3',5'-Dichloromethotrexate; Methotrexate, dichloro-; NSC 145883; NSC 29630

Base Information

• Chemical Name: 3',5'-Dichloromethotrexate; Methotrexate, dichloro-; NSC 145883; NSC 29630
• CAS No.: 528-74-5
• Molecular Formula: C20H20 Cl2 N8 O5
• Molecular Weight: 523.335
• NSC Number: 29630
• DSSTox Substance ID: DTXSID80859457
• ChEMBL ID: CHEMBL33308
• Mol file: 528-74-5.mol

Synonyms:NSC29630;Glutamic acid,5-dichloro-4-([(2,4-diamino-6-pteridinyl)methyl]methylamino)benzoyl)-;Glutamic acid,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-;Amethopterin,5'-dicloro-;Amethopterin,5'-dichloro-;CHEMBL33308;SCHEMBL160042;DTXSID80859457;3',5'-Dichloromethotrexate;Methotrexate, dichloro-;NSC 145883;NSC 29630;WLN: T66 BN DN GN JNJ CZ EZ H1N1&R BG FG DVMYVQ2VQ;N-[3,4-diamino-6-pteridinylmethyl)methylamino]benzoyl]glutamic acid;Glutamic acid,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-, L-;L-Glutamic acid,5-dichloro-4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-;N-(3,5-Dichloro-4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)glutamic acid

Chemical Property of 3',5'-Dichloromethotrexate; Methotrexate, dichloro-; NSC 145883; NSC 29630

Chemical Property:

• Refractive Index: 1.7350 (estimate)
• PSA: 210.54000
• Density: 1.637g/cm³
• LogP: 3.12850
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 9
• Exact Mass: 522.0933712
• Heavy Atom Count: 35
• Complexity: 770

Purity/Quality:

98%min ^*data from raw suppliers

DICHLOROMETHOTREXATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=C(C=C(C=C3Cl)C(=O)NC(CCC(=O)O)C(=O)O)Cl

Technology Process of 3',5'-Dichloromethotrexate; Methotrexate, dichloro-; NSC 145883; NSC 29630

There total 3 articles about 3',5'-Dichloromethotrexate; Methotrexate, dichloro-; NSC 145883; NSC 29630 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: 80.0%

methotrexate disodium salt (7413-34-5,7532-09-4,15475-56-6) → 3',5'-dichloro-methotrexate (528-74-5,88442-77-7)

Guidance literature:

With tert-butylhypochlorite; In acetic acid; at 25 ℃; for 1h;

DOI:10.1021/jo01291a034

Reference yield:

N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid (59-05-2) → 3',5'-dichloromethotrexate (528-74-5,88442-77-7)

Guidance literature:

With chlorine; formamide;

DOI:10.1021/ja01150a041 DOI:10.1021/ja01520a049

Reference yield:

→ 3',5'-dichloro-methotrexate (528-74-5,88442-77-7)

Guidance literature:

eines 36Cl-haltigen Praep.;

DOI:10.1002/jps.2600500418

upstream raw materials:

N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid

methotrexate disodium salt

Refernces

• 1、 Martinelli, Jack E.,Chaykovsky, Michael. "Aromatic Chlorination of p-Aminobenzoic Acid Derivatives. Improved Syntheses of Mono- and Dichloromethotrexate". . p. 527 - 529. Retrieved 2007/10/02.