947-04-6

Basic information

• Product Name: CYCLODODECANONE ISOOXIME
• Synonyms: 12-amino-dodecanoicacilactam;1-Aza-2-cyclotridecanone;2-Oxo-dodecamethylenimine;Aza-cyclotridecan-2-on;Azacyclotridecan-2-one;Cyclododecalactam;Dodecalactam;Dodecanoic acid, 12-amino-, lactam
• CAS NO: 947-04-6
• Molecular Formula: C12H23NO
• Molecular Weight: 197.32
• EINECS: 213-424-8
• Product Categories: Organics;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactams;Organic Building Blocks
• Mol File: 947-04-6.mol

Chemical Properties

• Melting Point: 150-153 °C(lit.)
• Boiling Point: 334.44°C (rough estimate)
• Flash Point: 195 °C
• Appearance: /
• Density: 0.9415 (rough estimate)
• Vapor Pressure: 0.000453mmHg at 25°C
• Refractive Index: 1.4400 (estimate)
• PKA: 16.91±0.20(Predicted)
• Water Solubility: 223mg/L at 20℃
• BRN: 122031
• CAS DataBase Reference: CYCLODODECANONE ISOOXIME(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLODODECANONE ISOOXIME(947-04-6)
• EPA Substance Registry System: CYCLODODECANONE ISOOXIME(947-04-6)

Safety Data

• RIDADR: 3257
• WGK Germany: 1
• RTECS: CL6940000
• HazardClass: IRRITANT
• Hazardous Substances Data: 947-04-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
CYCLODODECANONE ISOOXIME is used as a chemical intermediate for the synthesis of various compounds and materials. Its unique structure and properties make it a valuable component in the development of new chemical products and processes.
Used in Pharmaceutical Industry:
CYCLODODECANONE ISOOXIME is used as a building block in the synthesis of pharmaceutical compounds. Its reactivity and versatility allow for the creation of new drugs with potential therapeutic applications.
Used in Research and Development:
CYCLODODECANONE ISOOXIME is used as a research compound in academic and industrial laboratories. Its unique properties and reactivity make it an interesting subject for scientific investigations and the development of new technologies.

Preparation

One route to dodecyllactam is from butadiene as follows: Butadiene is trimerized with a Ziegler-Natta catalyst to give 1,5,9-cyclododecatriene which is then hydrogenated to cyclododecane. Dodecyllactam is then obtained by a series of reactions similar to those used to prepare caprolactam from cyclohexane.

Health Hazard

The acute oral LD50 was 2,330 mg/kg bw (rat) with central nervous system stimulation (trembling, convulsive twitches, ataxia) as the main clinical sign appearing at about 1,580 mg/kg bw. The dermal LD50 was greater than 2,000 mg/kg bw (rat). Decreased food consumption and stagnation of body weight development were noted. Validacute inhalation studies are not available. Azacyclotridecan-2-one was not irritating to the rabbit skin or eye (OECD TG 404, 405). It was not sensitizing in aguinea pig maximization test (OECD TG 406; 1981).

Purification Methods

Azacyclotridecan-2-one crystallises from CHCl3 and is stored over P2O5 in a vacuum desiccator. [Beilstein 26/1 V 566.]

InChI:InChI=1/C12H23NO/c14-12-10-8-6-4-2-1-3-5-7-9-11-13-12/h1-11H2,(H,13,14)

Synthetic route

cyclododecanone oxime (946-89-4) → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine In acetonitrile for 1h; Product distribution / selectivity; Heating / reflux;	100%
With 1,3,5-trichloro-2,4,6-triazine In Isopropylbenzene; Cyclooctan at 113℃; for 0.5h; Product distribution / selectivity;	100%
With 1,3,5-trichloro-2,4,6-triazine In octane at 113℃; for 1h; Product distribution / selectivity;	100%

cyclooctanone oxime (1074-51-7) + cyclododecanone oxime (946-89-4) → 2-azacyclononanone (935-30-8) + 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine In Cyclooctan at 113℃; for 0.5h; Product distribution / selectivity;	A 50% B 100%

cyclododecanone oxime (946-89-4) + 2,4-dichloro-6-cyclododecylidene'aminooxy-1,3,5-triazine → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
In acetonitrile	100%

cyclododecanone oxime (946-89-4) + 2-chloro-4,6-bis(cyclododecylidene-aminooxy)-1,3,5-triazine (1178530-68-1) → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With hydrogenchloride In acetonitrile	100%

azacyclotridec-10-en-2-one → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr;	99%

cyclododecanone (830-13-7) → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With sodium azide; sulfuric acid In ethyl acetate at 60 - 77℃; for 2h; Reagent/catalyst; Solvent; Temperature;	98%
With sodium azide; sulfuric acid; silica gel at 60℃; for 0.5h; Schmidt reaction;	95%
With hydroxylamine hydrochloride In benzonitrile at 90℃; for 12h; Beckmann Rearrangement; Inert atmosphere;	95%

cyclododecanone oxime hydrochloride (3046-04-6) → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With sulfuric acid for 0.416667h; Product distribution / selectivity;	95.1%

C15H31NOSi (136848-31-2) → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
silver hexafluoroantimonate; antimonypentachloride In dichloromethane; acetonitrile for 3h; Heating;	77%
With silver hexafluoroantimonate; antimonypentachloride In acetonitrile for 3h; Heating;	77%

1-[3-(tritylthio)propanoyl]-1-azacyclotridecan-2-one → 2-azacyclotridecanone (947-04-6) + 1-thia-5-azacycloheptadecane-4,17-dione

