29215-49-4

Usage

Uses

Used in Organic Synthesis:
1-Chloro-9-iodononane is utilized as a reagent in organic synthesis for the conversion of alcohols to alkyl chlorides, a process that is crucial for the formation of various organic compounds. Its unique structure allows for specific reactions that are not easily achievable with other reagents.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 1-Chloro-9-iodononane serves as an intermediate in the production of various drugs. Its ability to participate in a wide array of chemical reactions contributes to the synthesis of complex molecular structures required for medicinal compounds.
Used in Agrochemical Production:
Similarly, in the agrochemical sector, 1-Chloro-9-iodononane is employed as an intermediate for the synthesis of pesticides and other agricultural chemicals. Its role in creating specific chemical entities is essential for developing effective products for crop protection and enhancement.
Overall, 1-Chloro-9-iodononane's applications span across different industries, highlighting its importance in the synthesis of a broad spectrum of chemical products, from pharmaceuticals to agrochemicals, due to its unique structural attributes and reactivity.

Synthetic route

1,9-dichlorononane (821-99-8) → 1-iodo-9-chlorononane (29215-49-4)

Conditions	Yield
With sodium iodide In acetone for 3h; Heating;	19%
With acetone; sodium iodide
With sodium iodide

ethene (74-85-1) + Chloroiodomethane (593-71-5) → 1-iodo-9-chlorononane (29215-49-4)

Conditions	Yield
With water; dibenzoyl peroxide at 95℃; under 367754 - 441305 Torr;
With water; dibenzoyl peroxide at 95℃; under 367754 - 441305 Torr;

1,9-Nonanediol (3937-56-2) → 1-iodo-9-chlorononane (29215-49-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; thionyl chloride 2: acetone; NaI View Scheme

diethyl azelate (624-17-9) → 1-iodo-9-chlorononane (29215-49-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper chromite / 270 °C / 154457 Torr / Hydrogenation 2: pyridine; thionyl chloride 3: acetone; NaI View Scheme

1-iodo-9-chlorononane (29215-49-4) + 1-octynyllithium (21433-45-4) → 1-chloroheptadec-10-yne (56554-75-7)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature;	30%

n-octyne (629-05-0) + 1-iodo-9-chlorononane (29215-49-4) → 1-chloroheptadec-10-yne (56554-75-7)

Conditions	Yield
With ammonia; sodium amide

1-iodo-9-chlorononane (29215-49-4) + sodium acetylide (1066-26-8) → 11-chloro-1-undecyne (29043-93-4)

Conditions	Yield
With ammonia In diethyl ether

1-iodo-9-chlorononane (29215-49-4) + oct-1-ynyl sodium → 1-chloroheptadec-10-yne (56554-75-7)

Conditions	Yield
With ammonia

1-iodo-9-chlorononane (29215-49-4) + oct-1-ynyl sodium → 11-octadecynoic acid (19220-40-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 30 percent / HMPT / Ambient temperature 2: 37 percent / NaI / acetone / Heating 3: 1.) EtMgBr, Mg / 1.) THF, reflux, 3 h, 2.) THF, RT, overnight View Scheme

1-iodo-9-chlorononane (29215-49-4) + oct-1-ynyl sodium → 11-octadecynoic acid, methyl ester (26543-37-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 30 percent / HMPT / Ambient temperature 2: 37 percent / NaI / acetone / Heating 3: 1.) EtMgBr, Mg / 1.) THF, reflux, 3 h, 2.) THF, RT, overnight View Scheme

1-iodo-9-chlorononane (29215-49-4) + oct-1-ynyl sodium → 1-hydroxy octadec 11-yne (84999-79-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 30 percent / HMPT / Ambient temperature 2: 37 percent / NaI / acetone / Heating 3: 1.) EtMgBr, Mg / 1.) THF, reflux, 3 h, 2.) THF, RT, overnight 5: LiAlH4 / tetrahydrofuran / 4.5 h / Ambient temperature View Scheme

1-iodo-9-chlorononane (29215-49-4) + oct-1-ynyl sodium → octadec-11-ynyl acetate (154131-72-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: 30 percent / HMPT / Ambient temperature 2: 37 percent / NaI / acetone / Heating 3: 1.) EtMgBr, Mg / 1.) THF, reflux, 3 h, 2.) THF, RT, overnight 5: LiAlH4 / tetrahydrofuran / 4.5 h / Ambient temperature 6: 70 percent / pyridine View Scheme

