Cas no 822-87-7 (2-chlorocyclohexan-1-one)

2-chlorocyclohexan-1-one structure
2-chlorocyclohexan-1-one structure
Product Name:2-chlorocyclohexan-1-one
CAS No:822-87-7
MF:C6H9ClO
MW:132.588061094284
MDL:MFCD00001626
CID:39977
PubChem ID:13203
Update Time:2024-10-27

2-chlorocyclohexan-1-one Chemical and Physical Properties

Names and Identifiers

    • 2-CHLOROCYCLOHEXANONE
    • 2-chloro-cyclohexanon
    • alpha-Chlorocyclohexanone
    • 2-Chloro-1-cyclohexanone
    • 2-Chlorocyclohexanone (stabilized with HQ)
    • 2-Chlorocyclohexan-1-one
    • 2-Chlorocyclohexanone (stabilized with HQ + CaCO3)
    • 2-CHLOROCYCLOHEXANONE , STABILIZED WITH CALCIUM CARBONATE
    • MAGNESIUM OXIDE
    • Cyclohexanone,2-chloro-, (?à)-
    • (?à)-2-Chloro-1-cyclohexanone
    • (?à)-2-Chlorocyclohexanone
    • NSC 12439
    • a-Chlorocyclohexanone
    • CYCLOHEXANONE, 2-CHLORO-
    • 2-Chlorocyclohexonone
    • .alpha.-Chlorocyclohexanone
    • CCHNWURRBFGQCD-UHFFFAOYSA-N
    • 2-chloro-cyclohexanone
    • 2-chlorocylohexanone
    • 2-chlorocyclohexanon
    • 2-chloro cyclohexanone
    • WLN: L6VTJ BG
    • DSSTox_CID_1530
    • 2-chloro-cyclohexan-1-one
    • DSSTox_RID_76200
    • DSSTox_GSID_21530
    • 2-Chlorocyclohexanone (ACI)
    • Cyclohexanone, 2-chloro-, (±)- (ZCI)
    • (±)-2-Chloro-1-cyclohexanone
    • (±)-2-Chlorocyclohexanone
    • α-Chlorocyclohexanone
    • CS-W013402
    • AKOS016889127
    • FT-0632986
    • UNII-1134E5H2KV
    • Q27251237
    • AC1582
    • AS-57502
    • EINECS 212-505-5
    • 1134E5H2KV
    • CHEMBL3183260
    • (+/-)-2-CHLORO-1-CYCLOHEXANONE
    • SCHEMBL186361
    • NSC-12439
    • AKOS001133267
    • Tox21_200522
    • (+/-)-2-CHLOROCYCLOHEXANONE
    • Z94598693
    • EN300-18889
    • MFCD00001626
    • NCGC00248671-01
    • CAS-822-87-7
    • NCGC00258076-01
    • DTXCID001530
    • DTXSID1021530
    • NSC12439
    • SY038921
    • 2-CHLOROCYCLOHEXANONE, (+/-)-
    • F0001-2107
    • NS00022820
    • 822-87-7
    • 2-Chlorocyclohexanone, 98%
    • BBL011103
    • 2-Chlorocyclohexanone stabilized over calcium carbonate/magnesium oxide
    • DB-056596
    • STK802347
    • 2-chlorocyclohexan-1-one
    • MDL: MFCD00001626
    • Inchi: 1S/C6H9ClO/c7-5-3-1-2-4-6(5)8/h5H,1-4H2
    • InChI Key: CCHNWURRBFGQCD-UHFFFAOYSA-N
    • SMILES: O=C1C(Cl)CCCC1
    • BRN: 774100

Computed Properties

  • Exact Mass: 132.03400
  • Monoisotopic Mass: 132.034
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 0
  • Complexity: 101
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 17.1
  • Surface Charge: 0
  • Tautomer Count: 3
  • XLogP3: 1.5

Experimental Properties

  • Color/Form: White crystals
  • Density: 1.161?g/mL?at 25?°C(lit.)
  • Melting Point: 23?°C (lit.)
  • Boiling Point: 107°C/50mmHg(lit.)
  • Flash Point: Fahrenheit: 179.6 ° f < br / > Celsius: 82 ° C < br / >
  • Refractive Index: n20/D 1.484(lit.)
  • Water Partition Coefficient: Insoluble in water.
  • PSA: 17.07000
  • LogP: 1.73690
  • Solubility: Insoluble in water, soluble in alcohol and ether

2-chlorocyclohexan-1-one Security Information

  • Symbol: GHS07
  • Prompt:warning
  • Signal Word:Warning
  • Hazard Statement: H315,H317,H319,H335
  • Warning Statement: P261,P280,P305+P351+P338
  • Hazardous Material transportation number:UN 3335 9
  • WGK Germany:3
  • Hazard Category Code: 36/37/38-43
  • Safety Instruction: S26-S36/37-S37/39
  • FLUKA BRAND F CODES:10-19
  • RTECS:GW1225000
  • Hazardous Material Identification: Xi
  • TSCA:Yes
  • Storage Condition:<0°C
  • Risk Phrases:R36/37/38

