Conditions | Yield |
---|---|
With acetic acid; triethylamine for 3h; Temperature; Reagent/catalyst; Concentration; Reflux; | 95% |
Conditions | Yield |
---|---|
With dmap; 1,1'-carbonyldiimidazole In tetrahydrofuran for 16h; Reflux; Inert atmosphere; | 91% |
phthalic anhydride
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester
thalidomide
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 150℃; for 2h; Reagent/catalyst; Microwave irradiation; | 91% |
In 2,2,2-trifluoroethanol at 150℃; for 2h; Solvent; | 91% |
With sodium acetate; acetic acid for 6h; Reflux; |
Conditions | Yield |
---|---|
With Glutamic acid; ammonium acetate at 150℃; for 0.166667h; Reagent/catalyst; Microwave irradiation; Sealed tube; Green chemistry; | A 90% B 7% |
carbon monoxide
(+/-)-α-aminoglutarimide
1,2-dibromobenzene
thalidomide
Conditions | Yield |
---|---|
With palladium diacetate; triethylamine; catacxium A In N,N-dimethyl acetamide at 100℃; under 22502.3 Torr; for 30h; Autoclave; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With dmap; ammonium chloride at 150℃; for 0.166667h; Microwave irradiation; Sealed tube; Green chemistry; | 86% |
Conditions | Yield |
---|---|
With thiourea for 0.25h; Microwave irradiation; | 85% |
Conditions | Yield |
---|---|
With urea at 170 - 180℃; for 0.75h; | 75% |
With urea at 180℃; | 70% |
Stage #1: N-phthaloylglutamic acid anhydride With ammonia In N,N-dimethyl-formamide at 25℃; for 14h; Stage #2: With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 100℃; for 1h; | 68.3% |
2-[2,6-dioxo-5-(toluene-4-sulfonyl)-piperidin-3-yl]-isoindole-1,3-dione
thalidomide
Conditions | Yield |
---|---|
With sodium amalgam at 20℃; for 4h; | 72% |
Conditions | Yield |
---|---|
Stage #1: L-glutamine; phthalic acid dimethyl ester With pyridine at 20 - 85℃; for 6h; Stage #2: With 1,1'-carbonyldiimidazole at 40℃; for 2h; Stage #3: With hydrogenchloride In ethanol; water at 5 - 25℃; for 4h; pH=7; Product distribution / selectivity; | 72% |
Conditions | Yield |
---|---|
Stage #1: phthalic anhydride; L-glutamine In ISOPROPYLAMIDE at 20 - 80℃; for 6h; Stage #2: With 1,1'-carbonyldiimidazole In ISOPROPYLAMIDE at 20 - 90℃; for 4h; Product distribution / selectivity; | 71% |
Stage #1: phthalic anhydride; L-glutamine In 1-methyl-pyrrolidin-2-one at 20 - 80℃; for 6h; Stage #2: With 1,1'-carbonyldiimidazole In 1-methyl-pyrrolidin-2-one at 20 - 90℃; for 4h; Product distribution / selectivity; | 65% |
Stage #1: phthalic anhydride; L-glutamine In DMF (N,N-dimethyl-formamide) at 20 - 80℃; for 6h; Stage #2: With 1,1'-carbonyldiimidazole In DMF (N,N-dimethyl-formamide) at 20 - 90℃; for 4h; Product distribution / selectivity; | 63% |
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In ISOPROPYLAMIDE at 20 - 90℃; for 4h; Product distribution / selectivity; | 71% |
With 1,1'-carbonyldiimidazole In 1-methyl-pyrrolidin-2-one at 20 - 90℃; for 4h; Product distribution / selectivity; | 65% |
With 1,1'-carbonyldiimidazole In dimethyl sulfoxide at 20 - 90℃; for 4h; Product distribution / selectivity; | 62% |
Conditions | Yield |
---|---|
With ammonium acetate In diphenylether at 170 - 175℃; for 0.75h; Reagent/catalyst; Solvent; Temperature; | 65.57% |
With urea In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Solvent; Temperature; Reflux; | 42.5% |
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester
benzene-1,2-dicarboxylic acid
thalidomide
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; | 62% |
Conditions | Yield |
---|---|
Stage #1: L-glutamine; Phthaloyl dichloride With pyridine at 10 - 15℃; for 4h; Stage #2: With 1,1'-carbonyldiimidazole at 20℃; for 4h; Stage #3: With hydrogenchloride In water at 5 - 20℃; for 4h; pH=7; Product distribution / selectivity; | 58% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 80℃; for 24h; | 55% |
With triethylamine In tetrahydrofuran for 48h; Heating / reflux; | 54% |
Conditions | Yield |
---|---|
at 170 - 180℃; |
Conditions | Yield |
---|---|
for 0.316667h; Microwave irradiation; |
Conditions | Yield |
---|---|
With phosphate buffer In water at 37℃; pH=7.4; Kinetics; |
Conditions | Yield |
---|---|
With phosphate buffer In water at 37℃; pH=7.4; Kinetics; |
Conditions | Yield |
---|---|
With phosphate buffer In water at 37℃; pH=7.4; Kinetics; |
2-[1-(4-methoxybenzyl)-2,6-dioxopiperidin-3-yl]isoindoline-1,3-dione
thalidomide
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In acetonitrile at 20℃; for 5h; | 34 mg |
