610-09-3

Basic information

• Product Name: cis-Hexahydrophthalic acid
• Synonyms: CIS-1,2-CYCLOHEXANEDICARBOXYLIC;(1R)-Cyclohexane-1β,2β-dicarboxylic acid;(1R,2S)-1,2-Cyclohexanedicarboxylic acid;cis-1,2-Cyclohexanedicarboxylic acid,98%;cis-1,2-Cyclohexanedicarboxylic acid, 98% 25GR;(1R,2S)-cyclohexane-1,2-dicarboxylic acid;1,2-Cyclohexanedicarboxylicacid, (1R,2S)-rel-;is-1,2-Cyclohexanedicarboxylic acid
• CAS NO: 610-09-3
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• EINECS: -0
• Mol File: 610-09-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 188-192 °C
• Boiling Point: 262.49°C (rough estimate)
• Flash Point: 250°C
• Appearance: white crystals
• Density: 1.2104 (rough estimate)
• Refractive Index: 1.4455 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Benzene,Ethanol,Methanol,Ether
• PKA: pK1:4.34 ;pK2:6.76 (20°C)
• Water Solubility: >2g/L(20 oC)
• BRN: 2049754
• CAS DataBase Reference: cis-Hexahydrophthalic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cis-Hexahydrophthalic acid(610-09-3)
• EPA Substance Registry System: cis-Hexahydrophthalic acid(610-09-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25-37-26
• Hazardous Substances Data: 610-09-3(Hazardous Substances Data)

Usage

Chemical Properties

white crystals

Purification Methods

It is purified by recrystallisation from EtOH or H2O. [Smith & Byrne J Am Chem Soc 72 4406 1950, Abell J Org Chem 22 769 1957, Beilstein 9 III 3812, 9 IV 2801.]

Synthetic route

cyclohexane-1,2-dicarbonitrile (34112-17-9) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With hydrogenchloride In water for 24h; Inert atmosphere; Reflux;	65%

cis-cyclohexane-1,2-dicarbonitrile (28907-20-2) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + cis-Cyclohexan-dicarbonsaeure-1,2-monoamid (207518-98-7) + cis-2-carbamoylcyclohexanecarboxylic acid

Conditions	Yield
With Rhodococcus rhodochrous IFO 15564; water Yield given. Yields of byproduct given. Title compound not separated from byproducts;	A 26% B n/a C n/a
With Rhodococcus rhodochrous IFO 15564; water Yields of byproduct given;	A 24% B n/a C n/a

phthalic anhydride (85-44-9) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With hydrogen; oxygen; acetic acid

cyclohex-1-ene-1,2-dicarboxylic acid (635-08-5) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With sodium amalgam; sodium carbonate

cyclohexane-1,1,2,2-tetracarboxylic acid tetraethyl ester (50708-48-0) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With potassium hydroxide

cyclohex-3-ene-1,2-dicarboxylic acid (25079-83-8, 38765-76-3, 38765-77-4) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

(1RS,2SR)-dimethyl 4-oxocyclohexane-1,2-dicarboxylate (13990-96-0, 13991-44-1, 90927-39-2) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With hydrogenchloride; zinc

benzene-1,2-dicarboxylic acid (88-99-3) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With hydrogenchloride; acetic acid; platinum Hydrogenation;
With hydrogen; acetic acid; platinum
With ethanol; platinum Hydrogenation;

ethanol (64-17-5) + furan-2,3,5(4H)-trione pyridine (1:1) + cis-hexahydrophthalimide (7506-66-3) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
Behandeln bei Raumtemperatur;

cis-bicyclo[4.2.0]oct-7-ene (3806-82-4) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With potassium permanganate; sodium periodate; potassium carbonate

1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
In water for 5h; Heating;
With water Heating;
With acetic acid at 0℃;
With sodium hydroxide at 5℃;

carbon dioxide (124-38-9) + cyclohexene (110-83-8) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With In tetrahydrofuran under 760 Torr; Mechanism; Irradiation;
With Ni3(Ph2PCH2PPh2)3I2 Product distribution; Mechanism; Irradiation;

water (7732-18-5) + furan-2,3,5(4H)-trione pyridine (1:1) + cis-hexahydrophthalimide (7506-66-3) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
Behandeln bei Raumtemperatur;

