Production Method 1

556-82-1

870-63-3

Reaction Conditions

1.1 Solvents: Diethyl ether ;  rt → 0 °C
1.2 Reagents: Phosphorus tribromide ;  30 min, 0 °C
1.3 Reagents: Sodium chloride Solvents: Water

Reference

Studies on Taxadiene Synthase: Interception of the Cyclization Cascade at the Isocembrene Stage with GGPP Analogues

Chow, Siew Yin; et al, Journal of Organic Chemistry, 2005, 70(24), 9997-10003

Production Method 2

870-63-3

Reaction Conditions

1.1 Reagents: Bromine

Reference

Synthesis and application of coenzyme Q10

Mao, Jin; et al, Jingxi Yu Zhuanyong Huaxuepin, 2005, 13(10), 22-24

Production Method 3

870-63-3

Reaction Conditions

1.1 Reagents: Hydrogen bromide

Reference

Abnormal transformations of derivatives of isoprene and of β, γ-dimethylbutadiene

Claisen, L.; et al, Journal fuer Praktische Chemie (Leipzig), 1922, 105, 65-92

Production Method 4

4516-90-9

870-63-3

Reaction Conditions

1.1 Reagents: Bromine atom Solvents: Diethyl ether ,  Water

Reference

Sequential hydroformylation, aldol reactions: Stereochemical control towards the synthesis of the Labdane diterpenoid forskolin and related terpenoid natural products

Keraenen, Mark David, 2004, , ,

Production Method 5

115-18-4

870-63-3

Reaction Conditions

1.1 Reagents: Bromine atom Solvents: Water

Reference

Investigations in the Stereoselective Synthesis of Indole Alkaloids through Intramolecular Hetero-Diels-Alder Reactions

Fahlbusch, Karl-Georg, 1984, , ,

Production Method 6

870-63-3

Reaction Conditions

Reference

Reaction gas chromatography: study of the photodecomposition of halogenated hydrocarbons

Pacakova, V.; et al, Chromatographia, 1988, 25(7), 621-6

Production Method 7

29283-76-9

870-63-3

Reaction Conditions

Reference

Use of hydrogen chloride for the synthesis of organochlorine solvents

Kartashov, L. M.; et al, Khlorist. Vodorod v Khlororgan. Sinteze, 1987, 118, 118-42

Production Method 8

638-10-8

870-63-3

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride Solvents: Diethyl ether ;  3 h, 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C
2.1 Reagents: Hydrogen bromide Solvents: Dichloromethane ;  2 h, 0 °C

Reference

Scalable synthesis of the aroma compounds d6-β-ionone and d6-β-cyclocitral for use as internal standards in stable isotope dilution assays

Mosaferi, Shabnam; et al, Tetrahedron Letters, 2020, 61(51),

Production Method 9

638-10-8

870-63-3

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 3 h, -78 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C; 20 min, rt
2.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  1 h, 0 °C
2.2 Reagents: Water

Reference

Nickel-Catalyzed Regioselective Reductive Cross-Coupling of Aryl Halides with Polysubstituted Allyl Halides in the Presence of Imidazolium Salts

Zhang, Zhan; et al, Synlett, 2015, 26(20), 2784-2788

Production Method 10

182412-80-2

917-54-4

870-63-3

Reaction Conditions

1.1 Solvents: Diethyl ether
2.1 Reagents: Pyridine ,  Phosphorus tribromide Solvents: Diethyl ether
3.1 Reagents: Dibutyl sulfide ,  Silver tetrafluoroborate Solvents: Dichloromethane

Reference

Sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives

Brajeul, Solenn; et al, Tetrahedron Letters, 2007, 48(32), 5597-5600

Production Method 11

867-13-0

870-63-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  0 °C → rt; overnight, rt
1.2 Reagents: Water
2.1 Reagents: Lithium aluminum hydride Solvents: Diethyl ether ;  3 h, 0 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  0 °C
3.1 Reagents: Hydrogen bromide Solvents: Dichloromethane ;  2 h, 0 °C

Reference

Scalable synthesis of the aroma compounds d6-β-ionone and d6-β-cyclocitral for use as internal standards in stable isotope dilution assays

Mosaferi, Shabnam; et al, Tetrahedron Letters, 2020, 61(51),

Production Method 12

27934-32-3

870-63-3

Reaction Conditions

1.1 Reagents: Dibutyl sulfide ,  Silver tetrafluoroborate Solvents: Dichloromethane

Reference

Sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives

Brajeul, Solenn; et al, Tetrahedron Letters, 2007, 48(32), 5597-5600

Production Method 13

556-82-1

870-63-3

Reaction Conditions

1.1 Reagents: 1-Bromo-N,N,2-trimethyl-1-propen-1-amine Solvents: Chloroform-d ;  0 °C; 0 °C → rt; 30 min, rt

Reference

A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

Munyemana, Francois; et al, Tetrahedron, 2021, 89,

Production Method 14

870-63-3

Reaction Conditions

1.1 Reagents: Hydrogen bromide

Reference

The formation of cyclic ethers from olefinic alcohols. Part XIII. The oxidative cyclization of 5-methyl-4-hexen-1-ol, 6-methyl-5-hepten-2-ol, and 2,6-dimethyl-5-hepten-2-ol by means of lead tetraacetate