With ammonium cerium(IV) nitrate In water; acetonitrile for 5h; | 34 mg |
ethyl 2-(1,3-dioxoisoindolin-2-yl)acrylate
thalidomide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 72 percent / Na/Hg / 4 h / 20 °C View Scheme |
phthalimide
thalidomide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: triphenylphosphine; sodium acetate / toluene / 0.17 h / Heating 1.2: 78 percent / acetic acid / toluene / 18 h / Heating 2.1: sodium hydride / tetrahydrofuran / 0.08 h / 20 °C 2.2: 58 percent / tetrahydrofuran / 0.33 h / Heating 3.1: 6 percent sodium amalgam; sodium phosphate / methanol / 1 h / 20 °C 4.1: 34 mg / ceric ammonium nitrate / acetonitrile; H2O / 5 h View Scheme |
methyl 2-phthalimidoacrylate
thalidomide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.08 h / 20 °C 1.2: 58 percent / tetrahydrofuran / 0.33 h / Heating 2.1: 6 percent sodium amalgam; sodium phosphate / methanol / 1 h / 20 °C 3.1: 34 mg / ceric ammonium nitrate / acetonitrile; H2O / 5 h View Scheme |
1-p-methoxybenzyl-3-phthalimido-5-(p-toluenesulfonyl)piperidine-2,6-dione
thalidomide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 6 percent sodium amalgam; sodium phosphate / methanol / 1 h / 20 °C 2: 34 mg / ceric ammonium nitrate / acetonitrile; H2O / 5 h View Scheme | |
Multi-step reaction with 2 steps 1: Na2HPO4; 6 percent sodium amalgam / methanol / 1 h / 20 °C 2: 34 mg / aq. ceric ammonium nitrate / acetonitrile / 5 h / 20 °C View Scheme |
3-amino-1-(4-methoxy-benzyl)-5-(toluene-4-sulfonyl)-piperidine-2,6-dione
thalidomide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 450 mg / Et3N; 4 A molecular sieves / tetrahydrofuran / 2 h / Heating 2: Na2HPO4; 6 percent sodium amalgam / methanol / 1 h / 20 °C 3: 34 mg / aq. ceric ammonium nitrate / acetonitrile / 5 h / 20 °C View Scheme |
1-p-methoxybenzyl-3-tert-butoxycarbonylamino-5-(p-toluenesulfonyl)-piperidine-2,6-dione
thalidomide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: TFA / CH2Cl2 / 0.5 h / 20 °C 2: 450 mg / Et3N; 4 A molecular sieves / tetrahydrofuran / 2 h / Heating 3: Na2HPO4; 6 percent sodium amalgam / methanol / 1 h / 20 °C 4: 34 mg / aq. ceric ammonium nitrate / acetonitrile / 5 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With triethylamine In chloroform at 0 - 20℃; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate at 80℃; for 12h; Inert atmosphere; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
With 2C8H8N5O2(1-)*Cu(2+) In acetonitrile at 25℃; Resolution of racemate; | A 96% B 78% |
With N-[(S)-1-phenylethyl]carbamoyl-derivatized cyclofructan-6 column In ethanol; n-heptane; trifluoroacetic acid at 20℃; Resolution of racemate; | |
With chiral Ceramosphere RU-2 In methanol Resolution of racemate; |
thalidomide
tetramethylammonium fluoride
2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
Conditions | Yield |
---|---|
In 1-methyl-pyrrolidin-2-one at 160℃; for 12h; | 92% |
di-tert-butyl dicarbonate
thalidomide
1,3-dioxo-2-(1-tert.-butoxycarbonyl-2,6-dioxopiperidin-3-yl)isoindoline
Conditions | Yield |
---|---|
With dmap In 1,4-dioxane | 90% |
With 2-(Dimethylamino)pyridine In 1,4-dioxane |
thalidomide
3-(1-hydroxy-3-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione
Conditions | Yield |
---|---|
With acetic acid; zinc at 90℃; for 0.166667h; | 87% |
With aluminium amalgam; water; acetic acid In ethanol for 3h; Heating; |
Conditions | Yield |
---|---|
Stage #1: thalidomide With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: propargyl bromide In acetone; toluene at 20℃; for 48h; | 87% |
thalidomide
tosylethylazide
Conditions | Yield |
---|---|
Stage #1: thalidomide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.25h; Stage #2: tosylethylazide In N,N-dimethyl-formamide; mineral oil at 60℃; for 18h; | 84% |
Conditions | Yield |
---|---|
Stage #1: thalidomide With sodium hydride In dimethyl sulfoxide; mineral oil for 0.25h; Inert atmosphere; Stage #2: i-pentyl bromide In dimethyl sulfoxide; mineral oil at 20℃; Inert atmosphere; | 84% |
E-styryl iodide
thalidomide
Conditions | Yield |
---|---|
With palladium diacetate; potassium hydrogencarbonate at 100℃; regioselective reaction; | 83% |
Conditions | Yield |
---|---|
Stage #1: thalidomide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: (Z)-1-bromohex-4-ene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 79% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h; | 79% |
