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(R,R)-1,2-Bis(methanesulfonyloxymethyl)cyclohexane

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Name

(R,R)-1,2-Bis(methanesulfonyloxymethyl)cyclohexane

EINECS 1308068-626-2
CAS No. 186204-35-3 Density 1.271 g/cm3
PSA 103.50000 LogP 2.90680
Solubility N/A Melting Point N/A
Formula C10H20O6S2 Boiling Point 495.284 °C at 760 mmHg
Molecular Weight 300.397 Flash Point 253.339 °C
Transport Information N/A Appearance off-white solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 186204-35-3 ((R,R)-1,2-Bis(methanesulfonyloxymethyl)cyclohexane) Hazard Symbols N/A
Synonyms

(1R,2R)-1,2-Cyclohexanediylbis(methylene) dimethanesulfonate;

Article Data 10

(R,R)-1,2-Bis(methanesulfonyloxymethyl)cyclohexane Synthetic route

65376-05-8

(+)-(1R,2R)-trans-1,2-bis(hydroxymethyl)cyclohexane

124-63-0

methanesulfonyl chloride

186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

Conditions
ConditionsYield
With triethylamine at 0 - 5℃; Industrial scale;92.6%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;92%
With triethylamine In chloroform at 0 - 20℃; for 5h;90.8%
131-11-3

phthalic acid dimethyl ester

186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Raney nickel; methanol / 50 - 60 °C / 73550.8 Torr / Hydrogenation.Behandeln des Reaktionsprodukts mit methanol. Natriummethylat
2: LiAlH4; diethyl ether
3: (1R)-menthyl isocyanate
4: pyridine
View Scheme
76155-27-6

(+/-)-trans-2-(hydroxymethyl)cyclohexylmethanol

186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (1R)-menthyl isocyanate
2: pyridine
View Scheme
3205-35-4

dimethyl cyclohexane-trans-1,2-dicarboxylate

186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: LiAlH4; diethyl ether
2: (1R)-menthyl isocyanate
3: pyridine
View Scheme
46022-05-3

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

186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sulfuric acid / 18 h / 40 °C
2.1: diisobutylaluminium hydride / toluene / 6 h / -5 - 20 °C / Inert atmosphere
2.2: 13 h / -5 - 40 °C
3.1: triethylamine / chloroform / 5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 65 °C
2.1: triethylamine / dichloromethane / 0.42 h / 25 - 35 °C / Inert atmosphere
2.2: 3 h / -5 - 35 °C
View Scheme
Multi-step reaction with 4 steps
1: tetrahydrofuran / 1 h / 25 - 30 °C
2: tetrahydrofuran / 45 - 50 °C
3: sodium tetrahydroborate; water / tetrahydrofuran / 1 h
4: triethylamine / dichloromethane
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / 4 h / Reflux
2: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 40 °C / Reflux
3: triethylamine / dichloromethane / 1.5 h / 20 °C
View Scheme
140459-96-7

(1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester

186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: diisobutylaluminium hydride / toluene / 6 h / -5 - 20 °C / Inert atmosphere
1.2: 13 h / -5 - 40 °C
2.1: triethylamine / chloroform / 5 h / 0 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / tetrahydrofuran / 3 h / 40 °C / Reflux
2: triethylamine / dichloromethane / 1.5 h / 20 °C
View Scheme
186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

14805-29-9

(3aR,4S,7R,7aS)‑4,7‑methylene‑1H‑isoindole‑1,3(2H)-dione

((1R,2R)-2-(((3aR,4S,7R,7aS)-1,3-dioxohexahydro-1H-4,7-methanoisoindol-2(3H)-yl)methyl)cyclohexyl)methylmethanesulfonate

Conditions
ConditionsYield
With potassium carbonate In isopropyl alcohol for 4h;99%
186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

111-42-2

2,2'-iminobis[ethanol]

1421374-96-0

(3aR,7aR)-2,2-bis(2-hydroxyethyl)octahydro-1H-isoindolium mesylate

Conditions
ConditionsYield
With sodium carbonate In chlorobenzene Reflux;99%
186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

87691-87-0

3-(1-piperazinyl)-1,2-benzisothiazole

186204-37-5

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate

Conditions
ConditionsYield
With calcium hydroxide In isopropyl alcohol for 20h; Reflux; Industrial scale;97.3%
With potassium carbonate In water; acetonitrile at 82℃; for 3h; Temperature; Concentration; Solvent;91%
With sodium carbonate In acetonitrile at 80 - 85℃; for 24h;89.5%

3-(1-piperazinyl)-1,2-benzoisothiazole hydrochloride

186204-35-3

(1R,2R)-(-)-trans-cyclohexane-1,2-diylbis(methylene)dimethanesulfonate

186204-37-5

(3aR,7aR)-4’-(benzo[d]isothiazol-3-yl)octahydrospiro[isoindole-2,1’-piperazin]-2-ium methanesulfonate

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; Temperature;92.4%

(R,R)-1,2-Bis(methanesulfonyloxymethyl)cyclohexane Specification

The (R,R)-1,2-Bis(methanesulfonyloxymethyl)cyclohexane, with the CAS registry number 186204-35-3, is also known as (1R-trans)-1,2-Cyclohexanedimethanol dimethanesulfonate. It belongs to the product category of Sulfur & Selenium Compounds. This chemical's molecular formula is C10H20O6S2 and molecular weight is 300.39. What's more, its systematic name is called (1R,2R)-1,2-Cyclohexanediylbis(methylene) dimethanesulfonate. 

Physical properties about (R,R)-1,2-Bis(methanesulfonyloxymethyl)cyclohexane are: (1)ACD/LogP: 0.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.79; (4)ACD/LogD (pH 7.4): 0.79; (5)ACD/BCF (pH 5.5): 2.35; (6)ACD/BCF (pH 7.4): 2.35; (7)ACD/KOC (pH 5.5): 64.11; (8)ACD/KOC (pH 7.4): 64.11; (9)#H bond acceptors: 6; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 103.5 Å2; (13)Index of Refraction: 1.482; (14)Molar Refractivity: 67.38 cm3; (15)Molar Volume: 236.387 cm3; (16)Surface Tension: 45.57 dyne/cm; (17)Density: 1.271 g/cm3; (18)Flash Point: 253.339 °C; (19)Enthalpy of Vaporization: 73.385 kJ/mol; (20)Boiling Point: 495.284 °C at 760 mmHg; (21)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=S(=O)(OC[C@@H]1CCCC[C@H]1COS(=O)(=O)C)C
(2) InChI: InChI=1S/C10H20O6S2/c1-17(11,12)15-7-9-5-3-4-6-10(9)8-16-18(2,13)14/h9-10H,3-8H2,1-2H3/t9-,10-/m0/s1
(3) InChIKey: JIHKCHWEXXZTOU-UWVGGRQHSA-N

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