cis-Cyclohexane-1,2-dicarboxylic anhydride supplier

Name
CIS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE
EINECS 236-086-3
CAS No. 13149-00-3
Article Data24
CAS DataBase
Density 1.236 g/cm³
Solubility
Melting Point 32-34 °C(lit.)
Formula C₈H₁₀O₃
Boiling Point 283.351 °C at 760 mmHg
Molecular Weight 154.166
Flash Point 143.909 °C
Transport Information
Appearance white to almost white cryst. low melting solid
Safety 23-24-26-37/39
Risk Codes 41-42/43
Molecular Structure
Hazard Symbols Xn
Synonyms 1,2-Cyclohexanedicarboxylicanhydride, cis- (8CI);1,3-Isobenzofurandione, hexahydro-, cis-;cis-1,2-Cyclohexanedicarboxylic anhydride;cis-Cyclohexane-1,2-dicarboxylicacid anhydride;cis-Hexahydrophthalic anhydride;rel-(3aR,7aS)-Hexahydroisobenzofuran-1,3-dione;
PSA 43.37000
LogP 0.87620

Synthetic route

: 935-79-5
cis-1,2,3,6-tetrahydrophthalic anhydride

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In 1,4-dioxane for 24h;	96%
With acetic acid; platinum Hydrogenation;
With ethyl acetate; platinum Hydrogenation;
With silica gel; nickel at 130℃; Hydrogenation;
With nickel; ethyl acetate Hydrogenation;

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

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

Conditions

Conditions	Yield
With Isopropenyl acetate; Montmorillonite KSF for 0.0666667h; Irradiation;	94%
With Isopropenyl acetate; Montmorillonite KSF for 0.0666667h; Product distribution; Irradiation; var. microwave lenghts, var. reaction time, other carboxylic diacids;	94%
With 4-methyl-morpholine; methyl chloroformate In tetrahydrofuran at 20℃; for 0.25h;
With 2,6-bis[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenylboronic acid In propiononitrile	99 %Spectr.

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

: 2305-32-0
trans-1,2-cyclohexanedicarboxylic acid

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

Conditions

Conditions	Yield
With acetyl chloride

: 14166-21-3
(+/-)-trans-1,2-cyclohexanedicarboxylic anhydride

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

Conditions

Conditions	Yield
at 200℃;

: 2305-32-0
trans-1,2-cyclohexanedicarboxylic acid

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

Conditions

Conditions	Yield
With trifluoroacetic anhydride

: 46022-05-3
(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

Conditions

Conditions	Yield
With 2,6-bis[(2,2,6,6-tetramethylpiperidin-1-yl)methyl]phenylboronic acid In propiononitrile stereoselective reaction;	89 %Spectr.

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 6939-71-5
hexahydro-isobenzo[c]furan-1-one

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	100%
With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 5h;	91%
With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 2h;	85%

: 67-56-1
methanol

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 1687-29-2
dimethyl cis-1,2-cyclohexanedicarboxylate

Conditions

Conditions	Yield
With sulfuric acid at 20 - 60℃;	100%
With sulfuric acid
With thionyl chloride for 4h; Inert atmosphere; Reflux;

: 67-56-1
methanol

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 88335-92-6
(1S,2R)-2-(methoxycarbonyl)cyclohexanecarboxylic acid

Conditions

Conditions	Yield
at 100℃; for 1h;	100%
With polymer-supported Cinchona-based sulfonamide In mBTE at 20℃; for 3h; optical yield given as %ee; enantioselective reaction;	99%
Stage #1: methanol; 1,2-cis-cyclohexanedicarboxylic anhydride; C28H31N3O3S In di-isopropyl ether at -20℃; for 4h; Stage #2: With hydrogenchloride In di-isopropyl ether; water Product distribution / selectivity;	99%

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 6294-84-4, 92116-89-7, 92116-90-0
cis-1-carboxy-2-(aminocarboxyl)-2-cyclohexane

Conditions

Conditions	Yield
With ammonium hydroxide at 25℃;	100%
With ammonium hydroxide	88%
With ammonia In water
With ammonium hydroxide