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2-chlorocyclohexan-1-one Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Carbon tetrachloride ,  Water ;  20 - 25 °C
Reference
Synthesis of 2-halogenated cyclic ketones
Kashparov, V. P.; et al, Izvestiya Vysshikh Uchebnykh Zavedenii, 2008, (5), 58-60

Production Method 2

Reaction Conditions
1.1 Reagents: 1H-Imidazolium, 1-methyl-3-octyl-, (trichloride) (1:1) ;  30 min, 0 °C
Reference
Alkylimadazolium chloride: a medium of chlorine absorption and chlorination
Shi, Shenyi; et al, Youji Huaxue, 2011, 31(2), 227-230

Production Method 3

Reaction Conditions
1.1 Catalysts: Lead tetraacetate ,  Calcium chloride Solvents: Methanol ;  22 °C
Reference
Lead(IV) Acetate1
Mihailovic, Mihailo Lj.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 4

Reaction Conditions
1.1 Reagents: Chlorosuccinimide Catalysts: Iridium, di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopen… Solvents: Tetrahydrofuran ,  Water ;  24 h, rt
Reference
Iridium-Catalyzed 1,3-Hydrogen Shift/Chlorination of Allylic Alcohols
Ahlsten, Nanna; et al, Angewandte Chemie, 2013, 52(24), 6273-6276

Production Method 5

Reaction Conditions
1.1 Reagents: Piperidine, lithium salt (1:1) Solvents: Diethyl ether ,  Tetrahydrofuran ;  -78 °C
Reference
Lithium piperidide
Snieckus, Victor; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, 1, 1-2

Production Method 6

Reaction Conditions
1.1 Reagents: Cupric chloride Solvents: Dimethylformamide
Reference
Syntheses of α-chloroketones by reaction of silyl enol ethers with copper(II) chloride and iron(III) chloride
Ito, Yoshihiko; et al, Journal of Organic Chemistry, 1980, 45(10), 2022-4

Production Method 7

Reaction Conditions
1.1 Reagents: Hydrochloric acid Solvents: Dichloromethane ,  Water
Reference
Ring-Fused Cyclopropanone N,O-Acetals. Electrochemical Preparation and Their Reactivities under Acidic Conditions
Chiba, Toshiro; et al, Journal of Organic Chemistry, 1999, 64(7), 2516-2519

Production Method 8

Reaction Conditions
1.1 Reagents: Chlorotrimethylsilane ,  Chromium trioxide Solvents: Carbon tetrachloride
Reference
Oxidation of olefins using chromic anhydride-chlorotrimethylsilane. A convenient synthesis of α-chloro ketones
Lee, Jong Gun; et al, Tetrahedron Letters, 1989, 30(2), 193-6

Production Method 9

Reaction Conditions
Reference
Product class 6: α-hetero-substituted ketones
Suffert, J., Science of Synthesis, 2005, 26, 869-969

Production Method 10

Reaction Conditions
1.1 Reagents: Ethylmagnesium bromide Solvents: Tetrahydrofuran
1.2 Reagents: Ammonium chloride Solvents: Water
Reference
Ligand exchange reaction of sulfoxides in organic synthesis: a new synthesis of α-chloro ketones from carbonyl compounds with one-carbon homologation
Satoh, Tsuyoshi; et al, Tetrahedron, 1995, 51(3), 703-10

Production Method 11

Reaction Conditions
1.1 Reagents: Hexachloroacetone Solvents: Benzene ;  30 min, 0 °C; 0 °C → rt; 1 h, rt
1.2 Reagents: Acetic acid ,  Sodium acetate Solvents: Water ;  1 h, reflux
Reference
Heterolytic and homolytic reactions of polyhalogenated carbonyl compounds
Laskovics, Frederick Mark, 1977, , ,

Production Method 12

Reaction Conditions
1.1 Solvents: Diethyl ether
2.1 Reagents: Phosphoric acid
Reference
Halogenation of enamines - synthesis of β-halo iminium halides
Seufert, Walter; et al, Chemische Berichte, 1979, 112(5), 1670-6

Production Method 13

Reaction Conditions
1.1 Reagents: Mercuric chloride ,  Iodine Solvents: Dichloromethane
Reference
Mercury(II) chloride-iodine. A useful reagent for the direct and regiospecific synthesis of α-iodo carbonyl compounds
Barluenga, Jose; et al, Synthesis, 1986, (8), 678-80

Production Method 14

Reaction Conditions
1.1 Reagents: Lead tetraacetate ,  Calcium chloride Solvents: Methanol ;  rt
Reference
Lead(IV) acetate
Mihailovic, Mihailo Lj.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2005, 1, 1-8

Production Method 15

Reaction Conditions
1.1 Reagents: Methanol ,  Dimethyl sulfoxide ,  Oxalyl chloride ,  Triethylamine Solvents: Dichloromethane
Reference
Reaction of epoxides with activated DMSO reagent. General method for synthesis of α-chloro carbonyl compounds: application in asymmetric synthesis of (3S)-2,3-oxidosqualene
Raina, Sushil; et al, Tetrahedron, 1995, 51(8), 2467-76

