Product Name

  • Name

    Thalidomide

  • EINECS 200-031-1
  • CAS No. 50-35-1
  • Article Data47
  • CAS DataBase
  • Density 1.503 g/cm3
  • Solubility <0.1 g/100 mL at 22 °C in water
  • Melting Point 269-271 °C
  • Formula C13H10N2O4
  • Boiling Point 509.7 °C at 760 mmHg
  • Molecular Weight 258.233
  • Flash Point 262.1 °C
  • Transport Information UN 2811 6.1/PG 3
  • Appearance white solid
  • Safety 53-22-26-36/37/39-45
  • Risk Codes 46-61-21-25-62
  • Molecular Structure Molecular Structure of 50-35-1 (Thalidomide)
  • Hazard Symbols ToxicT
  • 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;
  • PSA 83.55000
  • LogP 0.35450

Synthetic route

phthalic anhydride
85-44-9

phthalic anhydride

rac-α-aminoglutarimide hydrochloride
24666-56-6

rac-α-aminoglutarimide hydrochloride

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With acetic acid; triethylamine for 3h; Temperature; Reagent/catalyst; Concentration; Reflux;95%
(S)-2-phthalimidoglutaramic acid
3343-29-1

(S)-2-phthalimidoglutaramic acid

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With dmap; 1,1'-carbonyldiimidazole In tetrahydrofuran for 16h; Reflux; Inert atmosphere;91%
phthalic anhydride
85-44-9

phthalic anhydride

(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester
31140-42-8

(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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;
phthalic anhydride
85-44-9

phthalic anhydride

A

phthalimide
136918-14-4

phthalimide

B

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With Glutamic acid; ammonium acetate at 150℃; for 0.166667h; Reagent/catalyst; Microwave irradiation; Sealed tube; Green chemistry;A 90%
B 7%
carbon monoxide
201230-82-2

carbon monoxide

(+/-)-α-aminoglutarimide
2353-44-8

(+/-)-α-aminoglutarimide

1,2-dibromobenzene
583-53-9

1,2-dibromobenzene

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With palladium diacetate; triethylamine; catacxium A In N,N-dimethyl acetamide at 100℃; under 22502.3 Torr; for 30h; Autoclave; Inert atmosphere;87%
phthalic anhydride
85-44-9

phthalic anhydride

Glutamic acid
617-65-2

Glutamic acid

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With dmap; ammonium chloride at 150℃; for 0.166667h; Microwave irradiation; Sealed tube; Green chemistry;86%
N-phthaloyl-L-glutamic acid
340-90-9

N-phthaloyl-L-glutamic acid

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With thiourea for 0.25h; Microwave irradiation;85%
N-phthaloylglutamic acid anhydride
3343-28-0

N-phthaloylglutamic acid anhydride

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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
671787-01-2

2-[2,6-dioxo-5-(toluene-4-sulfonyl)-piperidin-3-yl]-isoindole-1,3-dione

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With sodium amalgam at 20℃; for 4h;72%
L-glutamine
56-85-9

L-glutamine

phthalic acid dimethyl ester
131-11-3

phthalic acid dimethyl ester

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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%
phthalic anhydride
85-44-9

phthalic anhydride

L-glutamine
56-85-9

L-glutamine

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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%
2-phthalimidoglutaramic acid
7607-72-9

2-phthalimidoglutaramic acid

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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%
N-phthalylglutamic acid
6349-98-0

N-phthalylglutamic acid

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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
31140-42-8

(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

benzene-1,2-dicarboxylic acid
88-99-3

benzene-1,2-dicarboxylic acid

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation;62%
L-glutamine
56-85-9

L-glutamine

Phthaloyl dichloride
88-95-9

Phthaloyl dichloride

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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%
phthalic anhydride
85-44-9

phthalic anhydride

(RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate

(RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 80℃; for 24h;55%
With triethylamine In tetrahydrofuran for 48h; Heating / reflux;54%
acetic anhydride
108-24-7

acetic anhydride

2-phthalimidoglutaramic acid
7607-72-9

2-phthalimidoglutaramic acid

thalidomide
50-35-1

thalidomide

urea
57-13-6

urea

N-phthaloylglutamic acid anhydride
3343-28-0

N-phthaloylglutamic acid anhydride

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
at 170 - 180℃;
phthalic anhydride
85-44-9

phthalic anhydride

L-glutamine
56-85-9

L-glutamine

A

thalidomide
50-35-1

thalidomide

B

Pyroglutamic acid
149-87-1

Pyroglutamic acid

Conditions
ConditionsYield
for 0.316667h; Microwave irradiation;
2-aminoacetic acid-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2,6-dioxo-piperidin-1-yl]methyl ester hydrochloride

