Production Method 1

768-95-6

935-56-8

Reaction Conditions

1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  rt; 18 h, rt

Reference

Preparation of tripartite androgen receptor eliminators useful for treating an androgen receptor signaling-mediated diseases

, World Intellectual Property Organization, , ,

Production Method 2

25236-60-6

935-56-8

Reaction Conditions

1.1 Reagents: Iron chloride (FeCl3) Solvents: Dichloromethane ;  5 min, rt

Reference

Iron(III)-Catalyzed Halogenations by Substitution of Sulfonate Esters

Ortega, Nuria; Feher-Voelger, Andres; Brovetto, Margarita; Padron, Juan I.; Martin, Victor S.; et al, Advanced Synthesis & Catalysis, 2011, 353(6), 963-972

Production Method 3

281-23-2

935-56-8

Reaction Conditions

1.1 Reagents: Carbon tetrachloride Catalysts: Acetonitrile ,  Tris(acetylacetonato)manganese Solvents: Carbon tetrachloride ;  1 h, 200 °C

Reference

Chlorination of adamantane and its derivatives by carbon tetrachloride in the presence of manganese, vanadium, and molybdenum-containing catalysts

Khusnutdinov, R. I.; Shchadneva, N. A.; Baiguzina, A. R.; Lavrent'eva, Yu. Yu.; Burangulova, R. Yu.; et al, Neftekhimiya, 2004, 44(2), 148-155

Production Method 4

281-23-2

935-56-8

Reaction Conditions

1.1 Reagents: Sulfuric acid Solvents: Carbon tetrachloride

Reference

Biologically active polycycloalkanes. 1. Antiviral adamantane derivatives

Aigami, Koji; Inamoto, Yoshiaki; Takaishi, Naotake; Hattori, Kenichi; Takatsuki, Akira; et al, Journal of Medicinal Chemistry, 1975, 18(7), 713-21

Production Method 5

768-95-6

935-56-8

Reaction Conditions

1.1 Reagents: Chloroform ,  Polyisoprene Catalysts: Titanium ,  Iron(III) acetylacetonate Solvents: Chloroform ;  0.5 h, 25 °C

Reference

Chlorination method and catalyst system for the synthesis of 1- and 2-chloroadamantanes from 1- and 2-adamantanols and chloroform

, Russian Federation, , ,

Production Method 6

828-51-3

935-56-8

Reaction Conditions

1.1 Reagents: tert-Butyl hypochlorite Catalysts: Silver(1+), bis(1,10-phenanthroline-κN1,κN10)-, (T-4)-, 1,1,1-trifluoromethanesu… Solvents: Acetonitrile ;  3 h, rt

Reference

Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids

Wang, Zhentao; Zhu, Lin; Yin, Feng; Su, Zhongquan; Li, Zhaodong; et al, Journal of the American Chemical Society, 2012, 134(9), 4258-4263

Production Method 7

768-95-6

935-56-8

Reaction Conditions

1.1 Reagents: Carbon tetrachloride ,  Phosphine, [4-(1R,2R,4R)-bicyclo[2.2.1]hept-5-en-2-ylphenyl]diphenyl-, rel-, tri… Solvents: Dichloromethane

Reference

ROMPgel-Supported Triphenylphosphine with Potential Application in Parallel Synthesis

Aarstad, Erik; Barrett, Anthony G. M.; Hopkins, Brian T.; Koebberling, Johannes, Organic Letters, 2002, 4(11), 1975-1977

Production Method 8

768-92-3

935-56-8

Reaction Conditions

1.1 Reagents: Titanium tetrachloride Solvents: Dichloromethane

Reference

Halogen-exchange reactions between alkyl fluorides and boron trihalides or titanium tetrahalides. A convenient synthesis of alkyl halides from alkyl fluorides

Namavari, Mohammad; Satyamurthy, N.; Barrio, Jorge R., Journal of Fluorine Chemistry, 1995, 72(1), 89-93

