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

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Name

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

EINECS 670-321-4
CAS No. 46022-05-3 Density 1.315 g/cm3
PSA 74.60000 LogP 0.96200
Solubility N/A 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 N/A Appearance N/A
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 46022-05-3 ((1R,2R)-(-)-1,2-CYCLOHEXANEDICARBOXYLIC ACID) Hazard Symbols IrritantXi
Synonyms

1,2-Cyclohexanedicarboxylicacid, (1R-trans)-;(-)-trans-1,2-Cyclohexanedicarboxylic acid;(1R,2R)-Cyclohexane-1,2-dicarboxylic acid;

Article Data 24

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

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

46022-05-3

(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In water800 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
ConditionsYield
With hydrogenchloride In water
2305-32-0

trans-1,2-cyclohexanedicarboxylic acid

46022-05-3

(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With acetic acid; sodium nitrite In dimethyl sulfoxide at 40℃; for 8h; Inert atmosphere;
46022-05-3

(1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid

Conditions
ConditionsYield
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
ConditionsYield
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

Conditions
ConditionsYield
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
ConditionsYield
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

(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

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