Conditions | Yield |
---|---|
With hydrogen; nickel In N,N-dimethyl-formamide at 95℃; under 33752.7 Torr; for 3h; Product distribution; Further Variations:; Catalysts; Pressures; Temperatures; Solvents; Catalytic hydrogenation; | 88% |
With sodium amalgam Erhitzen des entstehenden Gemisches der stereoisomeren Hexahydrophthalsaeuren im Vakuum auf 210-220grad; anhydride of/the/ cis-hexahydrophthalic acid; |
(1R,2S)-cyclohexane-1,2-dicarboxylic acid
1,2-Cyclohexanedicarboxylic acid-anhydride
Conditions | Yield |
---|---|
beim Schmelzen; anhydride of/the/ cis-hexahydrophthalic acid; |
Conditions | Yield |
---|---|
With acetic anhydride Dehydration; |
1,2-Cyclohexanedicarboxylic acid-anhydride
Conditions | Yield |
---|---|
at 210 - 220℃; anhydride of/the/ cis-hexahydrophthalic acid; |
1,2-Cyclohexanedicarboxylic acid-anhydride
Conditions | Yield |
---|---|
With acetyl chloride anhydride of/the/ dextrorotatory trans-hexahydrophthalic acid; |
benzene-1,2-dicarboxylic acid
A
phthalic anhydride
B
2-methyl-1-cyclohexanecarboxylic acid
C
1,2-Cyclohexanedicarboxylic acid-anhydride
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; hydrogen In 1,4-dioxane at 219.84℃; under 51680.2 Torr; for 12h; |
Conditions | Yield |
---|---|
With acetic acid for 18h; Reflux; | 100% |
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane 1.) 30 min, 0 deg C, 2.) 1 h, RT; | 99% |
tert-butyl 4-[4-amino-6-(pyrazin-2-ylamino)-2,4'-bipyridin-2'-yl]piperazine-1-carboxylate
1,2-Cyclohexanedicarboxylic acid-anhydride
2-({[2'-[4-(tert-butoxycarbonyl)piperazin-1-yl]-6-(pyrazin-2-ylamino)-2,4'-bipyridin-4-yl]amino}carbonyl)cyclohexanecarboxylic acid
Conditions | Yield |
---|---|
With pyridine; dmap In N,N-dimethyl-formamide at 100℃; for 48h; | 99% |
With pyridine; dmap In N,N-dimethyl-formamide at 100℃; for 48h; | 99% |
1,2-Cyclohexanedicarboxylic acid-anhydride
3,3-diallylhexahydroisobenzofuran-1(3H)-one
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Inert atmosphere; chemoselective reaction; | 99% |
6-methylheptanol
1,2-Cyclohexanedicarboxylic acid-anhydride
diisooctyl cyclohexane-1,2-dicarboxylate
Conditions | Yield |
---|---|
With C9H21NO3S*H2O4S at 160 - 180℃; for 2.5h; Temperature; | 98.8% |
7-methyl-1-octanol
1,2-Cyclohexanedicarboxylic acid-anhydride
1,2-cyclohexane dicarboxylic acid di-isononylester
Conditions | Yield |
---|---|
With acetic anhydride at 180 - 230℃; under 760.051 Torr; for 3h; Temperature; | 98.5% |
at 180 - 200℃; for 2h; Temperature; | 98.7% |
titanium(IV) isopropylate at 250℃; under 3.75038 - 570.057 Torr; for 5h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 9h; | 98% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 18h; | 98% |
2,4-Dimethoxybenzylamine
1,2-Cyclohexanedicarboxylic acid-anhydride
Conditions | Yield |
---|---|
With acetic acid for 4h; Reflux; | 98% |
methanol
1,2-Cyclohexanedicarboxylic acid-anhydride
(1S,2R)-2-(methoxycarbonyl)cyclohexanecarboxylic acid
Conditions | Yield |
---|---|
With N-((1R,2R)-2-(dimethylamino)-1-(4-nitrophenyl)-3-(trityloxy)propyl)-3,5-bis-(trifluoromethyl)benzamide In tert-butyl methyl ether at 20℃; for 60h; Inert atmosphere; enantioselective reaction; | 97% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 9h; | 96% |
Conditions | Yield |
---|---|
With acetic acid for 3h; Reflux; | 96% |
2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid (3-amino-propyl)-amide
1,2-Cyclohexanedicarboxylic acid-anhydride
2-{3-[(2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carbonyl)-amino]-propylcarbamoyl}-cyclohexanecarboxylic acid
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 25℃; for 48h; | 94% |
1,2-Cyclohexanedicarboxylic acid-anhydride
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
C22H34O10
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 9h; | 94% |
With base at 0 - 20℃; for 9h; |
1-(3-(chloromethyl)phenyl)-2-hydroxy-2-methylpropan-1-one
1,2-Cyclohexanedicarboxylic acid-anhydride
C19H24O6
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; | 94% |
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; | 94% |
tryptamine
1,2-Cyclohexanedicarboxylic acid-anhydride
2-(2-(1H-indol-3-yl)ethyl)-octahydro-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With triethylamine In toluene for 36h; Inert atmosphere; Dean-Stark; Reflux; | 94% |
Conditions | Yield |
---|---|
With [Zn(BH4)2(py)] In tetrahydrofuran for 0.8h; Heating; | 93% |
With lithium aluminium tetrahydride | 90% |
With potassium borohydride; magnesium chloride In tetrahydrofuran; toluene at 100℃; for 24h; | 84.3% |
