(1R,2R)-1,2-Cyclohexanedicarboxylic acid supplier

Name
(1R,2R)-(-)-1,2-CYCLOHEXANEDICARBOXYLIC ACID
EINECS 670-321-4
CAS No. 46022-05-3
Article Data24
CAS DataBase
Density 1.315 g/cm³
Solubility
Melting Point 184 °C
Formula C₈H₁₂O₄
Boiling Point 384.075 °C at 760 mmHg
Molecular Weight 172.181
Flash Point 200.254 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,2-Cyclohexanedicarboxylicacid, (1R-trans)-;(-)-trans-1,2-Cyclohexanedicarboxylic acid;(1R,2R)-Cyclohexane-1,2-dicarboxylic acid;
PSA 74.60000
LogP 0.96200

Synthetic route

: 3886-69-9
(R)-1-phenyl-ethyl-amine

: racemic trans-cyclohexane-1,2-dicarboxylic acid

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

B: C24H30N2O2

Conditions

Conditions	Yield
Stage #1: (R)-1-phenyl-ethyl-amine; racemic trans-cyclohexane-1,2-dicarboxylic acid In methanol at 0 - 35℃; Inert atmosphere; Stage #2: With hydrogenchloride In water Inert atmosphere; enantioselective reaction;	A 25% B n/a

...Expand

: (R,R)-1,2-cyclohexane dicarboxylic acid (R)-1-phenylethyl amine salt

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

Conditions

Conditions	Yield
With hydrogenchloride In water	800 mg
With sodium hydroxide In chloroform; water for 0.5h; pH=10 - 11;

: (x)C8H11N*C8H12O4

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

Conditions

Conditions	Yield
With hydrogenchloride In water

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

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 6.5 h / -70 - 20 °C / Resolution of racemate 2: hydrogenchloride / water View Scheme
With (R)-1-phenyl-ethyl-amine In methanol; isopropyl alcohol at 30 - 40℃;	29.4 g

: 2-(nitromethyl)cyclohexane-1-carbaldehyde

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2: acetic acid; sodium nitrite / dimethyl sulfoxide / 8 h / 40 °C / Inert atmosphere View Scheme

: 1292320-69-4
(1R,2R)-2-(nitromethyl)cyclohexane-1-carboxylic acid

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

Conditions

Conditions	Yield
With acetic acid; sodium nitrite In dimethyl sulfoxide at 40℃; for 8h; Inert atmosphere;

: 88-98-2, 2305-26-2, 15573-40-7, 50987-15-0, 51096-07-2, 51096-08-3
trans-cyclohex-4-ene-1,2-dicarboxylic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium; hydrogen / methanol / 30 - 35 °C 2.1: ethanol / 30 h / 35 - 75 °C 2.2: 1 h View Scheme

: 3886-69-9
(R)-1-phenyl-ethyl-amine

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

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

Conditions

Conditions	Yield
Stage #1: (R)-1-phenyl-ethyl-amine; trans-1,2-cyclohexanedicarboxylic acid In ethanol at 35 - 75℃; for 30h; Stage #2: With hydrogenchloride In water; ethyl acetate for 1h;

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

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

B: 610-10-6, 1687-30-5, 2305-32-0, 21963-41-7, 46022-05-3, 610-09-3
(1S,2S)-cyclohexane-1,2-dicarboxylic acid

Conditions

Conditions	Yield
With FS-Hydrodex β-6TBDM column Resolution of racemate;

: 88-98-2
cyclohex-4-ene-1,2-dicarboxylic acid

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen / methanol / 20 °C / Autoclave 2: methanol / 2.5 h / 20 °C 3: sodium hydroxide / water; chloroform / 0.5 h / pH 10 - 11 View Scheme

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

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

B: 610-10-6, 1687-30-5, 2305-32-0, 21963-41-7, 46022-05-3, 610-09-3
(1S,2S)-cyclohexane-1,2-dicarboxylic acid

Conditions

Conditions	Yield
Stage #1: dimethyl cis-1,2-cyclohexanedicarboxylate With sodium methylate In methanol for 4h; Inert atmosphere; Reflux; Stage #2: With water; sodium hydroxide at 75℃; for 4h; Inert atmosphere; Stage #3: With hydrogenchloride In water at 0 - 5℃; pH=2; Inert atmosphere; Optical yield = 16.399 %ee; diastereoselective reaction;

: racemic trans-cyclohexane-1,2-dicarboxylic acid

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

Conditions

Conditions	Yield
With (R)-1-phenyl-ethyl-amine at 5℃; Temperature;

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

: 135-19-3
β-naphthol

: trans-(1R,2R)-cyclohexane dicarboxylic acid di(2-naphthyl)ester

Conditions

Conditions	Yield
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine	100%
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride; triethylamine In dichloromethane Esterification;