: 108-91-8
cyclohexylamine

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 2-cyclohexylcarbamoyl-cyclohexanecarboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclohexylamine; 1,2-cis-cyclohexanedicarboxylic anhydride In N,N-dimethyl acetamide at 20℃; for 24h; Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h;	100%

: 75-64-9
tert-butylamine

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 2-tert-butylcarbamoyl-cyclohexanecarboxylic acid

Conditions

Conditions	Yield
Stage #1: tert-butylamine; 1,2-cis-cyclohexanedicarboxylic anhydride In N,N-dimethyl acetamide at 20℃; for 24h; Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h;	100%

: 67-56-1
methanol

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 2484-60-8, 2778-62-3, 7719-08-6, 52782-07-7, 88335-91-5, 88335-92-6, 96894-64-3, 111955-05-6
cis-2-methoxycarbonylcyclohexane-1-carboxylic acid

Conditions

Conditions	Yield
at 100℃; for 1h;	100%
With 1,4-diaza-bicyclo[2.2.2]octane
With magnetite nanoparticles In tert-butyl methyl ether at 20℃; for 18h; Inert atmosphere;
Reflux;
Heating;

: 67-56-1
methanol

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 88335-91-5
cyclohexane-1,2-dicarboxylic acid monomethyl ester

Conditions

Conditions	Yield
With 1-((1R,2R)-2-(dimethylamino)cyclohexyl)-3-phenylthiourea In diethyl ether at 20℃; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	99%
With tert-butyl methyl ether; C28H29N3O3S at 20℃; for 24h; enantioselective reaction;	99%
With 1,4-bis(dihydroquinidinyl)anthraquinone In diethyl ether at -20℃; for 48h;	97%

: 62-53-3
aniline

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

A: 26491-47-4
N-phenyltetrahydrophthalimide

B: 2-Phenylcarbamoyl-cyclohexanecarboxylic acid

Conditions

Conditions	Yield
Stage #1: aniline; 1,2-cis-cyclohexanedicarboxylic anhydride In N,N-dimethyl acetamide at 20℃; for 24h; Stage #2: In N,N-dimethyl acetamide; xylene at 140℃; for 48h;	A 97% B n/a

...Expand

: 557-20-0
diethylzinc

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: (1RS,2SR)-2-propionylcyclohexanecarboxylic acid

Conditions

Conditions	Yield
With [2,2]bipyridinyl; bis(acetylacetonate)nickel(II); trifluorotoluene In tetrahydrofuran; hexane at 0 - 20℃; for 48h;	96%
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0); 1-trifluoromethyl-4-vinyl-benzene In tetrahydrofuran at 0 - 23℃; for 12h; Product distribution; Further Variations:; Reagents;	92%

: 4276-09-9
(R)-2-amino-3-methylbutanol

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 122383-33-9
cis-(2'S)-(+)-N-<1-(1-methylethyl)-2-hydroxyethyl>-3a,4,5,6,7,7a-hexahydro-1H-isoindolimide

Conditions

Conditions	Yield
at 220℃; for 2.5h;	95%

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 100-51-6
benzyl alcohol

: 151434-99-0
(1R,2S)-cis-2-benzyloxycarbonyl-cyclohexane-1-carboxylic acid

Conditions

Conditions	Yield
With quinindine In toluene at -55℃; for 96h; Inert atmosphere; enantioselective reaction;	95%
tributylphosphine In [D3]acetonitrile for 24h;	70%
With quinindine In toluene at -50℃; for 120h; Inert atmosphere;	60%

: 151-18-8
2-cyanoethylamine

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 192824-58-1, 260435-04-9
3-(1,3-dioxo-octahydroisoindol-2-yl)propionitrile

Conditions

Conditions	Yield
at 200℃; for 0.5h;	95%

: 4389-45-1
3-methylantranilic acid

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 1185155-84-3
C16H17NO4

Conditions

Conditions	Yield
at 110℃; for 10h; Inert atmosphere; neat (no solvent);	95%

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 18886-85-6
(3aR,7aS)-2-hydroxyhexahydro-1H-isoindol-1,3(2H)-dione

