Crotyl bromide

Base Information

• Chemical Name: Crotyl bromide
• CAS No.: 29576-14-5
• Molecular Formula: C₄H₇Br
• Molecular Weight: 135.004
• Hs Code.: 29033990
• European Community (EC) Number: 225-332-5,629-607-4
• DSSTox Substance ID: DTXSID20885457
• Nikkaji Number: J150.776A,J610F
• Wikidata: Q20054510
• Mol file: 29576-14-5.mol

Synonyms:Crotyl bromide;29576-14-5;(E)-1-bromobut-2-ene;2-Butene, 1-bromo-, (2E)-;1-Bromo-2-butene;(E)-1-Bromo-2-butene;trans-crotyl bromide;4784-77-4;1-Bromo-but-2-ene;2-Butenyl bromide;trans-1-bromo-but-2-ene;(2E)-1-bromobut-2-ene;2-Butene, 1-broMo-, (2Z)- (9CI);39616-19-8;1-Crotyl bromide;2-Butene, 1-bromo-, (E)-;Crotyl bromidetech.85;2-Buteno, 1-bromo-;trans-1-Bromo-2-butene;E-crotyl bromide;(E)-2-butenyl bromide;(E)-1-bromo-but-2-ene;SCHEMBL78548;SCHEMBL78549;(2E)-1-Bromo-2-butene #;CROTYL BROMIDE TECH. 85;DTXSID20885457;MFCD00000248;AKOS025149600;AKOS025295359;Crotyl bromide, technical grade, 85%;B0562;A848889;A928949;J-017569;Q20054510;trans-1-Bromo-2-butene, 80% remainder 3-Bromo-1-butene

Chemical Property of Crotyl bromide

Chemical Property:

• Appearance/Colour: Clear light yellow to yellow-brown liquid
• Melting Point: -115.07°C (estimate)
• Refractive Index: n20/D 1.480(lit.)
• Boiling Point: 104.5 °C at 760 mmHg
• Flash Point: 11.1 °C
• PSA: 0.00000
• Density: 1.331 g/cm³
• LogP: 1.95740
• Storage Temp.: Refrigerator (+4°C) + Flammables area
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 133.97311
• Heavy Atom Count: 5
• Complexity: 30.6

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-Crotyl Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37-36/37/38
• Safety Statements: 16-26-27-36/37/39-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC=CCBr
• Isomeric SMILES: C/C=C/CBr
• Uses: 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.

Technology Process of Crotyl bromide

There total 43 articles about Crotyl bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(E/Z)-2-buten-1-ol (6117-91-5,542-72-3) → (E/Z)-crotyl bromide (4784-77-4,29576-14-5,39616-19-8)

Guidance literature:

With tetradecafluorohexane; phosphorus tribromide; In diethyl ether; at 20 ℃; for 12h;

DOI:10.1021/ol035391b

Reference yield: 67.7%

(Z)-2-Butene (590-18-1) → (E/Z)-crotyl bromide (4784-77-4,29576-14-5,39616-19-8) + 3-bromo-1-butene (22037-73-6) + 2,3-dibromobutane (5408-86-6) + meso-2,3-dibromo-butane (5780-13-2)

Guidance literature:

With bromine; for 0.133333h; under 0.5 - 10 Torr; Product distribution; Ambient temperature; Irradiation;

Reference yield: 66.0%

2-((E)-But-2-enyl)-1,3-diisopropyl-isourea (113984-37-5) → 1,3-diisopropylurea (4128-37-4) + 3-bromo-1-butene (22037-73-6) + (E)-1-Bromo-2-butene (4784-77-4,39616-19-8,29576-14-5)

Guidance literature:

With trifluorormethanesulfonic acid; tetrabutylammomium bromide; In dichloromethane; at 25 ℃; for 24h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)96534-1

upstream raw materials:

2-hydroxy-3-butene

3-bromo-1-butene

(E/Z)-2-buten-1-ol

buta-1,3-diene

Downstream raw materials:

1-butylene

butene-2

3-methylpent-4-en-2-ol

but-2ξ-enyl-(2,4-dimethyl-6-trans-propenyl-phenyl)-ether

Refernces

• 1、 Vedejs, E.,Dent, W. H.,Gapinski, D. M.,McClure C. K.. "Local Conformer Effects in Unsaturated Lactones". . p. 5437 - 5446. Retrieved 1987.
• 2、 Munyemana, Fran?ois,Patiny, Luc,Ghosez, Léon. "A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols". . . Retrieved 2021/06/07.
• 3、 Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.. "Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method". supporting information. p. 4176 - 4182. Retrieved 2021/02/01.