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Chemistry
Heterocyclic Building Blocks
Thiazoles
5-bromothiazole
5-Bromo-a,a-dimethyl-2-thiazolemethanol
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Thiazoles
Bromides Alcohols
5-bromothiazole

[ CAS No. 879488-37-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 879488-37-6
Chemical Structure| 879488-37-6
Chemical Structure| 879488-37-6
Structure of 879488-37-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 879488-37-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
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Product Citations

Product Details of [ 879488-37-6 ]

CAS No. :879488-37-6 MDL No. :MFCD18325135
Formula : C6H8BrNOS Boiling Point : -
Linear Structure Formula :- InChI Key :JTHVMHSSQOPBCP-UHFFFAOYSA-N
M.W : 222.10 Pubchem ID :22714306
Synonyms :

Calculated chemistry of [ 879488-37-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.44
TPSA : 61.36 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 1.72
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : 2.85
Consensus Log Po/w : 1.89

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.552 mg/ml ; 0.00249 mol/l
Class : Soluble
Log S (Ali) : -2.62
Solubility : 0.527 mg/ml ; 0.00237 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.4
Solubility : 0.88 mg/ml ; 0.00396 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.74

Safety of [ 879488-37-6 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 879488-37-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 879488-37-6 ]

[ 879488-37-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 362718-78-3 ]
  • [ 879488-37-6 ]
YieldReaction ConditionsOperation in experiment
With bromine; sodium hydrogencarbonate; In hexane; chloroform; ethyl acetate; Step 3: 5-Bromo-2-(1-hydroxy-1-methylethyl)thiazole. To a solution of 2-(1-methyl-1-[2-(trimethylsilyl)ethoxy]methoxy}ethyl)thiazole from Step 2 in chloroform (2 mL/mmol) at room temperature was added bromine (2 molar eq) and the resulting mixture was stirred for 1 hour. Solid sodium bicarbonate (0.55 eq) was added and the mixture was stirred for 5 hours. More sodium bicarbonate was added (0.55 eq) and stirring was continued for 18 hours. After a final addition of sodium bicarbonate (0.55 eq) the mixture was stirred for a further 5 hours, diluted with chloroform and the organic phase was washed with saturated aqueous sodium bicarbonate, then with water, dried and evaporated. The crude material was chromatographed, eluding with a 3:7 mixture of ethyl acetate and hexane to afford the desired product.
Reference： [1]Patent: US2003/114478,2003,A1
YieldReaction ConditionsOperation in experiment
1.6 g With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20.0℃; for 1.0h; General procedure: To a solution of 2-(methoxymethyl)thiazole (920 mg, 7.12 mmol) in N,N-dimethylformamide (5 mL) was added N-bromosuccinimide (1.9 g, 10.68 mmol).The mixture was stirred at room temperature for 1 hour. The mixture was diluted with ethyl acetate (50 mL),Then it was washed with water (50mL) and saturated brine (50mL), and then dried with anhydrous sodium sulfate,Filter and concentrate under reduced pressure to obtain crude product,The crude product was purified by column chromatography to obtain 5-bromo-2-(methoxymethyl)thiazole (900 mg) as a white solid.
  • 3
  • [ 879488-37-6 ]
  • [ 1066-54-2 ]
  • C11H17NOSSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 50.0℃; for 0.75h;Inert atmosphere; General procedure: Procedure C:CuT (0.218 g; 1.14 mmol), PdC12(PPh3)2 (0.401 g; 0.57 mmol), (trimethylsilyl)ethynyl acetylene (5.71 mmol) and the iodo derivative (5.71 mmol) are introduced in a two-necked round flask. The atmosphere is flushed with nitrogen during 30 mm, then degassed THF (50 mL) and degassed TEA (2 mL; 14.3 mmol) are added. The suspension is stirred undernitrogen atmosphere at 50C for 45 mm. After concentration to dryness, the residue is then purified by CC (Hept-EA). Preparation BI: 2-(5-ethynylthiazol-2-yl)propan-2-ol:Starting from <strong>[879488-37-6]2-(5-bromothiazol-2-yl)propan-2-ol</strong> (0.429 g, 1.87 mmol; commercial) and proceeding in analogy to Procedure C (Sonogashira coupling, 76% yield) and Preparation H. step H.ii (TMS cleavage, 68% yield), the title compound was obtained, after purification by CC (Hept-EtOAc), as an yellowish solid (0.118 g). ‘HNMR(d6-DMSO) ö: 7.91 (s, 1H); 6.15 (s, 1H); 4.68 (s, 1H); 1.48 (s, 6H). MS (ESI, mlz): 168.00 [M+Hj for C8H9NOS; tp = 0.62 mm.
Reference： [1]Patent: WO2015/132228,2015,A1 .Location in patent: Page/Page column 71; 113; 114
  • 4
  • [ 879488-37-6 ]
  • (R)-4-((R)-1-((1-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]
  • (R)-4-((R)-1-((1-cyclopropyl-5-(2-(2-hydroxypropan-2-yl)thiazol-5-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.5% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; at 100.0℃; for 2.0h;Microwave irradiation; Inert atmosphere; Sealed tube; To a microwave tube equipped with a stirring bar, (R)-4-((R)-1-((1-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one (100 mg, 0.243 mmol), <strong>[879488-37-6]2-(5-bromothiazol-2-yl)propan-2-ol</strong> (80 mg, 0.36 mmol), 1,2-dimethoxyethane (3 mL), 1 N Na2CO3 aqueous solution (1.08 mL, 1.08 mmol) were added, the mixture was bubbled N2 for 5 minutes before Pd(PPh3)4 (20.8 mg, 0.018 mmol) was added. The tube was sealed and heated in an oil bath at 100 C. for 2 hrs. DCM (200 mL) was added and the resulting mixture was washed with saturated NaHCO3 aqueous solution (20 mL×4), brine (20 mL×1), dried over anhydrous Na2SO4, filtered, removed solvents in vacuo. The resulting residue was passed a ISCO silica gel column (MeOH:DCM=5:95) to give off-white solids, 51.5 mg (yield 33.5%).
Reference： [1]Patent: KR2016/37198,2016,A .Location in patent: Paragraph 2049-2051
  • 5
  • [ 879488-37-6 ]
  • (R)-4-((R)-1-((3-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]
  • (R)-4-((R)-1-((3-cyclopropyl-6-(2-(2-hydroxypropan-2-yl)thiazol-5-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
15.1% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 100.0℃; for 2.0h;Microwave irradiation; Inert atmosphere; Sealed tube; To a microwave tube equipped with a stirring bar, (R)-4-((R)-1-((3-cyclopropyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (167.0 mg, 0.405 mmol), <strong>[879488-37-6]2-(5-bromothiazol-2-yl)propan-2-ol</strong> (90.0 mg, 0.405 mmol), 1,2-dimethoxyethane (2 mL), 1 N Na2CO3 aqueous solution (0.55 mL, 0.55 mmol) were added, the mixture was bubbled N2 for 5 minutes before Pd(PPh3)4 (10.6 mg, 0.009 mmol) was added. The tube was sealed and heated in an oil bath at 100 C. for 2 hrs. DCM (200 mL) was added and the resulting mixture was washed with saturated NaHCO3 aqueous solution (20 mL×4), brine (20 mL×1), dried over anhydrous Na2SO4, filtered, removed solvents in vacuo. The resulting residue was passed a ISCO silica gel column (MeOH:DCM=5:95) to give brown solids, 26.1 mg (yield 15.1%).
Reference： [1]Patent: KR2016/37198,2016,A .Location in patent: Paragraph 2079-2081

