure to give product as a white solid (16.60 g, 96percent yield): mp 95°-100° C.; 1 H NMR (DMSO-d6) 4.00(t, 2H, J=6.28 Hz), 3.36(t, 2H, J=6.29 Hz), 2.81(s, 3H)ppm; IR (KBr) 3400, 2960, 2750, 2420, 1730, 1580, 1460, 1390, 1310, 1270, 1200, 1150, 1165, 1005, 990, 900, 860, 710 cm-1.
87% With thionyl chloride In chloroform at 0 - 50℃; for 17 h; Inert atmosphere To a solution of 2-(methylamino)ethanol (400 pL, 5.00 mmol, 1.0 equiv.) in chloroform (50 mL)was added, under argon at 0°C, thionyle chloride (1.09 mL, 15.0 mmol, 3.0 equiv.). After 17 h of stirring at 50°C, the solvent was concentrated until approximatively 10 mL, then diethyl ether (40 mL) was added to precipitate the compound which was collected on a fritglass, washed several times diethyl ether and dried with a vane pump during one night to afford compound A0219 (567 mg, 4.36 mmol) as a white solid in 87percent yield which was used in the next step without further purification. 1H NMR (400 MHz, MeOD) 5 3.91 (t, J = 5.4 Hz, 2H, CH2CI), 3.42 (t, J = 5.4 Hz, 2H, CH2N), 2.77 (s, 3H, CH3N). 13C NMR (100 MHz, MeOD) 551.46 (CH2N), 40.22 (CH2CI), 33.64 (CH3N).
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 14, p. 2672 - 2680
[2] Patent: US5233031, 1993, A,
[3] Chemical and Pharmaceutical Bulletin, 2002, vol. 50, # 7, p. 941 - 959
[4] Journal of the Chemical Society. Dalton Transactions, 2001, # 8, p. 1306 - 1318
[5] Journal of medicinal chemistry, 1992, vol. 35, # 17, p. 3246 - 3253
[6] Patent: WO2015/140337, 2015, A1, . Location in patent: Page/Page column 33
[7] Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5429 - 5444
[8] Journal of the American Chemical Society, 2008, vol. 130, # 15, p. 5052 - 5053
[9] Organometallics, 2012, vol. 31, # 21, p. 7427 - 7433,7
[10] Chemische Berichte, 1905, vol. 38, p. 3132
[11] Patent: WO2007/25889, 2007, A2, . Location in patent: Page/Page column 37; 39-40; 42
[12] Journal of Polymer Science, Part A: Polymer Chemistry, 2014, vol. 52, # 5, p. 671 - 679
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