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| CAS No.: | 50-35-1 |
|---|---|
| Name: | Thalidomide |
| Article Data: | 47 |
| Molecular Structure: | |
|
|
|
| Formula: | C13H10N2O4 |
| Molecular Weight: | 258.233 |
| Synonyms: | Phthalimide,N-(2,6-dioxo-3-piperidyl)- (6CI,7CI,8CI);1,3-Dioxo-2-(2,6-dioxopiperidin-3-yl)isoindoline;3-Phthalimidoglutarimide;Celgene;Contergan;Distaval;K 17;Kevadon;Myrin;N-Phthaloylglutamimide;Pantosediv;Quetimid;Sauramide;Softenil;Suaramide;Talimol;Thalomid;a-(N-Phthalimido)glutarimide;a-N-Phthalylglutaramide;a-Phthalimidoglutarimide; |
| EINECS: | 200-031-1 |
| Density: | 1.503 g/cm3 |
| Melting Point: | 269-271 °C |
| Boiling Point: | 509.7 °C at 760 mmHg |
| Flash Point: | 262.1 °C |
| Solubility: | <0.1 g/100 mL at 22 °C in water |
| Appearance: | white solid |
| Hazard Symbols: |
 T
|
| Risk Codes: | 46-61-21-25-62 |
| Safety: | 53-22-26-36/37/39-45 |
| Transport Information: | UN 2811 6.1/PG 3 |
| PSA: | 83.55000 |
| LogP: | 0.35450 |
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| 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% |
- 85-44-9
phthalic anhydride
- 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester
- 50-35-1
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% |
- 201230-82-2
carbon monoxide
- 2353-44-8
(+/-)-α-aminoglutarimide
- 583-53-9
1,2-dibromobenzene
- 50-35-1
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% |
- 671787-01-2
2-[2,6-dioxo-5-(toluene-4-sulfonyl)-piperidin-3-yl]-isoindole-1,3-dione
- 50-35-1
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% |
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Chemistry
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
History
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.
Toxicity Data With Reference
| 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. |
Consensus Reports
EPA Genetic Toxicology Program.
Safety Profile
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.
Specification
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.