2-aminoacetic acid-[3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-2,6-dioxo-piperidin-1-yl]methyl ester hydrochloride

A

formaldehyd
50-00-0

formaldehyd

B

glycinate
23297-34-9

glycinate

C

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
With phosphate buffer In water at 37℃; pH=7.4; Kinetics;
2-methylamino(propionic acid)-[3-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-2,6-di-oxo-piperidine-1-yl-methyl]ester hydrochloride

2-methylamino(propionic acid)-[3-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-2,6-di-oxo-piperidine-1-yl-methyl]ester hydrochloride

A

formaldehyd
50-00-0

formaldehyd

B

thalidomide
50-35-1

thalidomide

C

(S)-2-Methylamino-propionic acid anion

(S)-2-Methylamino-propionic acid anion

Conditions
ConditionsYield
With phosphate buffer In water at 37℃; pH=7.4; Kinetics;
2-amino-3-methylbutyric acid-[3-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-2,6-dioxo-piperidine-1-yl-methyl]ester hydrochloride

2-amino-3-methylbutyric acid-[3-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-2,6-dioxo-piperidine-1-yl-methyl]ester hydrochloride

A

formaldehyd
50-00-0

formaldehyd

B

thalidomide
50-35-1

thalidomide

C

L-valinate
17333-21-0

L-valinate

Conditions
ConditionsYield
With phosphate buffer In water at 37℃; pH=7.4; Kinetics;
2-[1-(4-methoxybenzyl)-2,6-dioxopiperidin-3-yl]isoindoline-1,3-dione
222713-07-7

2-[1-(4-methoxybenzyl)-2,6-dioxopiperidin-3-yl]isoindoline-1,3-dione

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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
24249-89-6

ethyl 2-(1,3-dioxoisoindolin-2-yl)acrylate

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / Na/Hg / 4 h / 20 °C
View Scheme
phthalimide
136918-14-4

phthalimide

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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
26878-24-0

methyl 2-phthalimidoacrylate

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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
485817-55-8

1-p-methoxybenzyl-3-phthalimido-5-(p-toluenesulfonyl)piperidine-2,6-dione

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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
485817-54-7

3-amino-1-(4-methoxy-benzyl)-5-(toluene-4-sulfonyl)-piperidine-2,6-dione

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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
485817-52-5

1-p-methoxybenzyl-3-tert-butoxycarbonylamino-5-(p-toluenesulfonyl)-piperidine-2,6-dione

thalidomide
50-35-1

thalidomide

Conditions
ConditionsYield
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
thalidomide
50-35-1

thalidomide

O-acetylsalicyloyl chloride
5538-51-2

O-acetylsalicyloyl chloride

2-acetoxy-N-(2,6-dioxopiperidin-3-yl)benzamide

2-acetoxy-N-(2,6-dioxopiperidin-3-yl)benzamide

Conditions
ConditionsYield
With triethylamine In chloroform at 0 - 20℃;98%
1,4-dioxane
123-91-1

1,4-dioxane

ethyl 2-(2-bromophenyl)-2-diazoacetate
1398179-24-2

ethyl 2-(2-bromophenyl)-2-diazoacetate

thalidomide
50-35-1

thalidomide

ethyl 2-(2-bromophenyl)-2-(2-(2-(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)ethoxy)ethoxy)acetate

ethyl 2-(2-bromophenyl)-2-(2-(2-(3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)ethoxy)ethoxy)acetate

Conditions
ConditionsYield
With potassium carbonate at 80℃; for 12h; Inert atmosphere; Schlenk technique;98%
thalidomide
50-35-1

thalidomide

A

(R)-thalidomide
2614-06-4

(R)-thalidomide

B

(S)-thalidomide
841-67-8

(S)-thalidomide

Conditions
ConditionsYield
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
50-35-1

thalidomide

tetramethylammonium fluoride
373-68-2

tetramethylammonium fluoride

2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
42472-93-5

2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 160℃; for 12h;92%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

thalidomide
50-35-1

thalidomide

1,3-dioxo-2-(1-tert.-butoxycarbonyl-2,6-dioxopiperidin-3-yl)isoindoline
220460-69-5

