10513-98-1

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione,2,2'-(1,6-hexanediyl)bis-
• Synonyms: Phthalimide,N,N'-hexamethylenedi- (6CI,7CI,8CI); 1,6-Bis(phthalimido)hexane;N,N'-Hexamethylenebisphthalimide; N,N'-Hexamethylenediphthalimide; NSC 76816
• CAS NO: 10513-98-1
• Molecular Formula: C22H20 N2 O4
• Molecular Weight: 376.412
• Mol File: 10513-98-1.mol

Chemical Properties

• Boiling Point: 552.7°Cat760mmHg
• Flash Point: 247.2°C
• Density: 1.321g/cm³
• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione,2,2'-(1,6-hexanediyl)bis-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione,2,2'-(1,6-hexanediyl)bis-(10513-98-1)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione,2,2'-(1,6-hexanediyl)bis-(10513-98-1)

Safety Data

• Hazardous Substances Data: 10513-98-1(Hazardous Substances Data)

Usage

Molecular Structure

1H-Isoindole-1,3(2H)-dione,2,2'-(1,6-hexanediyl)bisconsists of a central isoindole-1,3-dione core and two 1,6-hexanediyl chains attached to each of the nitrogen atoms.

Physical Properties

It is a bright yellow to orange crystalline solid.

Uses

Mainly used in the production of dyes and pigments. Also utilized in the synthesis of pharmaceuticals, plastics, and organic compounds.

Handling Precautions

It may have adverse health effects if not managed properly, so it is important to handle 1H-Isoindole-1,3(2H)-dione,2,2'-(1,6-hexanediyl)bis- with care.

Upstream product

• 629-03-8 1 ,6-dibromohexane 
• 1074-82-4 potassium phtalimide 
• 124-09-4 1,6-Hexanediamine 
• 85-44-9 phthalic anhydride 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 347885-68-1 4-bromo-1-tosylpiperidine 
• 136918-14-4 phthalimide 

Downstream Products

• 29237-59-0 hexamethylenediphthalamidoethylenediamine 
• 124-09-4 1,6-Hexanediamine 

Relevant articles and documents

New arylpiperazines with flexible versus partly constrained linker as serotonin 5-HT1A/5-HT7 receptor ligands

A series of new long-chain arylpiperazine (LCAP) derivatives with flexible and partly constrained alkyl linker were synthesized and investigated in vitro as potential serotonin 5-HT1A and 5-HT7 receptor ligands. The compounds were prepared by a two-step procedure using naphthalimide and 2H-1,3-benzoxazine-2,4(3H)-dione as imides, and 1-(2-methoxyphenyl)piperazine (o-OMe-PhP) and 1,2,3,4-tetrahydroisoquinoline (THIQ) as amine pharmacophores. Modifications of the spacer structure included introduction of flexible penta- and hexamethylene chains as well as partly constrained m- and p-xylyl moieties. In general, the new compounds were more active at the 5-HT1A than at the 5-HT7 receptor, and the o-OMe-PhP derivatives displayed higher affinities than their respective THIQ analogs. The spacer modifications had little effect on the observed in vitro activities. Within the o-OMe-PhP series, except for a small binding reduction for ligands containing the m-xylyl moiety, there was no substantial change in the compounds' potency at both receptors, while for the THIQ derivatives a clear structure-activity relationship was visible only for the interaction of the compounds with the 5-HT7 receptor, which strongly favored flexible analogs. New LCAP derivatives with flexible and partly constrained alkyl linker were tested as potential serotonin 5-HT1A and 5-HT7 receptor ligands. The spacer structure was modified by introduction of flexible penta- and hexamethylene chains and partly constrained m- and p-xylyl moieties. The new compounds were more active at the 5-HT1A than at the 5-HT7 receptor. o-OMe-PhP derivatives displayed higher affinities than their respective THIQ analogs. The spacer modifications had little effect on the observed in vitro activities. Copyright

Nickel-Catalyzed reductive cross-Coupling of unactivated alkyl halides

A Ni-catalyzed reductive approach to the cross-coupling of two unactivated alkyl halides has been successfully developed. The reaction works efficiently for primary and secondary halides, with at least one being bromide. The mild reaction conditions allow for excellent functional group tolerance and provide the C(sp3)-C(sp3) coupling products in moderate to excellent yields.

Thalidomide analogs from diamines: Synthesis and evaluation as inhibitors of TNF-α production

Fourteen thalidomide analogs bearing two phthalimido units were prepared in high yields (83-94%) by condensation of different diamines with phthalic or 3-nitrophthalic anhydride. An in vitro investigation of the compounds as inhibitors of the TNF-α production was performed. The inhibition was higher for compounds bearing amino and nitro groups and was modulated by increasing the size of the spacers between the phthalimide groups.

Photoresponsive Crown Ethers. Part 14. Photoregulated Crown-Metal Complexation by Competitive Intramolecular Tail(Ammonium)-biting

New photoresponsive crown ethers (1H+) having a crown ether ring and an ammoniumalkyl +-(CH2)n, n = 4,6,10> group attached to the two sides of an azobenzene have been synthesized.These photoresponsive 'tail-biting' crown ethers have been designed so that intramolecular 'biting' of the ammonium group to the crown can only occur upon photoisomerisation to the cis-forms.In the thermal cis-trans isomerisation, the first-order rate constants for cis-(1H+) were smaller by 1.6 - 2.2 -fold than those for (1) (the analogous free amines).Moreover, this rate increased with increasing added K+ concentration.This suggests that the ammonium tail is intramolecularly bound to the crown ether ring in cis-(1H+).This intramolecular 'biting' is further reflected in the relative affinities of (1H+) for alkali-metal cations.The affinities were markedly reduced by u.v.-light irradiation and in particular, cis-(1H+)(n=6) and cis-(1H+)(n=10) showed almost no metal-binding ability.This marked difference in the metal-binding ability was used to generate the light-controlled systems for the passive or active ion-transport of ions across a liquid membrane.