31844-98-1

Basic information

• Product Name: 1-BROMO-1-BUTENE
• Synonyms: 1-BROMO-1-BUTENE;TRANS-1-BROMO-1-BUTENE;1-bromo-1-buten;1-bromobut-1-ene;1-BROMO-1-BUTENE MIXTURE OF ISOMERS;1 - Bromo - 1 - butene (cis - trans)
• CAS NO: 31844-98-1
• Molecular Formula: C₄H₇Br
• Molecular Weight: 135
• EINECS: 250-836-7
• Mol File: 31844-98-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: -115.07°C (estimate)
• Boiling Point: 88.08°C (estimate)
• Flash Point: 14.5 °C
• Appearance: /
• Density: 1.3119
• Vapor Pressure: 53.4mmHg at 25°C
• Refractive Index: 1.4530
• CAS DataBase Reference: 1-BROMO-1-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-1-BUTENE(31844-98-1)
• EPA Substance Registry System: 1-BROMO-1-BUTENE(31844-98-1)

Safety Data

• Hazardous Substances Data: 31844-98-1(Hazardous Substances Data)

Usage

General Description

1-Bromo-1-butene is a chemical compound with the molecular formula C4H7Br. It is a colorless liquid with a slightly sweet odor, and is commonly used as a reagent in organic synthesis. 1-BROMO-1-BUTENE is a type of alkene, or unsaturated hydrocarbon, and the bromine atom is attached to the first carbon of the butene chain. 1-Bromo-1-butene is flammable and can react violently with strong oxidizing agents, so it must be handled and stored carefully. It is also considered to be harmful if swallowed, inhaled, or absorbed through the skin, and can cause irritation to the respiratory system, skin, and eyes. In industry, 1-bromo-1-butene is used as a starting material for the synthesis of other organic compounds and is also used in the production of pharmaceuticals and agrochemicals.

InChI:InChI=1/C4H7Br/c1-2-3-4-5/h3-4H,2H2,1H3

Synthetic route

pent-2-enoic acid (626-98-2, 13991-37-2, 16666-42-5) → (E)/(Z)-1-bromo-1-butene (31844-98-1)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; tetraethylammonium bromide In dichloromethane at 20℃; for 10h;	90%

2.3-dibromo-n-valeric acid → (E)/(Z)-1-bromo-1-butene (31844-98-1) + α-bromo-β-ethyl-acrylic acid

Conditions	Yield
With pyridine

acide dibromo-2,3 pentanoique (79912-57-5) → (E)/(Z)-1-bromo-1-butene (31844-98-1) + 2-bromo-pent-2-enoic acid (98021-78-4)

Conditions	Yield
With pyridine

butane, 1,1,2-tribromo- (3675-68-1) → (E)/(Z)-1-bromo-1-butene (31844-98-1)

Conditions	Yield
With ethanol; zinc higher-boiling 1-bromo-butene-(1);
With ethanol; zinc lower-boiling 1-bromo-butene-(1);

butyraldehyde (123-72-8) → (E)/(Z)-1-bromo-1-butene (31844-98-1)

Conditions	Yield
With phosphorus trichloride dibromide; sodium ethanolate

1,2-dibromobutane (533-98-2, 130232-89-2, 130232-90-5) → (E)/(Z)-1-bromo-1-butene (31844-98-1) + higher-boiling 1-bromo-buten-(1) and 2-bromo-butene-(1)

Conditions	Yield
With ethanol; sodium phenoxide man trennt das Isomeren-Gemisch durch fraktionierte Destillation mit Alkohol, Zerlegung der erhaltenen Azeotropen mit Wasser und nochmalige Destillation; lower-boiling 1-bromo-butene-(1);

1,2-dibromobutane (533-98-2, 130232-89-2, 130232-90-5) → (E)/(Z)-1-bromo-1-butene (31844-98-1) + lower-boiling 1-bromo-buten-(1) and 2-bromo-butene-(1)

Conditions	Yield
With ethanol; sodium phenoxide man trennt das Isomeren-Gemisch durch fraktionierte Destillation mit Alkohol, Zerlegung der erhaltenen Azeotropen mit Wasser und nochmalige Destillation; higher-boiling 1-bromo-butene-(1);

trans-2-pentenoic acid (13991-37-2) → (E)/(Z)-1-bromo-1-butene (31844-98-1)