Mihailovic, Mihailo L.; et al, Journal of the Serbian Chemical Society, 1986, 51(1), 1-7

Production Method 15

115-18-4

870-63-3

Reaction Conditions

1.1 Reagents: Acetyl bromide Solvents: Dichloromethane ;  1 h, rt

Reference

A novel one-pot conversion of allyl alcohols into primary allyl halides mediated by acetyl halide

Kishali, Nurhan; et al, Helvetica Chimica Acta, 2008, 91(1), 67-72

Production Method 16

115-18-4

870-63-3

Reaction Conditions

1.1 Reagents: Hydrogen bromide Solvents: Water ;  rt; 60 min, rt

Reference

Three-component three-bond forming cascade via palladium photoredox catalysis

Bellotti, Peter; et al, Chemical Science, 2021, 12(5), 1810-1817

Production Method 17

556-82-1

23162-64-3

870-63-3

Reaction Conditions

1.1 Catalysts: Triphenylphosphine

Reference

Stereospecific, R2AlCl-promoted intramolecular ene reaction of a 1,6-dienoate: evidence for a concerted mechanism

Oppolzer, Wolfgang; et al, Helvetica Chimica Acta, 1984, 67(3), 730-8

Production Method 18

77-48-5

870-63-3

Reaction Conditions

1.1 Reagents: Chlorine

Reference

Studies on formation of volatile chlorinated organic compounds by aqueous chlorination of aromatic hydrocarbons

Sayato, Yasuyoshi; et al, Suishitsu Odaku Kenkyu (1978-1991), 1987, 10(9), 547-54

Production Method 19

1826-67-1

870-63-3

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  3 h, -78 °C; -78 °C → rt
1.2 Reagents: Water ;  cooled
2.1 Reagents: Acetyl bromide Solvents: Dichloromethane ;  1 h, rt

Reference

A novel one-pot conversion of allyl alcohols into primary allyl halides mediated by acetyl halide

Kishali, Nurhan; et al, Helvetica Chimica Acta, 2008, 91(1), 67-72

Production Method 20

27934-31-2

870-63-3

Reaction Conditions

1.1 Reagents: Pyridine ,  Phosphorus tribromide Solvents: Diethyl ether
2.1 Reagents: Dibutyl sulfide ,  Silver tetrafluoroborate Solvents: Dichloromethane

Reference

Sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives

Brajeul, Solenn; et al, Tetrahedron Letters, 2007, 48(32), 5597-5600

Production Method 21

638-10-8

870-63-3

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  3 h, -78 °C; 1 h, -78 °C; -78 °C → 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  -20 °C; rt
2.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  15 - 30 min, 0 °C
2.2 Reagents: Ammonium chloride Solvents: Water

Reference

Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors

Liu, Jia-Li; et al, Organic Letters, 2020, 22(18), 7369-7372

Production Method 22

36032-75-4

870-63-3

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -70 °C
1.2 0.5 h, -50 °C; 2 h, rt
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  15 min, 0 °C; 0.5 h, rt
2.2 Reagents: Sodium sulfate Solvents: Water ;  0.5 h, rt
3.1 Reagents: Hydrogen bromide Solvents: Dichloromethane ,  Water ;  1.5 h

Reference

Preparation of [1,2,3,4,5-13C5]-5-amino-4-oxopentanoic acid (ALA) - design of a synthetic scheme to prepare any 13C- and 15N-isotopomer with high isotopic enrichment

Shrestha-dawadi, Prativa Bade; et al, European Journal of Organic Chemistry, 2003, (23), 4654-4663

Production Method 23

867-13-0

870-63-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  rt; 30 min, rt
1.2 Solvents: Tetrahydrofuran ;  0 °C; rt
2.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ;  3 h, -78 °C; 1 h, -78 °C; -78 °C → 0 °C
2.2 Reagents: Hydrochloric acid Solvents: Water ;  -20 °C; rt
3.1 Reagents: Phosphorus tribromide Solvents: Diethyl ether ;  15 - 30 min, 0 °C
3.2 Reagents: Ammonium chloride Solvents: Water

Reference

Visible-Light-Promoted Intramolecular α-Allylation of Aldehydes in the Absence of Sacrificial Hydrogen Acceptors