1,3-dioxo-2-(1-tert.-butoxycarbonyl-2,6-dioxopiperidin-3-yl)isoindoline

Conditions
ConditionsYield
With dmap In 1,4-dioxane90%
With 2-(Dimethylamino)pyridine In 1,4-dioxane
thalidomide
50-35-1

thalidomide

3-(1-hydroxy-3-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione
58585-25-4

3-(1-hydroxy-3-oxo-1,3-dihydro-isoindol-2-yl)-piperidine-2,6-dione

Conditions
ConditionsYield
With acetic acid; zinc at 90℃; for 0.166667h;87%
With aluminium amalgam; water; acetic acid In ethanol for 3h; Heating;
thalidomide
50-35-1

thalidomide

propargyl bromide
106-96-7

propargyl bromide

2-[2,6-dioxo-1-(prop-2-yn-1-yl)piperidin-3-yl]isoindoline-1,3-dione

2-[2,6-dioxo-1-(prop-2-yn-1-yl)piperidin-3-yl]isoindoline-1,3-dione

Conditions
ConditionsYield
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
50-35-1

thalidomide

tosylethylazide
113738-22-0

tosylethylazide

(±)-2-(1-(2-azidoethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

(±)-2-(1-(2-azidoethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
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%
thalidomide
50-35-1

thalidomide

i-pentyl bromide
107-82-4

i-pentyl bromide

2-(1-(4-methylpentyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

2-(1-(4-methylpentyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
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
42599-24-6

E-styryl iodide

N-(quinolin-8-yl)but‐3‐enamide

N-(quinolin-8-yl)but‐3‐enamide

thalidomide
50-35-1

thalidomide

(E)-3-((3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl)-5-phenyl-N-(quinolin-8-yl)pent-4-enamide

(E)-3-((3-(1,3-dioxoisoindolin-2-yl)-2,6-dioxopiperidin-1-yl)methyl)-5-phenyl-N-(quinolin-8-yl)pent-4-enamide

Conditions
ConditionsYield
With palladium diacetate; potassium hydrogencarbonate at 100℃; regioselective reaction;83%
(Z)-1-bromo-4-hexene
63281-98-1

(Z)-1-bromo-4-hexene

thalidomide
50-35-1

thalidomide

C19H20N2O4

C19H20N2O4

Conditions
ConditionsYield
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%
thalidomide
50-35-1

thalidomide

i-pentyl bromide
107-82-4

i-pentyl bromide

2-(1-isopentyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

2-(1-isopentyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h;79%
2-fluoroethyl bromide
762-49-2

2-fluoroethyl bromide

thalidomide
50-35-1

thalidomide

(±)-2-(1-(2-fluoroethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

(±)-2-(1-(2-fluoroethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
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%
carbon disulfide
75-15-0

carbon disulfide

thalidomide
50-35-1

thalidomide

C14H9N2O4S2(1-)

C14H9N2O4S2(1-)

Conditions
ConditionsYield
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
33657-49-7

chloromethyl n-butyrate

thalidomide
50-35-1

thalidomide

2-(1-butyroyloxymethyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

2-(1-butyroyloxymethyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
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
50-35-1

thalidomide

(R,S)-2-(1-(hydroxymethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
145945-21-7

(R,S)-2-(1-(hydroxymethyl)-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
With formaldehyd In water at 25℃; Reflux;74%
thalidomide
50-35-1

thalidomide

1,3-dioxo-2-(2-oxo-6-thioxopiperidin-3-yl)isoindoline

1,3-dioxo-2-(2-oxo-6-thioxopiperidin-3-yl)isoindoline

Conditions
ConditionsYield
With Lawessons reagent In toluene for 12h; Heating / reflux;73%
thalidomide
50-35-1

thalidomide

methyl iodide
74-88-4

methyl iodide

2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
42472-93-5

2-(1-methyl-2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;72.3%

Thalidomide Chemical Properties

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

Thalidomide 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.

Thalidomide 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.

Thalidomide Consensus Reports

EPA Genetic Toxicology Program.

Thalidomide 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.

Thalidomide 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.

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