Conditions	Yield
Stage #1: 1-[3-(tritylthio)propanoyl]-1-azacyclotridecan-2-one With trifluoroacetic acid In dichloromethane for 0.05h; Inert atmosphere; Stage #2: With chlorotriisopropylsilane In dichloromethane for 0.5h; Inert atmosphere; Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 18h; Reagent/catalyst;	A 4% B 56%

12-Aminododecanoic acid (693-57-2) → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With triethylamine; N-Hexadecyl-2-chloropyridinium iodide In 1,2-dichloro-ethane at 70℃; for 24h;	50%
With di(n-butyl)tin oxide In 1,3,5-trimethyl-benzene for 24h; Heating;	25%
With triethylamine; N-Hexadecyl-2-chloropyridinium iodide In 1,2-dichloro-ethane at 70℃; for 24h; Mechanism; also with N-methyl-2-chloropyridinium iodide, effect of micelles;

cyclododecanone oxime (946-89-4) + N-cyclohexylidenemethylamine (6407-35-8) → caprolactam (105-60-2) + 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With 1,3,5-trichloro-2,4,6-triazine In Isopropylbenzene at 113℃; for 1.58333h; Product distribution / selectivity;	A 20% B 50%

cyclotridecyne (5601-68-3) → 2-azacyclotridecanone (947-04-6)

Conditions	Yield
With nitromethane; trifluoromethylsulfonic anhydride; acetic acid In formic acid at 80 - 120℃;	42%

(Z)-4,5,6,7,8,9,10,11,12,13-decahydro-1-oxa-3a-azacyclopentacyclotridecene-2,3-dione → 3-allylazacyclotridecan-2-one + 2-azacyclotridecanone (947-04-6) + (E)-azacyclotridec-3-en-2-one + 14-allyl-4,5,6,7,8,9,10,11,12,13-decahydro-1-oxa-3a-azacyclopentacyclotridecene-2,3-dione (831227-11-3)

Conditions	Yield
Stage #1: (Z)-4,5,6,7,8,9,10,11,12,13-decahydro-1-oxa-3a-azacyclopentacyclotridecene-2,3-dione With allyl methyl carbonate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In chloroform; acetonitrile for 48h; Heating / reflux; Stage #2: With sodium methylate In methanol at 0℃; for 1h; Stage #3: With hydrogenchloride In water; ethyl acetate	A 11% B 6% C 5% D 25%

methyl 12-aminododecanoate (53005-24-6) → 2-azacyclotridecanone (947-04-6) + 12-Aminododecanoic acid (693-57-2)

Conditions	Yield
With whole-cells or crude cell extract of recombinant E.coli BL21 (DE3) (pCom10_T31) In ethanol for 0.5h; pH=10; aq. buffer; Enzymatic reaction;	A 13% B n/a

Upstream product

• 946-89-4 cyclododecanone oxime 
• 6407-35-8 N-cyclohexylidenemethylamine 
• 112-77-6 (Z)-9-octadecenoyl chloride 
• 112-80-1 cis-Octadecenoic acid 
• 1074-51-7 cyclooctanone oxime 
• 1129-90-4 cyclododecyne 
• 5601-68-3 cyclotridecyne 
• 1501-82-2 cyclododecene 
• 943-93-1 1,2-epoxy-5,9-cyclododecadiene 
• 286-99-7 1,2-epoxycyclododecane 
• 4904-61-4 cyclododeca-1,5,9-triene 
• 53005-24-6 methyl 12-aminododecanoate 
• 3046-04-6 cyclododecanone oxime hydrochloride 
• 1178530-67-0 2,4-dichloro-6-cyclododecylidene-aminooxy-1,3,5-triazine 

Downstream Products

• 5498-70-4 1-methyl-1-azacyclotrideca-2-one 
• 4068-53-5 1-benzyloxyacetyl-azacyclotridecan-2-one 
• 1561902-79-1 C₃₁H₄₀N₄O₈*ClH 
• 1561903-67-0 C₃₂H₄₂N₄O₈*ClH 

Relevant articles and documents

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

A process for preparing laurolactam

A novel process for the preparation of laurolactam (laurolactam) is disclosed. More specifically, cyclo dodecanone (C) as a starting material. 12 H22 O Is a process for the preparation of laurolactam with won -pot reactions (one-pot reaction) by adding a hydroxyl ammonium compound and an inorganic acid.

Efficient nitriding reagent and application thereof

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Synthesis of macrocyclic and medium-sized ring thiolactonesviathe ring expansion of lactams

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Chlorotropylium Promoted Conversions of Oximes to Amides and Nitriles

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Nitromethane as a nitrogen donor in Schmidt-type formation of amides and nitriles

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Water-dispersible polyamide powder

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Process for preparing polymers from monomers comprising laurolactam

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METHOD FOR MANUFACTURING CYCLODODECANONE AND APPARATUS FOR MANUFACTURING THE SAME

A method for manufacturing cyclododecanone according to the present invention has an effect of having a significantly high conversion rate of cyclododecene and selectivity of cyclododecanone, can minimize the cost used for equipment and processes, is practical, and has an advantageous effect on industrial mass production compared to the prior art by significantly reducing a reaction residence time and a required reaction volume of a reactor.COPYRIGHT KIPO 2019

Process for producing laurolactam and its synthesis apparatus

A method for manufacturing laurolactam and a synthesis apparatus thereof according to the present invention have a remarkably high conversion rate of raw materials and selectivity of a target compound, have an effect of synthesizing the target compound with a high yield and high purity, can minimize costs used for equipment and processes, are practical, and have an advantage of being more simplified compared to the prior art.COPYRIGHT KIPO 2019