29215-49-4

Basic information

• Product Name: 1-Chloro-9-iodononane
• Synonyms: Nonane, 1-chloro-9-iodo-
• CAS NO: 29215-49-4
• Molecular Formula: C₉H₁₈ClI
• Molecular Weight: 288.60
• Mol File: 29215-49-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 283.354 °C at 760 mmHg
• Flash Point: 125.168 °C
• Density: 1.392 g/cm3
• CAS DataBase Reference: 1-Chloro-9-iodononane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-9-iodononane(29215-49-4)
• EPA Substance Registry System: 1-Chloro-9-iodononane(29215-49-4)

Safety Data

• Hazardous Substances Data: 29215-49-4(Hazardous Substances Data)

Usage

General Description

1-Chloro-9-iodononane is an organic chemical compound with the molecular formula C9H18ClI. It consists of a nonane backbone with a chlorine atom and an iodine atom attached at the 1st and 9th carbon positions, respectively. 1-Chloro-9-iodononane is commonly used in organic synthesis as a reagent for the conversion of alcohols to alkyl chlorides, and in the preparation of other organic compounds. It is also used as an intermediate in the production of pharmaceuticals and agrochemicals. 1-Chloro-9-iodononane is a valuable chemical for various industrial applications due to its ability to undergo a variety of chemical reactions and its potential for creating different types of compounds.

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

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

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 articles and documents

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.