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

Description

CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE is an organic compound that serves as an intermediate in the synthesis of various chemical products. It is characterized by its pale yellow or light beige to yellow-brownish color and plays a significant role in the chemical industry due to its ability to be transformed into useful compounds.

Uses

Used in Chemical Synthesis:
CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE is used as an intermediate in the chemical synthesis process for creating cis-Captafol (C175740), which is a fungicide. Its role in this application is crucial, as it aids in the development of a product that helps protect crops from fungal infections, ensuring better agricultural yields.
Used in Pharmaceutical Industry:
CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE is also used as a building block in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable component in the development of new drugs, contributing to advancements in the medical field.
Used in Pesticide Industry:
In the pesticide industry, CIS-1,2,3,6-TETRAHYDROPHTHALIMIDE is used as a key component in the production of cis-Captafol, a fungicide that helps control fungal diseases in crops. Its application in this industry is essential for maintaining the health and productivity of agricultural plants, which in turn supports the global food supply.

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

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

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 
• 180979-42-4 ((1R,2S)-2-Aminomethyl-cyclohexyl)-methanol 
• 180979-41-3 [(1R,6S)-6-(aminomethyl)cyclohex-3-en-1-yl]methanol 
• 180790-26-5 N-((1S,6R)-6-Hydroxymethyl-cyclohex-3-enylmethyl)-methanesulfonamide 
• 180790-21-0 (1R,2S)-2-Methanesulfonylaminocarbonyl-cyclohexanecarboxylic acid isopropyl ester 
• 180790-20-9 (1R,6S)-6-Methanesulfonylaminocarbonyl-cyclohex-3-enecarboxylic 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).