Name: Hexahydrophthalic anhydride
SKU: 85-42-7

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Basic Information

Molecular Structure:
CAS No.:	85-42-7
Name:	Hexahydrophthalic anhydride
Article Data:	25

Formula:	C₈H₁₀O₃
Molecular Weight:	154.166
Synonyms:	1,2-Cyclohexanedicarboxylicanhydride (6CI,8CI);1,2-Cyclohexanedicarboxylic acid anhydride;Araldite HT904;Araldite HT 907;Araldite HY 907;Araldite HY 925;Araldite Hardener HY925;Cyclohexanedicarboxylic anhydride;EP 400B;Epilox H 11-01;HHPA;HY 925;Hexahydro-1,3-isobenzofurandione;Hexahydrophthalic acid anhydride;1,3-Isobenzofurandione, hexahydro-;Lekutherm Hardener H;MH 700E;NSC 8622;RikacidHH;Rikacid HH-A;Rikacid HHPA;Rikacid MH 700E;Rutadur AG;Rutapox HX;
EINECS:	201-604-9
Density:	1.236 g/cm³
Melting Point:	32-34 °C(lit.)
Boiling Point:	283.351 °C at 760 mmHg
Flash Point:	143.909 °C
Solubility:	Miscible with benzene, toluene, acetone, carbon tetrachloride, chloroform, ethanol and ethyl acetate; slightly soluble in petroleum ether
Appearance:	Colorless and clear viscous liquid
Hazard Symbols:	Xn
Risk Codes:	41-42/43
Safety:	23-24-26-37/39
Transport Information:	UN 3335
PSA:	43.37000
LogP:	0.87620

Synthetic route

: 2426-02-0
3,4,5,6-Tetrahydrophthalic anhydride

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

Conditions

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;

: 610-09-3
(1R,2S)-cyclohexane-1,2-dicarboxylic acid

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

Conditions

Conditions	Yield
beim Schmelzen; anhydride of/the/ cis-hexahydrophthalic acid;

: 1687-30-5
cyclohexane-1,2-dicarboxylic acid

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

Conditions

Conditions	Yield
With acetic anhydride Dehydration;

anhydride of/the/ inactive trans-hexahydrophthalic acid: anhydride of/the/ inactive trans-hexahydrophthalic acid

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

Conditions

Conditions	Yield
at 210 - 220℃; anhydride of/the/ cis-hexahydrophthalic acid;

dextrorotatory trans-hexahydrophthalic acid: dextrorotatory trans-hexahydrophthalic acid

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

Conditions

Conditions	Yield
With acetyl chloride anhydride of/the/ dextrorotatory trans-hexahydrophthalic acid;

: 88-99-3
benzene-1,2-dicarboxylic acid

A: 85-44-9
phthalic anhydride

B: 7077-04-5, 10479-51-3, 56586-13-1
2-methyl-1-cyclohexanecarboxylic acid

C: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In 1,4-dioxane at 219.84℃; under 51680.2 Torr; for 12h;

...Expand

: 2393-23-9
4-methoxy-benzylamine

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

: 2-(4-methoxybenzyl)hexahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With acetic acid for 18h; Reflux;	100%

: 7005-72-3
4-chlorodiphenyl ether

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

: 2-[4-(4-Chloro-phenoxy)-benzoyl]-cyclohexanecarboxylic acid

Conditions

Conditions	Yield
With aluminium trichloride In dichloromethane 1.) 30 min, 0 deg C, 2.) 1 h, RT;	99%

: 1370453-11-4
tert-butyl 4-[4-amino-6-(pyrazin-2-ylamino)-2,4'-bipyridin-2'-yl]piperazine-1-carboxylate

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

: 1370456-54-4
2-({[2'-[4-(tert-butoxycarbonyl)piperazin-1-yl]-6-(pyrazin-2-ylamino)-2,4'-bipyridin-4-yl]amino}carbonyl)cyclohexanecarboxylic acid

Conditions

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%

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

: potassium trifluoro(prop-1-en-2-yl)borate

: 1418757-97-7
3,3-diallylhexahydroisobenzofuran-1(3H)-one

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Inert atmosphere; chemoselective reaction;	99%

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Specification

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: Harmful 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%.

1,3-Isobenzofurandione, hexahydro- can be prepared by cyclohex-1-ene-1,2-dicarboxylic acid anhydride at the temperature of 95 °C

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%.

1,3-Isobenzofurandione, hexahydro- can be used to produce 2-trichloroacetyl-1-cyclohexanecarboxylic acid at the temperature of 60 °C

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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Specification