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C86405

Sigma-Aldrich

Crotyl bromide

technical grade, 85% (mixture of cis & trans)

Synonym(s):

trans-1-Bromo-2-butene

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About This Item

Linear Formula:
CH3CH=CHCH2Br
CAS Number:
29576-14-5
Molecular Weight:
135.00
Beilstein/REAXYS Number:
1361394
MDL number:
MFCD00000248
UNSPSC Code:
12352100
PubChem Substance ID:
24893087
NACRES:
NA.22

grade

technical grade

Quality Level

100

assay

85% (mixture of cis & trans)

form

liquid

refractive index

n20/D 1.480 (lit.)

bp

97-99 °C (lit.)

density

1.312 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]\C(C)=C(\[H])CBr

InChI

1S/C4H7Br/c1-2-3-4-5/h2-3H,4H2,1H3/b3-2+

InChI key

AVMHMVJVHYGDOO-NSCUHMNNSA-N

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Application

Crotyl bromide is a general organic reagent that can be used in the total synthesis of biologically important natural products and their derivatives such as (+)-artemisinin, plakortone E and (−)-horsfiline.
It can also be used to prepare analogs of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, hexoses and pseudo-indoxyl derivatives.

Other Notes

remainder 3-bromo-1-butene

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

51.8 °F - closed cup

flash_point_c

11 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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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A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses.
Audouard C.
Organic Letters, 6(23), 4269-4272 (2004)
Synthesis of pseudo-indoxyl derivatives via sequential Cu-catalyzed SN Ar and Smalley cyclization.
Goriya Y and Ramana CV.
Chemical Communications (Cambridge, England), 49(57), 6376-6378 (2013)
A concise synthesis of (+)-artemisinin.
Zhu C and Cook SP.
Journal of the American Chemical Society, 134(33), 13577-13579 (2012)
Efficient Enantioselective Total Synthesis of (−)?Horsfiline.
Hong S.
Chemistry?A European Journal , 19(29), 9599-9605 (2013)
Total synthesis and absolute stereochemistry of plakortone E.
Akiyama M.
Tetrahedron Letters, 47(14), 2287-2290 (2006)

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