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Alcohols

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols are Weakly Basic • Alcohols as Acids • Alcohols Convert Acyl Chlorides into Esters • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alcoholysis of Anhydrides • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldol Addition • Alkene Hydration • Alkene Hydration • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Appel Reaction • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Carboxylic Acids React with Alcohols to Form Esters • Chloroalkane Synthesis with SOCI2 • Chromium Reagents for Alcohol Oxidation • Chugaev Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Convert Esters into Aldehydes Using a Milder Reducing Agent • Convert Haloalkanes into Alcohols by SN2 • Corey-Kim Oxidation • Decarboxylation of 3-Ketoacids Yields Ketones • Decomposition of Lithium Aluminum Hydride by Protic Solvents • Dess-Martin Oxidation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylations Using Alcohols • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • General Reactivity • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Grignard Reagents Transform Esters into Alcohols • Haloalcohol Formation from an Alkene Through Electrophilic Addition • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Halogenation of Alkenes • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hiyama Cross-Coupling Reaction • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydroboration-Oxidation • Hydroboration-Oxidation • Hydrolysis of Haloalkanes • Jones Oxidation • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Martin's Sulfurane Dehydrating Reagent • Methylation of Ammonia • Methylation of Ammonia • Mitsunobu Reaction • Moffatt Oxidation • Osmium Tetroxide Reacts with Alkenes to Give Vicinal Diols • Osmium TetroxideReacts with Alkenes to Give Vicinal Diols • Oxidation of Alcohols by DMSO • Oxymercuration-Demercuration • Preparation of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkoxides with Alkyllithium • Preparation of Amines • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Alcohols • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Ring Opening of an Oxacyclopropane by Lithium Aluminum Hydride • Ritter Reaction • Sharpless Olefin Synthesis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Swern Oxidation • Synthesis of Alcohols from Tertiary Ethers • Synthesis of an Alkyl Sulfonate • The Nucleophilic Opening of Oxacyclopropanes • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Transesterification • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vicinal Anti Dihydroxylation of Alkenes • Williamson Ether Syntheses
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