14475-60-6

Basic information

• Product Name: N-methylbutane-1,4-diamine
• Synonyms: N-methylbutane-1,4-diamine;N-Methylputrescine;4-Methylamino-1-butanamine
• CAS NO: 14475-60-6
• Molecular Formula: C₅H₁₄N₂
• Molecular Weight: 102.18
• Mol File: 14475-60-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-methylbutane-1,4-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-methylbutane-1,4-diamine(14475-60-6)
• EPA Substance Registry System: N-methylbutane-1,4-diamine(14475-60-6)

Safety Data

• Hazardous Substances Data: 14475-60-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 6651, 1988 DOI: 10.1016/S0040-4039(00)82421-1

Upstream product

• 5394-18-3 2-(4-bromobutyl)isoindoline-1,3-dione 
• 103-67-3 benzyl-methyl-amine 
• 50-00-0 formaldehyd 
• 110-60-1 1,4-diaminobutane 
• 18807-73-3 N-benzyloxycarbonyl-1,4-butanediamine hydrochloride 
• 7544-87-8 2-Methylimino-pyrrolidin-hydrochlorid 
• 31058-09-0 4-methylamino-butyronitrile 

Downstream Products

• 120-94-5 1-Methylpyrrolidine 
• 1384353-29-0 C₃₃H₄₅N₃O₄ 

Relevant articles and documents

Enzymatic aminopropylation of certain secondary amines

Two unusual aminopropyl acceptors found in a survey of putrescine binding sites of mammalian spermidine synthase, N-methylputrescine (I) and 4-aminomethylpiperidine (II), were examined for their aminopropyl derivatives. Studies under In vitro incubation conditions suggested that the aminopropyl derivatives of the secondary amine of I and II, N4-methylspermidine (Is) and 1-N-(3-aminopropyl)-4-aminomethylpiperidine (IIs), and of the primary amine of I and II, N8-methy]spermidine (Ip) and 4-[N-(3-aminopropyl)aminomethyl]piperidine (IIp), respectively, were biosynthesized by rat spermidine synthase. Studies on the cell culture system of cultured rat hepatoma (HTC) cells treated with α-difluoromethylornithine, an ornithine decarboxylase inhibitor, clearly showed the presence of Is and Ip when I was administered, and IIs and IIp when II was administered, with no detection of putrescine or spermidine. These results suggested that mammalian spermidine synthase can transfer the anunop}opyl moiety of decarboxylated S-adenosylmethionine to certain secondary amines in living cells.

CONVENIENT ROUTES TO ALKYL-SUBSTITUTED POLYAMINES

Alkyl-substituted polyamines, valuable for biological studies, can be prepared from N-phenylmethoxycarbonyl-1,4-diaminobutane (1b) and N-phenylmethoxycarbonyl-4-azidobutanamine (4a) by utilising the following reactions: (i) reduction of the phenylmethoxycarbonyl group to methyl by borane and (ii) combination of the Staudinger and aza-Wittig reactions .