Production Method 16

Reaction Conditions
1.1 Catalysts: Methane, 1,1′-thiobis-, compd. with chlorine (1:1) Solvents: Dichloromethane
1.2 Catalysts: Triethylamine
Reference
Dimethyl Sulfide-Chlorine
Murray, William V., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 17

Reaction Conditions
1.1 Reagents: Toluene Catalysts: Titanium tetrachloride Solvents: Dichloromethane ;  rt
Reference
Titanium(IV) chloride
Gundersen, Lise-Lotte; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007, 1, 1-26

Production Method 18

Reaction Conditions
Reference
Convenient preparative method of α-chloroketones
Kuwajima, Isao; et al, Chemistry Letters, 1973, (2), 197-200

Production Method 19

Reaction Conditions
1.1 Reagents: Hexachloroacetone Solvents: Acetonitrile ;  30 min, 0 °C; 0 °C → rt; 1 h, rt
1.2 Reagents: Acetic acid ,  Sodium acetate Solvents: Water ;  1 h, reflux
Reference
Heterolytic and homolytic reactions of polyhalogenated carbonyl compounds
Laskovics, Frederick Mark, 1977, , ,

Production Method 20

Reaction Conditions
1.1 Catalysts: Graphite ,  Ammonium tungsten hydroxide oxide ((NH4)6W6(OH)7O17) Solvents: Water ;  15 min, rt
1.2 Reagents: Hydrogen peroxide Solvents: Water ;  rt; 11 h, rt → 70 °C
Reference
Ammonium Tungstate as an Effective Catalyst for Selective Oxidation of Alcohols to Aldehydes or Ketones with Hydrogen Peroxide under Water - A Synergy of Graphene Oxide
Fu, Huihui; et al, Synlett, 2018, 29(4), 447-451

Production Method 21

Reaction Conditions
1.1 Catalysts: Levulinic acid ,  Hydrochloric acid ,  Water ;  4 h, rt → 75 °C
Reference
Conversion of α,α'-dichlorodiazene dioxides using levulinic acid under solvent-free conditions to α-chloroketones through a three-step domino process
Vimala, B. C.; et al, Journal of Chemical Sciences (Bangalore, 2009, 121(6), 1011-1015

Production Method 22

Reaction Conditions
1.1 Reagents: Sulfuryl chloride ,  Sulfuryl chloride fluoride
Reference
Synthetic methods and reactions. 123. Preparation of α-chloro ketones from enol silyl ethers with sulfuryl chloride fluoride and sulfuryl chloride
Olah, George A.; et al, Journal of Organic Chemistry, 1984, 49(11), 2032-4

Production Method 23

Reaction Conditions
1.1 Reagents: Cesium chloride Catalysts: Fluorotrimethylsilane Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ;  3 h, 23 °C
Reference
Development of a generic activation mode: nucleophilic α-substitution of ketones via oxy-allyl cations
Vander Wal, Mark N.; et al, Chemical Science, 2013, 4(8), 3075-3079

Production Method 24

Reaction Conditions
Reference
Metal-catalyzed organic photoreactions. One-step synthesis of chlorinated ketones from olefins by the photo-oxidation in the presence of iron(III) chloride
Murayama, Eigoro; et al, Chemistry Letters, 1978, (2), 161-4

Production Method 25

Reaction Conditions
1.1 Reagents: Hydrochloric acid ,  Water Solvents: Water
Reference
Synthesis and thermolysis of 2-amino-1-cycloalkenylsulfonium salts
Vilsmaier, Elmar; et al, Chemische Berichte, 1979, 112(8), 2997-3006

Production Method 26

Reaction Conditions
1.1 Reagents: Trichloroisocyanuric acid Catalysts: Tempo Solvents: Dichloromethane ;  rt; 10 min, rt
1.2 Reagents: Methanol ;  rt; 2 h, rt
Reference
Direct Conversion of Alcohols to α-Chloro Aldehydes and α-Chloro Ketones
Jing, Yuanyuan; et al, Organic Letters, 2014, 16(18), 4932-4935

Production Method 27

Reaction Conditions
Reference
Product class 6: α-hetero-substituted ketones
Suffert, J., Science of Synthesis, 2005, 26, 869-969

Production Method 28

Reaction Conditions
1.1 Reagents: Sodium chloride Catalysts: Lead tetraacetate
Reference
Lead(IV) acetate/metal halide reagents; I. Synthesis of α-haloketones
Motohashi, Shigeyasu; et al, Synthesis, 1982, (12), 1021-3

Production Method 29

Reaction Conditions
1.1 Reagents: Phosphorus oxychloride Solvents: Acetonitrile ,  Sulfolane ;  10 h, reflux; cooled
1.2 Reagents: Water Solvents: Diethyl ether ;  cooled
Reference
A new approach to the synthesis of α-chlorocycloalkanones
Li, Xing Hai; et al, Chinese Chemical Letters, 2007, 18(12), 1476-1478

2-chlorocyclohexan-1-one Raw materials

2-chlorocyclohexan-1-one Preparation Products

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