2-chloro-N-(2-chloroethyl)-N-methylethanamine;hydron;chloride

Base Information

• Chemical Name: 2-chloro-N-(2-chloroethyl)-N-methylethanamine;hydron;chloride
• CAS No.: 55-86-7
• Molecular Formula: C5H11Cl2N . Cl H
• Molecular Weight: 192.516
• Hs Code.: 2921196190
• Mol file: 55-86-7.mol

Synonyms:SCHEMBL15532070;AKOS015833252

Chemical Property of 2-chloro-N-(2-chloroethyl)-N-methylethanamine;hydron;chloride

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 108-111 °C(lit.)
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 110.3°C at 760 mmHg
• PKA: pKa 6.43 (Uncertain)
• Flash Point: 20.5°C
• PSA: 3.24000
• Density: 1.106g/cm³
• LogP: 2.19780
• Storage Temp.: −20°C
• Sensitive.: Hygroscopic
• Solubility.: H2O: very soluble
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 191.003532
• Heavy Atom Count: 9
• Complexity: 43.7

Purity/Quality:

98% ^*data from raw suppliers

Mechlorethamine hydrochloride 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 45-46-28-34-42/43-27/28-61
• Safety Statements: 53-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [H+].CN(CCCl)CCCl.[Cl-]
• Description: Nitrogen mustard (HN) was developed in three formulations: HN-1, HN-2, and HN-3. HN-1 was the first to be produced in the late 1920s and early 1930s. Originally, it was developed as a pharmaceutical and used to remove warts before it became a military agent. Agent H-2 was developed as a military agent and became a pharmaceutical. HN-3 was designed as a military mustard agent and is the only one that remains in military use. Therefore, this section will only cover the characteristics of HN-3 mustard agent. HN-3 is colorless to pale yellow with a butter-almond odor. The chemical formula for nitrogen mustard agent HN-3 is N(CH2CH2Cl)3. It will otherwise be ineffective against stopping the damage to the body.
• Uses: xanthine oxidase/dehydrogenase inhibitor It has been used as an antineoplastic. A nitrogen mustard prepared by action of thionyl chloride on 2,2’(methylimino)- diethanol in trichloroethylene. Mechlorethamine hydrochloride USP (Mustargen)is used to treat Hodgkin’s disease; non-Hodgkin’s lymphomas; lymphosarcoma; cancer of breast, ovary, lung; neoplastic effusion.
• Indications: Mechlorethamine (Mustargen) is a cytotoxic alkylating agent. Topical application of freshly prepared aqueous solutions are used in patients with early stages of cutaneous T-cell lymphoma. A major disadvantage to the use of this drug is the rapid induction of allergic contact dermatitis in some patients. Mechlorethamine (nitrogen mustard; Mustargen), a derivative of the war gas sulfur mustard, is considered to be the first modern anticancer drug. In the early 1940s it was discovered to be effective in the treatment of human lymphomas.
• Biological Functions: Mechlorethamine is still used in regimens for cancers of the blood (e.g., Hodgkin's disease, chronic myelocytic, or chronic lymphocytic leukemia); fortunately, however, safer and still highly potent antineoplastic agents are now available.
• Clinical Use: Mechlorethamine is the only aliphatic nitrogen mustard currently on the U.S. market. Its use is limited by extremely high reactivity, which leads to rapid and nonspecific alkylation of cellular nucleophiles and excessive toxicity. It is a severe vesicant, and if accidental skin contact occurs, the drug must be inactivated with 2% sodium thiosulfate (Na2S2O3) solution.

Technology Process of 2-chloro-N-(2-chloroethyl)-N-methylethanamine;hydron;chloride

There total 5 articles about 2-chloro-N-(2-chloroethyl)-N-methylethanamine;hydron;chloride 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: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + bis-(2-chloroethyl)amine hydrochloride (821-48-7) → mechlorethamine hydrochloride (55-86-7)

Guidance literature:

With formic acid; at 100 - 120 ℃; for 3.33333h;

Reference yield: 99.0%

2-[2-hydroxyethyl(methyl)amino]ethanol hydrochloride (54060-15-0) → mechlorethamine hydrochloride (55-86-7)

Guidance literature:

With thionyl chloride; In chloroform; for 2h; Heating;

DOI:10.1021/jm000050e

Reference yield: 99.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + formic acid (64-18-6) + bis-(2-chloroethyl)amine hydrochloride (821-48-7) → mechlorethamine hydrochloride (55-86-7)

Guidance literature:

In water; at 100 ℃; for 3h; Reflux;

DOI:10.1039/c3dt52037d

upstream raw materials:

formaldehyd

bis-(2-chloroethyl)amine hydrochloride

N-Methyldiethanolamine

2-[2-hydroxyethyl(methyl)amino]ethanol hydrochloride

Downstream raw materials:

4-ethanesulfonyl-4-(4-methoxy-phenyl)-1-methyl-piperidine

4-(4-chloro-2-fluorophenyl)-4-cyano-1-methylpiperidine

2-chloroethanal

formaldehyd

Refernces

• 1、 Kushakova,Chernobroviy,Kuznetsov,Garabadgiu. "Preparation of 1-amino-4-methylpiperazine". . p. 1546 - 1549. Retrieved 2004.
• 2、 Choi, Jong-Hoo,Schloerer, Nils E.,Berger, Josefine,Prechtl, Martin H. G.. "Synthesis and characterisation of ruthenium dihydrogen complexes and their reactivity towards B-H bonds". . p. 290 - 299. Retrieved 2014.
• 3、 -. "TIN COMPOUND, TIN PRECURSOR COMPOUND FOR FORMING A TIN-CONTAINING LAYER, AND METHODS OF FORMING A THIN LAYER USING THE SAME". Paragraph 0034. . Retrieved 2020/08/05.
• 4、 Brune, Veronika,Hegemann, Corinna,Mathur, Sanjay. "Molecular Routes to Two-Dimensional Metal Dichalcogenides MX2 (M = Mo, W; X = S, Se)". . p. 9922 - 9934. Retrieved 2019/08/26.