(3aR,7aS)-hexahydroisobenzofuran-1-one (89395-29-9) + Cr2O3-H2SO4 → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

phthalic anhydride (85-44-9) + acetic acid (64-19-7) + hydrogen + platinum black → 8-oxabicyclo[4,3,0]nonane-7-one (2611-01-0) + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + (+-)-cis-2-methyl-cyclohexanecarboxylic acid (7076-91-7)

acetic acid (64-19-7) + benzene-1,2-dicarboxylic acid (88-99-3) + hydrogen + platinum black → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

anhydride of/the/ inactive trans-hexahydrophthalic acid → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
at 210 - 220℃; man loest in Soda und faellt mit verd. Schwefelsaeure;

cis-cyclohexene-(4)-dicarboxylic acid-(1.2)-anhydride → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With acetic acid; platinum Hydrogenation.Behandlung des Reaktionsprodukts mit heissem Wasser;

cyclohex-4-ene-1,2-dicarboxylic acid (88-98-2) + palladium + barium sulfate + natrium carbonate → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
Hydrogenation; cis-Δ4-tetrahydrophthalic acid;

benzene-1,2-dicarboxylic acid (88-99-3) + rhodium/ coal → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
With water at 80℃; Hydrogenation;

cyclohex-1-ene-1,2-dicarboxylic acid (635-08-5) + sodium amalgam → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

cyclohex-1-ene-1,2-dicarboxylic acid (635-08-5) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + inactive trans-hexahydrophthalic acid

Conditions	Yield
With sodium amalgam; sodium carbonate

1,4-dibromo-butane (110-52-1) + tetraethyl ethane-1,1,2,2-tetracarboxylate (632-56-4) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-cyclohexane-dicarboxylic acid-(1.2)

Conditions	Yield
With ethanol; sodium ethanolate Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge und Erhitzen der erhaltenen Tetracarbonsaeure auf 200grad;

(1S,2R)-2-(methoxycarbonyl)cyclohexanecarboxylic acid (88335-92-6) + alcoholic NaOH-solution → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

(+/-)-cis-cyclohexene-(3)-dicarboxylic acid-(1.2)-dichloride → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous acetone 2: acetic acid; platinum / Hydrogenation View Scheme

(+/-)-4-oxo-cyclohexane-1r,2c-dicarboxylic acid (54639-71-3, 90954-18-0) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
Multi-step reaction with 2 steps 2: zinc; aqueous HCl View Scheme

1,3-cyclooctadiene (186983-16-4) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / Irradiation 2: NaIO4, KMnO4, aq. K2CO3 View Scheme

+ cis-(+/-)-5-iodoperhydrophthalic acid + tri-n-butyl-tin hydride (688-73-3) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3)

Conditions	Yield
In 1,2-dimethoxyethane; hexane; ethyl acetate

benzene-1,2-dicarboxylic acid (88-99-3) → (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With 10% Rh/C; hydrogen In isopropyl alcohol at 60℃; under 3800.26 Torr; for 7h; optical yield given as %de;
With water; hydrogen at 60℃; under 37503.8 Torr; for 1h; Autoclave;	A n/a B n/a

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → trans-1,2-cyclohexanedicarboxylic acid (2305-32-0)

Conditions	Yield
With sodium hydroxide In water at 150℃; under 2280.15 Torr; for 72h; Reagent/catalyst; Concentration; Autoclave;	95.5%
With hydrogenchloride at 180℃;
With phosphoric acid
With sulfuric acid

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → 1,2-cis-cyclohexanedicarboxylic anhydride (13149-00-3)

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.

