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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

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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