1469-48-3

Basic information

• Product Name: CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE
• Synonyms: CIS-D-TETRAHYDROPHTHALIMIDE;CIS-4-CYCLOHEXEN-1,2-DICARBOXYLIC ACID IMIDE;CIS-4-CYCLOHEXENE-1,2-DICARBOXYIMIDE;CIS-4-TETRAHYDROPHTHALIMIDE;4-Cyclohexene-1,2-dicarboximide, cis- (8CI);cis-d4-Tetrahydrophthalimide;1,2,3,6-Tetrahydro ;4-CYCLOHEXENE-1,2-CARBOXIMIDE(CIS)
• CAS NO: 1469-48-3
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16
• EINECS: 215-999-0
• Product Categories: Diels-Alder Adducts
• Mol File: 1469-48-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 129-133 °C(lit.)
• Boiling Point: 336.8 °C at 760 mmHg
• Flash Point: 178 °C
• Appearance: Pale yellow or light beige to yellow-brownish or flakes/Powder or Flakes
• Density: 1.228 g/cm³
• Vapor Pressure: 0.00011mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 11.69±0.20(Predicted)
• BRN: 82338
• CAS DataBase Reference: CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE(1469-48-3)
• EPA Substance Registry System: CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE(1469-48-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21
• Safety Statements: 7-36/37/39-24/25
• WGK Germany: 3
• RTECS: GW4635000
• Hazardous Substances Data: 1469-48-3(Hazardous Substances Data)

Usage

Chemical Properties

pale yellow or light beige to yellow-brownish

Uses

cis-Tetrahydrophthalimide is an intermediate to synthesize cis-Captafol (C175740), which was used as a fungicide.

InChI:InChI=1/C8H9NO2/c10-7-5-3-1-2-4-6(5)8(11)9-7/h1-2,5-6H,3-4H2,(H,9,10,11)/t5-,6+

Upstream product

• 136918-14-4 phthalimide 
• 935-79-5 cis-1,2,3,6-tetrahydrophthalic anhydride 

Downstream Products

• 14599-59-8 captan 
• 100060-32-0 N,N-(cis-cyclohex-4-ene-1,2-dicarbonyl)-β-alanine-nitrile 
• 2555-11-5 (+/-)-cis-octahydro-isoindol-1-one 
• 141340-71-8 N-benzyloxymethyl-cis-1,2,3,6-tetrahydrophthalimide 
• 66050-03-1 cis-2-benzyl-1,3,3a,4,7,7a-hexahydro-1,3-isoindoledione 
• 145159-68-8 adipaldehyde-3,4-dicarboximide bis(phenylhydrazone) 
• 145159-69-9 adipaldehyde-3,4-dicarboximide bis(2-chlorophenylhydrazone) 
• 2144-87-8 (cis)-2,3,3a,4,7,7a-hexahydro-1H-isoindole 
• 7506-66-3 cis-hexahydrophthalimide 
• 180790-20-9 (1R,6S)-6-Methanesulfonylaminocarbonyl-cyclohex-3-enecarboxylic acid isopropyl ester 
• 180790-21-0 (1R,2S)-2-Methanesulfonylaminocarbonyl-cyclohexanecarboxylic acid isopropyl ester 

Relevant articles and documents

Photo decomposition of captan and difolatan

-

An expedient and convenient approach for one-pot synthesis of 1H-isoindole-1,3(2H)-diones

An easy and expedient method for the one-pot synthesis of 1H-isoindole-1,3(2H)-diones has been developed by the reaction of the corresponding cyclic anhydrides with guanidinium chloride as a nitrogen source in the presence of FeCl3 as a catalyst under mild reaction conditions.

Nonreductive enantioselective ring opening of N-(methylsulfonyl)dicarboximides with diisopropoxytitanium α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5- dimethanolate

The bicyclic and tricyclic meso-N-(methylsulfonyl)dicarboximides 1a-f are converted enantioselectively to isopropyl [(sulfonamido)carbonyl]-carboxylates 2a-f by diisopropoxytitanium TADDOLate (75-92% yield; see Scheme 3). The enantiomer ratios of the products are between 86:14 and 97:3, and recrystallization from CH2Cl2/hexane leads to enantiomerically pure sulfonamido esters 2 (Scheme 3). The enantioselectivity shows a linear relationship with the enantiomer excess of the TADDOL employed (Fig. 3). Reduction of the ester and carboxamide groups (LiAlH4) and additional reductive cleavage of the sulfonamido group (Red-Al) in the products 2 of imide-ring opening gives hydroxy-sulfonamides 3 and amino alcohols 4, respectively (Scheme 4). The absolute configuration of the sulfonamido esters 2 is determined by chemical correlation (with 2a, b; Scheme 6), by the X-ray analysis of the camphanate of 3e (Fig. I), and by comparative 19F-NMR analysis of the Mosher esters of the hydroxy-sulfonamides 3 (Table I). A general proposal for the assignment of the absolute configuration of primary alcohols and amines of Formula HXCH2CHR1R2, X = O, NH, is suggested (see 11 in Table I). It follows from the assignment of configuration of 2 that the Re carbonyl group of the original imide 1 is converted to an isopropyl ester group. This result is compatible with a rule previously put forward for the stereochemical course of reactions involving titanium TADDOLate activated chelating electrophiles (12 in Scheme 7). A tentative mechanistic model is proposed (13 and 14 in Scheme 7).