Home Cart Sign in  
Chemical Structure| 70260-17-2 Chemical Structure| 70260-17-2

Structure of 70260-17-2

Chemical Structure| 70260-17-2

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 70260-17-2 ]

CAS No. :70260-17-2
Formula : C5H5BrOS
M.W : 193.06
SMILES Code : OCC1=C(Br)C=CS1
MDL No. :MFCD06202660
InChI Key :IXULCOYQSDIBFO-UHFFFAOYSA-N
Pubchem ID :12479011

Safety of [ 70260-17-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 70260-17-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 5
Fraction Csp3 0.2
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 38.15
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

48.47 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.84
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.44
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.85
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

1.29
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.07
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.9

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.34
Solubility 0.881 mg/ml ; 0.00456 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.06
Solubility 1.67 mg/ml ; 0.00864 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.35
Solubility 0.86 mg/ml ; 0.00446 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.46 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.25

Application In Synthesis of [ 70260-17-2 ]

* 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.

  • Upstream synthesis route of [ 70260-17-2 ]

[ 70260-17-2 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 930-96-1 ]
  • [ 70260-17-2 ]
YieldReaction ConditionsOperation in experiment
100%
Stage #1: With sodium tetrahydroborate In methanol at 0℃; for 2 h;
Stage #2: With ammonium chloride In ethyl acetate
To a solution of 3- bromothiophene-2-carbaldehyde (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 firs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.
100% With sodium tetrahydroborate In methanol at 0℃; for 2 h; [00473] To a solution of 3-bromothiophene-2-carbaldehyde (6) (500 mg, 2.62 mmol) in methanol (10 mL) was added sodium borohydride (169 mg, 4.47 mmol) in small portions at 0 °C and the reaction was stirred for 2 hrs. The solvent was evaporated and the residue partitioned between ethyl acetate (20 mL) and 10percent ammonium chloride solution (10 mL). The organic layer was washed with water (10 mL), dried over sodium sulfate and evaporated. The title compound (505 mg, 2.62 mmol, 100percent) was obtained as a yellow oil.
92% With sodium tetrahydroborate In ethanol at 0 - 20℃; for 24 h; Inert atmosphere Stirring of 3-bromothiophene-2-carboxaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) at 0 ° C under argon, and adding sodium borohydride (NaBH 4 , 3.4 g, 90.1 mmol) and stirred at room temperature for 24 hours. An aqueous solution of ammonium chloride was added to the oily solid obtained by concentration of the reaction mixture under reduced pressure, and the organic layer was extracted with ethyl acetate. After the extract was dried over magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure to give a crude material. The crude product was purified by a silica gel column chromatography (ethyl acetate / hexane (volume ratio) = 2 / 8) to thereby obtain 3-bromothiophene-2-methanol (the compound (3-1), The yield was 9.3 g, and the yield was 92percent)
92% at 0 - 20℃; for 24 h; Inert atmosphere A solution of 3-bromothiophene-2-carboxaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) was stirred at 0 ° C under an argon atmosphere, and sodium borohydride (NaBH 4 , 3.4 g, 90.1 mmol) and stirred at room temperature for 24 hours. An aqueous solution of ammonium chloride was added to the obtained oily solid, and the organic layer was extracted with ethyl acetate. After the extract was dried over magnesium sulfate and filtered, the filtrate was concentrated under reduced pressure to give a crude material. The crude product was purified by silica gel column chromatography (ethyl acetate / hexane (volume ratio) = 2/8), whereby 3-bromothiophene-2-methanol (the compound (3) -1), yield 9.3 g, yield 92percent).
92% With sodium tetrahydroborate In ethanol at 0 - 20℃; for 24 h; Inert atmosphere In an argon environment,A solution of 3-bromothiophene-2-carbaldehyde (compound (2-1), 10 g, 52.3 mmol) / ethanol (EtOH, 200 mL) was stirred at 0 ° C.Sodium borohydride (NaBH4, 3.4 g, 90.1 mmol) was added on one side.Stir at room temperature for 24 hours.The oily solid obtained by concentrating the reaction liquid under reduced pressure is added to an aqueous solution of ammonium chloride.The organic layer was extracted with ethyl acetate.Drying the extract with magnesium sulfate,After filtering,The filtrate was concentrated under reduced pressure to give a crude product.The crude product was purified by column chromatography (ethyl acetate/hexane (volume ratio) = 2/8).And the target compound 3-bromothiophene-2-methanol was obtained.(Compound (3-1), yield 9.3 g, yield 92percent).