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → cis-cyclohexane-1,2-dicarboxylic acid chloride (60901-05-5)

Conditions	Yield
With phosphorus pentachloride Ambient temperature;	93%
With thionyl chloride; N,N-dimethyl-formamide for 41h;	78%
With pyridine; thionyl chloride Ambient temperature;
With thionyl chloride

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → potassium cis-1,2-cyclohexanedicarboxylate

Conditions	Yield
With potassium hydroxide In diethyl ether; water at 35 - 40℃; for 0.5h; pH=7;	92%

1,2-bis(4'-pyridyl)ethane (4916-57-8) + zinc(II) nitrate hexahydrate + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → [Zn2(e,a-cis-1,2-cyclohexanedicarboxylate)2(H2O)(μ-1,2-bis(4-pyridyl)ethane)]*4H2O

Conditions	Yield
With NH4OH In ethanol; water mixt. of C6H10(CO2H)2, NH4OH and Zn salt dissolved in H2O; carefully layered with EtOH soln. of 1,2-bis(4-pyridyl)ethane; crystd. for 1 wk; elem. anal.;	91.2%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → disodium cis-1,2-cyclohexanedicarboxylate

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 35 - 40℃; for 0.5h; pH=7;	90%
With sodium hydroxide In water at 70℃; for 0.833333h;	85%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → dilithium cis-1,2-cyclohexanedicarboxylate

Conditions	Yield
With lithium hydroxide In water at 75℃; for 0.666667h;	90%

n-butyl formate (592-84-7) + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → cis-Cyclohexane-1,2-dicarboxylic acid monobutyl ester + cis-Cyclohexane-1,2-dicarboxylic acid dibutyl ester

Conditions	Yield
With Dowex 50Wx2 In octane at 100℃; for 17h; Esterification;	A 89% B 5%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → ammonium cis-1,2-cyclohexanedicarboxylate

Conditions	Yield
With ammonia In diethyl ether; water at 35 - 40℃; for 0.5h; pH=7;	86%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + allyl bromide (106-95-6) → diprop-2-en-1-yl (1R,2S)-cyclohexane-1,2-dicarboxylate (46872-42-8)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	85%
Stage #1: (1R,2S)-cyclohexane-1,2-dicarboxylic acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Inert atmosphere; Stage #2: allyl bromide With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	85%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → cis-1,2-cyclohexanedimethanol (15753-50-1)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; Inert atmosphere;	84%

zinc(II) sulfate heptahydrate + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → zinc cis-1,2-cyclohexanedicarboxylate

Conditions	Yield
Stage #1: (1R,2S)-cyclohexane-1,2-dicarboxylic acid With lithium hydroxide In water at 50℃; for 0.333333h; Stage #2: zinc(II) sulfate heptahydrate In water at 85℃; for 0.833333h;	81%

uranyl nirate hexahydrate + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + tetraphenylphosphonium bromide (2751-90-8) + acetonitrile (75-05-8) → [NH4][PPh4][(UO2)8(cis-1,2-cyclohexanedicarboxylate)9(H2O)6]*3H2O

Conditions	Yield
In water at 140℃; Sealed tube;	79%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → calcium cis-1,2-cyclohexanedicarboxylate

Conditions	Yield
With calcium hydroxide In water at 85℃; for 1h;	78%

C40H44N2Si2 (915698-88-3) + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → C40H44N2Si2*C8H12O4

Conditions	Yield
In methanol for 6h; Heating;	76%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → magnesium cis-1,2-cyclohexanedicarboxylate

Conditions	Yield
With magnesium oxide In water at 75℃; for 0.833333h;	73%

cadmium(II) nitrate hexahydrate + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → [Cd(cis-1,2-cyclohexanedicarboxylate)(1,2-bis(4-pyridyl)ethylene)]n (1309059-90-2)

Conditions	Yield
With NH4OH In ammonia; acetonitrile aq. NH3; soln. of cis-1,2-cyclohexanedicarboxylic acid and Cd(NO3)2*6H2O in aq. NH3 layered with soln. of 1,2-bis(4-pyridyl)ethene in MeCN, system storedfor 3 wk; crystals isolated; elem. anal.;	70.6%

ferrous(II) sulfate heptahydrate + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → [Fe(II)(e,e-trans-cyclohexane-1,2-dicarboxylate)]

