Diethyl acetamidomalonate
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Diethyl acetamidomalonate
structure -
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CAS No:
1068-90-2
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Formula:
C9H15NO5
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Chemical Name:
Diethyl acetamidomalonate
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Synonyms:
Propanedioic acid,2-(acetylamino)-,1,3-diethyl ester;Malonic acid,acetamido-,diethyl ester;Propanedioic acid,(acetylamino)-,diethyl ester;Diethyl acetamidomalonate;Acetamidomalonic acid diethyl ester;Diethyl (acetylamino)malonate;Diethyl 2-acetamidomalonate;Diethyl (N-acetylamino)malonate;Diethyl α-(acetylamino)malonate;(Acetylamino)malonic acid diethyl ester;2-(Acetylamino)propanedioic acid diethyl ester;Diethyl 2-acetylaminomalonate;NSC 7645;2-Acetylamino-malonic acid diethyl ester;(Acetylamino)propanedioic acid diethyl ester;Diethyl 2-(acetylamino)propanedioate;Diethyl 2-(acetamido)propanedioate;1,3-Diethyl 2-acetamidopropanedioate;Diethyl acetoamidomalonate;2088923-16-2
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CAS No:
Diethyl acetamidomalonate Basic Attributes
217.22
217.22
213-952-9
4VDX81E00W
7645
DTXSID6061446
CRYSTALS FROM ALCOHOL OR BENZENE-PETROLEUM ETHER
29241900
Characteristics
81.7
0.3
White crystalline powder
1.2850 (rough estimate)
95-96 °C
185 °C @ Press: 20 Torr
185°C/20mm
1.4640 (estimate)
soluble in chloroform and methanol. Slightly soluble in water.
Store at RT.
0.000565mmHg at 25°C
eye-rbt 500 mg/24H MLD 28ZPAK -,130,72
Safety Information
IRRITANT
3
R36
39-36-26-44
OO0360000
Xi
Stable under normal temperatures and pressures.
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
H302
|Warning|H302 (71.43%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 21 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Diethyl acetamidomalonate Use and Manufacturing
Diethyl 2-aminomalonate hydrochloride (1 .69 g, 8.0 mmol) and triethylamine (3.4 mL, 24 mmol, 3.0 eq.) were dissolved in dichloromethane (120 mL) at 0 °C. Then acetylchloride (0.57 mL, 8.0 mmol, 1 .0 eq.) was added under stirring and stirring was continued overnight while the mixture was allowed to warm up to r.t. The mixture was diluted with dichloromethane (100 mL) and washed with 1 M HCI (3 * 60 mL). The aqueous phase was extracted with dichloromethane (2 Alternatively, diethyl 2-aminomalonate hydrochloride (21 .4 g, 100 mmol) and triethylamine (56 ml_, 400 mmol, 4.0 eq.) were dissolved in dichloromethane (500 mL) and stirred with acetic anhydride (9.5 mL, 100 mmol, 1.0 eq.) at 0 °C and overnight at r.t. The mixture was washed with brine (2 The above crude product was dissolved in a mixture of 79 volume parts of acetic acid, 25 volume parts of acetic anhydride and 3.5 volume parts of carbon tetrachloride and, under stirring, 27 parts of zinc dust was added at a temperature not exceeding 45°C. 1.1 Diethyl 2-acetamidomalonate[0138] Alternatively, diethyl 2-aminomalonate hydrochloride (21.4 g, 100 mmol) and triethylamine (56 mL, 400 mmol, 4.0 eq.) were dissolved in dichloromethane (500 mL) and stirred with acetic anhydride (9.5 mL, 100 mmol, 1.0 eq.) at 0° C. and overnight at r.t. The mixture was washed with brine (2×200 mL) and dried over MgSO1.1 Diethyl 2-acetamidomalonate10133] Diethyl 12-aminomalonate hydrochloride (1.69 g, 8.0 mmol) and triethylamine (3.4 mL, 24 mmol, 3.0 eq.) were dissolved in dichloromethane (120 mL) at 0° C. Then acetylchloride (0.57 mL, 8.0 mmol, 1.0 eq.) was added under stirring and stirring was continued overnight while the mixture was allowed to warm up to tt. The mixture was diluted with dichloromethane (100 mL) and washed with 1 M RC1 (3x60 mL). The aqueous phase was extracted with dichioromethane (2x60 mL) and the combined organic layer was dried over MgSO4. Afier evaporation of the solvent in vacuo the product was isolated as a pure white solid. Yield: 1.68 g (96percent).0 09_otito 7t10134] M.p.: 96° C. (lit. 97° C.)10135] ‘R NMR (300 MRz, CDC13): ö [ppm]: 1.30 (t, 3Hii=7.1 Rz, 6R, 7-CR3, 9-CR3), 2.08 (s, 3R, 5-CR3), 4.27 (m, 4R, 6-CR2, 8-CR2), 5.18 (d, 3JHH=7.1 Rz, 1R, 2-CR), 6.67(d, Rz, 1R, 2-NR).10136] ‘3C-NMR (75 MRz, CDC13) ö [ppm]: 14.0 (q, C-7, C-9), 22.8 (q, C-5), 56.5 (d, C-2), 62.6 (t, C-6, C-8), 166.5 (s, C-i, C-3), 169.9 (s, C-4).10137] Exact mass (ESI): C9R15NO5+Na: calcd.240.0842, found 240.0824.Example 5 In a 250 mL round bottom flask, to 4 g (18.90 mmol) of diethylaminomalonate hydrochloride 5 were added 9.43 mL (0.885 g mL
Propanedioic acid, 2-(acetylamino)-, 1,3-diethyl ester: ACTIVE
Computed Properties
Molecular Weight:217.22
XLogP3:0.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:217.09502258
Monoisotopic Mass:217.09502258
Topological Polar Surface Area:81.7
Heavy Atom Count:15
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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