Conditions

Conditions	Yield
With hydroxyammonium sulfate; sodium hydroxide In water at 90℃; for 1.25h;	94%
With hydroxylamine sulfate; sodium hydroxide In water at 90℃; for 2.25h;	94%
With hydroxyammonium sulfate; sodium hydroxide In water at 90℃; for 2.25h;	94%
With methanol; hydroxylamine
With water; hydroxylamine

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 15753-50-1
cis-1,2-cyclohexanedimethanol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Reflux;	94%
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Heating;	89.4%
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reduction; Heating;	88%

: 593-51-1
methylamine hydrochloride

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 83248-53-7
2-methylhexahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With sodium acetate In acetic acid for 24h; Heating;	94%

: 141329-76-2
(S)-1-phenyl-3,3-bis(trifluoromethyl)propan-1,3-diol

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 141329-77-3
(1R,2S)-Cyclohexane-1,2-dicarboxylic acid mono-((S)-4,4,4-trifluoro-3-hydroxy-1-phenyl-3-trifluoromethyl-butyl) ester

Conditions

Conditions	Yield
With sodium hydride In toluene at -78℃; for 1h; Product distribution; other ς-symmetric cyclic dicarboxylic acid anhydride and glutaric anhydrides, other reagents; var. reaction conditions;	94%

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 65376-02-5
(1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C77H108O6P2 In ethyl acetate at 80℃; for 20h; Inert atmosphere; Glovebox; enantioselective reaction;	94%
Multi-step reaction with 3 steps 1.1: toluene / 1 h / 20 °C 2.1: ZnCl2; HMDS / toluene / 2 h / Heating 3.1: chiral 2-methyl-1-oxa-3-aza-2-boracyclopenta[a]indene; BH3*THF / tetrahydrofuran / 18 h / 25 °C 3.2: NaBH4 / ethanol / 4 h / 50 °C 3.3: aq. H2SO4 / 2 h / 80 °C View Scheme

: 29540-84-9
4-chlorophenyl trifluoromethanesulfonate

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 52240-18-3, 52240-19-4
cis-2-(4-chlorobenzoyl)cyclohexane-1-carboxylic acid

Conditions

Conditions	Yield
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0); chloro-trimethyl-silane; zinc(II) iodide; zinc In N,N-dimethyl acetamide at 80℃; for 12h; Inert atmosphere; Sealed tube;	94%

: 74-89-5
methylamine

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 117307-10-5
(S)-trans-N-methylcyclohexane-1,2-dicarboximide

Conditions

Conditions	Yield
With acetyl chloride In ethanol for 0.166667h; Inert atmosphere; Reflux;	93%

: 100-46-9
benzylamine

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 66050-00-8
2-benzylhexahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
at 200℃; for 0.5h;	92%
Stage #1: benzylamine; 1,2-cis-cyclohexanedicarboxylic anhydride In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: With 1,1,1,3,3,3-hexamethyl-disilazane; zinc(II) chloride In toluene for 2h; Inert atmosphere; Reflux;	74%

: 77-86-1
2-amino-2-hydroxymethyl-1,3-propanediol

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

polymer; monomer(s): cis-1,2-cyclohexanedicarboxylic anhydride; tris(hydroxymethyl)aminomethane: polymer; monomer(s): cis-1,2-cyclohexanedicarboxylic anhydride; tris(hydroxymethyl)aminomethane

Conditions

Conditions	Yield
at 110℃; for 5h;	92%

: 108-88-3
toluene

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: cis-2-(4-methylbenzoyl)cyclohexane-1-carboxylic acid

Conditions

Conditions	Yield
With aluminium trichloride	91.8%
With aluminium trichloride

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 71-43-2
benzene

: 86528-42-9
(1S*,2R*)-2-benzoylcyclohexane-1-carboxylic acid

Conditions

Conditions	Yield
With aluminium trichloride	91%
With aluminium trichloride In dichloromethane Friedel-Crafts acylation; Heating;	20%