Conditions	Yield
(i) Br2, (UV-irradiation), (ii) (heating in Py); Multistep reaction;

pyridine (110-86-1) + acide dibromo-2,3 pentanoique (79912-57-5) → (E)/(Z)-1-bromo-1-butene (31844-98-1) + 2-bromo-Δ2-pentenoic acid

methylmagnesium bromide (75-16-1) + 1,3-dibromopropene (627-15-6) → (E)/(Z)-1-bromo-1-butene (31844-98-1)

Conditions	Yield
higher-boiling 1-bromo-butene-(1);

butyraldehyde (123-72-8) + PCl3Br2 → (E)/(Z)-1-bromo-1-butene (31844-98-1)

Conditions	Yield
Behandeln des Reaktionsprodukts mit Natriumaethylat;

1-bromo-2-butanol (2482-57-7) + phosphorus pentoxide → (E/Z)-crotyl bromide (4784-77-4, 29576-14-5, 39616-19-8) + (E)/(Z)-1-bromo-1-butene (31844-98-1)

diethyl ether (60-29-7) + methylmagnesium bromide (75-16-1) + 1,3-dibromopropene (627-15-6) → methane (34557-54-5) + (E)/(Z)-1-bromo-1-butene (31844-98-1) + ethane (74-84-0) + buta-1,3-diene (106-99-0)

Conditions	Yield
Produkt5: Octadien-(2.6);

(E)/(Z)-1-bromo-1-butene (31844-98-1) + (2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol (125975-53-3, 147220-48-2, 116996-54-4) → (R)-1-((tert-butyldiphenylsilyl)oxy)oct-7-en-3-ol

Conditions	Yield
Stage #1: (E)/(Z)-1-bromo-1-butene With magnesium; ethylene dibromide In tetrahydrofuran Grignard Reaction; Reflux; Inert atmosphere; Stage #2: (2S)-O-(tert-butyldiphenylsilyl)-1,2-epoxybutan-4-ol With copper(l) iodide In tetrahydrofuran at -78 - 0℃; for 1.08333h; Cooling with acetone-dry ice;	99%

(E)/(Z)-1-bromo-1-butene (31844-98-1) + 2',4'-dihydroxychalcone (1776-30-3, 25515-43-9) → C19H18O3

Conditions	Yield
With potassium carbonate In acetone at 25 - 30℃; Irradiation;	87.5%

(E)/(Z)-1-bromo-1-butene (31844-98-1) + 2',4'-dihydroxychalcone (1776-30-3, 25515-43-9) → C23H24O3

Conditions	Yield
With potassium carbonate In acetonitrile at 25 - 30℃; Irradiation;	85.6%

(E)/(Z)-1-bromo-1-butene (31844-98-1) + (hex-5-enyl)magnesium bromide (30043-41-5) → deca-3,9-diene (92230-34-7)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 30℃;	79.5%

(E)/(Z)-1-bromo-1-butene (31844-98-1) + trimethylsilylacetylene (1066-54-2) → (E)-1-trimethylsilyl-3-hexen-1-yne (60216-44-6)

Conditions	Yield
Stage #1: trimethylsilylacetylene With ethylmagnesium bromide In tetrahydrofuran at 65℃; for 1h; Substitution; Stage #2: With zinc(II) chloride In tetrahydrofuran at 20℃; for 0.5h; Transmetallation; Stage #3: (E)/(Z)-1-bromo-1-butene; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 58h; Cross-coupling;	66%

(E)/(Z)-1-bromo-1-butene (31844-98-1) + n-propylmagnesium bromide (927-77-5) → trans-3-heptene (14686-14-7)

Conditions	Yield
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 30℃;	61%

(E)/(Z)-1-bromo-1-butene (31844-98-1) + 4-penten-1-ylmagnesium bromide (34164-50-6) → trans nona-1,3-diene (60024-69-3)

Conditions	Yield
palladium dichloride In tetrahydrofuran at 30℃;	57%

(E)/(Z)-1-bromo-1-butene (31844-98-1) → 3,5-Octadiene (7348-75-6)

Conditions	Yield
With [2,2]bipyridinyl; (2,2'-bipyridine)nickel(II) dibromide In various solvent(s) at 20℃; electrochemical reaction, magnesium anode, gold gauze cathode, -1,2 V;	50%

formic acid (64-18-6) + (E)/(Z)-1-bromo-1-butene (31844-98-1) → trans-2-pentenoic acid (13991-37-2)

Conditions	Yield
With palladium diacetate; acetic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane In N,N-dimethyl-formamide at 100℃; Inert atmosphere; Schlenk technique;	39%

