Production Method 1

4333-56-6

24388-23-6

873-49-4

Reaction Conditions

1.1 Reagents: Ethanamine, N-methyl-, lithium salt Catalysts: 2723559-03-1 Solvents: Benzene ;  24 h, 25 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  25 °C

Reference

Air-Stable Iron-Based Precatalysts for Suzuki-Miyaura Cross-Coupling Reactions between Alkyl Halides and Aryl Boronic Esters

Wong, Alexander S.; et al, Organic Process Research & Development, 2021, 25(11), 2461-2472

Production Method 2

13943-33-4

873-49-4

Reaction Conditions

1.1 Reagents: Zinc Catalysts: Iron tetraphenylporphyrin chloride Solvents: Tetrahydrofuran ;  4 h, 60 °C

Reference

Carbene reactivity from alkyl and aryl aldehydes

Zhang, Lumin ; et al, Science (Washington, 2022, 377(6606), 649-654

Production Method 3

873-49-4

Reaction Conditions

1.1 Reagents: Triethylaluminum Solvents: Hexane ,  Perfluorohexane ;  rt; 58 h, rt

Reference

Cyclopropanation of alkenes with CH2I2/Et3Al by the phase-vanishing method based on fluorous phase screen

Matsubara, Hiroshi; et al, Journal of Fluorine Chemistry, 2008, 129(10), 951-954

Production Method 4

873-49-4

Reaction Conditions

1.1 Reagents: 2,4,6-Trichlorophenol ,  Diethylzinc Solvents: Dichloromethane
1.2 -

Reference

New family of cyclopropanating reagents: synthesis, reactivity, and stability studies of iodomethylzinc phenoxides

Charette, Andre B.; et al, Angewandte Chemie, 2000, 39(24), 4539-4542

Production Method 5

873-49-4

Reaction Conditions

1.1 Reagents: Azobisisobutyronitrile ,  Diethylzinc Solvents: Benzene

Reference

Simmons-Smith cyclopropanation reaction

Charette, Andre B.; et al, Organic Reactions (Hoboken, 2001, 58,

Production Method 6

23719-80-4

873-49-4

Reaction Conditions

1.1 Catalysts: (SP-4-3)-[1-[Bis(1,1-dimethylethyl)phosphino]-1′-[bis(tricyclo[3.3.1.13,7]dec-1-… Solvents: Tetrahydrofuran ;  5 min, rt
1.2 rt; 4 h, rt
1.3 Reagents: Water ;  rt

Reference

Tunable Unsymmetrical Ferrocene Ligands Bearing a Bulky Di-1-adamantylphosphino Motif for Many Kinds of Csp2-Csp3 Couplings

Xu, Guolin; et al, ACS Catalysis, 2022, 12(9), 5123-5135

Production Method 7

411235-57-9

873-49-4

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Palladium Solvents: Ethanol ,  Water ;  25 °C

Reference

Single-Atomic Pd Embedded 2D g-C3N4 Homogeneous Catalyst Analogs for Efficient LMCT Induced Full-Visible-Light Photocatalytic Suzuki Coupling

Jia, Xiaoxia; et al, ChemistrySelect, 2022, 7(40),

Production Method 8

411235-57-9

873-49-4

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Tricyclohexylphosphine ,  Palladium diacetate Solvents: Toluene ,  Water ;  24 - 48 h, 110 °C

Reference

Cooperative NHC/Photoredox Catalyzed Ring-Opening of Aryl Cyclopropanes to 1-Aroyloxylated-3-Acylated Alkanes

Zuo, Zhijun; et al, Angewandte Chemie, 2021, 60(48), 25252-25257

Production Method 9

4392-26-1

873-49-4

Reaction Conditions

1.1 Reagents: 9-Borabicyclo[3.3.1]nonane ,  Sodium hydroxide ,  Water Solvents: Water

Reference

Formation of carbon-carbon and carbon-heteroatom bonds via organoboranes and organoborates

Negishi, Ei-Ichi; et al, Organic Reactions (Hoboken, 1985, 33,

Production Method 10

14874-70-5

873-49-4

Reaction Conditions

1.1 Solvents: Dichloromethane

Reference

Synthesis and characterization of a stable iron-methylene complex; methylene activation by electron transfer catalysis (ETC)

Roger, Christophe; et al, Journal of the Chemical Society, 1989, (21), 1598-600

Production Method 11

16919-18-9

127522-73-0

873-49-4

Reaction Conditions

1.1 Solvents: 1,4-Dioxane

Reference

S-Alkylation of α-thioether iron compounds by trityl cation and [Fe(η-C5Me5)(CO)2(CH2)]+

