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ChemicalBook--->CAS DataBase List--->2550-36-9

2550-36-9

2550-36-9 Structure

2550-36-9 Structure
IdentificationMore
[Name]

Cyclohexylmethyl bromide
[CAS]

2550-36-9
[Synonyms]

BROMOMETHYLCYCLOHEXANE
CYCLOHEXYLMETHYL BROMIDE
HEXAHYDROBENZYL BROMIDE
Bromocyclohexylmethane
1-CYCLOHEXYL-1-BROMOMETHANE
Cyclohexane, (bromomethyl)-
CYCLOHEXYLMETHYBROMIDE
1-(Bromomethyl)cyclohexane
[Molecular Formula]

C7H13Br
[MDL Number]

MFCD00001509
[Molecular Weight]

177.08
[MOL File]

2550-36-9.mol
Chemical PropertiesBack Directory
[Appearance]

Light yellow liquid
[Boiling point ]

76-77 °C26 mm Hg(lit.)
[density ]

1.269 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.492(lit.)
[Fp ]

135 °F
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[solubility ]

soluble in Chloroform, Ethyl Acetate
[form ]

Liquid
[color ]

Clear light yellow
[Water Solubility ]

Insoluble in water.
[BRN ]

635738
[InChI]

InChI=1S/C7H13Br/c8-6-7-4-2-1-3-5-7/h7H,1-6H2
[InChIKey]

UUWSLBWDFJMSFP-UHFFFAOYSA-N
[SMILES]

C1(CBr)CCCCC1
[CAS DataBase Reference]

2550-36-9(CAS DataBase Reference)
[NIST Chemistry Reference]

Cyclohexane, (bromomethyl)-(2550-36-9)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[RIDADR ]

UN 1993 3/PG 3
[WGK Germany ]

3
[HazardClass ]

3
[PackingGroup ]

III
[HS Code ]

29035990
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Phosphorus tribromide-->Cyclohexanemethanol-->Cyclohexylmethyl 4-methylbenzenesulfonate-->Toluene-->Pyridine-->CYCLOHEXYLMAGNESIUM CHLORIDE-->Bromocyclohexane-->CYCLOHEXYLMAGNESIUM BROMIDE-->Cyclohexanecarboxaldehyde
[Preparation Products]

1-(CYCLOHEXYLMETHYL)PIPERAZINE-->Cyclohexane, 1-bromo-2-(bromomethyl)--->N-PENTADECYLCYCLOHEXANE-->ISOBUTYLCYCLOBUTANE-->CYCLOHEPTYL BROMIDE-->BROMOMETHYLENECYCLOHEXANE 96-->Cyclohexylacetic acid-->1-METHYL-1-CYCLOHEXENE-->1-N-(cyclohexylmethyl)benzene-1,2-diamine-->N-(cyclohexylmethyl)-1H-indol-6- amine
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Cyclohexylmethyl bromide(2550-36-9).msds
Hazard InformationBack Directory
[Chemical Properties]

Light yellow liquid
[Uses]

(Bromomethyl)cyclohexane is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals.
[Synthesis]

Cyclohexanemethanol

100-49-2

Cyclohexylmethyl bromide

2550-36-9

The general procedure for the synthesis of bromomethylcyclohexane from cyclohexanemethanol is as follows: 1.4 kg of cyclohexanemethanol (colorless liquid), 8.4 L of toluene, and 969.8 g of pyridine were added to a 20 L four-neck flask. The reaction system was cooled to 0 to 10 °C, and then a mixture of 1.66 kg of phosphorus tribromide with 7 L of toluene was slowly added with controlled titration rate to keep the reaction temperature below 5 °C. The dropwise addition process was completed in about 1 hour. Subsequently, the reaction system was warmed to room temperature and the reaction was continued with stirring for 10 hours. Upon completion of the reaction, the system was cooled to below 20 °C and about 2.5 L of 5% sodium hydroxide solution was slowly added dropwise, followed by the addition of 1.85 kg of solid sodium hydroxide to form a mixture. Liquid-liquid separation was carried out and the aqueous phase was extracted twice with 4 L of toluene. The organic phases were combined and washed with saturated brine, and the washed organic phase was dried with anhydrous sodium sulfate. The dried organic phase was concentrated to give 1.73 kg of crude product. The crude product was purified by distillation under reduced pressure to give 722.8 g of bromomethylcyclohexane with 97.5% purity in 33.3% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 3.82 (m, 1H), 1.79-1.53 (m, 6H), 1.13-0.90 (m, 6H).

[References]

[1] Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2901 - 2910
[2] Patent: US2016/319312, 2016, A1. Location in patent: Paragraph 0083
[3] Journal of the American Chemical Society, 1926, vol. 48, p. 2392
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1906, vol. 142, p. 344
[5] Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 548
Spectrum DetailBack Directory
[Spectrum Detail]

Cyclohexylmethyl bromide(2550-36-9)MS
Cyclohexylmethyl bromide(2550-36-9)1HNMR
Cyclohexylmethyl bromide(2550-36-9)IR1
Cyclohexylmethyl bromide(2550-36-9)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

Cyclohexylmethyl bromide, 96%(2550-36-9)
[Alfa Aesar]

(Bromomethyl)cyclohexane, 98%(2550-36-9)
[Sigma Aldrich]

2550-36-9(sigmaaldrich)
[TCI AMERICA]

(Bromomethyl)cyclohexane,>95.0%(GC)(2550-36-9)
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