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128007

Sigma-Aldrich

1,5-Dibromopentane

97%

Synonym(s):

Pentamethylene dibromide

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About This Item

Linear Formula:
Br(CH2)5Br
CAS Number:
111-24-0
Molecular Weight:
229.94
Beilstein:
1209245
EC Number:
203-849-7
MDL number:
MFCD00000268
UNSPSC Code:
12352100
PubChem Substance ID:
24847812
NACRES:
NA.22

vapor density

8 (vs air)

Assay

97%

form

liquid

refractive index

n20/D 1.512 (lit.)

bp

110 °C/15 mmHg (lit.)

mp

−34 °C (lit.)

density

1.688 g/mL at 25 °C (lit.)

SMILES string

BrCCCCCBr

InChI

1S/C5H10Br2/c6-4-2-1-3-5-7/h1-5H2

InChI key

IBODDUNKEPPBKW-UHFFFAOYSA-N

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General description

1,5-Dibromopentane is a growth supplement for Yarrowia lipolytica 3589, a tropical marine yeast.

Application

1,5-Dibromopentane can be used to prepare:
  • Derivatives of 5-pyrazolones.
  • O-alkylated phloroglucinol derivatives, which forms the core of poly(alkyl aryl ether) dendrimers.
  • Intermediate for dezocine viz, (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone using 1-methyl-7-methoxy-2-tetralone.

1,5-Dibromopentane was used in the preparartion of 1,5-di-Grignard reagent. It was also used in the synthesis of novel spirocyclic pyrrolidones.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

174.2 °F - closed cup

Flash Point(C)

79 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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J. Chem. Soc. Perkin Trans. II, 2217-2217 (1992)
Wieslaw M Kazmierski et al.
Bioorganic & medicinal chemistry letters, 12(23), 3431-3433 (2002-11-07)
We have developed concise and efficient syntheses of novel spirocyclic pyrrolidones 1-3, which involve the alkylation of pyrrolidone precursor 13 with 1,5-dibromopentane, 16 and 15, followed by an in situ lactamization. Conjugates of 1 and 2 with P1'/P2' hydroxy-indanolamine moiety
Aakanksha Vatsal et al.
Yeast (Chichester, England), 28(10), 721-732 (2011-09-10)
Yarrowia lipolytica 3589, a tropical marine yeast, grew aerobically on a broad range of bromoalkanes varying in carbon chain length and differing in degree and position of bromide group. Amongst the bromoalkanes studied, viz. 2-bromopropane (2-BP), 1-bromobutane (1-BB), 1,5-dibromopentane (1,5-DBP)
1, 5-Bis (4-dithiocarboxylate-5-hydroxypyrazolyl) pentane Derivatives of 5-Pyrazolones
Avila C, et al.
Journal of Heterocyclic Chemistry, 42(4), 595-597 (2005)
Akimitsu Miyaji et al.
Physical chemistry chemical physics : PCCP, 22(33), 18595-18605 (2020-08-14)
Formate dehydrogenase from Candida boidinii (EC.1.2.1.2; CbFDH) is a commercially available enzyme and can be easily handled as a catalyst for the CO2 reduction to formate in the presence of NADH, single-electron reduced methylviologen (MV+˙) and so on. It was
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