55382-85-9

Basic information

• Product Name: DICYCLOHEXYLIODOBORANE
• Synonyms: Dicyclohexyliodoborane solution;DICYCLOHEXYLIODOBORANE, 0.5M SOLUTION IN HEXANES;Dicyclohexylboryl iodide;Dicyclohexyliodoborane 97%;Dicyclohexyliodoborane solution 0.5 M in hexanes;DICYCLOHEXYLIODOBORANE
• CAS NO: 55382-85-9
• Molecular Formula: C₁₂H₂₂BI
• Molecular Weight: 304.02
• Product Categories: Boranes;Reduction;Synthetic Reagents
• Mol File: 55382-85-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 68-69 °C
• Flash Point: 86 °F
• Appearance: /
• Density: 1.325 g/mL at 25 °C(lit.)
• CAS DataBase Reference: DICYCLOHEXYLIODOBORANE(CAS DataBase Reference)
• NIST Chemistry Reference: DICYCLOHEXYLIODOBORANE(55382-85-9)
• EPA Substance Registry System: DICYCLOHEXYLIODOBORANE(55382-85-9)

Safety Data

• Hazard Codes: C,F,N,Xn
• Statements: 11-14-20/21/22-34-40-42/43-10-67-65-62-51/53-48/20-38
• Safety Statements: 16-26-27-36/37/39-45-23-62-61-36/37
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 55382-85-9(Hazardous Substances Data)

Usage

Uses

Reactant for:Preparation of vinyloxyboranes

Synthetic route

bis(cyclohexanyl)borane (1568-65-6) → B-iododicyclohexylborane (55382-85-9)

Conditions	Yield
With I2 In hexane	80%

tricyclohexylborane (1088-01-3) → B-iododicyclohexylborane (55382-85-9)

Conditions	Yield
With iodine

tricyclohexylborane (1088-01-3) + iodine (7553-56-2) → B-iododicyclohexylborane (55382-85-9)

(CH3)2SnSe (55382-84-8) + B-iododicyclohexylborane (55382-85-9) → bis(dicyclohexylboryl)selenane (55462-47-0)

Conditions	Yield
In hexane byproducts: (CH3)2SnI2; 2 h mixing at 25°C; evapn.; distn. at 100-110°C; recrystn.;	51%
In hexane byproducts: (CH3)2SnI2; 2 h mixing at 25°C; evapn.; distn. at 100-110°C; recrystn.;	51%

B-iododicyclohexylborane (55382-85-9) → dicyclohexylhydroxyborane (2628-46-8)

Conditions	Yield
With water

B-iododicyclohexylborane (55382-85-9) → dicyclohexylboron chloride (36140-19-9)

Conditions	Yield
With antimony(III) chloride

ethynyldimagnesium dibromide (4301-15-9) + B-iododicyclohexylborane (55382-85-9) → (cyclo-C6H11)2BCCB(cyclo-C6H11)2 + BrIMg

B-iododicyclohexylborane (55382-85-9) + hexamethylcyclotristannaselenane (58258-49-4) → bis(dicyclohexylboryl)selenane (55462-47-0) + dimethyltin diiodide (2767-49-9)

B-iododicyclohexylborane (55382-85-9) + antimony(III) chloride (10025-91-9) → dicyclohexylboron chloride (36140-19-9)

Methyl 4-pentenoate (818-57-5) + B-iododicyclohexylborane (55382-85-9) → C18H31BO2

Conditions	Yield
With triethylamine In pentane at 0℃; for 0.166667h; Inert atmosphere;

B-iododicyclohexylborane (55382-85-9) → N-cyclohexyl-cyclohexanamine (101-83-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: H2O View Scheme

B-iododicyclohexylborane (55382-85-9) → cyclohexyl ethyl acetate (21722-83-8)

(2-methylcyclohex-1-en-1-yl)methyl 4-(3-(2-methoxy-2-oxoethyl)-2-(((perfluorobutyl)sulfonyl)oxy)cyclopent-1-en-1-yl)butanoate + B-iododicyclohexylborane (55382-85-9) → C36H50BF9O7S

Conditions	Yield
With triethylamine In dichloromethane at -78℃; for 1h; Inert atmosphere;

(2-methylcyclohex-1-en-1-yl)methyl propionate (1626423-86-6) + B-iododicyclohexylborane (55382-85-9) → C23H39BO2

Conditions	Yield
With triethylamine In dichloromethane at -78℃; for 1h; Inert atmosphere;

Upstream product

• 1088-01-3 tricyclohexylborane 
• 7553-56-2 iodine 
• 1568-65-6 bis(cyclohexanyl)borane 

Downstream Products

• 2628-46-8 dicyclohexylhydroxyborane 
• 36140-19-9 dicyclohexylboron chloride 
• 55462-47-0 bis(dicyclohexylboryl)selenane 
• 2767-49-9 dimethyltin diiodide 
• 21722-83-8 cyclohexyl ethyl acetate 
• 101-83-7 N-cyclohexyl-cyclohexanamine 

Relevant articles and documents

Bis(bicyclo(2.2.2)octyl)haloboranes

A novel class of enolboration reagents represented by the formula wherein each R is the same or different alkyl or cycloalkyl, B is boron, X is halo, R' is lower alkyl and / indicates that R2 BX is preferably employed in the presence of R'3 N are disclosed. Methods of enolborating a wide variety of organic carbonyl compounds are also provided. Further, new bis(bicyclo[2.2.2.]octyl)haloboranes are efficacious for enolboration.