Conditions | Yield |
---|---|
Stage #1: thalidomide With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2-fluoroethyl bromide In N,N-dimethyl-formamide at 20℃; for 72h; | 77% |
Conditions | Yield |
---|---|
Stage #1: carbon disulfide; thalidomide In methanol at 0 - 5℃; for 4h; Stage #2: With sodium hydroxide In methanol for 8h; | 74.6% |
chloromethyl n-butyrate
thalidomide
Conditions | Yield |
---|---|
Stage #1: thalidomide With caesium carbonate In DMF (N,N-dimethyl-formamide) Stage #2: chloromethyl n-butyrate In DMF (N,N-dimethyl-formamide) at 20℃; for 20h; | 74% |
thalidomide
(R,S)-2-(1-(hydroxymethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
Conditions | Yield |
---|---|
With formaldehyd In water at 25℃; Reflux; | 74% |
thalidomide
Conditions | Yield |
---|---|
With Lawessons reagent In toluene for 12h; Heating / reflux; | 73% |
thalidomide
methyl iodide
2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere; | 72.3% |
Molecular Structure of Thalidomide (CAS NO.50-35-1):
IUPAC Name: 2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione
Molecular Formula: C13H10N2O4
Molecular Weight: 258.229500 g/mol
H bond acceptors: 6
H bond donors: 1
#Freely Rotating Bonds: 1
Polar Surface Area: 74.76Å2
Index of Refraction: 1.646
Molar Refractivity: 62.35 cm3
Molar Volume: 171.7 cm3
Surface Tension: 69.9 dyne/cm
Enthalpy of Vaporization: 78.04 kJ/mol
Vapour Pressure: 1.65E-10 mmHg at 25°C
Density: 1.503 g/cm3
Melting Point: 269-271 °C
Boiling Point: 509.7 °C at 760 mmHg
Flash Point: 262.1 °C
Water solubility: <0.1 g/100 mL at 22 °C
EINECS: 200-031-1
Categories: Intermediates & Fine Chemicals; Pharmaceuticals; API's; Cytokine signaling
One source have suggested that Thalidomide (CAS NO.50-35-1) had been developed under the direction of a Nazi scientist in 1944, other sources have suggested that it may have been first synthesised by British scientists at the University of Nottingham in 1949.
1. | cyt-hmn:lym 1 mg/L | AMSVAZ Acta Medica Scandinavica. 177 (1965),783. | ||
2. | dns-rat-ipr 80 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 171 (1970),109. | ||
3. | orl-rat LD50:113 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 14 (1969),515. | ||
4. | skn-rat LD50:1550 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 14 (1969),515. | ||
5. | orl-mus LD50:2000 mg/kg | LIFSAK Life Sciences. 3 (1964),721. | ||
6. | ipr-mus LDLo:800 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 23 (1972),288. |
EPA Genetic Toxicology Program.
Safety Information of Thalidomide (CAS NO.50-35-1):
Hazard Codes: T
Risk Statements: 46-61-21-25-62
R46:May cause heritable genetic damage.
R61:May cause harm to the unborn child.
R21:Harmful in contact with skin.
R25 :Toxic if swallowed.
R62:Risk of impaired fertility.
Safety Statements: 53-22-26-36/37/39-45
S53:Avoid exposure - obtain special instructions before use.
S22:Do not breathe dust.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: TI4375000
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion. Moderately toxic by skin contact and intraperitoneal routes. Human teratogenic effects by ingestion: developmental abnormalities of the musculoskeletal and cardiovascular systems. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic and teratogenic data. Human mutation data reported. It was commonly used as a prescription drug in Europe in the late 1950s and early 1960s. Its use was discontinued because it was discovered to cause serious congenital abnormalities in the fetus, notably amelia and phocomelia (absence or deformity of the limbs, including hands and feet) when taken by a woman during early pregnancy. When heated to decomposition it emits toxic fumes of NOx. Used as a sedative and hypnotic.
Thalidomide , with CAS number of 50-35-1, can be called Phthalimide,N-(2,6-dioxo-3-piperidyl)- (6CI,7CI,8CI) ; 1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline ; 3-Phthalimidoglutarimide ; Contergan ; N-(2,6-Dioxo-3-piperidyl)phthalimide ; N-Phthaloylglutamimide ; a-(N-Phthalimido)glutarimide ; a-Phthalimidoglutarimide . It is a white powder. Thalidomide (CAS NO.50-35-1) is a sedative-hypnotic and multiple myeloma medication found to have an inhibitory effect on morning sickness,insomnia, coughs, colds and headaches, but it may lead to severe birth defects if it is taken during pregnancy.
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