Production Method 9

768-95-6

935-56-8

Reaction Conditions

1.1 Reagents: Tin tetrachloride

Reference

A simple method for the conversion of adamantyl, benzyl and benzyhydryl alcohols to their corresponding bromides and chlorides and the transhalogenation of adamantyl, benzyl, benzhydryl and tertiary alkyl bromides and chlorides

Amrollah-Madjdabadi, A.; Pham, Tung N.; Ashby, E. C., Synthesis, 1989, (8), 614-16

Production Method 10

2094-72-6

935-56-8

Reaction Conditions

1.1 Reagents: Carbon tetrachloride ,  Sodium pyrithione Catalysts: 4-(Dimethylamino)pyridine Solvents: Carbon tetrachloride

Reference

Synthesis of bridgehead halides by Barton halodecarboxylation

Della, Ernest W.; Tsanaktsidis, John, Australian Journal of Chemistry, 1989, 42(1), 61-9

Production Method 11

281-23-2

935-56-8

Reaction Conditions

1.1 Reagents: Carbon tetrachloride Catalysts: Acetonitrile ,  Tris(acetylacetonato)manganese ;  1 h, 200 °C

Reference

Method of synthesis of 1-chloroadamantane and chlorodiamantanes

, Russian Federation, , ,

Production Method 12

118334-83-1

935-56-8

Reaction Conditions

1.1 Reagents: Dabco Solvents: Carbon tetrachloride ,  tert-Butanol ,  Water

Reference

Photochemical chlorodecarboxylation via an electron transfer mechanism

Okada, Keiji; Okamoto, Kazushige; Oda, Masaji, Journal of the Chemical Society, 1989, (21), 1636-7

Production Method 13

612058-38-5

935-56-8

Reaction Conditions

1.1 Reagents: Diisopropyl azodicarboxylate Solvents: Dichloromethane ;  1 min, rt
1.2 Reagents: Chlorotrimethylsilane ;  15 min, rt

Reference

Alkylphosphinites as Synthons for Stabilized Carbocations

Ochmann, Lukas ; Kessler, Mika L.; Schreiner, Peter R., Organic Letters, 2022, 24(7), 1460-1464

Production Method 14

828-51-3

935-56-8

Reaction Conditions

1.1 Reagents: tert-Butyl hypochlorite Catalysts: Silver(1+), bis(1,10-phenanthroline-κN1,κN10)-, (T-4)-, 1,1,1-trifluoromethanesu… Solvents: Acetonitrile ;  rt

Reference

Catalytic Decarboxylation/Carboxylation Platform for Accessing Isotopically Labeled Carboxylic Acids

Tortajada, Andreu ; Duan, Yaya; Sahoo, Basudev ; Cong, Fei; Toupalas, Georgios; et al, ACS Catalysis, 2019, 9(7), 5897-5901

Production Method 15

281-23-2

935-56-8

Reaction Conditions

1.1 Reagents: Carbon tetrachloride Catalysts: Iron(III) acetylacetonate Solvents: Ethanol ;  6 h, 160 °C

Reference

Method of producing 1-chloroadamantane

, Russian Federation, , ,

Production Method 16

768-95-6

935-56-8

Reaction Conditions

1.1 Reagents: Benzil ,  Chlorodimethylsilane Catalysts: Indium trichloride Solvents: Dichloromethane ;  82 h, rt

Reference

Direct chlorination of alcohols: synthesis of ethyl 3-chloro-3-phenylpropanoate [benzenepropanoic acid, β-chloro-, ethyl ester]

Yasuda, Makoto; Yamasaki, Satoshi; Onishi, Yoshiyuki; Baba, Akio, Organic Syntheses, 2006, 83, 38-44

Production Method 17

768-95-6

935-56-8

Reaction Conditions

1.1 Reagents: Benzil ,  Chlorodimethylsilane Catalysts: Indium trichloride Solvents: Dichloromethane ;  82 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt

