2-Chloroethylamine

Base Information

• Chemical Name: 2-Chloroethylamine
• CAS No.: 689-98-5
• Molecular Formula: C2H6 Cl N
• Molecular Weight: 79.5293
• Hs Code.: 2921199090
• UNII: P7YLY3O329
• DSSTox Substance ID: DTXSID10218977
• Nikkaji Number: J25.725G
• Wikidata: Q27286339
• ChEMBL ID: CHEMBL1190279
• Mol file: 689-98-5.mol

Synonyms:2-chloroethylamine;2-chloroethylamine hydrochloride;2-chloroethylamine monohydrochloride;ethanamine, 2-chloro-, hydrochloride (1:1)

Chemical Property of 2-Chloroethylamine

Chemical Property:

• Melting Point: 146-148 °C
• Refractive Index: 1.4202 (estimate)
• Boiling Point: 90.19°C (rough estimate)
• PKA: 8.25±0.10(Predicted)
• PSA: 26.02000
• Density: 0.9313 (rough estimate)
• LogP: 0.88420
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 79.0188769
• Heavy Atom Count: 4
• Complexity: 10

Purity/Quality:

99% ^*data from raw suppliers

2-chloroethanamine >95% ^*data from reagent suppliers

Safty Information:

• Safety Statements: Unstable and may polymerize explosively. When heated to decompo"> − and NOx. See also AMINES and CHLORIDES." target="_blank">Unstable and may polymerize explosively. When heated to decompo

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCl)N
• General Description: 2-Chloroethylamine (2-Chloroethanamine) is a substituted ethylamine derivative used in the synthesis of mitomycin C and porfiromycin analogues, where it serves as a functional group at position 7 to modulate antitumor activity. In this study, it was among the tested compounds, but the abstract highlights that other analogues, such as mercaptoethylamine and fluoroethylamine, demonstrated superior potency and reduced leukopenic effects compared to mitomycin C. While 2-chloroethylamine contributed to the structural exploration of these derivatives, the findings suggest that its antitumor performance was less notable than some of the other modified ethylamines examined. The research underscores the importance of specific substituents in optimizing therapeutic efficacy while minimizing toxicity.

Technology Process of 2-Chloroethylamine

There total 8 articles about 2-Chloroethylamine 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:

hydrogenchloride (7647-01-0,15364-23-5) + N-(2-Hydroxyethyl)phthalimide (3891-07-4) → benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + chloroethylamine (689-98-5)

Guidance literature:

at 180 - 200 ℃;

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + N-(2-chlroethyl)phthalimide (6270-06-0) → benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + chloroethylamine (689-98-5)

Guidance literature:

at 180 ℃;

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + N-[2-(2,4-dimethyl-phenoxy)-ethyl]-phthalimide (690648-63-6) + acetic acid (64-19-7,77671-22-8) → 2,4-Xylenol (105-67-9) + chloroethylamine (689-98-5)

Guidance literature:

at 160 ℃;

upstream raw materials:

Dechloroethylcyclophosphamide

ilfosfamide

(2-chloro-ethyl)-phosphoramidic acid mono-(3-amino-propyl) ester

(2-chloro-ethyl)-phosphoramidic acid mono-[3-(2-chloro-ethylamino)-propyl] ester

Downstream raw materials:

4-(2-AMINOETHYL)MORPHOLINE

ethyl N-(2-chloroethyl)carbamate

N,N-dibenzyl-2-chloroethanamine

N-(2-chloro-ethyl)-benzamide

Refernces

Mitomycin C and porfiromycin analogues with substituted ethylamines at position 7

10.1021/jm00355a004

The research focuses on the development and evaluation of analogues of mitomycin C and porfiromycin with substituted ethylamines at position 7. These analogues were synthesized and tested for their antitumor activities against various mouse tumors, including P-388 leukemia, L-1210 leukemia, and B-16 melanoma. The study aimed to identify compounds that are at least as potent as mitomycin C but with reduced leukopenic effects. Key chemicals involved in the research include mitomycin C, porfiromycin, and a variety of ethylamine derivatives such as 2-phenylethylamine, 2-chloroethylamine, 2-hydroxyethylamine, and others with different functional groups at the 2-position of the ethylamine. The analogues were prepared using mitomycin A or N-methyl-mitomycin A as starting materials and various amines for substitution. The synthesized compounds were then purified, characterized, and tested for their biological activities. The results showed that some analogues exhibited better antitumor activity and reduced leukopenia compared to mitomycin C, with notable examples being the mercaptoethylamine analogue (8) and the fluoroethylamine analogue (4). The study also explored structure-activity relationships, finding a limited correlation between the potency of the analogues and their hydrophilicity.