Guerchais, Veronique; et al, Journal of the Chemical Society, 1989, (20), 1554-6

Production Method 12

74-95-3

873-49-4

Reaction Conditions

1.1 Reagents: Zinc Catalysts: 2640824-21-9 Solvents: Mesitylene ,  1,2-Dimethoxyethane ;  30 h, 60 °C

Reference

Structure and Methylene Transfer Reactivity of Thiolate-Bridged Dichromium Methylene Complexes Derived from Dihalomethane via Cleavage of Two Carbon-Halogen Bonds

Wei, Nianmin; et al, Organometallics, 2021, 40(10), 1434-1442

Production Method 13

80-11-5

873-49-4

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Methanol ,  Water
1.2 Solvents: Dimethylformamide
1.3 Catalysts: Palladium diacetate Solvents: Diethyl ether ,  Tetrahydrofuran ;  15 - 30 min, 25 °C
1.4 Reagents: Acetic acid

Reference

Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane

Dallinger, Doris; et al, Journal of Organic Chemistry, 2016, 81(14), 5814-5823

Production Method 14

49675-43-6

873-49-4

Reaction Conditions

Reference

The flash thermolysis of γ-sultines

Durst, Tony; et al, Journal of the Chemical Society, 1979, (4), 950-2

Production Method 15

60188-44-5

873-49-4

Reaction Conditions

1.1 Catalysts: Bis(acetylacetonato)nickel Solvents: Tetrahydrofuran

Reference

Nickel-catalyzed cyclopropanation of alkenes via methylene transfer from lithiated tert-butyl methyl sulfone

Gai, Yonghua; et al, Synlett, 1991, (1), 56-7

Production Method 16

4333-56-6

24388-23-6

873-49-4

Reaction Conditions

1.1 Reagents: Ethanamine, N-methyl-, lithium salt Catalysts: 2413474-02-7 (THF-deficient (≈ 0.75)) Solvents: Benzene ;  24 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Rational Design of an Iron-Based Catalyst for Suzuki-Miyaura Cross-Couplings Involving Heteroaromatic Boronic Esters and Tertiary Alkyl Electrophiles

Crockett, Michael P.; et al, Angewandte Chemie, 2020, 59(13), 5392-5397

Production Method 17

67966-89-6

873-49-4

Reaction Conditions

Reference

The photolysis of 2-phenylthietane 1,1-dioxides; preparation of substituted cyclopropanes

Finlay, John D.; et al, Synthesis, 1978, (8), 579-80

Production Method 18

17714-42-0

873-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide

Reference

Electrical effects of cycloalkyl groups

Hahn, Roger C.; et al, Journal of the American Chemical Society, 1968, 90(13), 3404-15

Production Method 19

17714-42-0

873-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide

Reference

Cyclopropylbenzene

Corbin, Thomas F.; et al, Organic Syntheses, 1964, 44, 30-3

Production Method 20

3360-52-9

873-49-4

Reaction Conditions

1.1 Reagents: 9-Borabicyclo[3.3.1]nonane ,  Sodium hydroxide ,  Water Solvents: Water

Reference

Formation of carbon-carbon and carbon-heteroatom bonds via organoboranes and organoborates

Negishi, Ei-Ichi; et al, Organic Reactions (Hoboken, 1985, 33,

Production Method 21

411235-57-9

873-49-4

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Tricyclohexylphosphine ,  Palladium diacetate Solvents: Toluene ,  Water ;  3 h, 100 °C

Reference

Cyclopropylboronic acid: synthesis and Suzuki cross-coupling reactions

Wallace, Debra J.; et al, Tetrahedron Letters, 2002, 43(39), 6987-6990

Production Method 22

3234-51-3

873-49-4

Reaction Conditions

1.1 Reagents: Diethylaluminum chloride ,  Magnesium Catalysts: Iron chloride (FeCl3) Solvents: Diethyl ether

Reference

Methylenation of carbonyl compounds with methylenedimagnesium iodide in the presence of diethylaluminum chloride

Dzhemilev, U. M.; et al, Izvestiya Akademii Nauk SSSR, 1989, (11), 2562-5

Production Method 23

3234-51-3

873-49-4

Reaction Conditions

1.1 Solvents: Dimethylformamide

Reference

A Novel Cathode Material for Cathodic Dehalogenation of 1,1-Dibromo Cyclopropane Derivatives

Guetz, Christoph; et al, Chemistry - A European Journal, 2015, 21(40), 13878-13882