: 67-56-1
methanol

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

: 140459-96-7
(1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 2h; Reflux;	99%
With sulfuric acid at 40℃; for 18h;	97%
With sulfuric acid at 40℃; for 24h; Cooling with ice;	91%

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

: 85-42-7, 13149-00-3, 14166-21-3, 31982-85-1, 71749-03-6, 97233-90-4
trans-1,2-cyclohexanedicarboxylic anhydride

Conditions

Conditions	Yield
With acetyl chloride	98%
With acetic anhydride at 80℃; for 1h;
With acetic anhydride at 80℃; for 1h;

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

: 65376-05-8
(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

Conditions

Conditions	Yield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 0℃; for 5h; Reflux;	88.4%
With Red-Al In tetrahydrofuran; toluene for 5h; Inert atmosphere; Reflux;	85.2%
Multi-step reaction with 2 steps 1: diethyl ether 2: LiAlH4 / diethyl ether View Scheme

: uranyl nirate hexahydrate

: cadmium(II) nitrate tetrhydrate

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

: O2U(2+)*2C8H10O4(2-)*Cd(2+)*3H2O

Conditions

Conditions	Yield
In water; acetonitrile at 140℃; Autoclave; High pressure;	85%

...Expand

: cadmium(II) nitrate tetrhydrate

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

: 1135-32-6
trans-1,2-bis(4-pyridyl)ethylene

: C8H10O4(2-)*2C12H10N2*3H2O*Cd(2+)

Conditions

Conditions	Yield
In water at 140℃; for 72h; Sealed tube;	83%

...Expand

: 186581-53-3, 908094-01-9
diazomethane

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

: 140459-96-7
(1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester

Conditions

Conditions	Yield
In diethyl ether at 0℃; Inert atmosphere;	75%
In diethyl ether
In diethyl ether

: uranyl nirate hexahydrate

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

: O2U(2+)*C8H10O4(2-)

Conditions

Conditions	Yield
With silver nitrate In water; acetonitrile at 140℃; Reagent/catalyst; Autoclave; High pressure;	75%

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

: (R,R)-trans-2-aminocyclohexanecarboxylic acid hydrochloride

Conditions

Conditions	Yield
Stage #1: (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid With acetyl chloride Heating; Stage #2: With ammonia In dichloromethane at 20℃; Stage #3: With bis-[(trifluoroacetoxy)iodo]benzene In water; acetonitrile at 20℃; Further stages.;	74%

: nickel(II) chloride hexahydrate

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

: 1135-32-6
trans-1,2-bis(4-pyridyl)ethylene

: C8H10O4(2-)*2C12H10N2*3H2O*Ni(2+)

Conditions

Conditions	Yield
In water at 140℃; for 72h; Sealed tube;	73.2%

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

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

: 233661-54-6
(1R,2R)-2-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid

Conditions

Conditions	Yield
Multistep reaction.;	67%

: cobalt(II) chloride hexahydrate

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

: 1135-32-6
trans-1,2-bis(4-pyridyl)ethylene

: Co(2+)*C8H10O4(2-)*2C12H10N2*3H2O

Conditions

Conditions	Yield
In water at 140℃; for 72h; Sealed tube;	65%

...Expand

: cadmium(II) nitrate tetrhydrate

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

: 9,10-di(1-H-imidazol-1-yl)-anthracene

: [Cd(9,10-di(1H-imidazol-1-yl)anthracene)(1,2-chdc)]n

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide at 120℃; for 72h; Sealed tube;	63%

...Expand

: uranyl nirate hexahydrate

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

: 1779-49-3
Methyltriphenylphosphonium bromide

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: [PPh3Me][H2NMe2]3[(UO2)4(R-t-1,2-chdc)6]·H2O

Conditions

Conditions	Yield
In water at 140℃; for 168h; Autoclave; High pressure;	57%

...Expand

: 4916-57-8
1,2-bis(4'-pyridyl)ethane

: nickel(II) chloride hexahydrate

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

: C8H10O4(2-)*5H2O*Ni(2+)*C12H12N2

Conditions

Conditions	Yield
With sodium hydroxide In water at 110℃; for 48h; Sealed tube;	52%

...Expand

: 553-26-4
4,4'-bipyridine

: copper(II) perchlorate hexahydrate

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

: 3C10H8N2*3Cu(2+)*2C8H11O4(1-)*2C8H10O4(2-)*4H2O

Conditions

Conditions	Yield
In water at 110℃; for 72h; Sealed tube;	49%

...Expand

: cadmium(II) nitrate tetrhydrate

: 357429-12-0
1,4-bis(pyridin-4-ylmethyl)piperazine

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

: [Cd2(trans-1,2-cyclohexanedicarboxylate)2(bis(4-pyridylmethyl)piperazine)]n

Conditions

Conditions	Yield
With sodium hydroxide In water at 120℃; for 48h; High pressure;	43%

