(+)-Thalidomide

Base Information

• Chemical Name: (+)-Thalidomide
• CAS No.: 2614-06-4
• Molecular Formula: C13H10 N2 O4
• Molecular Weight: 258.233
• Hs Code.: 2925190090
• European Community (EC) Number: 636-759-5
• UNII: QN61H68KLK
• DSSTox Substance ID: DTXSID6046971
• Nikkaji Number: J15.228E
• Wikidata: Q27131492
• Metabolomics Workbench ID: 61909
• ChEMBL ID: CHEMBL558551
• Mol file: 2614-06-4.mol

Synonyms:(R)-Thalidomide;(+)-Thalidomide;(R)-(+)-thalidomide;D-Thalidomide;2614-06-4;R-(+)-Thalidomide;Thalidomide, (R)-;NSC 91729;QN61H68KLK;2-[(3R)-2,6-dioxopiperidin-3-yl]isoindole-1,3-dione;CHEBI:61917;Phthalimide, N-(2,6-dioxo-3-piperidyl)-, D-(+)-;(R)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;1H-Isoindole-1,3(2H)-dione, 2-(2,6-dioxo-3-piperidinyl)-, (R)-;2-[(3R)-2,6-dioxopiperidin-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione;Phthalimide, N-(2,6-dioxo-3-piperidyl)-, (+)-;2-[(3R)-2,6-dioxopiperidin-3-yl]-1H-isoindole-1,3(2H)-dione;2-[(3~{R})-2,6-bis(oxidanylidene)piperidin-3-yl]isoindole-1,3-dione;NSC-91729;(R)-(D)-Thalidomide;R-(D)-THALIDOMIDE;UNII-QN61H68KLK;SCHEMBL41641;rac-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione;BIDD:ER0498;CHEMBL558551;(+)-(R)-THALIDOMIDE;DTXSID6046971;BDBM65362;N-(alpha-Glutarimido)-phthalimide;N-(I+/--Glutarimidyl)phthalimide;CCG-36381;HY-14658B;AKOS040736366;LS-109464;(+)-Thalidomide, >=98% (HPLC), powder;CS-0021929;EN300-7507077;J-016277;Q27131492;1H-Isoindole-1,3(2H)-dione,2-[(3R)-2,6-dioxo-3-piperidinyl]-;1H-ISOINDOLE-1,3(2H)-DIONE, 2-((3R)-2,6-DIOXO-3-PIPERIDINYL)-;2-((3R)-2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE;6EL

Chemical Property of (+)-Thalidomide

Chemical Property:

• Vapor Pressure: 1.65E-10mmHg at 25°C
• Melting Point: 269-271°C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 509.7°C at 760 mmHg
• PKA: 10.70±0.40(Predicted)
• Flash Point: 262.1°C
• PSA: 83.55000
• Density: 1.503g/cm³
• LogP: 0.35450
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO: soluble
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 258.06405680
• Heavy Atom Count: 19
• Complexity: 449

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(+)-Thalidomide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 61-22
• Safety Statements: 53-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC(=O)C1N2C(=O)C3=CC=CC=C3C2=O
• Isomeric SMILES: C1CC(=O)NC(=O)[C@@H]1N2C(=O)C3=CC=CC=C3C2=O
• Uses: Optically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative. Optically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative Thalidomide has been used to study its teratogenic effects in chicken embryos and human embryonic cells. This study reported that thalidomide causes limb defects by stabilizing PTEN, inhibiting the expression of Akt and activating caspase-dependent apoptosis. Thalidomide has also been used for studying glutathione mediated teratogenic resistance in mouse embryos.

Technology Process of (+)-Thalidomide

There total 2 articles about (+)-Thalidomide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

phthalic anhydride (85-44-9) → (R)-thalidomide (2614-06-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, 4 Angstroem molecular sieves / tetrahydrofuran / 2 h / Heating

2: 89 percent / H₂ / 10percent Pd/C / methanol / 2 h

3: 80 percent / bromoacetophenone, DMAP, Et₃N / acetonitrile / 2 h / Ambient temperature

With dmap; 4 A molecular sieve; hydrogen; triethylamine; α-bromoacetophenone; palladium on activated charcoal; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1016/0957-4166(95)00155-I

Reference yield:

(S)-thalidomide (841-67-8) → (S)-4-phthalimidoglutaramic acid (2614-08-6,2820-40-8) + (R)-thalidomide (2614-06-4) + α-(o-carboxybenzamido)-L-glutarimide (131-68-0,29883-18-9) + (S)-2-phthalimidoglutaramic acid (3343-29-1,2110-19-2,174591-46-9)

Guidance literature:

human serum albumin; In phosphate buffer; at 37 ℃; pH=7.40; Further Variations:; Catalysts; catalyst, buffer concentration; Kinetics;

DOI:10.1021/tx9801817

Reference yield:

(R)-thalidomide (2614-06-4) → (R)-4-phthalimidoglutaramic acid (2614-09-7,2820-40-8) + (S)-thalidomide (841-67-8) + (R)-2-phthalimidoglutaramic acid (2110-19-2,174591-46-9) + α-(o-carboxybenzamido)-D-glutarimide (131-68-0,29883-18-9)

Guidance literature:

human serum albumin; In phosphate buffer; at 37 ℃; pH=7.40; Further Variations:; Catalysts; pH-values; catalyst, buffer concentration; Kinetics;

DOI:10.1021/tx9801817

upstream raw materials:

(S)-thalidomide

phthalic anhydride

Downstream raw materials:

(R)-4-phthalimidoglutaramic acid

(S)-thalidomide

(R)-2-phthalimidoglutaramic acid

α-(o-carboxybenzamido)-D-glutarimide

Refernces

• 1、 Robin, Sylvie,Zhu, Jiarong,Galons, Herve,Pham-Huy, Chuong,Claude, Jean Roger,et al.. "A Convenient Asymmetric Synthesis of Thalidomide". . p. 1249 - 1252. Retrieved 2007/10/02.