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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:
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

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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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Total synthesis and absolute stereochemistry of plakortone E.
Akiyama M.
Tetrahedron Letters, 47(14), 2287-2290 (2006)
Efficient Enantioselective Total Synthesis of (−)?Horsfiline.
Hong S.
Chemistry?A European Journal , 19(29), 9599-9605 (2013)
A concise synthesis of (+)-artemisinin.
Zhu C and Cook SP.
Journal of the American Chemical Society, 134(33), 13577-13579 (2012)
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)

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