1-iodo-9-chlorononane (29215-49-4) + oct-1-ynyl sodium → 1-iodoheptadec-10-yne (154131-70-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 30 percent / HMPT / Ambient temperature 2: 37 percent / NaI / acetone / Heating View Scheme

1-iodo-9-chlorononane (29215-49-4) + oct-1-ynyl sodium → <3H>-vaccenic acid

Conditions	Yield
Multi-step reaction with 4 steps 1: 30 percent / HMPT / Ambient temperature 2: 37 percent / NaI / acetone / Heating 3: 1.) EtMgBr, Mg / 1.) THF, reflux, 3 h, 2.) THF, RT, overnight 4: tritium / Pd/CaCO3/Pb View Scheme

1-iodo-9-chlorononane (29215-49-4) + oct-1-ynyl sodium → <3H>-vaccenyl acetate

Conditions	Yield
Multi-step reaction with 7 steps 1: 30 percent / HMPT / Ambient temperature 2: 37 percent / NaI / acetone / Heating 3: 1.) EtMgBr, Mg / 1.) THF, reflux, 3 h, 2.) THF, RT, overnight 5: LiAlH4 / tetrahydrofuran / 4.5 h / Ambient temperature 6: 70 percent / pyridine 7: tritium, pyridine / Lindlar catalyst / toluene / 1 h View Scheme

1-iodo-9-chlorononane (29215-49-4) → 11-octadecynoic acid (19220-40-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amide; liquid NH3 2: ethanol / und Verseifen des Reaktionsprodukts mit siedender wss.-alkoh.NaOH View Scheme

1-iodo-9-chlorononane (29215-49-4) → 17-chloro-heptadeca-4,7-diyne (93543-12-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: liq. NH3 / diethyl ether 2: (i) EtMgBr, THF, (ii) /BRN= 1736285/, CuCl, THF View Scheme

1-iodo-9-chlorononane (29215-49-4) → 17-chloro-heptadeca-4c,7c-diene (93478-59-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: liq. NH3 / diethyl ether 2: (i) EtMgBr, THF, (ii) /BRN= 1736285/, CuCl, THF 3: iBu2AlH / heptane View Scheme

1-iodo-9-chlorononane (29215-49-4) → cis,cis-Octadeca-11,14-diensaeuremethylester (18287-24-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: liq. NH3 / diethyl ether 2: (i) EtMgBr, THF, (ii) /BRN= 1736285/, CuCl, THF 3: iBu2AlH / heptane 4: (i) EtMgBr, ether, (ii) /BRN= 1900390/ 5: diethyl ether View Scheme

1-iodo-9-chlorononane (29215-49-4) → 11-cis,14-cis-octadecadienoic acid (17027-31-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: liq. NH3 / diethyl ether 2: (i) EtMgBr, THF, (ii) /BRN= 1736285/, CuCl, THF 3: iBu2AlH / heptane 4: (i) EtMgBr, ether, (ii) /BRN= 1900390/ View Scheme

1-iodo-9-chlorononane (29215-49-4) → 11,12,14,15-Tetrabromo-octadecanoic acid

Conditions	Yield
Multi-step reaction with 5 steps 1: liq. NH3 / diethyl ether 2: (i) EtMgBr, THF, (ii) /BRN= 1736285/, CuCl, THF 3: iBu2AlH / heptane 4: (i) EtMgBr, ether, (ii) /BRN= 1900390/ 5: Br2 / petroleum ether View Scheme

Upstream product

• 821-99-8 1,9-dichlorononane 
• 74-85-1 ethene 
• 593-71-5 Chloroiodomethane 
• 3937-56-2 1,9-Nonanediol 
• 624-17-9 diethyl azelate 

Downstream Products

• 19220-40-7 11-octadecynoic acid 
• 18287-24-6 cis,cis-Octadeca-11,14-diensaeuremethylester 
• 84999-79-1 1-hydroxy octadec 11-yne 
• 26543-37-3 11-octadecynoic acid, methyl ester 

Relevant academic research and scientific papers

Studies in pheromone biosynthesis: Preparation of 3H labelled precursors of Drosophila pheromones

Two synthetic schemes were designed giving access to tritium labelled potential precursors of Drosophila pheromones. An intermediate in the first scheme allowed the preparation of [3H]-labelled vaccenyl acetate.