References: [1] Patent: WO2011/156640, 2011, A2, . Location in patent: Page/Page column 134.
[2] Patent: WO2013/86451, 2013, A2, . Location in patent: Paragraph 00473.
[3] Patent: TW2018/43157, 2018, A, . Location in patent: Paragraph 0229-0232.
[4] Patent: TW2018/41922, 2018, A, . Location in patent: Paragraph 0239; 0240; 0241; 0242.
[5] Patent: TW2018/41923, 2018, A, . Location in patent: Paragraph 0213; 0214; 0215; 0216.
[6] Journal of the American Chemical Society, 2014, vol. 136, # 19, p. 7132 - 7139.
[7] Chemical Communications, 2015, vol. 51, # 18, p. 3842 - 3845.
  • 2
  • [ 7311-64-0 ]
  • [ 70260-17-2 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride; sodium chloride In tetrahydrofuran; water A/Preparation of 3-Bromo-2-hydroxymethyl-thiophene:
2-(3-Bromothienyl)carboxylic acid (7 g; 34 mmoles) is dissolved in 25 ml of anhydrous THF. A solution of aluminium hydride AlH3 in anhydrous THF (2 M; 42 ml; 84 mmoles) is added slowly at a temperature of 0° C.
At the end of the addition, the reaction mixture is refluxed for 3 hours.
After cooling to 0° C., water (200 ml) and hydrochloric acid (1N, 150 ml) are added.
The mixture is decanted and the aqueous phase extracted with 3*150 ml of tert-butyl methyl ether.
The organic phases are combined and then washed with 150 ml of a saturated solution of sodium chloride, dried over magnesium sulphate and filtered.
The solvent is evaporated under reduced pressure.
The desired product is obtained as a brown oil and is used as such in the next step.
Yield: 95percent; Physical characteristics: * NMR1H: (CD3OD) 4.69 ppm (s; 2H); 6.95 ppm (d; 1H, J=5.2 Hz); 7.39 ppm (d; 1H, J=5.2 Hz).
* NMR13C: (DMSO-d6) 57.80 ppm; 106.28 ppm; 126.11 ppm; 129.80 ppm; 141.15 ppm. * MS: (EI, 70 eV); 194/192 (M+*; 80percent); 177/175 (30percent); 113 (50percent); 98 (60percent); 85 (100percent).
73% With sodium hydroxide; borane In tetrahydrofuran; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate b.
3-Bromo-2-thiophenemethanol
A stirred, ice-water chilled solution of 90.0 g of 3-bromo-2-thiophenecarboxylic acid and 600 ml of sieve dried tetrahydrofuran was treated at 5° C. with 962 ml of borane in tetrahydrofuran (1.04M solution) over 2 hours (nitrogen atmosphere), with exclusion of moisture.
The stirred solution and cooling bath were allowed to equilibrate to ambient temperature overnight.
The stirred, chilled (10° C.) solution was treated dropwise with 150 ml methanol over 2 hours and then with 100 ml of 10percent sodium hydroxide.
After concentration, the residue was diluted with water, adjusted to pH=8 with 10percent sodium hydroxide solution and extracted with ether (2*300 ml).
The combined dried (over anhydrous sodium sulfate) ethereal phase was concentrated.
Distillation gave 61 g (73percent) of product, b.p. 79°-82° C. (0.38 mm).
Analysis:
Calculated for C5 H5 BrOS: 31.11percentC; 2.61percentH. Found: 31.30L percentC; 2.70percentH.
References: [1] Patent: US6525040, 2003, B1, .
[2] Patent: US4560701, 1985, A, .
  • 3
  • [ 26137-08-6 ]
  • [ 70260-17-2 ]
References: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 14, p. 2319 - 2332.
[2] Patent: US6528510, 2003, B1, .
  • 4
  • [ 872-31-1 ]
  • [ 67-56-1 ]
  • [ 70260-17-2 ]
References: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 18, p. 2661 - 2668.
  • 5
  • [ 62224-14-0 ]
  • [ 70260-17-2 ]
References: [1] Patent: US6340759, 2002, B1, . Location in patent: Example 259.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 70260-17-2 ]

Bromides

Chemical Structure| 7311-64-0

A116048 [7311-64-0]

3-Bromothiophene-2-carboxylic acid

Similarity: 0.79

Chemical Structure| 29421-99-6

A378787 [29421-99-6]

4-Bromo-5-methylthiophene-2-carboxylic acid

Similarity: 0.79

Chemical Structure| 16694-18-1

A141112 [16694-18-1]

4-Bromo-2-thiophenecarboxylic acid

Similarity: 0.73

Chemical Structure| 26137-08-6

A255746 [26137-08-6]

Methyl 3-bromothiophene-2-carboxylate

Similarity: 0.72

Chemical Structure| 930-96-1

A253098 [930-96-1]

3-Bromothiophene-2-carboxaldehyde

Similarity: 0.71

Alcohols

Chemical Structure| 699-12-7

A392356 [699-12-7]

2-(Phenylthio)ethanol

Similarity: 0.53

Chemical Structure| 6317-56-2

A148279 [6317-56-2]

(4-(Phenylthio)phenyl)methanol

Similarity: 0.52

Chemical Structure| 1122660-25-6

A150480 [1122660-25-6]

4-(5-(3-Hydroxyphenyl)thiophen-2-yl)-2-methylphenol

Similarity: 0.51

Chemical Structure| 5556-22-9

A185351 [5556-22-9]

Methyl 3-hydroxy-5-methyl-2-thiophenecarboxylate

Similarity: 0.50

Chemical Structure| 116539-57-2

A463778 [116539-57-2]

(R)-3-(Methylamino)-1-(thiophen-2-yl)propan-1-ol

Similarity: 0.50