Conditions	Yield
With Et3N In water High Pressure; under hydrothermal conditions; mixt. of FeSO4*7H2O, ligand, Et3N and deionized H2O sealed in autoclave; heated at 160°C for 2 d; crystals isolated; elem. anal.;	65%

uranyl nirate hexahydrate + [Ni(1,4,8,11-tetra-azacyclotetradecane)(NO3)2] + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → [UO2(cis-1,2-cyclohexanedicarboxylate)2Ni(1,4,8,11-tetraazacyclotetradecane)(H2O)]

Conditions	Yield
In water; N,N-dimethyl-formamide at 140℃; High pressure;	65%

zinc nitrate tetrahydrate + 1,4-bis(pyridin-4-ylmethyl)piperazine (357429-12-0) + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + water (7732-18-5) → {[Zn2(cis-1,2-cyclohexanedicarboxylate)2(bis(4-pyridylmethyl)piperazine)]•6H2O}n

Conditions	Yield
With sodium hydroxide at 120℃; for 48h; Sealed tube; High pressure;	62%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + isopropyl alcohol (67-63-0) → (1R*,2S*)-diisopropyl cyclohexane-1,2-dicarboxylate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 60℃; Inert atmosphere; Sealed tube;	61%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + aniline (62-53-3) → cis-2-phenyl-octahydroisoindole-1,3-dione (92670-99-0)

Conditions	Yield
microwave irradiation;	60%

spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidine]-5,6-dione (959701-71-4) + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → spiro[naphtho[1,2-b][1,4]oxathiine-2,4'-piperidinium]-5,6-dione cis-2-carboxycyclohexanecarboxylate

Conditions	Yield
In acetonitrile at 80℃;	60%

zinc(II) nitrate hexahydrate + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + trans-1,2-bis(4-pyridyl)ethylene (1135-32-6) → [Zn2(μ-e,a-cis-1,2-cyclohexanedicarboxylate)2(μ-1,2-bis(4-pyridyl)ethylene)]*2H2O

Conditions	Yield
With NH4OH In water; acetone mixt. of C6H10(CO2H)2, NH4OH and Zn salt dissolved in H2O; carefully layered with acetone soln. of 1,2-bis(4-pyridyl)ethylene; crystd. for 1 wk; elem. anal.;	54%

zinc(II) nitrate hexahydrate + 1,3-di(4-pyridyl)propane (17252-51-6) + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → [Zn2(μ-e,a-cis-1,2-cyclohexanedicarboxylate)2(μ-1,3-bis(4-pyridyl)propane)2Zn2(μ-cis-1,2-C6H10(CO2)2)2(H2O)2]*MeCN*2H2O

Conditions	Yield
With NH4OH In further solvent(s) mixt. of C6H10(CO2H)2, NH4OH and Zn salt dissolved in H2O; carefully layered with soln. of 1,2-bis(4-pyridyl)propane in acetone-MeOH-EtOH; crystd. for 1 wk; elem. anal.;	52%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + L-2-aminohexanoic acid-methyl ester hydrochloride (3844-54-0) → C22H38N2O6

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 1h;	52%

(1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + benzylamine (100-46-9) → 2-benzylhexahydro-1H-isoindole-1,3(2H)-dione (66050-00-8)

Conditions	Yield
microwave irradiation;	50%

zinc(II) nitrate hexahydrate + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) + 1,3-bis(1H-imidazol-4-yl)benzene (794485-43-1) → [Zn(1,3-di(1H-imidazol-4-yl)benzene)(cis-1,2-cyclohexanedicarboxylic acid)]

Conditions	Yield
With sodium hydroxide In water at 100℃; for 72h; High pressure;	49%

hexadecylamine (143-27-1) + (1R,2S)-cyclohexane-1,2-dicarboxylic acid (610-09-3) → C40H78N2O2

Conditions	Yield
Stage #1: (1R,2S)-cyclohexane-1,2-dicarboxylic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: hexadecylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	49%