Production Method 24

34782-55-3

873-49-4

Reaction Conditions

Reference

Preparation of cyclopropanes from α,β-unsaturated aldehydes, esters, and ketones

Chang, Yeong-Ho; et al, Journal of Organic Chemistry, 1978, 43(2), 373-4

Production Method 25

74-95-3

873-49-4

Reaction Conditions

1.1 Reagents: Lanthanum Catalysts: Iodine Solvents: Tetrahydrofuran ;  5 h, 67 °C

Reference

Lanthanum metal-assisted cyclopropanation of alkenes with gem-dihaloalkanes

Nishiyama, Yutaka; et al, Tetrahedron Letters, 2007, 48(36), 6405-6407

Production Method 26

74-95-3

873-49-4

Reaction Conditions

1.1 Reagents: Copper ,  Zinc Solvents: Diethyl ether ;  reflux

Reference

Simmons-Smith cyclopropanation reaction

Charette, Andre B.; et al, Organic Reactions (Hoboken, 2001, 58,

Production Method 27

873-49-4

Reaction Conditions

Reference

Sultones and Sultines via a Julia-Kocienski Reaction of Epoxides

Smith, Geoffrey M. T.; et al, Angewandte Chemie, 2015, 54(50), 15236-15240

Production Method 28

873-49-4

Reaction Conditions

1.1 Reagents: Dysprosium iodide (DyI2) Solvents: Tetrahydrofuran ;  0 °C; 0 °C → 50 °C; 6 h, 50 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Utility of Dysprosium Diiodide and Metallic Dysprosium as Reductants in Cyclopropanation Reactions of Alkenes with Dichloromethane

Xiang, Xu; et al, Organometallics, 2008, 27(8), 1959-1962

Production Method 29

873-49-4

Reaction Conditions

1.1 Reagents: Dimethylacetamide ,  Zinc Catalysts: Nickel, [μ-[(1,2,3,4-η:1,4,5,6-η)-benzene]][μ-[N,N′-[(1,8-naphthyridine-2,7-diyl… Solvents: Dichloromethane ;  43 h, 22 °C

Reference

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes

Zhou, You-Yun; et al, Angewandte Chemie, 2016, 55(9), 3171-3175

Production Method 30

873-49-4

Reaction Conditions

1.1 Catalysts: Tungsten(1+), carbonyl[1,1′-(η2-1,2-ethynediyl)bis[benzene]][hydrotris(1H-pyrazo…

Reference

Synthesis and Reactivity of Tungsten(II) Methylene Complexes

Gunnoe, T. Brent; et al, Organometallics, 1997, 16(22), 4865-4874

Cyclopropylbenzene Raw materials

• Diazald
• Phosphate(1-),hexafluoro-
• Borate(1-),tetrafluoro-
• Benzene,(1,3-dibromopropyl)-
• [1-(Benzenesulfonyl)cyclopropyl]benzene
• Cyclopropylboronic acid
• Dibromomethane
• 1-Phenylallyl Chloride (Stabilized with MEHQ)
• Benzene, [1-(chloromethyl)ethenyl]-
• Iodomethyl Benzoate
• Cyclopropylmagnesium Bromide (0.5M solution in THF)
• Bromocyclopropane
• 1,2-Oxathiolane, 5-phenyl-, 2-oxide
• Phenylboronic Acid Pinacol Ester
• (2,2-dibromocyclopropyl)benzene
• Propane, 2-methyl-2-(methylsulfonyl)-, ion(1-), lithium (9CI)
• Thietane, 2-phenyl-, 1,1-dioxide
• Iron(1+), dicarbonyl[methyl(triphenylmethyl)sulfonium η-methylide][(1,2,3,4,5-η)-1,2,3,4,5-pentylmethyl-2,4-cyclopentadien-1-yl]- (9CI)

Cyclopropylbenzene Preparation Products

• Cyclopropylbenzene (873-49-4)

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• 5. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzene and substituted derivatives
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives

• 2214-14-4(Benzene,(1-methylcyclopropyl)-)
• 56363-36-1(Benzene, 1-methyl-4-(2-phenylcyclopropyl)-, cis-)
• 56363-35-0(Benzene, 1-methyl-4-(2-phenylcyclopropyl)-, trans-)
• 58774-39-3(Benzene,[(2-phenylcyclopropyl)methyl]-)
• 121954-61-8(Benzene,1-(1-methylethyl)-3-propyl-)
• 3145-76-4(1-Methyl-2-phenylcyclopropane)
• 1138-47-2(Benzene,1,1'-(1R,2R)-1,2-cyclopropanediylbis-, rel-)
• 22975-62-8(Benzene,1-(1-methylethyl)-4-propyl-)
• 5070-01-9(Benzene, [(1R,2R)-2-methylcyclopropyl]-, rel-)
• 41380-88-5(Benzene,1-cyclopropyl-3-(1-methylethyl)-)