Liu, Jia-Li; et al, Organic Letters, 2020, 22(18), 7369-7372

Production Method 24

867-13-0

870-63-3

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  0 °C; 2 h, 0 °C
1.2 0 °C; overnight, rt
2.1 Reagents: Diisobutylaluminum hydride Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 3 h, -78 °C
2.2 Reagents: Ammonium chloride Solvents: Water ;  0 °C; 20 min, rt
3.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  1 h, 0 °C
3.2 Reagents: Water

Reference

Nickel-Catalyzed Regioselective Reductive Cross-Coupling of Aryl Halides with Polysubstituted Allyl Halides in the Presence of Imidazolium Salts

Zhang, Zhan; et al, Synlett, 2015, 26(20), 2784-2788

Production Method 25

105-36-2

870-63-3

Reaction Conditions

1.1 3 h, 130 - 140 °C
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -70 °C
2.2 0.5 h, -50 °C; 2 h, rt
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  15 min, 0 °C; 0.5 h, rt
3.2 Reagents: Sodium sulfate Solvents: Water ;  0.5 h, rt
4.1 Reagents: Hydrogen bromide Solvents: Dichloromethane ,  Water ;  1.5 h

Reference

Preparation of [1,2,3,4,5-13C5]-5-amino-4-oxopentanoic acid (ALA) - design of a synthetic scheme to prepare any 13C- and 15N-isotopomer with high isotopic enrichment

Shrestha-dawadi, Prativa Bade; et al, European Journal of Organic Chemistry, 2003, (23), 4654-4663

Production Method 26

26732-90-1

870-63-3

Reaction Conditions

1.1 Reagents: Formaldehyde ,  Potassium carbonate Solvents: Water
2.1 Solvents: Diethyl ether
3.1 Reagents: Pyridine ,  Phosphorus tribromide Solvents: Diethyl ether
4.1 Reagents: Dibutyl sulfide ,  Silver tetrafluoroborate Solvents: Dichloromethane

Reference

Sulfonium salts as prenyl, geranyl, and isolavandulyl transfer agents towards benzoylphloroglucinol derivatives

Brajeul, Solenn; et al, Tetrahedron Letters, 2007, 48(32), 5597-5600

1-bromo-3-methyl-but-2-ene Raw materials

• Triethyl phosphonoacetate
• 1,3-Dibromo-5,5-dimethylhydantoin
• 5-Hepten-2-one,6-methyl-3-methylene-
• Methyllithium (1.6M in Diethyl Ether)
• Ethyl bromoacetate
• 3-Methyl-2-buten-1-ol
• ethyl 3-methylbut-2-enoate
• 1,1,1,3,3,3-Hexabromoacetone
• Lithium, 1-propenyl- (9CI)
• Acetic acid, (diethylphosphinyl)-, ethyl ester
• 3-Buten-1-ol, 2-methyl-
• vinylmagnesium bromide solution
• 1,1-Dimethyl-2-propen-1-ol
• 5-Hepten-2-ol, 2,6-dimethyl-3-methylene-
• 2,4-Pentanedione, 3-(3-methyl-2-butenyl)-
• 3-(Bromomethyl)-2,6-dimethyl-2,5-heptadiene

1-bromo-3-methyl-but-2-ene Preparation Products

• 1-bromo-3-methyl-but-2-ene (870-63-3)

• 1. An approach to biodegradable star polymeric architectures using disulfide coupling?
  Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. Davis Chem. Commun., 2008, 6582-6584
• 2. An investigation into the origin of variations in photovoltaic performance using D–D–π–A and D–A–π–A triphenylimidazole dyes with a copper electrolyte?
  Govind Reddy Mol. Syst. Des. Eng., 2021,6, 779-789
• 3. An amorphous carbon nitride/NiO/CoN-based composite: a highly efficient nonprecious electrode for supercapacitors and the oxygen evolution reaction?
  Huifang Yang,Haoran Guo,Peidong Fan,Xinpan Li,Wenlu Ren,Rui Song Nanoscale, 2020,12, 7024-7034
• 4. Aggregation-induced emission leading to two distinct emissive species in the solid-state structure of high-dipole organic chromophores?
  Felix Witte,Philipp Rietsch,Nithiya Nirmalananthan-Budau,Florian Weigert,Jan P. G?tze,Ute Resch-Genger,Siegfried Eigler,Beate Paulus Phys. Chem. Chem. Phys., 2021,23, 17521-17529
• 5. An integrated system for field analysis of Cd(ii) and Pb(ii) via preconcentration using nano-TiO2/cellulose paper composite and subsequent detection with a portable X-ray fluorescence spectrometer?
  Xiaofeng Lin RSC Adv., 2016,6, 9002-9006

• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Organobromides Organobromides
• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Organobromides
• Solvents and Organic Chemicals Organic Compounds Acids/Esters
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

Chemical Profile of 1-bromo-3-methyl-but-2-ene (CAS No. 870-63-3)

1-bromo-3-methyl-but-2-ene, identified by its Chemical Abstracts Service number (CAS No. 870-63-3), is a significant organic compound widely utilized in synthetic chemistry and pharmaceutical research. This molecule, characterized by a bromine substituent on a branched alkene backbone, exhibits unique reactivity that makes it a valuable intermediate in the synthesis of more complex molecules.