Reference

Indium-Catalyzed Direct Chlorination of Alcohols Using Chlorodimethylsilane-Benzil as a Selective and Mild System

Yasuda, Makoto; Yamasaki, Satoshi; Onishi, Yoshiyuki; Baba, Akio, Journal of the American Chemical Society, 2004, 126(23), 7186-7187

Production Method 18

768-95-6

935-56-8

Reaction Conditions

1.1 Reagents: Triphenylphosphine ,  Selenium, dichlorodimethyl-, (T-4)- Solvents: Chloroform

Reference

Triphenylphosphine/Dichloroselenurane: A new reagent for a selective conversion of alcohols into alkyl chlorides

Drabowicz, Jozef; Luczak, Jerzy; Mikolajczyk, Marian, Journal of Organic Chemistry, 1998, 63(25), 9565-9568

Production Method 19

768-95-6

935-56-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  2 h, rt

Reference

2-Ethyl-3-(4-hydroxybenzoyl)benzofuran compounds and their preparation, pharmaceutical compositions and use in the treatment of hyperuricemia and gout

, China, , ,

Production Method 20

24375-05-1

935-56-8

Reaction Conditions

Reference

Thermolysis of N,N-dihalo derivatives of bridgehead and neopentylamines to the corresponding halides

Roberts, John T.; Rittberg, Barry R.; Kovacic, Peter; Scalzi, Francis V.; Seely, Michael J., Journal of Organic Chemistry, 1980, 45(26), 5239-43

1-Chloroadamantane Raw materials

• Tricyclo[3.3.1.13,7]decan-1-ol,1-methanesulfonate
• Adamantane
• 1-Fluoroadamantane
• PHOSPHINOUS ACID, DIPHENYL-, TRICYCLO[3.3.1.13,7]DEC-1-YL ESTER
• 1-Adamantanol
• adamantane-1-carbonyl chloride
• Tricyclo[3.3.1.13,7]decane-1-carboxylic acid, 1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl ester
• Tricyclo[3.3.1.13,7]decan-1-amine, N,N-dichloro-
• Adamantane-1-carboxylic acid

1-Chloroadamantane Preparation Products

• 1-Chloroadamantane (935-56-8)

• 1. An integrated system for field analysis of Cd(ii) and Pb(ii) via preconcentration using nano-TiO2/cellulose paper composite and subsequent detection with a portable X-ray fluorescence spectrometer?
  Xiaofeng Lin RSC Adv., 2016,6, 9002-9006
• 2. An air-stable organometallic polymer containing titanafluorene moieties obtained by the Sonogashira–Hagihara cross-coupling polycondensation?
  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043
• 3. An antioxidant self-healing hydrogel for 3D cell cultures?
  Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei Tao J. Mater. Chem. B, 2020,8, 1383-1388
• 4. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210
• 5. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554

• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Organochlorides Organochlorides
• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Organochlorides
• Solvents and Organic Chemicals Organic Compounds Organic Halides

• 1445-98-3(1-Chloro-1-ethylcyclohexane)
• 27011-46-7(Tricyclo[4.3.1.13,8]undecane,1-chloro-)
• 16641-30-8(Naphthalene,1,6-dichlorodecahydro-1,6-dimethyl-4-(1-methylethyl)-, (1S,4S,4aS,6S,8aR)-)
• 10207-94-0(Naphthalene,1,6-dichlorodecahydro-1,6-dimethyl-4-(1-methylethyl)-, (1S,4S,4aS,6R,8aS)-)
• 1123-39-3(Bicyclo[2.2.2]octane,1,4-dichloro-)
• 931-78-2(Cyclohexane,1-chloro-1-methyl-)
• 352431-55-1(1-Chloroadamantane-d15)
• 27621-71-2(Cyclohexane,1,4-dichloro-1-methyl-4-(1-methylethyl)-)
• 1073-15-0(Cyclohexane, 1-chloro-1,4-dimethyl-)
• 30899-14-0(Bicyclo[2.2.1]heptane,chloro- (9CI))