2-Bromo-3-methylbutyric acid

Base Information

• Chemical Name: 2-Bromo-3-methylbutyric acid
• CAS No.: 565-74-2
• Deprecated CAS: 10323-40-7
• Molecular Formula: C₅H₉BrO₂
• Molecular Weight: 181.029
• Hs Code.: 29159080
• European Community (EC) Number: 209-291-0
• NSC Number: 6967,167
• UNII: M69LGV465C
• DSSTox Substance ID: DTXSID30870617
• Nikkaji Number: J6.513G
• Wikidata: Q27283553
• Mol file: 565-74-2.mol

Synonyms:2-bromoisovaleric acid;2-bromoisovaleric acid, (+-)-isomer;2-bromoisovaleric acid, (R)-isomer;2-bromoisovaleric acid, (S)-isomer;2-bromoisovaleric acid, sodium salt;alpha-bromoisovaleric acid

Chemical Property of 2-Bromo-3-methylbutyric acid

Chemical Property:

• Appearance/Colour: White to beige crystalline powder or chunks
• Vapor Pressure: 0.024mmHg at 25°C
• Melting Point: 39-42 °C(lit.)
• Refractive Index: 1.4790 (estimate)
• Boiling Point: 229.999 °C at 760 mmHg
• PKA: 3.00±0.10(Predicted)
• Flash Point: 88.917 °C
• PSA: 37.30000
• Density: 1.513 g/cm³
• LogP: 1.49050
• Solubility.: alcohol: soluble(lit.)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 179.97859
• Heavy Atom Count: 8
• Complexity: 90.4

Purity/Quality:

99% ^*data from raw suppliers

2-Bromo-3-methylbutyric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 21/22-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)Br
• Uses: 2-Bromo-3-methylbutyric acid was used to study the conjugation of glutathione (GSH) with (R)-and (S)-α-bromoisovaleric acid (BI) in the rat 1 . 2-Bromo-3-methylbutyric acid has been used in the preparation of optically active N-methylvalines.

Technology Process of 2-Bromo-3-methylbutyric acid

There total 33 articles about 2-Bromo-3-methylbutyric acid 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: 97.0%

3-methylbutyric acid (503-74-2) → 2-bromoisovaleric acid (10323-40-7,565-74-2)

Guidance literature:

With bromine; phosphorus trichloride; for 4.5h; Heating;

DOI:10.1039/b618540a

Reference yield: 81.0%

D,L-valine (516-06-3,25609-85-2,7004-03-7,921-10-8) → 2-bromoisovaleric acid (10323-40-7,565-74-2)

Guidance literature:

With pyridinium polyhydrogen fluoride; potassium bromide; sodium nitrite; for 48h; Ambient temperature;

DOI:10.1002/hlca.19830660404

Reference yield: 73.0%

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) → (R)-2-bromoisovaleric acid (76792-22-8,10323-40-7,26782-75-2,565-74-2)

Guidance literature:

With sulfuric acid; potassium bromide; sodium nitrite; at 0 - 20 ℃;

upstream raw materials:

3-methylbutyric acid

2-bromo-3-methyl-butyraldehyde

dibromoacetonitrile

isobutyraldehyde

Downstream raw materials:

ethyl 2-bromoisovalerate

2-methoxy-3-methylbutanoic acid

3-Methylbutenoic acid

2-hydroxy-3-methylbutanoic acid

Refernces

• 1、 Wu, Peng,Zhang, Mengjie,Zhang, Yinjun,Wang, Zhao,Zheng, Jianyong. "A novel lipase from Aspergillus oryzae catalyzed resolution of (R,S)-ethyl 2-bromoisovalerate". . p. 231 - 238. Retrieved 2019/12/27.
• 2、 Takatsuji, Ryo,Shinbara, Koki,Katoh, Takayuki,Goto, Yuki,Passioura, Toby,Yajima, Ryo,Komatsu, Yamato,Suga, Hiroaki. "Ribosomal Synthesis of Backbone-Cyclic Peptides Compatible with in Vitro Display". supporting information. . Retrieved 2019/02/14.