: 4,4'-diamino-4''-cyanotriphenylamine

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 1416570-70-1
4,4'-di(1,2-cyclohexanedicarboxyimido)-4''-cyanotriphenylamine

Conditions

Conditions	Yield
With acetic acid at 140℃; for 3h;	91%

: 109459-38-3
diphenyl boric ester of (R)-2-methoxy-1-phenylethanol

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: Cyclohexane-1,2-dicarboxylic acid mono-((R)-2-methoxy-1-phenyl-ethyl) ester

Conditions

Conditions	Yield
With diphenylboryl triflate In toluene at 0℃; for 61h;	90%

: 62-53-3
aniline

: 13149-00-3
1,2-cis-cyclohexanedicarboxylic anhydride

: 92670-99-0
cis-2-phenyl-octahydroisoindole-1,3-dione

Conditions

Conditions	Yield
Stage #1: aniline; 1,2-cis-cyclohexanedicarboxylic anhydride In tetrahydrofuran at 40℃; for 0.5h; Inert atmosphere; Stage #2: at 190℃; for 4h; Inert atmosphere;	90%
Stage #1: aniline; 1,2-cis-cyclohexanedicarboxylic anhydride In tetrahydrofuran at 40℃; for 0.5h; Inert atmosphere; Stage #2: at 190℃; for 4h; Inert atmosphere;	86%
at 200℃; for 2h;	36%

cis-Cyclohexane-1,2-dicarboxylic anhydride Chemical Properties

Chemical Name: cis-1,2-Cyclohexanedicarboxylic anhydride
IUPAC NAME: 3a,4,5,6,7,7a-Hexahydro-2-benzofuran-1,3-dione
CAS No.: 13149-00-3
EINECS: 236-086-3
Molecular Formula: C₈H₁₀O₃
Molecular Weight: 154.16 g/mol
Melting Point: 32-34 °C(lit.)
Density: 1.235 g/cm³
Flash Point: 143.9 °C
Boiling Point: 283.4 °C at 760 mmHg
Sensitive: Moisture Sensitive
Following is the structure of Hexahydrophthalic anhydride (CAS No.13149-00-3):

Product Categories about Hexahydrophthalic anhydride (CAS No.13149-00-3) is refer to Pharmaceutical Intermediates
The chemical synonymous of Hexahydrophthalic anhydride (CAS No.13149-00-3) are cis-1,2-Cyclohexanedicarboxylic anhydride (HHPA) ; 1,3-Isobenzofurandione, hexahydro-, (3ar,7as)-rel- ; cis-1,2-Cyclohexanedecarboxylicanhydride ; cis-1,2-Cyclohexanedicarboxylic anhydride ; cis-Hexahydrophthalic anhydride ; cis-HHPA ; cis-Cyclohexane-1,2-dicarboxylic anhydride ; Hexahydrophthalic acid anhydride

cis-Cyclohexane-1,2-dicarboxylic anhydride Uses

Hexahydrophthalic anhydride (CAS No.13149-00-3) is used as a curing agent, adhesives, plasticizers for coating and epoxy resin.

cis-Cyclohexane-1,2-dicarboxylic anhydride Safety Profile

Hazard Codes: Harmful Xn
Risk Statements about Hexahydrophthalic anhydride (CAS No.13149-00-3):
R41:Risk of serious damage to the eyes.
R42/43:May cause sensitization by inhalation and skin contact.
Safety Statements about Hexahydrophthalic anhydride (CAS No.13149-00-3):
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.
Attention:
1. Storage: Store in a cool, dry place. Store in a tightly closed container.
2. Handling: Use only in a well-ventilated area. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.

Product Name

CIS-1,2-CYCLOHEXANEDICARBOXYLIC ANHYDRIDE

Synthetic route

cis-Cyclohexane-1,2-dicarboxylic anhydride Chemical Properties

cis-Cyclohexane-1,2-dicarboxylic anhydride Uses

cis-Cyclohexane-1,2-dicarboxylic anhydride Safety Profile

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