...Expand

: uranyl nirate hexahydrate

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

: 2751-90-8
tetraphenylphosphonium bromide

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: [PPh4][UO2(trans-(R)-1,2-cyclohexanedicarboxylate)(HCOO)]*(H2O)

Conditions

Conditions	Yield
In water at 140℃; Autoclave; High pressure;	38%

...Expand

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

: 472-15-1
Betulinic acid

: 1221184-26-4
3β-O-[(1'R,2'R)-2'-carboxycyclohexanecarbonyl]betulinic acid

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	35%

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

: 5970-45-6
zinc(II) acetate dihydrate

: 3Zn(2+)*2C8H10O4(2-)*2HO(1-)

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 110℃; for 72h;	32.3%

: 366-18-7
[2,2]bipyridinyl

: uranyl nirate hexahydrate

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

: O2U(2+)*C8H10O4(2-)*C10H8N2

Conditions

Conditions	Yield
In water; acetonitrile at 140℃; Autoclave; High pressure;	27%

...Expand

: 17455-13-9
18-crown-6 ether

: uranyl nirate hexahydrate

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

: 7732-18-5
water

: potassium nitrate

: [(uranyl)10(potassium)5((1R,2R)-trans-1,2-cyclohexanedicarboxylate)4(oxalate)10(18-crown-6)5(OH)(H2O)3] tetrahydrate

Conditions

Conditions	Yield
at 140℃; for 730.5h; High pressure;	27%

...Expand

: 13126-12-0
rubidium nitrate

: uranyl nirate hexahydrate

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

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: [H2NMe2][(UO2)4Rb3(R-trans-1,2-cyclohexanedicarboxylate)6(H2O)1.75]*DMF

Conditions

Conditions	Yield
In water at 150℃; High pressure;	24%

...Expand

: 7631-99-4
sodium nitrate

: uranyl nirate hexahydrate

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

: 2O2U(2+)*3C8H10O4(2-)*2Na(1+)*2H2O

Conditions

Conditions	Yield
With 18-crown-6 ether In water; acetonitrile at 140℃; Autoclave; High pressure;	21%

...Expand

: 143-27-1
hexadecylamine

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

: C40H78N2O2

Conditions

Conditions	Yield
Stage #1: (1R,2R)-(-)-trans-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;	11%

: lead(II) nitrate

: uranyl nirate hexahydrate

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

: 2O2U(2+)*3C8H10O4(2-)*4H2O*Pb(2+)

Conditions

Conditions	Yield
In water; acetonitrile at 140℃; Autoclave; High pressure;	11%

...Expand

: caesium nitrate

: uranyl nirate hexahydrate

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

: [(UO2)4Cs4(R-trans-1,2-cyclohexanedicarboxylate)6(H2O)4]·3H2O

Conditions

Conditions	Yield
In methanol; water at 150℃; High pressure;	10%

...Expand

: 366-18-7
[2,2]bipyridinyl

: copper nitrate hemi(pentahydrate)

: uranyl nirate hexahydrate

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

: O2U(2+)*2C8H10O4(2-)*C10H8N2*Cu(2+)*3H2O

Conditions

Conditions	Yield
In water; acetonitrile at 140℃; Autoclave; High pressure;	9%

...Expand

(1R,2R)-1,2-Cyclohexanedicarboxylic acid Specification

The 1,2-Cyclohexanedicarboxylicacid, (1R,2R)-, with the CAS registry number 46022-05-3, is also known as Cyclohexane-1,2-dicarboxylic acid, trans. It belongs to the product categories of Carboxylic Acids (Chiral); Chiral Building Blocks; Synthetic Organic Chemistry. This chemical's molecular formula is C₈H₁₂O₄ and molecular weight is 172.1785. Its IUPAC name is called (1R,2R)-cyclohexane-1,2-dicarboxylic acid. The product should be sealed and stored in cool and dry place.

Physical properties of 1,2-Cyclohexanedicarboxylicacid, (1R,2R)-: (1)ACD/LogP: 0.61; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1.861; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 4; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.521; (11)Molar Refractivity: 39.885 cm³; (12)Molar Volume: 130.952 cm³; (13)Surface Tension: 57.832 dyne/cm; (14)Density: 1.315 g/cm³; (15)Flash Point: 200.254 °C; (16)Enthalpy of Vaporization: 69.461 kJ/mol; (17)Boiling Point: 384.075 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CCC(C(C1)C(=O)O)C(=O)O
(2)Isomeric SMILES: C1CC[C@H]([C@@H](C1)C(=O)O)C(=O)O
(3)InChI: InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h5-6H,1-4H2,(H,9,10)(H,11,12)/t5-,6-/m1/s1
(4)InChIKey: QSAWQNUELGIYBC-PHDIDXHHSA-N

Product Name

(1R,2R)-(-)-1,2-CYCLOHEXANEDICARBOXYLIC ACID

Synthetic route

(1R,2R)-1,2-Cyclohexanedicarboxylic acid Specification

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