The structural framework of 1-bromo-3-methyl-but-2-ene consists of a four-carbon chain with a double bond between the second and third carbons, a bromine atom attached to the first carbon, and a methyl group on the third carbon. This specific arrangement imparts distinct chemical properties, including moderate polarity due to the bromine atom and unsaturation from the double bond, which are leveraged in various synthetic pathways.

In recent years, 1-bromo-3-methyl-but-2-ene has garnered attention in the development of novel pharmaceutical agents. Its ability to undergo nucleophilic substitution reactions makes it an excellent precursor for constructing heterocyclic compounds, which are prevalent in many bioactive molecules. For instance, researchers have utilized this compound to synthesize derivatives with potential antimicrobial and anti-inflammatory properties. The bromine atom serves as a versatile handle for further functionalization, enabling the introduction of diverse pharmacophores.

The compound’s utility extends beyond pharmaceutical applications into agrochemical research. In this domain, 1-bromo-3-methyl-but-2-ene has been employed in the synthesis of herbicides and fungicides. The incorporation of its moiety into larger molecular structures enhances binding affinity to biological targets, improving the efficacy of crop protection agents. Recent studies have highlighted its role in developing next-generation pesticides with reduced environmental impact.

From a synthetic chemistry perspective, 1-bromo-3-methyl-but-2-ene is valued for its role in cross-coupling reactions, such as Suzuki-Miyaura and Heck couplings. These reactions facilitate the formation of carbon-carbon bonds, which are essential for constructing complex organic molecules. The presence of both a bromine atom and an unsaturated double bond allows for sequential functionalization, making it a versatile building block in multi-step syntheses.

Industrial applications of 1-bromo-3-methyl-but-2-ene include its use as a monomer or intermediate in polymer chemistry. While not as common as other olefins in polymer production, its unique structure can contribute to the development of specialty polymers with tailored properties. For example, its incorporation into certain polymer backbones can enhance thermal stability or mechanical strength.

The safety and handling of 1-bromo-3-methyl-but-2-ene are critical considerations in industrial and laboratory settings. Although it is not classified as a hazardous material under standard regulations, proper precautions must be taken to prevent exposure due to potential skin or eye irritation. Storage conditions should be controlled to avoid degradation or unwanted reactions with other chemicals.

Environmental impact assessments have been conducted to evaluate the persistence and toxicity of 1-bromo-3-methyl-but-2-ene in aquatic systems. Current research suggests that while it exhibits moderate biodegradability, its brominated nature may lead to bioaccumulation concerns under certain conditions. Thus, responsible disposal practices are essential to mitigate environmental risks.

In academic research circles, 1-bromo-3-methyl-but-2-ene continues to be explored for its potential in catalytic processes. Studies have demonstrated its utility as an intermediate in asymmetric synthesis, where chiral auxiliaries or catalysts can induce stereoselective transformations. This capability is particularly valuable in producing enantiomerically pure compounds, which are often required for pharmaceutical applications.

The future prospects for 1-bromo-3-methyl-but-2-ene appear promising, with ongoing investigations into its role in green chemistry initiatives. Efforts are underway to develop more sustainable synthetic routes that minimize waste and energy consumption while maintaining high yields. Such advancements would align with global trends toward environmentally conscious chemical manufacturing.

• 869-72-7(2-Pentene, 1-bromo-3-methyl-)
• 30432-16-7(1,4-Dibromo-2,3-bis(bromomethyl)but-2-ene)
• 57253-30-2((2e)-1-bromo-2-methyl-2-butene)
• 41178-84-1
• 34619-20-0(1,4-Dibromo-2,3-dimethyl-2-butene)
• 16526-18-4(2-Butene, 1,4-dibromo-2-methyl-, (Z)-)
• 58135-14-1(2,6-Octadiene, 1-bromo-7-methyl-, (2E)-)
• 18860-95-2((e)-1,4-dibromo-2-methylbut-2-ene)
• 5072-70-8(1-Bromo-2,3-dimethyl-2-butene, (Technical Grade))
• 16526-19-5(2-Butene, 1,4-dibromo-2-methyl-, (2E)-)