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Chlorodimedone

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Name

Chlorodimedone

EINECS N/A
CAS No. 7298-89-7 Density 1.17g/cm3
PSA 34.14000 LogP 1.55200
Solubility Insoluble in water. Melting Point 161-164 °C
Formula C8H11ClO2 Boiling Point 285.4 °C at 760 mmHg
Molecular Weight 174.627 Flash Point 119 °C
Transport Information N/A Appearance N/A
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 7298-89-7 (1,1-DIMETHYL-4-CHLORO-3,5-CYCLOHEXANEDIONE) Hazard Symbols N/A
Synonyms

Monochlorodimedone;2-chloro-5,5-dimethyl-cyclohexane-1,3-dione;1,3-Cyclohexanedione, 2-chloro-5,5-dimethyl-;2-Chlorodimedone;Monochlorodimedon;

Article Data 28

Chlorodimedone Synthetic route

126-81-8

dimedone

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane95%
With N-chloro-succinimide; toluene-4-sulfonic acid In dichloromethane at 0 - 20℃;91%
With N-chloro-succinimide In various solvent(s) at 20℃; for 0.5h;86%
126-81-8

dimedone

A

7298-86-4

2,2-dichloro-5,5-dimethylcyclohexane-1,3-dione

B

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

Conditions
ConditionsYield
With zinc chloride diethyl ether; iron(III)porphyrinate In dichloromethane for 0.5h;A 20%
B 74%
With sulfuryl dichloride In benzene at 25℃; for 18h;A 66%
B 26%
With potassium bromate; hydrogenchloride In N,N-dimethyl-formamide at 20℃; for 12h;A 10%
B 40%
With sodium hypochlorite; iron(III)porphyrinate; triethylbenzylammonium hypochlorite; acetic acid In dichloromethane for 0.5h; Product distribution; various iron(III)porphyrinate adducts, Lewis acids, various products and yields;
67-56-1

methanol

75-09-2

dichloromethane

1807-68-7

diazodimedone

A

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

B

3-hydroxy-5,5-dimethyl-2-methoxy-2-cyclohexen-1-one

C

2-chloro-3-(chloromethoxy)-5,5-dimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
dirhodium tetraacetate at 18 - 20℃; for 2h;A 65%
B 10%
C 6%
1807-68-7

diazodimedone

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

Conditions
ConditionsYield
With dirhodium tetraacetate; dichloromethane; saccharin at 0 - 20℃;61%
126-81-8

dimedone

A

3359-52-2

bis(4,4-dimethyl-2,6-dioxo-1-cyclohexyl) sulfide

B

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

Conditions
ConditionsYield
With SCl In benzene at 25℃; for 18h;A 5%
B 48%
126-81-8

dimedone

A

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

B

83538-02-7

2-Hydroxydimedon

Conditions
ConditionsYield
With 1H-imidazole; citrate-phosphate buffer; Mn-meso-tetrakis(3,5-disulphonatomesityl)porphyrinato; polyvinylpyridinium polymer (MnTMPS/PVP); dihydrogen peroxide; sodium chloride In water; acetonitrile for 1h; Product distribution; Ambient temperature; other reaction partner systems;A 9%
B 26%
7298-86-4

2,2-dichloro-5,5-dimethylcyclohexane-1,3-dione

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

Conditions
ConditionsYield
With acid aqueous solution; potassium iodide
With hydrogenchloride; tin(ll) chloride
With sodium acetate In acetic acid Heating;
Multi-step reaction with 2 steps
1: HCl / dimethylformamide / 0.08 h / 160 - 165 °C
2: NaOAc / acetic acid / Heating
View Scheme
7298-87-5

2-bromo-2-chloro-5,5-dimethylcyclohexane-1,3-dione

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

Conditions
ConditionsYield
With potassium hydroxide; urea
17554-71-1

2,4-dichloro-5,5-dimethyl-cyclohexane-1,3-dione

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

Conditions
ConditionsYield
With sodium acetate In acetic acid Heating;
126-81-8

dimedone

A

17530-69-7

3-chloro-5,5-dimethylcyclohex-2-en-1-one

B

56995-07-4

4',4',6,6-tetramethyl-6,7-dihydro-2'H,6'H-spiro[1,3-benzoxathiol-2,1'-cyclohexan]-2',4,6'(5H)-trion

C

7298-89-7

2-chloro-5,5-dimethyl-1,3-cyclohexanedione

D

C8H10Cl2O2S

Conditions
ConditionsYield
With thionyl chloride In benzene Product distribution; Ambient temperature; investigation of effect of reaction times on product distribution;

Chlorodimedone Specification

The Chlorodimedone, with the CAS registry number 7298-89-7, is also known as 1,3-Cyclohexanedione, 2-chloro-5,5-dimethyl-. This chemical's molecular formula is C8H11ClO2 and molecular weight is 174.62. What's more, its systematic name is 2-Chloro-5,5-dimethylcyclohexane-1,3-dione. 

Physical properties of Chlorodimedone are: (1)ACD/LogP: 0.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.4; (4)ACD/LogD (pH 7.4): -2.07; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 34.14 Å2; (13)Index of Refraction: 1.476; (14)Molar Refractivity: 42.08 cm3; (15)Molar Volume: 149.1 cm3; (16)Polarizability: 16.68×10-24cm3; (17)Surface Tension: 35.5 dyne/cm; (18)Density: 1.17 g/cm3; (19)Flash Point: 119 °C; (20)Enthalpy of Vaporization: 52.44 kJ/mol; (21)Boiling Point: 285.4 °C at 760 mmHg; (22)Vapour Pressure: 0.00281 mmHg at 25°.

Preparation: this chemical can be prepared by 5,5-Dimethyl-cyclohexane-1,3-dione at the ambient temperature. This reaction will need reagent KIO3 and ClSiMe3 and solvent dimethylformamide with the reaction time of 6 hours. The yield is about 82%.

chlorodimedone is prepared by 5,5-Dimethyl-cyclohexane-1,3-dione

Uses of Chlorodimedone: it can be used to produce 2-Acetoxy-6-hydroxy-4,4-dimethyl-2,5-cyclohexadien-1-one. It will need reagent NaH and solvent dimethylformamide. The yield is about 79%.

Use chlorodimedone to produce 2-Acetoxy-6-hydroxy-4,4-dimethyl-2,5-cyclohexadien-1-one

When you are using this chemical, please be cautious about it as the following:
Do not breathe dust and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1C(Cl)C(=O)CC(C)(C)C1
(2)Std. InChI: InChI=1S/C8H11ClO2/c1-8(2)3-5(10)7(9)6(11)4-8/h7H,3-4H2,1-2H3
(3)Std. InChIKey: VOBIHUAWDXUCPH-UHFFFAOYSA-N

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