Upstream product

• 85-44-9 phthalic anhydride 
• 25079-83-8 cyclohex-3-ene-1,2-dicarboxylic acid 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 3806-82-4 cis-bicyclo[4.2.0]oct-7-ene 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 124-38-9 carbon dioxide 
• 110-83-8 cyclohexene 
• 64-19-7 acetic acid 
• 635-08-5 cyclohex-1-ene-1,2-dicarboxylic acid 
• 110-52-1 1,4-dibromo-butane 
• 632-56-4 tetraethyl ethane-1,1,2,2-tetracarboxylate 
• 688-73-3 tri-n-butyl-tin hydride 
• 13990-96-0 (1RS,2SR)-dimethyl 4-oxocyclohexane-1,2-dicarboxylate 
• 1687-29-2 dimethyl cis-1,2-cyclohexanedicarboxylate 

Downstream Products

• 1687-29-2 dimethyl cis-1,2-cyclohexanedicarboxylate 
• 108-94-1 cyclohexanone 
• 98-89-5 Cyclohexanecarboxylic acid 
• 13149-00-3 1,2-cis-cyclohexanedicarboxylic anhydride 
• 7436-01-3 (1S)-trans-1,2-bis-(toluene-4-sulfonyloxymethyl)-cyclohexane 
• 21583-35-7 cis-Cyclohexane-1,2-dicarboxylic acid monobutyl ester 
• 1026611-68-6 2-(4-{(S)-2-[((1R,2S)-2-Carboxy-cyclohexanecarbonyl)-amino]-2-pentylcarbamoyl-ethyl}-phenoxy)-malonic acid dibenzyl ester 
• 31982-90-8 (1S,2S)-(+)-cyclohexane-1,2-dicarboxylic acid dimethyl ester 
• 568588-47-6 (1S,2S)-2-((S)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclohexanecarboxylic acid methyl ester 
• 568588-48-7 (1S,2S)-Cyclohexane-1,2-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] 
• 46021-27-6 (1S,2S)-cyclohexane-1,2-dicarbonyl dichloride 
• 66050-00-8 2-benzylhexahydro-1H-isoindole-1,3(2H)-dione 
• 2756-85-6 1-aminocyclohexane carboxylic acid 
• 5691-19-0 rac-trans-2-aminocyclohexanecarboxylic acid 

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Low-barrier hydrogen bonding in aqueous and aprotic solutions of dicarboxylic acids: Spectroscopic characterization

We present additional spectroscopic evidence for the formation of low- barrier hydrogen bonds (LBHBs) within vicinal and geminal dicarboxylic acid monoanions. Hydrogen cis-cyclohexane 1,2-dicarboxylate, displays low-field 1H NMR signals in apro

Enantioselective Synthesis of ((1 R,2 R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate

A concise, economical, and highly enantioselective synthesis of bismesylate intermediate of lurasidone HCl, an antipsychotic, has been developed. The key steps involved in the synthesis are thionyl chloride-catalyzed esterification of tetrahydrophthalic anhydride in MeOH, epimerization of cis to trans isomer, hydrolysis of the diester, resolution of the diacid, reduction with Red-Al, and finally bismesylation of the corresponding diol, which provided the desired intermediate ((1 R,2 R)-cyclohexane-1,2-diyl)bis(methylene) dimethanesulfonate in overall good yield.

Lipophilic oligopeptides for chemo- and enantioselective acyl transfer reactions onto alcohols

Inspired by the extraordinary selectivities of acylases, we envisioned the use of lipophilic oligopeptidic organocatalysts for the acylative kinetic resolution/desymmetrization of rac- and meso-cycloalkane-1,2-diols. Here we describe in a full account the discovery and development process from the theoretical concept to the final catalyst, including scope and limitations. Competition experiments with various alcohols and electrophiles show the full potential of the employed oligopeptides. Additionally, we utilized NMR and IR-spectroscopic methods as well as computations to shed light on the factors responsible for the selectivity. The catalyst system can be readily modified to a multicatalyst by adding other catalytically active amino acids to the peptide backbone, enabling the stereoselective one-pot synthesis of complex molecules from simple starting materials.