(E)/(Z)-1-bromo-1-butene (31844-98-1) → but-1-yne (107-00-6)

Conditions	Yield
With potassium hydroxide; ethanol at 180℃;

(E)/(Z)-1-bromo-1-butene (31844-98-1) → 1,1,2-tribromo-3-methoxy-propane

Conditions	Yield
With bromine

(E)/(Z)-1-bromo-1-butene (31844-98-1) → tris(1-butenyl)boroxine (24863-41-0)

Conditions	Yield
(i) Mg, (ii) B(OMe)3, (iii) phenothiazine; Multistep reaction;

(E)/(Z)-1-bromo-1-butene (31844-98-1) + 2-methyl-6-n-propylpyrazine (29444-46-0) → cis-3-methyl-5-n-propyl-2-(1-butenyl)-pyrazine (83568-49-4) + trans-3-methyl-5-n-propyl-2-(1-butenyl)-pyrazine (83568-51-8) + cis-5-methyl-3-n-propyl-2-(1-butenyl)-pyrazine (83568-47-2) + trans-5-methyl-3-n-propyl-2-(1-butenyl)-pyrazine (83568-50-7)

Conditions	Yield
With tert.-butyl lithium In tetrahydrofuran; diethyl ether; pentane 1.) -78 deg C, 15 min; 2.) r.t., 20 min; Title compound not separated from byproducts;

(E)/(Z)-1-bromo-1-butene (31844-98-1) + 11-dodecyn-1-yl acetate (53596-78-4) → (Z)-13-hexadecene-11-yn-1-yl acetate (78617-58-0) + (E)-13-hexadecene-11-yn-1-yl acetate (78617-59-1)

Conditions	Yield
With propylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) 1.) benzene, 2.) 16 h, RT; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

(E)/(Z)-1-bromo-1-butene (31844-98-1) + chloroform (67-66-3) + bromine (7726-95-6) → butane, 1,1,2-tribromo- (3675-68-1)

Conditions	Yield
lower-boiling 1-bromo-butene-(1);
higher-boiling 1-bromo-butene-(1);

(E)/(Z)-1-bromo-1-butene (31844-98-1) + bromine (7726-95-6) → 1-bromo-butene-(1) higher-boiling form

Conditions	Yield
am Sonnenlicht; Gleichgewicht.Irradiation; lower-boiling 1-bromo-butene-(1);

(E)/(Z)-1-bromo-1-butene (31844-98-1) + alcoholic KOH-solution → but-1-yne (107-00-6) + hydrogen bromide (10035-10-6, 12258-64-9)

Conditions	Yield
at 120 - 125℃; lower-boiling 1-bromo-butene-(1);
at 120 - 125℃; higher-boiling 1-bromo-butene-(1);

Upstream product

• 3675-68-1 butane, 1,1,2-tribromo- 
• 123-72-8 butyraldehyde 
• 60-29-7 diethyl ether 
• 75-16-1 methylmagnesium bromide 
• 627-15-6 1,3-dibromopropene 
• 2482-57-7 1-bromo-2-butanol 
• 533-98-2 1,2-dibromobutane 
• 626-98-2 pent-2-enoic acid 
• 110-86-1 pyridine 
• 79912-57-5 acide dibromo-2,3 pentanoique 
• 13991-37-2 trans-2-pentenoic acid 

Downstream Products

• 107-00-6 but-1-yne 
• 78617-58-0 (Z)-13-hexadecene-11-yn-1-yl acetate 
• 78617-59-1 (E)-13-hexadecene-11-yn-1-yl acetate 
• 7348-75-6 3,5-Octadiene 
• 10035-10-6 hydrogen bromide 
• 60216-44-6 1-trimethylsilyl-3-hexen-1-yne 
• 13991-37-2 trans-2-pentenoic acid 
• 3675-68-1 butane, 1,1,2-tribromo- 
• 14686-14-7 trans-3-heptene 

Relevant articles and documents

Novel system for decarboxylative bromination of α,β-unsaturated carboxylic acids with diacetoxyiodobenzene

A simple and mild method for the conversion of varieties of α,β-unsaturated carboxylic acids to the corresponding bromoalkenes using diacetoxyiodobenzene (IBD) in combination with tetraethyl-ammonium bromide (TEAB) at room temperature is discussed. Advantages of this system are short reaction time, easy work up and gave good to excellent yields.