1088-80-8

Basic information

• Product Name: Metamelfalan
• Synonyms: Metamelfalan;3-[Bis(2-chloroethyl)amino]-L-phenylalanine;3-[m-[Bis(2-chloroethyl)amino]phenyl]-L-alanine;L-m-Sarcolysin;m-L-SL;2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid;2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propionic acid;2-azanyl-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid
• CAS NO: 1088-80-8
• Molecular Formula: C₁₃H₁₈Cl₂N₂O₂
• Molecular Weight: 305.23
• Mol File: 1088-80-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 479.7°Cat760mmHg
• Flash Point: 243.9°C
• Appearance: /
• Density: 1.3587 (rough estimate)
• Vapor Pressure: 5.2E-10mmHg at 25°C
• Refractive Index: 1.6070 (estimate)
• CAS DataBase Reference: Metamelfalan(CAS DataBase Reference)
• NIST Chemistry Reference: Metamelfalan(1088-80-8)
• EPA Substance Registry System: Metamelfalan(1088-80-8)

Safety Data

• Hazardous Substances Data: 1088-80-8(Hazardous Substances Data)

Usage

Uses

Metamelfalan is an impurity of Melphalan (M216900). Melphalan (M216900) is an antineoplastic.

InChI:InChI=1/C13H18Cl2N2O2/c14-4-6-17(7-5-15)11-3-1-2-10(8-11)9-12(16)13(18)19/h1-3,8,12H,4-7,9,16H2,(H,18,19)/t12-/m0/s1

Upstream product

• 174019-19-3 L-N-acetyl-(m-bis-hydroxyethylamino)-phenylalanine methyl ester 
• 173558-68-4 L-N-acetyl-3-aminophenyl-alanine methyl ester 
• 621-44-3 3-nitro-L-tyrosine 
• 173558-69-5 (S)-2-Acetylamino-3-{3-[bis-(2-chloro-ethyl)-amino]-phenyl}-propionic acid methyl ester 

Downstream Products

• 38232-20-1 (S)-2-{(S)-3-{3-[Bis-(2-chloro-ethyl)-amino]-phenyl}-2-[((S)-pyrrolidine-2-carbonyl)-amino]-propionylamino}-pentanoic acid 
• 173558-64-0 N-trifluoroacetyl-L-propyl-L-m-sarcolysil-L-norvaline ethyl ester 
• 173558-63-9 trifluoroacetyl-L-propyl-m--L-phenylalanine 

Relevant articles and documents

Acidic coupling and aminolytic TFA cleavage approaches in a new synthesis of an L-m-sarcolysin containing antitumor tripeptide ester

L-propyl-L-m-[bis(chloroethyl)amino]-phenylalanyl-L-norvaline ethyl ester hydrochloride, 4 (and its 3H and 14C doubly-labeled version) was synthesized starting with reacting unprotected L-m-sarcolysin, 1, with TFA-Pro-Cl in an acidic system to yield TFA-Pro-L-m-sarcolysin, 2, which was transformed to the TFA-tripeptide ethyl ester, 3. Selective aminolytic cleavage of the TFA group with butylamine in abs. ethanol, followed by neutralization with HCl gave 4.