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253901

Sigma-Aldrich

5-Bromo-1-pentene

95%

Synonym(s):

1-Bromo-4-pentene, 4-Pentenyl bromide

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About This Item

Linear Formula:
Br(CH2)3CH=CH2
CAS Number:
1119-51-3
Molecular Weight:
149.03
Beilstein:
506077
EC Number:
214-281-4
MDL number:
MFCD00000264
UNSPSC Code:
12352100
PubChem Substance ID:
24855339
NACRES:
NA.22

Quality Level

200

Assay

95%

form

liquid

refractive index

n20/D 1.463 (lit.)

bp

126-127 °C/765 mmHg (lit.)

density

1.258 g/mL at 25 °C (lit.)

functional group

alkyl halide
allyl
bromo

storage temp.

2-8°C

SMILES string

BrCCCC=C

InChI

1S/C5H9Br/c1-2-3-4-5-6/h2H,1,3-5H2

InChI key

LPNANKDXVBMDKE-UHFFFAOYSA-N

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Application

5-Bromo-1-pentene was used in stereoselective synthesis of 7α-(3-carboxypropyl) estradiol. It was used in preparation of thioacetate 11 of sialic acid having thioglycosidic linkage. It was also used as staring material in recent syntheses of DL-histrionicotoxin and benzophenone-containing fatty acids.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

87.8 °F - closed cup

Flash Point(C)

31 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000134197
0000086667
BCCK6685
0000285601
BCBX5021

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Maheswaran S Karatholuvhu et al.
Journal of the American Chemical Society, 128(39), 12656-12657 (2006-09-28)
The synthesis of (+/-)-histrionicotoxin has been achieved in just nine steps using a two-directional synthesis strategy. Key reactions include a two-directional cross-metathesis, a tandem oxime formation/Michael addition/1,4-prototopic shift/[3 + 2]-cycloaddition cascade, a selective Z,Z-bisenyne formation, and a one-pot N-O and
M Adamczyk et al.
Steroids, 62(12), 771-775 (1998-01-22)
Alkylation of 3,17 beta-bis(2-trimethylsilyl)ethoxymethyl-1,3,5(10) estratriene-6-one (2) with 5-bromo-1-pentene using NaHMDS in THF afforded 3,17 beta-bis(2-trimethylsilyl)ethoxymethyl-7-alpha-(4'pentenyl)-1,3,5(10) estratriene-6-one (3) in excellent stereoselectivity (> 95% epimeric excess). Functionalization of the side chain in compound 3 was accomplished via ozonolysis, oxidation and esterification to
Jun-Ichi Sakamoto et al.
Bioorganic & medicinal chemistry letters, 17(3), 717-721 (2006-11-11)
An efficient synthesis of a series of carbosilane dendrimers uniformly functionalized with alpha-thioglycoside of sialic acid was accomplished. The results of a preliminary study on biological responses against influenza virus sialidases using thiosialoside clusters showed that some of the glycodendrimers
Yifan Dong et al.
Carbohydrate polymers, 221, 37-47 (2019-06-23)
Bile salts tend to form micelles in aqueous media and can thereby contribute to drug solubilization; they also exhibit crystallization inhibition properties that can stabilize supersaturated drug solutions. Herein, we explore conjugation of bile salts with polysaccharides to create new
Yonghong Gan et al.
The Journal of organic chemistry, 71(25), 9487-9490 (2006-12-02)
Syntheses of new benzophenone-containing fatty acids (FABPs) 1, 5, and 6 and a new route to FABP 3 are described. Combined with the known 2 and 4, these FABPs comprise a set of photoactivatable fatty acid analogues with the crosslinking
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