Stage #1: 1,2-Cyclohexanedicarboxylic acid-anhydride With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; Stage #2: With water In tetrahydrofuran | 75% |
With lithium aluminium tetrahydride In tetrahydrofuran 1.) 0 deg C, 1 h, 2.) r. t. overnight; | 55% |
Conditions | Yield |
---|---|
With pyridine for 12h; Heating; | 93% |
Conditions | Yield |
---|---|
With pyridine for 12h; Heating; | 92% |
Conditions | Yield |
---|---|
With pyridine for 12h; Heating; | 92% |
4-aminophenylacetic acid
1,2-Cyclohexanedicarboxylic acid-anhydride
4-(1,3-dioxo-hexahydro-2-isoindolinyl)phenylacetic acid
Conditions | Yield |
---|---|
With acetic acid at 120℃; for 2h; | 91.5% |
Conditions | Yield |
---|---|
With acetic acid at 120℃; for 2h; | 91.5% |
Conditions | Yield |
---|---|
In chloroform at 20℃; for 3h; | 90.9% |
2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid (2-amino-ethyl)-amide
1,2-Cyclohexanedicarboxylic acid-anhydride
2-{2-[(2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrole-3-carbonyl)-amino]-ethylcarbamoyl}-cyclohexanecarboxylic acid
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at 25℃; for 48h; | 90% |
Conditions | Yield |
---|---|
With pyridine for 10h; Heating; | 90% |
With acetic acid at 120℃; for 12h; Reflux; | |
With acetic acid for 4h; Reflux; |
Conditions | Yield |
---|---|
With ammonium acetate for 0.0125h; microwave heating; | 90% |
1,2-Cyclohexanedicarboxylic acid-anhydride
Conditions | Yield |
---|---|
With acetic acid at 140℃; for 3h; | 90% |
1. Introduction of Hexahydrophthalic anhydride
Hexahydrophthalic anhydride, with the CAS registry number 85-42-7, is also known as 1,2-Cyclohexanedicarboxylic acid anhydride, 1,3-Isobenzofurandione, hexahydro-. It belongs to the product categories of Diels-Alder Adducts; Organics. What's more, its systematic name is Hexahydro-2-benzofuran-1,3-dione. Hexahydrophthalic anhydride can be used as coatings, epoxy curing agent, polyester resin, adhesive, plasticizer, intermediate of plasticizers and insect repellents. This chemical should be sealed and stored in a cool, ventilated and dry place. Moreover, it should be protected from moisture, sunburn and fire.
2. Properties of Hexahydrophthalic anhydride
(1)ACD/LogP: 0.762; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.76; (4)ACD/LogD (pH 7.4): 0.76; (5)ACD/BCF (pH 5.5): 2.24; (6)ACD/BCF (pH 7.4): 2.24; (7)ACD/KOC (pH 5.5): 61.91; (8)ACD/KOC (pH 7.4): 61.91; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 43.37 Å2; (13)Index of Refraction: 1.502; (14)Molar Refractivity: 36.813 cm3; (15)Molar Volume: 124.728 cm3; (16)Polarizability: 14.594×10-24cm3; (17)Surface Tension: 42.23 dyne/cm; (18)Density: 1.236 g/cm3; (19)Flash Point: 143.909 °C; (20)Enthalpy of Vaporization: 52.227 kJ/mol; (21)Boiling Point: 283.351 °C at 760 mmHg; (22)Vapour Pressure: 0.003 mmHg at 25°C.
3. Structure Descriptors of Hexahydrophthalic anhydride
(1)SMILES: O=C1OC(=O)C2C1CCCC2
(2)Std. InChI: InChI=1S/C8H10O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h5-6H,1-4H2
(3)Std. InChIKey: MUTGBJKUEZFXGO-UHFFFAOYSA-N
4. Safety Information of Hexahydrophthalic anhydride
Hazard Symbols:Xn
Risk Codes:
R41:Risk of serious damage to the eyes.
R42/43:May cause sensitization by inhalation and skin contact.
Safety Description:
S23:Do not breathe vapour.
S24:Avoid contact with skin.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
5. Preparation of Hexahydrophthalic anhydride
Hexahydrophthalic anhydride can be prepared by cyclohex-1-ene-1,2-dicarboxylic acid anhydride at the temperature of 95 °C. This reaction will need reagent H2 and solvent dimethylformamide with the reaction time of 3 hours. This reaction will also need catalyst Raney-Ni. The yield is about 88%.
6. Uses of Hexahydrophthalic anhydride
Hexahydrophthalic anhydride can be used to produce 2-trichloroacetyl-1-cyclohexanecarboxylic acid at the temperature of 60 °C. It will need reagent dibenzo-18-crown-6 and solvent acetonitrile with the reaction time of 6 hours. The yield is about 81%.
7. Other details of Hexahydrophthalic anhydride
When you are using this chemical, please be cautious about it as the following:
Hexahydrophthalic anhydride has a risk of serious damage to eyes and it may cause sensitisation by inhalation and skin contact. You should not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). When using it, you must avoid contact with skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective gloves and eye/face protection.
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